I am going to try something this week that I have been meaning to do for a while.

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Drop your questions in the comments, and I will answer as many as possible.

Ask me about anything in these lanes:

• IRS representation. Keep it general, not specific to your client’s facts. I cannot give advice on a case I am not engaged in. But how a process works, how I would think about an approach, what I wish I had known earlier, all fair game.

• Practice management. Pricing, engagement letters, workflow, saying no, the stuff nobody teaches you.

• Technology and security. The tools I actually use, what is worth the money, how I think about the FTC Safeguards Rule, and keeping client data safe.

• Building a practice. How I got here, what I would do differently, what the first few years actually looked like.

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Where to find me this summer

A few places.

Tax Retreat 2026, San Antonio, June 3rd to 6th. I am co-presenting Built This Way: Technology, Infrastructure, and Security Decisions with Aaron Dickerson, CPA, on Thursday from 11:45 AM to 12:45 PM Central.

CSTC Summer Tax Symposium, June 7th to 10th in Reno at the Silver Legacy. I am teaching three sessions this year. Two on Tuesday: one on responding to IRS notices, and one on innocent spouse relief. Then, on Wednesday, I am joining Tom Gorczynski and Shannon Hall for a panel on closing a practice, which is timely given the succession-planning language in the proposed Circular 230 changes. Details and registration

CSEA Super Seminar, June 16th to 18th, also in Reno, at the Peppermill. I am attending this one, not speaking, so if you want to grab coffee and chat, hit me up. Conveniently, it lands right after CSTC, so you can make one trip out of both.

NATP Taxposium 2026, Cleveland, July 13th to 15th. I am teaching three sessions this year, spread across all three days, so I will be there from start to finish. Monday, I am presenting Fixing Common Errors in a Tax Practice. Tuesday is Cryptocurrency and Other Digital Asset Crimes. On Wednesday, I close out with Cybersecurity Best Practices for Tax Professionals. Early registration runs through June 12th before rates go up on June 13th, so if you are thinking about it, now is the time. Use code 26ROCK for $100 off your registration.

Hope to see you at one of the events. Always great to put a face with a subscriber.

Last week, I was getting a facial when I heard how someone had lost access to everything.

My esthetician was telling a story while he worked. He had lost his phone number. Not lost it in the casual sense. Lost it in the sense that someone else now had it. He woke up to dead service one morning, and by the time he figured out what was happening, the attacker had used the number to reset his banking credentials, drain several thousand dollars, and lock him out of every account he owned.

I lay there with my eyes closed and thought about how many people I know would not survive that week.

The attack has a name. It is called port-out fraud, and it is a close cousin of SIM swapping. SIM stands for Subscriber Identity Module, the chip or digital profile that links your phone number to your carrier. The two attacks get used interchangeably, but they are not the same thing. A SIM swap moves your number to a new SIM inside your current carrier. A port-out moves your number to an entirely different carrier. Same outcome either way. The attacker now receives your text messages and phone calls. Your phone goes dead. Theirs comes alive with your life on it.

From there, the script is depressingly simple. Click “forgot password” on a bank login. Receive the verification text. Walk in. Too much consumer security in 2026 still rests on the quiet assumption that the person holding your phone number is you.

The Numbers

This is not a fringe attack.

The Federal Bureau of Investigation’s Internet Crime Complaint Center, known as the IC3, logged 971 SIM-swap complaints and $17.4 million in reported losses in 2025. That is down from the $72.6 million peak reported in 2022, but the decline should not make anyone comfortable. Victims often report the downstream fraud: bank theft, crypto theft, fraudulent credit-card charges, or identity theft. The phone-number takeover can disappear inside the larger police report.

A Princeton study tested SIM-swap authentication practices across five U.S. prepaid wireless carriers and found that all five used authentication challenges that could be subverted.

One of the largest publicly reported examples remains what was widely reported to be the FTX hack in November 2022. More than $400 million in cryptocurrency was allegedly drained after attackers used a SIM-swapping scheme to take control of a target’s phone number. In March 2025, a law firm announced a $33 million arbitration award against T-Mobile over a customer whose cryptocurrency was stolen after a SIM-swap attack that the claim alleged the carrier should have stopped.

You do not have to be a crypto whale to be a target. You just have to have a bank account.

What the Carriers Will Not Tell You

FCC rules adopted in 2023 now require wireless providers to use stronger authentication for SIM-change and port-out requests, notify customers when those requests are made, and take additional steps to protect customers from SIM-swap and port-out fraud. In practice, these protections are often opt-in. The burden is still on you to go find the toggle.

Here is the checklist. Do this today.

1. Turn on port-out and SIM locks at your carrier. (The location of these settings can change.)

• Verizon: Sign in to the My Verizon app. Open Account, then Security settings. Enable both Number Lock and SIM Protection. Number Lock helps block port-outs. SIM Protection helps block SIM and device changes. Do both.

• AT&T: Open the AT&T app. Tap the person icon, scroll to Wireless Account Lock, and swipe to lock. AT&T also describes Wireless Account Lock as a control that disables certain account transactions and account changes.

• T-Mobile: Enable Account Takeover Protection or Port Out Protection for each line, and turn on SIM Protection where available. T-Mobile describes Account Takeover Protection as free protection against unauthorized ports, and its fraud guidance describes SIM Protection as a feature that prevents bad actors from moving your number to a new SIM card or eSIM.

2. Get every account you can off SMS-based two-factor authentication.

SMS stands for Short Message Service, the original text messaging protocol. Two-factor authentication, also called multi-factor authentication or MFA, is the second step a system asks for after your password. SMS as a second factor is the entire reason this attack pays. Move everything that matters to an authenticator app (Duo is my preference), a hardware key, or biometric passkeys. Banks, email, brokerage, social media, tax software, anywhere money lives or identity is verified.

The National Institute of Standards and Technology, known as NIST, does not ban SMS outright, but it treats phone-network-based authentication as restricted. NIST specifically tells verifiers to consider risk indicators such as device swaps, SIM changes, and number porting before sending an authentication code.

3. Set a real account PIN with your carrier.

A PIN, or Personal Identification Number, is the short numeric code a carrier representative will ask for before making changes to your account. Not your birthday. Not the last four of your Social Security number. Not the same PIN you use for your debit card. A unique, random number that exists only to authenticate carrier requests.

4. Lock the SIM itself.

On iPhone and Android, you can require a PIN to use the SIM after a reboot. Turn it on. It is one more layer between an attacker and your number.

Each carrier ships a SIM with a default PIN. Common default include: Verizon and AT&T 1111, and T-Mobile using 1234. Confirm your own default with your carrier before you enter anything, because three wrong attempts lock the SIM and force you to call for a PUK (PIN Unblocking Key) to recover it. Exhausting the PUK attempts can disable the SIM for good. Once you are in, change the default to a number only you know. Left at 1111 or 1234, the lock protects nothing.

Keep in mind that it will require a PIN before connecting to the cellular network. If you lose your phone, that can be problematic because a service such as Find My on iPhones would not update your location until the device reconnects.

5. Stop using your phone number as a recovery identifier.

Wherever a service lets you use app-based recovery instead of a phone number, switch. Treat the phone number as a partially public identifier, not a credential. Because that is what it has become.

But What About...

Two reasonable questions land hard once the toggles are flipped, and they deserve straight answers.

“Could not someone just log into my carrier account and turn the lock off?”

In theory, yes. In practice, the lock raises the bar substantially.

To turn off Number Lock or SIM Protection, an attacker now needs your actual carrier portal credentials, not just enough scraped personal information to social engineer a customer service representative. That shifts the attack from “make a convincing phone call” to “break into a specific online account.” Changes to SIM or port settings may also generate notifications, which give you a chance to catch the attack before the next domino falls. The FCC order requires customer notification for SIM-change and port-out requests.

The catch is that your carrier login is now a high-value credential in its own right. Treat it that way.

• Use a long, unique password from a password manager. Not the one you also use for streaming.

• Turn on MFA for the carrier account itself, and use an authenticator app or a passkey. Do not use SMS to the line you are trying to protect. That creates a circular dependency the attacker can exploit.

• Watch every carrier security email and text. Treat them like fire alarms, not spam.

Is the lock perfect? No. It forces an attacker to clear two hurdles instead of zero. Many opportunistic attackers will move on to an easier target.

“Does any of this work if I do not have a physical SIM card? I am on eSIM.”

Yes. The principle is identical.

An eSIM, or embedded SIM, is just a digital version of the same credential. The attack does not care whether the SIM is a piece of plastic or a software profile on your device. The attack targets the carrier’s verification process, which decides whose device gets to receive your number. Carriers can and do issue new eSIM profiles to a different device just as readily as they used to ship physical SIM cards in the mail. eSIM provisioning fraud is a documented and growing attack pattern.

Verizon’s SIM Protection materials state that the control can block transactions requiring a new physical SIM or eSIM. T-Mobile also describes SIM Protection as applying before changing to a new SIM card or moving an eSIM to a new device. Flip the toggle regardless of which kind of SIM you carry.

In some ways, eSIM-only phones may raise the stakes slightly. There is no longer a physical card to ship to a fraudulent address, which means one small friction in the old attack chain is gone. The toggle is the new friction.

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The Practitioner Footnote

For tax professionals reading this, this is very important.

If your Written Information Security Plan, or WISP, relies on SMS-based MFA to satisfy your Federal Trade Commission Safeguards Rule obligations under 16 C.F.R. Part 314, you have a single point of failure that a port-out call can dismantle. The Gramm-Leach-Bliley Act framework the Safeguards Rule sits on top of does not name SMS. It does require reasonable safeguards.

In my view, “reasonable” in 2026 no longer means relying on a six-digit code texted to a number that can be hijacked at a strip-mall phone store. The FTC Safeguards Rule, built on the Gramm-Leach-Bliley Act definition of a financial institution at 16 C.F.R. 314.2, classifies tax and accounting professionals as covered financial institutions and requires them to develop, implement, and maintain an information security program. The IRS guidance for practitioners restates that obligation in plainer terms.

Your practice management software, your e-filing portal, your bank, your email, your client portal. If any of those still default to SMS for the second factor, you are one phone call away from a breach notification you will not want to write.

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In Closing

My esthetician finished my facial. I paid, walked out into the parking lot, and made sure Number Lock and SIM Protection were turned on in the Verizon app before I drove away.

Go turn yours on. Then send this to someone who would not survive losing their phone number for a week. Sometimes it is the simple quick things that have a huge impact. As always, if you have any questions, let me know.

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I have a friend who uses Microsoft Edge and Bing (I think that was once a search engine?), I routinely give her a hard time because, well, it is fun. My spouse uses Firefox, and every time I sit down at his computer, I’m like, " What is this, 2000? Well, maybe they are on to something. (We can’t tell them that, though.)

Google Chrome has been up to something. Open File Explorer or Finder. Navigate to your Chrome user profile directory. Look for a folder called OptGuideOnDeviceModel. That folder is likely 4 gigabytes in size. You did not download it deliberately. You did not see a prompt. If you delete it, Chrome will quietly put it back the next time the right conditions trigger.

That file is Gemini Nano, Google’s on-device large language model. It is being deployed silently to any device that meets Google’s hardware threshold and triggers any feature that uses it. There was no consent prompt. There was no settings toggle until February of this year, and even now, the toggle is rolling out unevenly across operating systems and Chrome versions. Delete the file, and Chrome will redownload it the next time a triggering condition fires, unless you have first disabled the underlying flags. Security researcher Alexander Hanff documented the behavior, and outlets including The Verge, Tom’s Hardware, Android Authority, Gizmodo, and Malwarebytes have since confirmed it on Windows, macOS, and Linux.

Set the privacy lawyers and the EU regulators aside. As a pure security matter, the behavior pattern is the part that should bother you.

Pattern recognition

Walk through what Chrome actually did on your machine.

It downloaded several gigabytes of new code and data without notifying you. It installed that payload into a directory in your user profile that you almost certainly did not know existed. It did not ask whether you wanted the feature. It did not tell you what the file does. If you find the file and delete it, it puts the file back. The opt-out is buried behind two experimental flags in a developer settings page that no normal user will ever open, plus a Settings menu toggle that may or may not be present depending on your version.

There is a worse detail. Researchers analyzing Chrome’s internal feature flags found that the browser enables the OnDeviceModelBackgroundDownload flag before the corresponding user-facing settings are exposed. Translation: Chrome can begin pulling the model to your machine before any control surface exists for you to see it on, much less object to it. The setting that would let you say no is published after the fact.

Read the previous two paragraphs again with the vendor name redacted. Pretend you do not know who shipped this. The security community has a phrase for software that installs itself without consent, hides in obscure folders, persists across user removal, and ships its control surface after the install begins. The phrase is not flattering.

The argument that Google is a trusted vendor and therefore the behavior is acceptable inverts the security model. Trust is what allows you to install software in the first place. It is not what software is supposed to use to justify behavior you would otherwise reject. A trusted vendor that ships malware-shaped behavior is in some ways the worse outcome, because the defenses you have in place are less likely to flag it.

What actually triggers the download

The trigger pattern deserves its own attention. The model does not necessarily install the moment you launch Chrome on qualifying hardware. It downloads when something activates a feature that uses it.

A user clicking Help Me Write triggers it. A website you visit calling the Summarizer API triggers it. An extension you have installed requesting an Origin Trial token triggers it. AI-assisted tab grouping, autofill, smart paste, page summarization, on-device scam detection, and writing suggestions can all trigger it.

The set of conditions that can cause Chrome to begin pulling several gigabytes of code and weights to your computer is broader than most users would guess, and it includes conditions that third parties decide for you. Loading the wrong page is enough.

What the install expands

The presence of the model itself adds attack surface to your machine.

Gemini Nano on Chrome powers a growing list of features. Help Me Write. On-device scam detection. Smart paste. Page summarization. AI-assisted tab grouping. Autofill. Writing suggestions. A Summarizer API that any website you visit can call. Each of those is a code path that takes input and produces output, all running on your machine, all sharing the same underlying model.

For anyone with a security background, the relevant questions are the ones you would ask about any new local service. What inputs can reach it? What outputs can it produce? What other components on the system can interact with it? What is the audit trail when the service runs? Where are the logs?

Chrome has not made those answers easy to find. The Summarizer API is callable by any origin without a meaningful consent mechanism. Help Me Write integrates with text fields, including those inside web applications you may use for sensitive work. The model itself updates through Chrome’s existing update channel, which means the integrity of what runs on your machine is downstream of whatever Google decides to ship next, on whatever schedule Google chooses, with no separate review or approval step.

For most users, none of that matters in any practical sense. For anyone whose endpoint touches data they care about, it matters the same way any unaudited local service running with user privileges has always mattered.

The bigger pattern

Hanff connected the Chrome behavior to a broader trend across desktop platforms. Microsoft is embedding Copilot into Windows and Office on a similar trajectory. Anthropic’s Claude Desktop reportedly installed browser integration bridges across Chromium browsers without a prompt. The default posture for major software vendors right now is to ship AI features and explain them later, if at all.

This is not a one-time incident. It is the new operating mode. Your endpoint is not a stable artifact you configured once. It is a continuously mutating surface that vendors are reshaping in the background, on their schedule, for their priorities.

A security model that assumes your machine looks today the way it looked last quarter no longer holds. Periodic baseline review used to be a hygiene practice you could let slip without immediate consequence. It is now a first-order control. You cannot reason about your defenses if you do not know what is running.

The alternatives are different

Worth being precise about something. This is Chrome’s behavior, not Chromium’s.

Gemini Nano rides on Google’s Optimization Guide component update infrastructure. That infrastructure is a Google service that lives on top of Chromium, not inside it. Other Chromium-based browsers fork from upstream Chromium and strip out Google’s service layer, replacing it with their own. None of them inherit Chrome’s silent model deployment pipeline.

Microsoft Edge keeps its AI cloud-routed. Copilot in Edge sends prompts to Microsoft’s servers, the same way Chrome’s omnibox AI Mode does. No silent multi-gigabyte local model installed by the browser. Edge has its own issues, and Microsoft is pushing on-device AI hard at the operating system level on Copilot+ PCs, but that is OS-level deployment tied to specific hardware classes you bought deliberately, not browser-level silent install.

Brave strips Google services from Chromium aggressively and replaces them with its own privacy-focused versions. Brave’s AI assistant, Leo, is opt-in, defaults to cloud routing through an anonymizing reverse proxy, and supports a Bring Your Own Model option for users who want to run local models through Ollama. Local models in Brave are user-installed, not browser-installed.

Vivaldi went the other direction entirely. The CEO put it in writing last year that Vivaldi will not ship AI features in the browser. If your concern is exactly the pattern Chrome is establishing, Vivaldi is the most aligned Chromium browser available.

Opera, Arc, Dia, Comet, and the rest of the AI-forward Chromium browsers each handle integration differently. None has been documented doing the Chrome-style silent local install.

Firefox is not Chromium-based at all. Mozilla uses the Gecko rendering engine and operates under different governance from Google, Microsoft, or Apple. Firefox does have AI features, and it has explicit, documented user controls for them. As of Firefox 148, released in February of this year, an AI Controls panel in Settings lets users disable every generative AI feature in the browser with a single “Block AI enhancements” toggle. Smaller features like language translation and PDF alt text use local specialist ML models, but they are listed in the panel and individually toggleable. The optional sidebar chatbot routes to third-party providers the user picks (ChatGPT, Claude, Gemini, Copilot, or Mistral), not one Mozilla assigns. Mozilla has publicly committed to a kill switch approach for future AI features. None of this is a silent multi-gigabyte LLM install.

Safari is the other major non-Chromium browser, and it ships only on Apple platforms. Its AI integration is Apple Intelligence, which is an operating system layer rather than a browser feature. Apple Intelligence requires explicit opt-in, requires specific hardware (Apple silicon Macs, recent iPhones and iPads), runs many tasks on-device using Apple’s own model infrastructure, and routes more complex tasks to Apple’s Private Cloud Compute. Settings includes an Apple Intelligence Report panel that logs what was processed off-device. Whatever your view of Apple’s broader posture, none of this is the Chrome silent install pattern. The model deployment ships through OS updates with explicit consent flows, not through browser background downloads.

The point is not that any of these browsers is perfect. The point is that silent multi-gigabyte local model deployment is a Chrome decision, not a Chromium constraint. If you switch off Chrome, you do not inherit this problem.

Check your own machine

Before you act, verify what is actually sitting on your disk.

On macOS, open Terminal and run:

du -sh ~/Library/Application\ Support/Google/Chrome/OptGuideOnDeviceModel/

That returns the total size of the folder including everything inside it. If you prefer Finder, press Cmd + Shift + G, paste in ~/Library/Application Support/Google/Chrome/OptGuideOnDeviceModel/, then right-click the version subfolder inside and choose Get Info to see the rolled-up size.

On Windows, press Win + R, paste in %LOCALAPPDATA%\Google\Chrome\User Data\OptGuideOnDeviceModel\, then hit Enter. In File Explorer, right-click the version subfolder, choose Properties, and read the size off the dialog.

A few things to know going in. The OptGuideOnDeviceModel folder contains a versioned subfolder with a name like 2025.8.8.1141, and the actual model lives one level deeper inside that. Alongside weights.bin you will find smaller sibling files including encoder_cache.bin, adapter_cache.bin, manifest.json, and _metadata. If you check the size of a single file rather than the whole folder, you may be looking at a sibling that is one or two hundred megabytes rather than the main weights. The file you want to verify, specifically, is weights.bin. Reports across the major coverage put it in the 2GB to 4GB range, with Google itself acknowledging that the exact size varies by Chrome version and hardware tier.

Mine was exactly 4.0 gigabytes. That number landed without notice on a network managed end-to-end with endpoint protection on every machine. If your number is similar, your defenses missed it, too.

That is the article in one sentence.

What to do this week

You have two paths. They are not mutually exclusive.

If you are staying with Chrome:

1. Open Chrome. Type chrome://flags in the address bar. Find optimization-guide-on-device-model and set it to Disabled. Find prompt-api-for-gemini-nano and set it to Disabled. Restart Chrome when prompted.

   1. Set to disabled

      

   2. Set both disabled

      

2. Go to Settings > System and look for an “On-device AI” or “Use AI features in Chrome” toggle. The rollout is uneven across versions and operating systems, so this option may or may not be present. If it is, switch it off.

   1. 

3. Navigate to the OptGuideOnDeviceModel folder using the paths mentioned above. Delete its contents. With the flags disabled, Chrome will not redownload the model.

4. Review your endpoint protection logs and network monitoring for the past several months. A 4GB download from Google’s servers should have left a trace. If your tools did not flag or even log the event, you have a visibility problem worth fixing on its own merits.

5. Put a recurring quarterly task on your calendar. Walk through what is actually installed on each of your machines, compared to what you assume is installed. If the comparison surprises you, you have just learned something useful.

If you are leaving Chrome, and you should consider it:

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The friction has dropped close to zero. Brave, Edge, Vivaldi, and Firefox all import bookmarks, passwords (You should be using a dedicated password manager), extensions, and history from Chrome in a couple of clicks. Most extensions you use will work in any Chromium browser unchanged. A small number of sites still test only against Chrome, and the workaround is to keep Chrome installed for those specific cases with AI features disabled per the steps above, and run something else as your daily driver.

Three reasonable paths:

• Brave is the easiest recommendation for practitioners who want a Chrome-equivalent experience with adversarial privacy defaults. Drop-in replacement for daily use.

• Vivaldi is the recommendation for practitioners who specifically want a browser whose vendor has publicly refused to ship AI features. Most aligned with the concern this article raises.

• Firefox or LibreWolf are the recommendations for practitioners who want out of the Chromium monoculture entirely. Firefox has added some local AI features but they are opt-in and not deployed Chrome-style. LibreWolf strips them. Different rendering engine, different governance.

• Safari is the natural recommendation for Mac, iPhone, and iPad users already in the Apple ecosystem. Apple Intelligence is hardware-gated, opt-in, and surfaces what it does. Different engine, different governance, opposite deployment posture from Chrome.

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None of them is perfect. All of them are better on the specific axis at issue here than Chrome is right now.

The takeaway

The takeaway is not that Google is uniquely guilty. When I was reading about this earlier, I remarked to a friend that “Big tech is so #$*&# corrupt,” and his response was “Especially a company that once had the motto don't be evil.” Major software vendors have collectively decided that pushing AI features as default-on, opt-out-buried features is acceptable. They are correct that most users will not push back. They are wrong about whether the behavior is fine.

You do not have to accept it on the machines you control. The simplest move this week is to stop using Chrome as your daily driver. The longer move is to apply the same scrutiny to everything else running on your endpoints with your privileges. Both are overdue.

What browser are you using?

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There is so much noise about AI right now. Half the feeds I open are people insisting it changes everything. The other half are people insisting it is hype that will pass. Both are partially right, and both are missing the part that actually matters: how you use it.

I get the same question, in different shapes, from people who have tried these tools and walked away frustrated.

“Why does mine come out generic?”

The answer is almost never the AI. It is almost always the prompt.

I have a line I keep coming back to, and it is the only one I want you to remember from this article: AI is a magnifier. Smart in, smarter out. Sloppy in, sloppier out. (That is a sharper version of my original line, which was: if you are smart, you will be smarter; if you are dumb, you will be dumber.) The model is not the bottleneck. The prompt is.

This is true whether you are using Claude, ChatGPT, Gemini, Copilot, or whatever new tool will be on the front page next week. The interface changes. The logos change. The pricing changes. The fundamental skill of asking the tool a question worth answering does not.

I have heard the same complaint from people in completely different fields. A doctor who tried it once and gave up because “it just told me obvious things.” A real estate agent who said it kept producing “generic listing copy that sounds like every other listing.” A small business owner who said it was “fine for grammar but useless for anything real.”

In all three cases, I asked to see the prompt. In all three cases, the prompt was one sentence long.

Learning a new tool requires an investment of time. A small one, but real. We are now conditioned for instant gratification, which in my opinion is far more damaging than what AI will do.

You cannot ask a one-sentence question and expect a thoughtful, specific, useful answer. You would not accept that from a junior team member. You would not accept it from a contractor. You should not accept it from yourself when you are the one writing the prompt.

The Simple Method

The framework I use and teach is four letters. RCTF.

That stands for Role, Context, Task, Format. Every great prompt has all four. Skip one and the output drifts. Hit all four and the output stops looking like AI and starts looking like a deliverable.

R, Role

Tell the AI who it is supposed to be.

Not “you are a helpful assistant.” That is the default, and the default is mediocre. Tell it the actual role you want it to inhabit.

“Act as a senior tax advisor with twenty years of experience explaining complex tax issues to a client who does not understand taxes.”

“Act as a real estate agent writing a listing for a buyer, not a window-shopper.”

“Act as a financial advisor preparing for a difficult conversation with a retiree who lost money in the market.”

The role does two things at once. It activates a body of knowledge. It also sets a tone. A “senior tax advisor” sounds different from a “tax accountant.” A “patient teacher” sounds different from a “subject-matter expert.” Pick the role that matches what you actually need on the other side of the prompt.

C, Context

This is the part most people skip, and it is the part that matters most.

Give the AI the background. The situation. The constraints. The audience. The thing that is true about your specific case is not true about a generic case. Remember, though, do not use any PII about the client.

“My client is a W-2 employee earning around $180,000. They had a major life event this year, the sale of a primary home. They also had capital gains of $50,000 from various stock sales. They had no estimated payments because last year they got a refund. They are confused about why they owe.”

You can already feel the difference between that and a one-sentence “client wants to know why they owe.”

Context is where these tools turn from a search engine into something actually useful for your specific situation.

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T, Task

State the verb. Be specific.

Draft. Summarize. Compare. Analyze. Outline. Calculate. Critique.

The reason this matters is that AI tools default to “explain.” Ask a question, get an explanation. But explanations are usually not what you actually need. You need a draft. You need a comparison. You need a checklist. You need an outline. Tell it which one.

Pair the verb with a quantity. “Draft a 200-word reply.” “Outline a 5-section memo.” “Compare three options in a table.” Word counts and section counts are the cheapest way to make the output usable on the first pass.

F, Format

Tell the AI what shape the output should take.

A memo. An email. A bulleted list. A table. A one-page handout. A client-friendly explanation that avoids jargon. A table with three columns.

Format is the part where the output stops looking like AI and starts looking like the thing you need to send. You can paste it. You can print it. You can drop it into your client portal. The format is not an afterthought. It is the difference between “this is interesting” and “I am sending this.”

A Real Before-and-After

Here is the prompt most people write:

> “Write me an email explaining why my client owes more this year.”

Here is the same prompt with RCTF:

> “Act as a senior tax advisor explaining a tax outcome to a client. [Role] My client is a W-2 employee with an approximate income of $150,000 to $200,000. They asked why they owe more this year than expected. They had a major life event, the sale of a primary home, and no prior-year refund. They also had capital gains of $50,000 from various stock sales. [Context] Draft a 200-word reply in plain English. [Task] No jargon. Include one real-world analogy a non-accountant would understand. Tone: warm, expert, never condescending. End with ‘happy to chat more if helpful. Please book a meeting using the link in my email signature.’ [Format]”

The first prompt gets you a generic email. The second one gets you something close to what you would have written yourself, in roughly the time it takes to make a cup of coffee.

The difference is not the tool. It is the prompt.

The Moment That Always Lands

When I walk people through this, the moment that always lands is when someone tries an old prompt, then rewrites it with RCTF, then watches the second output. Their face changes. They get quiet. Then they say something like, “I have been blaming the wrong thing.”

That happens almost every time. Without exception.

People assume that getting better output means picking a smarter model, or upgrading to a paid plan, or learning some advanced technique they read about on Reddit. None of that is wrong, exactly. But all of it is downstream of the prompt.

A great prompt on a free model beats a sloppy prompt on the most expensive model in the world. Every single time.

Why This Is

Remember the small business owner I mentioned at the top, the one who said AI was useless for anything real? A few weeks after that conversation, she sent me a one-line follow-up. “I tried RCTF on my social media posts. They sound like me again.”

Same tool. Same business. Different prompt.

RCTF works whether you are drafting a contract, a recipe, a newsletter, or a toast. It does not care what you do for a living. It cares whether you respect the tool enough to use it well.

The people who get the most out of these tools are not the most technical people. They are the ones who treat the prompt like a brief to a junior associate. That is not a technology skill. It is a thinking skill, and, like any thinking skill, it improves with practice.

It also explains why some of the loudest skeptics are people who tried these tools once, got a generic answer, and concluded the technology was overhyped. They are not wrong about what they got. They are wrong about why they got it.

The Boundaries

A reminder, because the boundaries matter as much as the prompt.

If you are a tax professional, anonymize before you paste. No real names. No SSNs or EINs. No real dollar amounts. IRC §7216 and §6713 do not care which AI plan you are on, nor whether you toggled training off. Plan tier does not override federal law.

If you are not a tax professional, the same logic applies in every other context. Do not put client data, patient data, financial data, or anything else you would not put on a public website into an AI tool unless your firm has explicitly approved it. The chat window feels private, but that does not make it private.

And in every case, verify before you send. These tools can hallucinate citations, dates, and authority. The output looks confident even when it is wrong. We all know that being confidently wrong is still wrong. If you need an example of what this looks like, I can point you to some Facebook groups. You sign off on what reaches the client or the reader. Not the AI.

The Loop Back

The line I keep coming back to.

AI is a magnifier. Smart in, smarter out. Sloppy in, sloppier out.

The prompt is the part that decides which of those two you get. Not the model. Not the plan. Not the company building the tool. The prompt.

If you have been frustrated with AI tools, try this. Take the worst prompt you wrote this week, the one where you got a garbage answer and gave up. Rewrite it with Role, Context, Task, and Format. See what comes back. I would bet a coffee (a good coffee) that the difference is bigger than you expected.

Reply, comment, or email me. I read everything and do my best to respond.

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Me? I rewrite my own prompts more than I would like to admit. Every time I do, the output gets better. Every time I do not, I have only myself to blame.

What is the first prompt you are going to rewrite this week?

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If you are a tax professional, the companion to this article is a 12-prompt library structured around RCTF and ready to copy, customize, anonymize, and use. It covers client communications, IRS notice response templates, year-end planning letters by income segment, newsletter explainers, web copy, two interactive calculator specs, and an SOP-via-interview prompt that gets the process out of your head and into a document.

Paid Josh & Taxes subscribers can grab the PDF below.

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I have seen the same question, or some version of it, posted in a Facebook group dozens of times. “How do I handle X situation with the IRS?”

No context. No details. No specifics about the client, the issue, or what the person has already tried.

The responses come in fast. Most of them are variations of “need more info” or “what kind of notice?” A few people take a guess and give an answer that turns out to be wrong because they are solving a different problem than the one the asker had. The thread sprawls. Twenty replies later, somebody finally pulls enough information out of the original poster to give a real answer. By that point, half the responders have moved on, and the asker has waited a full day for help that could have arrived in ten minutes.

I have watched this pattern play out in tax practitioner groups, subreddits, X/Twitter posts, and LinkedIn discussions. The platform changes. The dynamic does not. Somebody asks a question that nobody can answer without a follow-up interview, and a small disaster of wasted time unfolds.

It also makes me forgiving of the people who post questions that make the rest of us want to throw our phones across the room. Nobody is born knowing how to ask a good question in a professional forum. It is a skill, and like most skills, you get better by paying attention to what works and what does not. What follows is what I have learned by watching what actually works.

The Problem

Every active group has a version of the same patterns. Someone posts a question that has already been answered dozens of times in the group. Someone else posts the same question in twelve different groups simultaneously. Someone asks a question so vague that answering it requires guessing what they actually want to know. Someone posts a screenshot of an error message with no context and expects a diagnosis.

This is not a character flaw. Most people who post these questions are stressed and stuck, trying to get unstuck as quickly as possible. They are not trying to waste anyone’s time. They just have not been taught that how you ask shapes what you get back.

Here is the thing that took me too long to figure out: asking a better question is not about being polite or following etiquette. It is about getting the answer you actually need. The people who ask well get help faster, get more useful help, and build relationships with the experts in the room. The people who ask poorly get ignored, get wrong answers, or get told to search the archives.

There is also a downstream cost that nobody talks about. The experts in any group have a finite amount of patience and time. Every time they answer the same poorly-framed question for the hundredth time, that patience erodes. Eventually, they stop answering at all, or they leave the group, and the quality of the whole place degrades. The people who ask well are not just helping themselves. They are helping the community survive.

Before You Post

The best question is the one you do not have to ask because you found the answer yourself in two minutes.

Search first. Every major platform has a search function. Facebook groups have one. Reddit has one. LinkedIn has one. Use it. Search for two or three keywords related to your question. If the question has been asked before, you will often find the answer and the thread where people discussed the edge cases. That thread is usually more useful than posting fresh, because you get to see how the answer holds up under follow-up questions.

If the search fails, check the pinned posts, the group rules, and any FAQ document the moderators have put together. A surprising number of common questions have dedicated resources that nobody reads. The moderators put those resources together because they were tired of answering the same question. Reward that effort by reading them.

Then check the source. If your question is about a specific product, platform, law, or tool, the authoritative source probably has a documentation page or a help center. Ten minutes with the actual source beats ten hours of crowdsourced guessing. The source is also usually more accurate than whatever the group remembers because the source updates while group memory does not.

There is also a category of questions that do not belong in a group at all. If you need legal advice for your specific situation, you need a lawyer. If you need medical advice, you need a doctor. Groups can give you general information, point you to resources, and share experiences.

If you have done all of that and still do not have an answer, now you can post. You will be in a much better position to ask a useful question because you will know exactly what you already ruled out.

How to Write the Question

Lead with the actual question. Not “Hi everyone, hope you are all having a great day, I have a weird situation.” Just the question. People are scanning. Give them something to scan.

Provide context in the next sentence or two. What are you trying to accomplish? What have you already tried? What does not work? Specifics matter more than you think. “My client got a notice” is not enough. “My client got a CP2000 proposing additional tax of $4,200 based on unreported 1099-NEC income. Do I need to file an amended return?” is something people can actually work with.

Include the details that would let someone answer without asking follow-up questions. If you are asking about software, mention the version. If you are asking about a process, mention what step you are on. If you are asking about a document, mention what kind and from what year. The goal is to let the first person who sees your question give you a useful answer instead of forcing them to interview you first.

Tell people what you have already tried. This is the single most underused move in question-asking. If you say “I tried X and it did not work because Y,” you save the responder from suggesting X. You also signal that you have done some thinking on your own, which makes people much more willing to invest time in helping you. A question that shows effort gets effort in return. A question that shows none gets none.

Skip the story. Nobody needs to know the entire history of your relationship with the client, your feelings about the situation, or your theory about why the other side is incompetent. That belongs in a different post, or in a different venue entirely. The question post is for the question.

Be specific about what you want. Are you looking for a citation? A recommended next step? A confirmation that your plan is reasonable? A second opinion? Say so. People want to help, but they cannot read your mind, and vague questions get vague answers.

A useful exercise: before you post, read your draft and ask yourself whether a stranger could answer it without asking you a single follow-up question. If the answer is no, you have more work to do. Add the missing context, cut the irrelevant context, and try again. Five minutes of editing on the front end saves an hour of back-and-forth on the back end.

On Being Rude

There are two flavors of rudeness in online groups, and both of them poison the well.

The first is the entitled asker. This is the person who posts a question and then gets annoyed that nobody has answered within an hour. The person who demands help without offering context. The person who responds to a clarifying question with “just tell me the answer.” The person who follows up with “bump” every two hours. The people in the group are not obligated to help you. They are volunteering their time and expertise for free. If you are rude about it, they will remember, and next time they will scroll past.

The thing about entitlement is that it is often invisible to the person displaying it. They are stressed, they need help, and the urgency feels like enough justification on its own. It is not. Your urgency is not anyone else’s problem. The people who answer questions well do it because they want to, not because they owe you anything. Treating them like staff is the fastest way to lose access to the only resource that was actually going to help you.

The second flavor is the smug answerer. “You should know this.” “This is basic.” “I have been doing this for 25 years.” That last one is my favorite, because sometimes the honest response is that you have been doing it wrong for 25 years and never noticed. Experience is not the same thing as being right. Years in the chair do not substitute for a citation.

The smug answerer is doing real damage even when their answer is technically correct. They are training newer members to stay quiet. They are teaching everyone who is watching that asking a question carries a social risk. The next person who has the same question will not ask it. They will guess, or they will get the answer wrong, or they will give up. The community gets smaller and dumber every time someone gets publicly shamed for asking.

If you have been doing this long enough that beginner questions annoy you, you have two choices. You can answer the question kindly and move on, or you can scroll past. Those are the only two options that do not actively harm the place you are participating in.

The AI Copy-Paste Problem

There is a newer version of bad answering, and it is getting worse.

Someone posts a question. Within minutes, another member pastes a response that is clearly the unedited output of an AI tool. Confident. Comprehensive. Authoritative-sounding. Often completely wrong, or right in a way that does not match the actual facts of the question, or right in general but missing the specific exception that makes it wrong here.

The person who posted the AI answer did not read it carefully. They did not verify it. They did not check whether the citations the AI included were real, because half the time they are not. They wanted to be the person who answered first. They wanted the social credit for knowing the thing. The accuracy of the answer was secondary to the appearance of having one.

This is a different failure mode than ordinary smugness, and it is more dangerous. The smug answerer who has been doing it wrong for 25 years at least believes their own answer. The AI-paste answerer is not even an actor in their own response. They are a delivery mechanism for output they did not check. The asker, who came to the group looking for human expertise, gets back a hallucinated regulation citation and a confident summary of a rule that no longer exists.

I am not anti-AI. I use AI tools every day. AI is genuinely useful when you treat it as a research partner that needs supervision. It is corrosive when you treat it as a vending machine that produces correct answers, because most of the time, it does not.

If you are going to use AI to help you answer a question in a group, the rules are simple. Read the output carefully. Verify any citation it produces by pulling up the actual source. Test the answer against the specific facts the asker provided. If the AI hedged, keep the hedges. If the AI cited a rule, confirm the rule exists and says what the AI claims. Then, if you are confident the answer is right, post it in your own words and disclose that you cross-checked it.

What you do not do is paste the raw output, slap your name on it, and walk away. That is not answering. That is laundering AI output through your professional reputation, and it damages both you and the group. The next time you post a real answer, the people who watched you paste a wrong AI response last week will discount it. You spent your credibility, and you got nothing in return except the brief satisfaction of being first.

Citations Over Feelings

When a question turns into a disagreement, the only thing that matters is the source.

If you are answering a question and you have a definitive answer, point to it. The statute. The regulation. The documentation. The reported decision. Whatever the authoritative source is in your field. “I have always done it this way” is not an answer. It is a personal habit dressed up as expertise.

If you are asking the question and someone gives you an answer with a source, read the source before you argue with them. Pull it up. Read the relevant section. Then decide whether it actually applies to your situation. If it does, you have your answer. If it does not, you can now explain specifically why your facts are different, which is a completely different conversation than “I do not think you are right.”

If you are answering and someone challenges you, produce the source or revise your position. Those are the only two options. Doubling down with more conviction does not make you more correct. It just makes the next person less likely to take your answers seriously.

There is a particular kind of failure mode that shows up in every professional group. Someone posts a confident answer. Someone else points out that the confident answer is wrong and provides a citation. The first person, instead of acknowledging the error, pivots to attacking the second person’s tone, credentials, or motivation. This is how a group loses its credibility. Every time it happens and goes unchallenged, the signal-to-noise ratio gets worse. The people who actually know what they are talking about start to leave, because they do not want to spend their time fighting people who are wrong but loud.

The fix is simple but unglamorous. When you are wrong, say so. “Good catch, I had that backwards.” “You are right, the rule changed.” “Let me reread the statute.” Those sentences cost nothing, and they buy you credibility. The people who are willing to be corrected publicly are the people whose answers other people start to trust.

This is how professional groups are supposed to work. The goal is to find the correct answer, not to win the thread. Everyone in the room benefits when the conversation stays anchored to what the source actually says. Everyone loses when it devolves into who feels more strongly about their position.

What Not to Do

Do not cross-post the same question in multiple groups at the same time. It annoys the people who are in all of those groups, it fragments the answers across multiple threads, and it signals that you are prioritizing speed over quality. If you have been waiting a day and the question is genuinely urgent, it is fine to try a different venue. But do not carpet-bomb. The people who do this almost always get worse answers than the people who pick one venue and ask carefully.

Do not post the question and then disappear. If someone asks you a follow-up, answer it. If someone gives you an answer that does not fit your situation, say why. The thread is a conversation, not a vending machine. The people who answer questions remember who engages and who ghosts. Engagement is currency in any group, and you spend it down every time you take an answer and run.

Do not argue with people who are trying to help you. You can push back on an answer if you think it is wrong. That is fine. But “that is not what I asked” when the person is answering what you actually asked is a good way to make sure nobody helps you next time. If the answers do not address your question, the most likely explanation is that your question was not clear, not that everyone misread it.

Do not post a screenshot of a long document and ask people to read it for you. If you want someone to review something, be specific about what part you have a question about and what the question is. Pointing at a wall of text and saying “thoughts?” is not a question. It is a request for unpaid labor.

Do not ask questions that would require someone to do your job for you. “How do I handle this entire case?” is not a question. It is a request for free consulting. Narrow it down. Pick the specific decision point you are stuck on, and ask about that.

Do not delete your post after you get the answer. The next person who has the same question will find your thread through search, and the answer will be valuable to them. Deleting it because you got what you needed is selfish in a way that is hard to articulate but easy to feel. The group helped you. Leave the answer behind for the next person.

After You Get an Answer

Thank the people who helped you. Not with a gif. Just a sentence. People remember who is gracious and who is not, and it matters more than you think the next time you need help.

If the answer solved your problem, say so. This helps the next person who finds your thread through a search. There is nothing more frustrating than reading a thread that ends with “got it, thanks!” and never finding out which of the four answers actually worked.

If you figured it out yourself before anyone responded, post the answer in your own thread. This is one of the most valuable things you can do for a group, and almost nobody does it. Your future self will be grateful when you search for the same problem two years from now and find your own answer waiting.

If you got an answer that was wrong and you eventually figured out the right one, come back and post the correction. This is harder than it sounds, because it requires admitting that the original answer did not work. Do it anyway. The next person who finds the thread needs the correction more than you needed your ego protected.

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The Part That Is Hard to Say Nicely

Some of the people who ask bad questions are not going to read this article, and if they did, they would not see themselves in it. That is fine. This article is not really for them.

It is for the person who has been in a group for a while, notices the patterns, and wants to do better. It is for the person who has asked a question recently that did not get the response they hoped for, and is wondering why. It is for anyone who has ever felt the low-grade frustration of watching a thread devolve because the original poster did not give anyone enough to work with.

Asking good questions is a professional skill. It is worth developing. The people who do it well get better answers, build stronger networks, and spend less time stuck. That is a real competitive advantage in any field.

It is also a skill that quietly signals everything else about how you work. People who ask precise, well-scoped questions in public are usually the same people who write good emails, run good meetings, and produce good work. The reverse is also true.

The way you ask a question in a Facebook group is a tiny window into how you operate everywhere else. People notice. They form opinions about who they would refer work to, who they would hire, and who they would partner with. None of this is fair, but all of it is real.

And if you are on the answering side, remember that you were a beginner once, too. A short reply pointing someone to the search function is more useful than a long reply about how they should have searched. We are all trying to get better at this.

The groups that thrive are the ones where the people asking questions take the time to ask them well, and the people answering take the time to answer kindly. That is not complicated. It is just rare. Be the kind of participant that makes the place better for everyone else, and the place will be better for you when you need it.

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Examples

Let’s talk about a few examples. I am changing names to protect the guilty

Yes, in fact, we have seen this. Had you utilized a search, you would have seen that 7 other people had similar fact patterns this week. This one is popping up daily and is admittedly annoying me.

I won’t mention the lady who does this routinely in certain Facebook groups. But it isn’t helpful, and some of us may talk about you.

No, just no.

If you recognized yourself in any of those examples, you are not alone. Everyone has been at least one of those people at some point. I have probably been all three on different days. The point is not to feel bad about it. The point is to notice the pattern and choose differently next time.

Asking well is a small discipline. So is answering well. Neither is hard, but both require a moment's pause before you hit post. That pause is the whole game.

The next time you are about to ask a question, take a beat. Search first. Write the question. Read it back. Ask whether a stranger could answer it without interviewing you. Then post.

The next time you are about to answer one, take a beat. Read the question carefully. Check the source. Resist the pull to be first. Ask whether the answer you are about to post would help the asker, or just make you feel useful.

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There is something that happens after April 15.

Motivation seems to evaporate. I feel it right now, sitting at my desk with a list of things I wanted to tackle the moment the deadline passed. The list is still there. The tasks are still real. Some of them are things I was genuinely excited about three weeks ago. And yet when I look at the list this morning, I cannot seem to make myself start.

For three months, I was up at 4:30 or 5:30 every morning. Seven days a week. No exceptions. That was the rhythm, and the rhythm worked because I was not just doing returns. I was building an office I love walking into. I was saying yes to new projects. I was teaching. I was writing. I was taking on opportunities I have wanted for years, and when a new one appeared, I said yes to that too. Because why would I not? This is the game. This is the part I love.

And then the deadline passed, and I hit a wall.

The Word I Hate to Use

I am going to use a word, and I am going to hate using it.

Entrepreneur.

The word is overused. It has been worn smooth by a decade of influencer content, hustle-bro podcasts, and LinkedIn posts with stock photos of sunrises. Every person who has ever sold a course on how to sell a course calls themselves one. I cringe writing it. I’ve almost deleted it twice.

But underneath all the noise, the word is pointing at something real, and I do not have a better one.

Some of us are almost addicted to it. Let’s be real, who doesn’t love some dopamine? It is not a career choice. It is part of our identity. We wake up thinking about business ideas. We go to bed thinking about business ideas. The shower is a think tank. The drive home is a think tank. The moments when normal people are decompressing are the moments we are mentally drafting the next thing. A piece of writing. A new service. A better workflow. A conversation we want to have. A problem we cannot stop turning over.

The idea of a 9 to 5 feels like prison to people like us. Not because we are lazy. Not because we are unwilling to show up. The opposite. It feels like prison because the structure itself is built on the assumption that you do the work someone else designed, on the timeline someone else set, for reasons that belong to someone else. For people wired like us, that is not stability. That is suffocation. Plus, the idea of someone telling me what to do, yeah, that’s a hard pass.

People who have never done this for themselves do not get it. They cannot. They hear “I love my work” and translate it in their heads to “I like my job,” which is not even close to the same thing. Loving your work means the work is not separate from you. It is how you think, how you process, how you make sense of the world. It is the thing you cannot stop doing even when you are trying to stop doing it.

Which brings me to the problem.

The Cost of Saying Yes

The thing that got me here is not the volume of returns. It is the volume of yes. Every new project I took on was something I wanted. Every opportunity I chased was one I had been working toward. The office is not a burden. It is the thing I have been building in my head for years, finally real. The teaching, the writing, the new directions, none of it is work I resent. All of it is work I chose. Enthusiastically.

But it turns out that saying yes to everything you love has the same cost as saying yes to everything you hate. Your body does not distinguish. Twelve hours of work on something that lights you up still costs twelve hours. Sustained enthusiasm is still sustained output. And when you stack a dozen things you love on top of each other, what you end up with is the same exhaustion as the person doing a dozen things they resent. You just get to the exhaustion later and feel guiltier about admitting it.

This is the trap for people wired this way. The work is not separate from us. The work is an expression of us. Turning it down feels like turning down some version of who we are. So we do not turn it down. We say yes. We keep saying yes. And somewhere around mid-April the body we have been ignoring sends up a flare and the motivation we were running on just, stops.

The Part We Do Not Like to Say Out Loud

Here is the other thing driving all of this, and I do not think we talk about it enough.

We are not going to live forever.

All of us are going to die. That is not a morbid observation. It is the most basic fact of being alive. And the older I get, the more I notice how much of my drive comes from a quiet awareness that the clock is running.

I am going to be honest about something. Within the span of a month, my family lost two of our dogs. One of which was while I was out of town last week. Gaga (gorgeous and profoundly empathetic) and Pinky (always happy and full of love). They were my parents’ dogs. If you have never lost an animal you loved, you might not understand what I am about to say, and that is okay. If you have, you already know.

I have always believed that losing furry family members hurts in a way that losing humans does not. I know how that sounds. Some of you are already rolling your eyes. People are complicated. Relationships with people are complicated. Even the best human in your life is, by definition, a person, which means there are edges and misunderstandings and the low-grade friction of two flawed beings trying to exist in proximity to each other. That friction is part of what makes human love meaningful. It is also what dulls it, around the edges, in small ways you do not notice until they are gone.

Dogs do not do that. Cats do not do that. Whatever was in their bowl this morning, they forgave you for it by dinner. Whatever mood you came home in, they met you at the door anyway. There is no edge. There is no friction. There is just presence. Uncomplicated and unconditional.

Losing them is a specific kind of grief, and I will not pretend it is not sitting in the background of everything I am writing here. It is part of why the wall hit as hard as it did. It is part of why the motivation disappeared after the April 15 deadline instead of April 30. Grief does not check your calendar. It waits until the adrenaline drops, and then it shows up.

So when I talk about the clock running, I am not being abstract. I watched it run out, twice, inside of a month. That has a way of rearranging your priorities, whether you asked it to or not. It’s weird. It’s life.

There are articles I want to write. Courses I want to teach. Clients I want to help. Ideas I want to build. The list is longer than the time I have, and I know it. So I say yes. So I wake up at 4:30 to 5:30. So I stack the plates until they bend.

The world is not making this any easier to ignore. On any given day, the headlines read like a fever dream. Wars grinding on. Institutions wobbling. The occasional reminder that nuclear Armageddon is, apparently, still on the menu. I try not to doomscroll, but I also cannot pretend I do not see it. None of us can. The uncertainty is part of the air we breathe now.

That awareness is both fuel and poison. It is fuel because it reminds me not to waste the days. It is poison because it convinces me I cannot afford to stop, even for a week, because what if the week I take off is one of the ones that mattered.

But here is the math I keep forgetting. If the time is short, then the time I spend exhausted and unable to start is time I have already lost. Grinding through a wall is not a good use of time. It is just burning it with the lights on. A week of actual rest, taken on purpose, gives me back weeks of real work on the other side. A month of half-powered grinding gives me nothing.

If we are going to live like the days are precious, we have to actually live like the days are precious. That includes the ones where we stop. That includes the ones where we grieve. That includes the ones where we sit with something hard instead of working around it.

“Just Get a Hobby”

Here is the part I want to say carefully, because it is the part most people get wrong.

Our spouses, partners, and friends who do not work for themselves do not understand this. They see us working all the time and they say things like, “Why do you work so much?” and “You should get a hobby.” They mean well. They love us. And they are missing something important.

For those of us who work for ourselves, the work is not a burden we are trying to escape. The work is how we are built. Creating and doing is what fuels us. Being in control of what we make, when we make it, and how we make it is not something we tolerate. It is something we need.

I know how that sounds. It sounds like one of those motivational posters in the break room of a company none of us would ever work for. “Create your own destiny.” “Be your own boss.” I cringe typing it. But underneath the bumper-sticker language, it is true. The thing that makes us capable of doing this work in the first place is the same thing that makes it hard for us to stop. We are not grinding (another word that is overused by “influencers” and “hustle culture” types) because we are miserable. We are grinding because building something is the most alive we ever feel.

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So when someone tells you to “just get a hobby,” or — my personal favorite (sarcasm)— “you should touch grass,” they are not wrong exactly. They are using the wrong language for the wrong audience. I roll my eyes every time. “Touch grass” is for people whose problem is that they spend too much time scrolling on a couch. That is not my problem. That has never been my problem. Now, am I on the couch on my phone? Yeah, but I’m not mindlessly scrolling. I’m intentional about it (eye roll).

A hobby, for people like us, is not a substitute for work. It is a smaller, lower-stakes version of the same instinct. Making something. Getting better at something. Being in control of something. A few months ago I decided to take up crocheting again. I learned when I was a kid. It is very relaxing. I bought some really cool yarn and then, like many things, moved on. I plan to get back to it because it was very much like meditation. My next project is perfecting the cappuccino.

That distinction matters. If you try to “rest” by doing nothing at all, you will be miserable within a day. I know because I have tried. What works is redirecting the impulse to make toward something small and low-stakes until your system recovers enough to take on the big stuff again.

What “Unplug” Actually Means

I want to push back on the word “unplug” for a second, because it gets used like it means one thing, and it does not.

For some people, unplugging means getting off social media. And sure, there is a version of that worth doing. The latest Twitter controversy does not need my attention. I rarely care anymore. I have not started one in a long time, and I do not miss the reflex. That part of the internet is just noise dressed up as importance, and walking away from it is almost always a net positive.

But I am not deleting my accounts. Because social media is also where a small group of friends lives. People who get what I am doing. People who actually understand why a reply from IRS Chief Counsel is exciting, or why a client makes me want to put my head through a wall. It is unrestrained humor. It is shop talk with people who speak the language. It is the closest thing a solo practitioner has to coworkers, except the coworkers are self-selected and genuinely fun.

That is not something I am trying to unplug from. That is one of the things keeping me sane.

So when I talk about unplugging this week, I do not mean silence. I do not mean a digital detox. I mean, stepping out of the content treadmill. I mean, closing the client email tab. I mean, not checking the practice management software to see what came in overnight. I mean, letting the algorithm-driven parts of my attention rest while keeping the friendships that actually sustain me.

Unplug from the parts that drain you. Keep the parts that fill you up. That is the distinction nobody explains when they tell you to “get off your phone.”

The Case for a Real Week Off

Most of us do not take a real week off after a stretch like this. We take a weekend. Maybe a long weekend. Then we are back at the desk, feeling vaguely behind and unsure why we cannot focus.

A weekend is not enough. A weekend is what you take after a hard Friday. Three months of 4:30 wake-ups chasing a dozen projects you love needs more than forty-eight hours to metabolize.

A week is different. A week is long enough for your brain to actually stop scanning for the next thing to say yes to. The first two days, you will still feel like something is wrong. You will keep checking your email. You will jump when your phone buzzes. You will feel a pull to start something, anything, because starting is how you are wired. Somewhere around day three or four, something shifts. The background noise quiets down. You start sleeping differently. You find yourself thinking about things other than work for extended periods without catching yourself.

That is when the rest actually starts working. And it is the part most of us never get to because we cut the break short.

What to Do With the Week

Here is the trap. If you do not plan the week, you end up scrolling your phone on the couch for seven days, wondering why you still feel terrible. Worse, if you are wired like me, you will just fill the silence with a new project by Wednesday.

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So here is what I would suggest. Pick three things before the week starts. One of them is a hobby. One of them is a place. One of them is something you want to learn. These become the guardrails that keep you from either collapsing into the couch or quietly starting a new venture by Wednesday afternoon.

I can tell you mine.

The hobby is the cappuccino. I got an espresso machine a while back, and I have been fumbling through it between client meetings for months. My first attempt looked like a dishwater latte wearing a hat. My second was worse. Next week I am going to actually practice. Not in ten-minute stolen windows. Mornings. With intention. I will be bad at it for a while, and that is the point.

The place does not have to be far. See something unfamiliar. Some of the best ideas I have ever had about my practice came to me when I was nowhere near my practice. That is not a coincidence. Distance from the work is how you see the work clearly.

The learning is whatever has been nagging at the edge of your attention for months. The book you keep meaning to read. The documentary you saved and never watched. The topic has nothing to do with the Internal Revenue Code. Let yourself be a beginner at something again. Reading a new Revenue Procedure is work. Learning why certain chords sound sad, or how long it takes ICBMs to reach their target (I’m mostly kidding, but hey, nuclear war has been an interest since I was a kid), or how to identify the birds at your feeder, is something else entirely. That kind of learning reminds you that your brain is a general-purpose instrument, not a tax machine.

Three things. Small enough to actually do. Specific enough that you cannot fake them. The hard part for me is that I will reach for something technology-related, which is fun but also creeps back into work territory. Technology and tax are the two things I love, and they both end up being work if I am not careful

Let the 4:30 Go. For a Week.

One more thing to the practitioners who, like me, ran on 4:30 wake-ups for the last three months.

Let it go. For a week. This morning, I finally got out of bed at almost 7 AM.

You earned the early mornings because the work demanded them. The work is not demanding them right now, and the reality is it never did; we all just made the choice to do it. Sleep until you wake up on your own. Do it for seven days and see what happens. I suspect that around day four, your body will start sleeping the way it is supposed to, and around day six, you will wake up naturally at a reasonable hour, feeling like yourself again.

The Work Will Still Be There

I know what some of you are thinking. You have representation cases waiting. You have extensions to work through. You have planning meetings on the calendar. You have new projects you are excited about. You cannot just disappear for a week.

You can. The work will still be there on the other side. Your clients will survive (and if you don’t, they will replace you). The opportunities you are chasing will still be chaseable. The projects you cannot wait to start will still be waiting. Nothing meaningful gets worse because you took a week to be a person.

What does get worse is you, if you never stop.

The Summer Ahead

Summer is going to be busy with lots of travel to conferences. June, I am teaching at CSTC Summer Tax Symposium. If you’re in Reno or want to be, check it out. I will also be attending CSEA Super Seminar in Reno.

Then, in July, there is the NATP Taxposium in Cleveland, Ohio.

I’m looking forward to teaching about Innocent Spouse Relief (Is there such a thing as an innocent spouse??), Cybersecurity, and a few other things.

A few webinars will land in between. I will post details as they go live.

Your Turn

So tell me. Are you feeling it too?

Did you hit the wall this week? What did you say yes to this year that you would say yes to all over again, even knowing the cost? Has someone in your life told you to “just get a hobby” or “touch grass” and made you want to roll your eyes so hard they got stuck? And what would happen if you gave yourself a week before you tried to start the next thing?

I want to hear it. Drop it in the comments. Tell me what hobby you are picking up, where you are going, and what you are learning. And if any of you have actually mastered the cappuccino, I could use some tips. Mine still looks like it lost a fight.

I have lots of fun content planned, AI, how-tos, etc. (maybe an announcement or two). I haven’t done a giveaway in a while. I enjoy giving stuff away. So, one lucky commenter will get 3 months free of Claude Pro. (But please, for the love of God, do not put client data in it.)

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On Tax Day, this distinction matters more than you think.

A friend/colleague in the tax world said something to me a while back that I have given a lot of thought to. It was one of those offhand comments that lands like a pebble in your shoe. You keep walking, but you can’t stop thinking about it.

I’m paraphrasing, but it was basically:

I spent the next few weeks pulling on that thread until it unraveled something I needed to see.

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The Polite Lie vs. The Caring Truth

Being nice is comfortable. It’s the path of least resistance. It’s telling someone what they want to hear because it’s easier than watching their face fall. It’s smiling and nodding and saying “yeah, that should be fine” when you know it won’t be.

Being kind is harder. Being kind is telling someone the truth, even when it’s inconvenient. Even when it makes the conversation awkward. Even when they might not like you as much afterward.

Nice is pleasant. Kind is useful.

Nice protects the relationship in the moment. Kind protects the person in the long run.

What This Looks Like in Tax Practice

I think about this distinction constantly now, especially today, April 15th, when the weight of filing season sits on everyone’s shoulders.

Being nice is telling a client, “Sure, we will get that filed, no problem.” Being kind is saying, “I am sorry, but this is after our deadline. We will file an extension and work on this after April 15th.”

Being nice is letting a colleague’s questionable position slide because you don’t want to create friction. Being kind is pulling them aside and saying, “Hey, I think there’s some exposure here. Let’s talk through it.”

Being nice is agreeing to take on one more client, one more extension, one more “quick question” because you don’t want to disappoint anyone. Being kind (to yourself, in this case) is saying, “I can’t do that well right now, and you deserve someone who can.”

Nice avoids the hard conversation. Kind starts it.

The Rabbit Hole

Once this idea was planted, I started seeing the nice-versus-kind split everywhere. In friendships. In business. In the way we talk to ourselves.

How many times have I been “nice” to myself by not confronting a habit that wasn’t serving me? How many times have I been “nice” to a client by softening a message so much that the actual point got lost?

The uncomfortable truth is that niceness can be a form of avoidance. It can masquerade as warmth while actually being a way to dodge responsibility. You get to feel good about yourself (”I didn’t want to hurt their feelings”) without actually helping anyone.

Kindness requires something niceness doesn’t. It requires courage. It requires caring more about the person’s outcome than about how they perceive you in the next five minutes.

Kindness Has a Longer Time Horizon

Here’s what I keep coming back to. Nice operates on a short clock. It’s optimized for right now. For this conversation. For today’s comfort level.

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Kind operates on a longer timeline. It asks, “What does this person need to hear so that six months from now, they’re in a better position?” Sometimes that’s encouragement. Sometimes it’s a reality check. Sometimes it’s a boundary.

The best mentors I’ve had in this profession were kind, not nice. They told me things I didn’t want to hear. They challenged positions I was attached to. They pushed back. And every single time, I was better for it. I've always loved people who tell me exactly what they think.

A Tax Day Reflection

Today, as the filing deadline lands and the dust starts to settle on another season, I want to challenge all of us (myself included) to audit something that doesn’t show up on a return.

Where are you being nice when you should be kind?

Where are you smoothing things over instead of saying what actually needs to be said?

Where are you choosing comfort over clarity?

The colleague who dropped this idea into my world probably doesn’t know how far it traveled. That’s often how the most important lessons arrive. Not in a seminar or a textbook, but in a passing comment from someone who cared enough to say the true thing instead of the easy thing.

That’s kindness. And it’s worth more than all the niceness in the world.

What are you changing for next tax season?

Me? I’m saying no more often. No to things that waste time. No to clients that I do not want to work with. Life is short, remember that.

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First, I want to acknowledge that, just like tax professionals, there are good mortgage professionals and bad ones. This is for the bad ones. The ones that cause many of us to order voodoo dolls.

We need to talk.

Not on your timeline. Not at 6:47 PM on a Tuesday with a breathless voicemail about how you need something “first thing tomorrow.” On my timeline. Right now. Because I have some things to say that are long overdue.

I know your world. Before I became a tax professional, I worked in mortgage banking. I also spent years in IT working with loan officers and brokers. I’ve seen the inside of your industry. So when I tell you that your behavior toward tax professionals is out of line, understand that I’m not speaking from ignorance. I’m speaking from experience.

Let’s start with the basics.

You Don’t Get to Call Me

You are not my client. My client is the borrower. The taxpayer. The person whose return you want me to hand over like it’s a takeout order from Chilis.

I can’t just send someone’s tax return to any person who calls my office and says they need it. There’s a federal law called Internal Revenue Code §7216. It governs the disclosure of tax return information. Violations carry criminal penalties. Not civil. Criminal.

That means I need written authorization from my client before I send you anything (or even confirm they are a client). Not a verbal okay. Not a text message. Not “they said it was fine when we were on the phone together.” Written consent that meets the requirements of the statute.

So when you call my office and get frustrated that I won’t email you a tax return on the spot, understand that I’m not being difficult. I’m following the law. You should try it sometime.

Stop Calling After Hours

My office has business hours. They exist for a reason. I am not on call for your loan pipeline. The fact that you promised your borrower a closing date before you had all the documentation is not my emergency.

Plan ahead. Request what you need early in the process. And when my office tells you the turnaround time, believe them.

Comfort Letters Are Not a Thing

I’ve talked about this in an article before, but it bears repeating. Let me explain again, when you ask me to write a letter “confirming” that my client’s income will continue, or that their business is “stable,” or that their self-employment income is “reliable,” you’re asking me to predict the future. I don’t do that. No credible tax professional does. We do not have a crystal ball. If I did, I’d pick the lottery numbers, retire, and move into the Four Seasons.

You want a comfort letter because your underwriter doesn’t want to do the actual work of analyzing the tax returns. That’s not my problem. I prepared the return. It speaks for itself. If your underwriter can’t read a Schedule C or a K-1, that’s a training issue on your end.

I’m not putting my license on the line so you can close a loan faster.

Stop Turning Our Clients Against Us

This one really ticks me off. When we won’t bend to your demands, some of you go back to the client and say things like, “Your tax person is holding up the process”, “If your tax guy would just write the letter, we could close,” or “You’re going to lose this house because your tax person will not cooperate.”

You are weaponizing our clients against us. You’re creating conflict in a professional relationship that predates your involvement and will outlast it. You’ll close this loan and move on. I’ll still be here preparing their returns for the next twenty years.

When you pit a client against their tax professional, you’re not just being unprofessional. You’re being reckless. Because if that client pressures us to do something unethical to satisfy your underwriter, you’ve just tried to make us complicit in your shortcut. (Spoiler alert: Most of us will not bend. You can disparage us until the cows come home, but the reality doesn’t change.)

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Let’s Talk About Security

You want me to email a full tax return. Unencrypted. To your aol.com address. Or to some generic inbox at a brokerage that has the cybersecurity posture of a child’s lemonade stand.

I have 30 years of IT experience. I’ve worked in your industry. I know how many of you handle sensitive data. I’ve seen the shared logins, the passwords on sticky notes, the Excel spreadsheet with every login you’ve ever had, and the complete absence of any data protection policy. And you want me to trust you with my client’s Social Security number, income details, and financial life?

As my 7-year-old nephew says, “No, thank you.” He says it with sarcasm, and I’m not sure where he got that.

If you want tax return information, we’ll deliver it securely. We will not email it.

And While We’re at It, Stop Encouraging Fraud

Some of you do this, and you know who you are. “Can’t you just move some income around?” “What if they didn’t claim that deduction this year?” “Can you amend the return to show higher income?”

You’re asking a licensed professional to commit tax fraud so you can earn a commission. Read that sentence again and think about what you’re doing.

I have ethical obligations. I have legal obligations. My license and my livelihood depend on following them. Your commission does not outweigh my professional responsibility. Not today. Not ever.

Here’s How This Actually Works

If you want to work with a tax professional, here’s the playbook:

Have your borrower contact us directly to authorize the release of their information. Give us a reasonable timeline. Accept the documents we provide as prepared. Don’t ask us to write letters predicting the future. Don’t call after hours. Don’t go around us to the client when you don’t get what you want.

Treat us like the licensed professionals we are, and you’ll find we’re pretty easy to work with. Keep treating us like an obstacle to your closing, and you’ll keep getting the resistance you’ve earned.

We’re not the problem here. We never were.

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I’ve created a one-page client handout you can customize for your own practice. It explains the mortgage document request process in plain language, covers Section 7216 authorization requirements, and sets expectations around comfort letters, security, and turnaround times. Swap in your firm name and contact info, and you’ve got something ready to hand to any client who tells you they’re buying or refinancing a home. You can download it below.

Mortgage Handout

53.2KB ∙ PDF file

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I’m making this available to all subscribers, not just paid, because this is something too many of us deal with often. If you find this kind of content valuable, please consider becoming a paid subscriber. It helps me keep putting out articles, tools, and resources like this one.

It is the middle of tax season. You are tired. Your inbox is a disaster. Your phone will not stop ringing. Every voicemail is from someone who needs something from you yesterday.

And in the middle of all of that, a potential client shows up. They have money. They have a real problem. They need help. Your brain does what it always does. It starts calculating. That is another return. That is another fee. That is the margin you need to hit this quarter.

I turned down a potential client last month. I said no.

It took me years to learn how to do that. When I started my practice, I said yes to everything. Every phone call was a potential invoice. Every consultation was a chance to keep the “lights on”. I needed every dollar, and I suspect you did too.

Here is what nobody tells you when you go into business. The clients you say yes to will define your practice. The clients you say no to will define your sanity.

Tax season is the worst time to make this decision and the most important time to make it. You are exhausted. People are demanding. Some of them are delusional about their situations.

That is exactly when you need to be the most intentional about who you take on.

Make a list. Check it twice. Know what your ideal client looks like before the phone rings, not after. Know your capacity. Know your limits. Know the types of work that energize you and the types that drain you. Because if you do not define those boundaries before tax season buries you, tax season will define them for you. And you will not like the result.

The Red Flags Are Quiet at First

Bad-fit clients do not announce themselves. They do not walk in wearing a sign. They show up like everyone else, with a problem and a willingness to pay you to fix it. The red flags are subtle. You have to learn what they look like, and that education is expensive.

The client who calls five times before the engagement letter is signed. The one who already knows the answer and just needs you to rubber-stamp it. The one who badmouths every professional who came before you. The one who treats your fee like an opening offer.

These are not difficult clients. These are clients telling you exactly who they are. Listen to them.

Let me give you two examples.

A few years ago, a taxpayer called me about an IRS collections case. Straightforward situation. He owed about $80,000, had the income to support an installment agreement, and needed someone to negotiate it. Perfect case for my practice. But in the first fifteen minutes of the consultation, he told me his last three practitioners were all incompetent, his ex-wife’s attorney was conspiring with the IRS, and he needed me to “fight” the Revenue Officer who was “out to get him.” Every answer I gave him was met with “but what about...” followed by something he read on the internet.

I passed. The next week, a client with a similar balance called. She had her documents organized. She listened. She asked good questions. She signed the engagement letter the same day.

Here is another one. A small-business owner called during the filing season last year. She needed three years of unfiled returns and wanted them done in two weeks. When I quoted the fee, she asked if I could do it for half because “it should not take that long.” When I explained the scope, she said her last preparer did it for less. When I held my fee, she asked if she could pay in installments spread over six months. Three red flags in one phone call. I wished her well and moved on.

The Math Never Works the Way You Think

When you are starting out, turning down a paying client feels like setting money on fire. Your brain runs the math in real time. That fee is rent. That fee is payroll. That fee is the software subscription you just renewed.

But your brain is running the wrong calculation.

The real math includes the hours you will spend managing unreasonable expectations. The emails at 10 PM on a Saturday. The scope creep that turns a straightforward engagement into a months-long negotiation over what was and was not included. The damage to your reputation when the client tells everyone you failed them, despite the fact that you delivered exactly what you promised.

Factor all of that in, and the “lost revenue” from saying no starts to look like the best money you never made.

Trust the Flinch

Every practitioner I know who has been doing this long enough has developed what I call the flinch. It is that feeling in the first ten minutes of a consultation where something is off. You cannot always name it. The client seems fine on paper. The case is in your wheelhouse. But something in your gut says walk away.

Trust that.

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I ignored the flinch early in my career. Every single time, I regretted it. Not sometimes. Every time. The flinch is your experience talking before your conscious brain catches up. It is pattern recognition built from every bad engagement, every painful collection effort, every client who made you question why you chose this work.

Your gut is not being dramatic. It is doing math that your spreadsheet cannot.

Saying No Is a Skill

Nobody teaches you this part. There is no CE course called “How to Turn Down Money Gracefully.” So here is what I have learned.

Be direct. “I do not think I am the right fit for your situation” is a complete sentence. You do not owe anyone a detailed explanation. The more you explain, the more you give them to argue with.

Refer out when you can. Sometimes the client is not a bad client. They are a bad client for you. A referral costs you nothing and builds goodwill with the colleague who takes it.

Do not negotiate with yourself after you have decided. If your answer is no, say no. Do not talk yourself into a “maybe” because the fee is attractive. The fee is always attractive. That is exactly how bad engagements start.

Something Better Is Coming

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I know how that sounds. Like a motivational poster. But I have found it to be reliably true.

Every time I have turned down work that was not right, something better showed up. Not because the universe rewards virtue with referrals (maybe it does send you something better). But because I had the capacity to take it. The hours I would have spent managing a bad-fit client were open for the right-fit client who called the following week.

You cannot take on good work if you are buried in bad work. And capacity is not just about hours on the calendar. It is about mental bandwidth. One bad client will consume the same energy as five good ones. You know this already. You are probably thinking about that client right now. We have all had those clients, and, to be honest, we probably have a few who should be disengaged.

Keep Notes

I keep notes on every call or meeting I have with a client. If it is a tax-preparation client, I may only talk to them once or twice a year. If the interaction is unpleasant, I make a note of it. When it is time to send out engagement letters, you do not have to send one to everyone. If someone is unpleasant, you can say no. Life is very short. Make the most of it.

The Permission You Did Not Ask For

If you are reading this and you have a specific client in mind, you already know the answer. You knew it during the consultation. You knew it when they called for the third time before signing the engagement letter. You knew it when they told you what their last accountant did wrong.

You do not need permission to protect your practice. You do not need permission to value your time.

But if you need to hear it from someone: say no. Mean it. And get back to the work that actually deserves you.

How do you handle clients who are not ideal?

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I was working on a case last month. I had IRS transcripts pulled up on one monitor, my notes on the other, and I needed to draft notes about the client’s compliance history. I knew exactly what I wanted to say. I could see the whole thing in my head. And I sat there typing it out, word by word, watching my thoughts back up behind my fingers like traffic.

That’s when it clicked. I wasn’t slow at typing. I was slow at typing compared to thinking.

I’ve spent thirty years in IT. I type fast. I’ve always typed fast. I was the last person who thought they needed a voice dictation tool. And I was wrong.

Wispr Flow has changed how I work. Not in a “nice productivity hack” way. In a “I can’t believe I was doing it the other way” way. But it comes with a serious caveat for anyone in our profession, and that caveat is what most of this article is about.

I’m also not the only fast typer who got converted. Ryan Reichert, EA, CFP, of Brass Tax Presentations, has been on the same journey. I asked him to share his experience, and he brought something to the table I wasn’t expecting.

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The Friction You Don’t Notice

Here’s what Wispr Flow does. You hit a hotkey. You talk. Clean, edited text appears wherever your cursor is. Email, Claude, CoCounsel, Word, Slack, your case management system, Facebook Messenger. It doesn’t care. It works everywhere. It runs on Mac, Windows, and iOS, with Android in limited release.

What separates it from the dictation you’ve been ignoring on your Mac since 2015 is what happens between your mouth and the screen. It strips filler words. If you restart a sentence mid-thought, it catches the correction instead of transcribing the false start. It learns your vocabulary. I’ve trained mine on “Section 7216” and “Form 2848” and “installment agreement” and all the other terms that make normal dictation tools choke. It adapts tone based on the app you’re dictating into, more formal in Outlook, more casual in Slack.

Pro costs $15 a month, or $12 a month on an annual plan. There’s a free tier capped at 2,000 words per week on desktop (1,000 on iPhone). Enterprise starts at $24 per user per month. All new accounts get a 14-day Pro trial, no credit card required.

But the pricing isn’t the point. The point is what happens to your work when the bottleneck between your brain and your screen disappears.

The biggest difference has been in AI prompting. I draft prompts now that I never would have typed. Long ones. Detailed ones. The kind where you walk the AI through the full context of a case, explain what you’ve already tried, describe what you’re looking for, and specify the format you want back. Nobody types a 300-word prompt. You shortcut it. You leave context on the table. But when you can just talk through it, you give the AI everything it needs, because the cost of being thorough dropped to zero.

Case notes after a client call used to be something I’d get to “in a minute,” which sometimes meant an hour later when half the details had faded. Now I hit the hotkey the second I hang up and talk through the whole conversation while it’s fresh. Content drafts, client emails, cover letters for IRS submissions, all faster, all with more detail than I’d have bothered to type. And because it works on iPhone too, I’ve caught myself dictating notes from the parking lot before I even get back to my desk.

I didn’t expect any of this. I expected to try it for a week and go back to my keyboard. That was months ago.

Ryan’s Experience

Ryan has been deep in the weeds, integrating AI into his continuing education work at Brass Tax Presentations. I asked him to share his experience independently because he’s thinking about this from a different angle, and because he’s honest about where the tool falls short.

Recently, we’ve been migrating our continuing education infrastructure to integrate AI where it makes sense. I’ve been a fast typer all of my life, but our adoption of AI has caused me to stop and think anytime I feel “friction” while working to see if there’s a better way for me to operate. So, as I’ve been prompting my tax research tool CoCounsel from Thomson Reuters or prompting Claude Code, by finding a way to get information out of my head faster I figured my prompts would be better off if I didn’t feel constrained by the time it took to type them.

There are A LOT of dictation services out there. But I wanted one that could meet the following requirements:

1) Cutting um’s and ah’s 2) Would notice when I made a mistake and rephrase and actually apply it while typing 3) That could be trained on the odd tax vocabulary I use constantly

After doing a ton of research, I ended up settling on WisprFlow.

This app has effectively removed all friction from typing and working with AI. And I LOVE it. As I use it, I’m teaching it new words, phrases, and formatting of my spoken word into a typed format. I like that it effectively exists in any application I want to use it with, with the click of a hotkey. It’s amazing.

However, I will say that until everyone makes a change, there is an obvious gap between my spoken word and my typed word. When I type, my voice tends to be far more formal, which is really important for writing. But if you ask any of my regular seminar attendees, they’ll tell you that I speak very casually, which helps to make the material more approachable. This is an odd catch-22 that I’m sure could be solved by using another service like Grammarly to help to formalize some of my spoken word translated by WisprFlow, but I’m not really sure.

AI technology is advancing so fast that I wouldn’t be surprised if, in a few months, it could formalize my words on the fly. I’m also pretty considerate about what I use it to dictate. Outside of education, I work with some high-profile tax clients, and I am VERY careful not to dictate that information, or to dictate and leave out sensitive information which I’ll then go and add later.

There are always complications when using AI for sensitive information, which I anticipate will also be worked out to push full-blown commercial use of AI, but I don’t think it’s a reason enough not to use these tools (while being considerate of security concerns).

-- Ryan Reichert, EA, CFP® | Brass Tax Presentations

Ryan raises something worth sitting with: the gap between your spoken voice and your written voice. When you type, you self-edit in real time. When you talk, you’re more relaxed. I’ve noticed the same thing. My dictated drafts need more editing than my typed ones. The substance is better, but the polish isn’t there yet. Wispr Flow’s Command Mode helps (you can highlight text and say “make this more formal”), and I think the AI models will close this gap soon enough. For now, know that your spoken drafts won’t read like your typed ones. Plan accordingly.

The Security Deep Dive

Every word you dictate through Wispr Flow leaves your computer. There is no local processing option. Your voice travels to external servers, gets processed by multiple third-party AI providers, including OpenAI, Anthropic, Cerebras, Baseten, and Fireworks AI, and the resulting text comes back to your device. All infrastructure runs on AWS in the US East region. All of it happens off your machine.

For a tax practitioner, that fact is where this conversation has to start.

The Controls That Matter

Wispr Flow gives you real privacy controls, and they’re meaningful. This isn’t security theater.

Privacy Mode is the most important toggle in the app. Enable it in Settings, Data and Privacy, and none of your dictation data (audio, transcripts, edits) is stored or used for model training by Wispr or any third party. Zero data retention. Process and discard. Available on every plan, including free.

Here’s what you need to know: Privacy Mode is not on by default. During onboarding, Wispr presents two choices: “Help improve Flow” and “Privacy Mode.” The default selection is “Help improve Flow,” which means your dictation data can be used for model training. If you clicked through onboarding without reading carefully, you are opted in to data collection. Go check your settings right now. Settings. Data and Privacy. Privacy Mode. Turn it on.

The HIPAA BAA is available on all plans and can be signed in-app on desktop and iOS. Signing the BAA permanently locks Privacy Mode on. You cannot turn it off afterward. That’s not a limitation. That’s good design. It removes the possibility that you or someone on your staff accidentally toggles Privacy Mode off and forgets to turn it back on. This is what I mean when I talk about systems over discipline. You’re not relying on yourself to remember to keep a toggle in the right position every day. You’re building a system where the safe configuration is permanent. Sign the BAA. Even if you don’t handle health information. Lock it in.

Context Awareness is the one to watch. When it’s on, Wispr Flow reads text from your active application window to improve transcription accuracy. Think about what that means if you’re staring at an IRS transcript or a client’s Form 433-A when you start dictating. Whatever’s on your screen could be transmitted to their servers alongside your voice data. You can toggle this off. I’d recommend you do when working with client files.

One more gotcha: if you submit a feedback or bug report through the app, the transcript text associated with that report may be transmitted to Wispr’s internal support systems regardless of Privacy Mode. If you’ve signed the BAA and you’re handling sensitive data, don’t submit bug reports that include active transcription windows.

Wispr states they have agreements with all third-party AI providers ensuring zero data retention on their end. They say they never sell your data. Their business model is software, not data. Even so, usage metadata (word counts, app names, device info, IP addresses) is still collected with Privacy Mode enabled. And the privacy policy contemplates data sharing in the event of an acquisition or merger. Wispr has raised significant venture capital. Companies at that stage get acquired. The privacy commitments that exist today are made by the company that exists today.

The Enterprise Documentation Gap

This is the part that frustrates me, and it’s a theme I keep coming back to.

What you get on Basic and Pro is functional: Privacy Mode, HIPAA BAA, Context Awareness toggle, TLS encryption. What’s behind the Enterprise paywall is different: SOC 2 Type II compliance documentation, ISO 27001 certification documentation, enforced Privacy Mode across your team, SSO/SAML, SCIM provisioning, a formal Data Processing Agreement, and configurable local data storage policies.

That second list isn’t the features you use every day. It’s the documentation you need when you’re building your WISP and you need to demonstrate you’ve vetted your vendors’ security controls. Without those audit reports, you’re pointing at a marketing page and hoping that counts.

I’ll also flag something odd. Wispr’s Trust Center and Enterprise page both say they’re SOC 2 Type II compliant. But their Security Overview help article says “Working toward SOC 2 Type II and ISO 27001 certifications.” That’s contradictory. If I’m doing a vendor assessment for my WISP, I need a clear answer on certification status, and the vendor’s own documentation shouldn’t contradict itself.

Wispr does maintain a public Trust Center through Delve, where you can request access to SOC 2 reports, penetration test reports, and other documentation. If you’re on Basic or Pro, it’s worth submitting a request to see if they’ll share regardless of plan tier. The FTC Safeguards Rule requires you to document how your service providers protect client data. You need those documents in your files.

This isn’t unique to Wispr Flow. It’s systemic across SaaS. The compliance documentation small businesses need is consistently locked behind pricing tiers designed for organizations with hundreds of seats. I’ve written about this before and I’ll keep writing about it until it changes.

Section 7216 and PII

Here’s where I need you to pay attention. If you haven’t read the article I contributed to last week with Tom Gorczynski, it is a must read.

Tom Talks Taxes

AI and the §7216 Disclosure and Use Rules

Many tax professionals are experimenting with artificial intelligence (AI) tools, such as ChatGPT and Claude, in their tax practices to help with client and administrative tasks…

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3 months ago · 7 likes · 12 comments · Thomas A. Gorczynski and Josh Youngblood, EA, CRETS

Under Section 7216, a tax return preparer cannot disclose tax return information to a third party without the taxpayer’s consent. The penalties are real. It’s a misdemeanor with potential criminal penalties and fines.

Now think about what happens when you dictate case notes through Wispr Flow. You say a client’s name. You reference their Social Security number. You talk about income figures, filing statuses, and assessment balances. That information is being transmitted to servers operated by five different AI companies. Is that a disclosure under Section 7216? That’s a question worth asking. The answer probably depends on your specific circumstances and the data involved. But the question exists, and most practitioners haven’t thought to ask it.

Let’s be practical. You’re on the phone with a client discussing their wage garnishment. You hang up. You hit the hotkey and start rattling off notes. Their name, their SSN, the balance they owe, the levy source. That’s a reflex. And it’s a reflex that sends all of that to cloud servers.

Ryan gets this right. He dictates around sensitive information and backfills the specifics later. That’s the correct approach. But it requires building a habit, and habits are only as reliable as the person maintaining them on a Tuesday afternoon when they’re four cases deep and running behind.

This is where systems over discipline comes back. You can’t rely on yourself to remember not to say a Social Security number out loud every single time. But you can sign the BAA (locking Privacy Mode permanently), turn off Context Awareness, and build a workflow where PII gets typed, not spoken. Structure the system so the safe path is the default path.

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The Verdict

Wispr Flow is the best voice dictation tool I’ve used. It removed a bottleneck I didn’t know I had. It has made me faster, made my AI prompts dramatically better, and changed how I think about the gap between having an idea and getting it on screen. Ryan’s experience confirms what I’ve been seeing.

But “best tool I’ve used” and “use it without thinking” aren’t the same thing.

If you have a Written Information Security Plan (and you should, because the FTC Safeguards Rule requires it, and when you renew your PTIN, you state that you understand that requirement), voice dictation tools need to be in it. Not as a footnote. As a documented vendor with a documented risk assessment. Document what data the tool could capture, where it’s processed, what controls you’ve enabled, and what residual risks remain.

Use Wispr Flow with Privacy Mode locked on. Use it with the BAA signed. Use it with Context Awareness off when you’re in client files. Build the habit of dictating around PII rather than through it. Say “the client” instead of their name. Say “their identifier” instead of their SSN. Fill in the specifics manually. And check your settings, because the defaults aren’t configured the way you’d want them.

I use Wispr Flow every day. I recommend it. And I recommend it with respect for what it can do if you’re not paying attention.

Here is an offer for a free month of the pro version. (I get a free month if you use it.)

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Editor's Note: After this article was drafted, a Substack investigation accused Delve, the platform that hosts Wispr Flow's Trust Center and compliance badges, of systematically misleading customers about their compliance status. The allegations include fabricating audit evidence and routing certifications through firms that rubber-stamp reports without independent review. Delve has denied the claims, calling them misleading. TechCrunch and other outlets have covered the story. This does not mean Wispr Flow's SOC 2 Type II certification is fraudulent. But Wispr Flow's public compliance documentation is hosted on a platform whose credibility is now being actively questioned. If you are evaluating Wispr Flow's security posture for your WISP, this is something to be aware of. I will update this article as the situation develops.

If you spend any time in tax professional Facebook groups, you’ve seen the posts. Confession, sometimes at night, to unwind, some friends (you know who you are), and I may peruse the groups a bit. It is terrifying to say the least. Someone’s pitching their “service bureau” with promises of passive income, white-labeled software, and the ability to build an empire without preparing another return. The comments fill up with fire emojis and “DM me for details.”

And if you’ve been doing this long enough, you’ve also seen the other posts. The ones from preparers who got burned. The ones asking why their EFIN was compromised. The ones wondering where all those fees came from that got pulled out of their client’s refund.

Let’s talk about what a service bureau actually is, where the model works, where it goes wrong, and why the real problem is bigger than any single bureau.

What Is a Service Bureau?

A tax service bureau is a reseller of professional tax preparation software. A tax professional contracts with an established software company (CrossLink, TaxSlayer Pro, Sigma Tax Pro, UltimateTax, and others), purchases software licenses at a discounted rate, brands the software with their own logo, and resells it to other preparers at a markup.

The bureau is supposed to provide more than just software. Training, support, bank product onboarding, the kind of personalized service a large vendor can’t offer every small office. The idea isn’t inherently bad. Some service bureaus are run by credentialed, experienced professionals who genuinely support their preparers.

The problem is how easy it is to become one without being any of those things.

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Follow the Money

Service bureaus don’t make money from a single source. They stack fees. And the people absorbing those fees often don’t know the full picture.

Software license fees. The bureau buys licenses at a discount and resells them at whatever price they choose. Some charge $1,000 or more per license per year. One accelerator program encourages bureau owners to sell ten licenses at $1,000 renewal fees each, collecting $10,000 the following year without making a single new sale.

Service bureau fees. Every time a preparer files a bank product return, the bureau collects a fee directly from the taxpayer’s refund. Bureau owners can set this fee up to $99 per funded return. One software provider disclosed an average total fee per funded bank product of roughly $93, and that’s before the preparer’s own fee gets deducted.

Revenue splits. Some bureaus take a percentage of the preparer’s preparation fees. Common splits are 70/30, 80/20, or 90/10, with the smaller number going to the bureau. If you’re giving up 10 to 30 percent of your prep fees to someone who sold you software, you should know exactly what you’re getting in return.

Add-on fees. Technology fees, transmitter fees, audit protection fees, e-filing fees. These stack on top of everything else.

Recent fee surveys put the national average for a simple Form 1040 with standard deduction in the low- to mid-$200s. Studies consistently show credentialed preparers charge more than non-credentialed ones, which makes sense given the education involved. But when a service bureau preparer charges a comparable fee and then layers on $99 in bureau fees, $44 in bank fees, and another $30 or $40 in technology and transmitter fees, a taxpayer expecting a $300 bill sees $450 or more come out of their refund.

The taxpayer doesn’t understand the breakdown. The preparer sometimes doesn’t either.

Who Gets to Be a Service Bureau?

This is where it gets uncomfortable.

Multiple service bureau programs advertise that there are no specific requirements to become a bureau owner. No credential. No experience. No exam. One major software provider states this explicitly on their website. If you’re “business-minded” and willing to pay, you’re in.

Some programs go further. “Nesting” arrangements let preparers who don’t have their own EFIN file returns under the bureau’s EFIN. One program advertises “no EFIN required” and offers preparers up to 60% of the preparation fee while working under the bureau’s credentials. Publication 3112 makes EFINs non-transferable and prohibits renting, leasing, or otherwise sharing them; providers who do so can be sanctioned, including suspension or expulsion from the e-file program. Yet EFIN sharing gets marketed as a feature.

If someone can’t pass the IRS suitability check on their own, possibly because of criminal history or compliance violations, the answer should not be to let them file returns under someone else’s number.

The accelerator programs pitch themselves as turnkey businesses. Pay a one-time fee, get white-labeled software, a custom logo, social media templates, and unlimited licenses. Testimonials talk about making $40,000 before tax season starts, just from selling software. One describes the model as “one of the easiest ways to make money in the tax industry without working so hard.” The focus is revenue generation, not return accuracy.

The Damage

Low-income taxpayers get hit hardest. The people most affected by fee stacking are taxpayers claiming the Earned Income Tax Credit. They can’t afford to pay up front. They need their refund the most. And they lose the largest percentage of it to fees they didn’t fully understand. This will only intensify now that, under Executive Order 14247, the IRS has generally stopped issuing paper refund checks for individuals and is pushing most taxpayers toward electronic refund options. More taxpayers steered toward bank products means more opportunities for fee stacking.

Ghost preparers thrive in this ecosystem. The IRS’s 2026 Dirty Dozen list, released March 5, includes ghost preparers at number eight. Ghost preparers file returns without signing them or including a PTIN, leaving taxpayers on the hook for everything on the return. When the barrier to entry is low enough, and EFIN sharing exists, ghost preparers operate under a bureau’s credentials without ever being individually accountable. In August 2025, a ghost preparer in Augusta, Georgia, was sentenced to 22 months in federal prison for fabricating income, charging percentage-based fees, and never providing clients with copies of their returns. This week, a preparer in Allentown, Pennsylvania, was charged in a $5.5 million fraud scheme on top of a prior $4.3 million scheme that had already resulted in prison time.

The data security gap is real. Under the Gramm-Leach-Bliley Act and the FTC’s Safeguards Rule, every tax return preparer is required to have a Written Information Security Plan. When a service bureau distributes software to dozens of preparers across multiple offices, who is responsible for the taxpayer data flowing through the system? Does the bureau have its own WISP? Do the individual preparers? Is anyone conducting risk assessments? In most cases, the answer is no.

The Number That Should End the Debate

The National Taxpayer Advocate’s 2026 Purple Book, released in January, includes a recommendation that Congress authorize the IRS to establish minimum standards for federal tax return preparers. The data behind that recommendation is hard to argue with.

In fiscal year 2024, 27.3% of EITC payments were estimated to be improper, totaling $15.9 billion. Among EITC returns prepared by paid preparers, 96% of the total dollar amount of audit adjustments was attributable to returns prepared by non-credentialed preparers.

Federal and state laws require licenses for lawyers, doctors, financial planners, barbers, and beauticians. Most paid tax return preparers have no competency requirement at all.

I want to be very clear about something: just because you are not licensed does not mean you are not competent. There are unlicensed tax preparers who know more and do a better job than licensed people. Having letters after your name does not mean you are all-knowing. Believe me! But having some minimum requirement in place would be a good start.

The IRS tried once. The Registered Tax Return Preparer program would have required testing and continuing education for unenrolled preparers. Loving v. IRS struck it down in 2014 because the court said the IRS lacked statutory authority. Congress has not given them that authority in the twelve years since. The Obama, first Trump, and Biden administrations all recommended it. A bipartisan Senate discussion draft from Finance Committee Chair Crapo and Ranking Member Wyden proposes increased preparer penalties, jumping the failure-to-sign penalty from $60 to $250 and the due diligence penalty from $635 to $1,000. Those are steps in the right direction, but penalties after the fact are not prevention.

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What Should Change

We need more people in the tax profession. Experienced practitioners are retiring, and the pipeline isn’t keeping up. Nobody disputes that. But there’s a difference between lowering barriers to entry and removing guardrails entirely.

Federal minimum competency standards for paid preparers. Testing and continuing education for anyone who prepares returns for compensation. Three administrations have recommended it. The National Taxpayer Advocate has recommended it. Congress needs to stop waiting.

Credential requirements for service bureau owners. If you’re distributing software, collecting fees from taxpayers’ refunds, and onboarding preparers under your brand, you should be an EA, CPA, or attorney.

Consistent EFIN enforcement. The rules already exist. Publication 3112 prohibits EFIN sharing. If the IRS deactivated EFINs aggressively when sharing is detected, the EFIN-as-a-service model collapses.

Transparent fee disclosure. Taxpayers should see a clear, itemized breakdown of every fee coming out of their refund before they consent to a bank product. Service bureau fees, technology fees, transmitter fees, and preparation fees listed separately, in plain language.

Practitioner due diligence. If you’re considering signing up with a service bureau, ask hard questions. What credentials does the owner hold? What fees hit your clients’ refunds? Are they asking you to use their EFIN? Do they have a WISP? What happens when a return gets flagged? If the answers are vague, or if the pitch is more about your revenue than your clients’ returns, walk away.

The Bottom Line

The service bureau model isn’t going away. It fills a real gap for independent preparers who need affordable software and support. But the absence of regulation, the nonexistent barrier to entry, and the incentive structure that rewards volume over quality have created an environment where exploitation thrives.

Every fraudulent return filed under a service bureau’s EFIN, every taxpayer who loses a chunk of their refund to fees they didn’t understand, every ghost preparer who fabricates credits and disappears after April 15 erodes the public trust that voluntary compliance depends on.

$15.9 billion in improper EITC payments tells us exactly what the cost of inaction looks like.

How We Can Fix It

I spend a lot of this article talking about what’s broken. We should always seek solutions to problems, or we are just complaining, and that doesn’t solve anything. I want to end with something that’s working.

I serve on the scholarship committee for the National Association of Enrolled Agents (NAEA), dedicated to helping aspiring enrolled agents reach their career goals. The foundation provides SEE exam prep course scholarships, reimbursement of exam registration fees, National Tax Practice Institute (NTPI) Level 1 scholarships for practitioners entering representation work, and college scholarships for students pursuing accounting and tax careers. The next scholarship window opens May 1.

If we want more qualified people in this profession, and we do, this is how we get them there. Not through a turnkey software package and a Facebook group. Through education, testing, continuing education, and mentorship. The license must mean something because you have to earn it. Personally, I also want to see more required education and stronger vetting to ensure quality. Getting a license is an important first step, but the learning never stops.

If you’d like to learn more or donate, visit the NAEA Education Foundation.

What are your thoughts? Have you been impacted by this?

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For those of you of a certain vintage, Claude rhymes with Maude. As in Bea Arthur. The woman who walked into a room said exactly what everyone was thinking, but nobody had the nerve to say, and dared you to disagree. She was loud. She was opinionated. She was unavoidable. And she changed the conversation just by showing up.

That is exactly what is happening right now with AI in our profession.

The Overnight Revelation That Wasn’t Overnight

It feels like the entire accounting and tax world woke up one Tuesday morning and collectively discovered artificial intelligence. My inbox is full of it. Social media is abuzz. Every conference, every webinar, every post from someone who six months ago couldn’t spell “API” is now an AI thought leader.

Here is the thing, though. This was not overnight. Some of us have been in these trenches for a while now. But I will give credit where it is due. The fact that our profession is finally paying attention? That matters. That is a big deal.

Claude, specifically, has become my go-to. I say that because the tool genuinely understands the nuance of what we do. It does not just spit out generic answers. It thinks.

I have used it to outline CE presentations, pressure-test arguments before submitting, review engagement letters, and even brainstorm better ways to structure my workflows in my practice. It is not replacing me. It is making me faster, sharper, and honestly, a little more creative in how I approach problems. The number of projects I have on the horizon from brainstorming is a little overwhelming but utterly exciting.

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And here is something else that matters to me. Anthropic, the company behind Claude, actually seems to have a backbone. They talk openly about AI safety, about responsible development, about the risks of the technology they are building. In a space full of companies racing to ship first and ask questions never, Anthropic is at least trying to have the conversation about guardrails before the wheels come off. And when the government came knocking, looking to use AI in ways that raised serious ethical questions, Anthropic pushed back. They did not just roll over for a contract or a handshake with power. That is a total Maude move. She never had any patience for people who refused to say the hard thing out loud, and she sure as hell was not going to smile and go along with something she knew was wrong just because the person asking had authority.

The Morning Rush

I wake up every morning now with a list of ideas that did not exist the night before. Processes I want to redesign. Client communications, I want to rethink. Workflows I want to tear apart and rebuild from scratch. That is not hyperbole. That is a normal Thursday. After a cappuccino, of course.

AI has turned my practice into a laboratory. Every engagement is a chance to ask, “Could this be better? Could this be faster? Could this be more accurate?” And the answer, almost every single time, is yes.

If you are a tax professional and you are not at least experimenting with these tools, I need you to hear this with all the love and respect I can muster: you are falling behind. Not next year. Not in five years. Right now.

But Let’s Not Be Stupid About It

And here is where I put on the brakes, because this is where most of the AI cheerleading falls apart.

We need to talk about what we are actually doing when we use these tools. Every prompt you type, every document you upload, every client name and Social Security number you feed into a system (DO NOT DO THAT!), that data goes somewhere. Do you know where? Do you know who has access to it? Do you know what the retention policy is?

If your answer to any of those questions is “I don’t know,” then you have a problem. And it is not a theoretical problem. It is a Circular 230 problem and a legal problem. It is a data breach problem. It is a “your client is suing you” problem. But, after a long day of CE, it will be something that we all talk about at the bar, so there is that.

I say this as someone with 30 years in IT and security. The enthusiasm is great. The ignorance about data security is terrifying. I do not say this as some smug tech guy with a god complex; I want people to understand technology and use it. But responsibly.

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Here is what you need to understand at a minimum before you let AI anywhere near your practice:

What data are you feeding it, and does your engagement letter cover that? Who owns the output? Where is the data stored, and for how long? Did you get a 7216 disclosure if needed? Is your state’s data privacy law even on your radar?

If you cannot answer those questions, stop. Learn. Then proceed.

The Monster in the Mirror

There is a real conversation to be had about what we are building here. AI is not just another software tool. It is a system that learns, adapts, and scales in ways our profession has never dealt with before. The IRS is using it. The states are using it. And they are not using it to necessarily make your life easier.

When I talk about “what monster are we creating,” I am not being dramatic. I am asking a genuine question that our profession has not seriously wrestled with yet. What happens when AI can prepare a return better than a human? What happens when the value proposition we have built our careers on gets automated?

The answer is not to hide from it. The answer is to be the one who understands it well enough to stay ahead of it.

The Bottom Line

AI, Claude included, is the most significant shift in how we practice since e-file. Maybe bigger. The professionals who embrace it responsibly will build practices that are faster, more accurate, and more profitable. The ones who ignore it will wonder what happened.

And the ones who use it recklessly, without understanding data security, without thinking about ethics, without considering the implications? They will be the cautionary tales the rest of us reference in our CE classes.

So yes, here comes Claude. And just like Maude, he is not asking for permission. He is not waiting for the profession to catch up. He is already in the room, already changing the conversation, and already making some people very uncomfortable.

The only question is whether you are going to change with it. I have more to say about this topic; stay tuned.

What are you most eager to learn about Claude? What have you done with it so far?

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It’s March. You’re deep in tax season. You’re exhausted, you’re behind, and somewhere between your fourteenth 1040 and your third cup of coffee (not medical advice), a thought creeps in that you’ve been pushing off since January:

Am I charging enough for this?

So you do what any reasonable professional does. You go to a Facebook group and ask what other practitioners charge for a basic 1040. Or a representation matter. Or a business return with three K-1s and a depreciation schedule that looks like it was prepared at 2AM.

And within four minutes, someone drops in with the classic: “We can’t discuss pricing. Sherman Act.”

Let me save you some time. That response is overstating the rule, and usually confusing conversation with coordination. Just like in tax law, context and nuance matter.

The Sherman Act Does Not Say What You Think It Says

Section 1 of the Sherman Antitrust Act prohibits competitors from entering into agreements to fix prices. That’s the keyword: agreements. Contracts. Combinations. Conspiracies. Coordinated action that restrains trade.

If you and I get on a call and decide we’re both going to charge $500 for an installment agreement and neither of us will go lower, that’s a problem. If a professional organization sets a fee schedule that members are expected to follow, that’s a problem. If competitors agree, explicitly or implicitly, to standardize pricing or avoid competing on price, that crosses the line.

But you, an individual practitioner, independently telling another practitioner what you charge? That’s not automatically price fixing. Absent an agreement to coordinate or restrain competition, sharing your own pricing information is not the same thing as collusion.

Now, there is nuance here. Trade associations and competitor groups must be careful. Repeated exchanges of sensitive pricing information, especially if they influence coordinated behavior, can raise antitrust concerns. Organizations often adopt strict policies to avoid even the appearance of impropriety. That caution makes sense from a risk-management standpoint.

But organizational caution has somehow mutated into a widespread belief that tax professionals cannot discuss pricing at all, anywhere, under any circumstances.

That belief is not supported by the statute. And it’s costing practitioners real money.

The Oil Change or the Spa Day

Here’s the thing about pricing that nobody wants to say out loud: price reflects the experience, not just the deliverable.

If getting your tax return done feels like getting an oil change, you’re going to shop on price. You want it done fast, done cheap, and you don’t care who does it as long as the car doesn’t explode when you drive away.

That’s a perfectly valid way to approach oil changes. Something I know very little about, I do know the 5-minute oil change is a marketing gimmick, and it always took more than 5 minutes.

But if getting your tax return done feels more like a spa day at the Four Seasons, you expect something different. You expect to be taken care of. You expect someone who knows your name, understands your situation, and doesn’t make you feel like you’re on an assembly line. And you’re willing to pay for that experience.

Both types of clients exist, and that is ok! The real question is which one you want to serve, and whether your pricing reflects the experience you’re actually delivering.

What I Pay My Therapist (and Why I Don’t Argue About It)

I’ll give you a personal example that has nothing to do with taxes. That’s the “Josh” part of this substack.

My therapist raises her rates pretty much every year. And I don’t blink. I don’t shop around. I don’t ask if she can match some rate I found online for a therapist who graduated last Tuesday. Although if I did, I’m pretty sure she would have a witty response.

Could I find someone who charges less? Absolutely. Would I get the same experience? Not a chance.

She knows my history. She understands how I think. She’s built a relationship with me over time, and that relationship has value far beyond the hourly rate.

That’s what a trusted adviser looks like.

And guess what? You are a trusted adviser, or at least you should be. Sometimes I feel like we offer a little therapy with tax, which is not always my strong suit.

If your clients see you the way I see my therapist, they’re not price shopping. They’re not comparing you to the guy running a $99 special out of a strip mall. They’re paying you because of the expertise, judgment, and relationship you provide.

So yes, raise your prices. Thoughtfully. Intentionally. Regularly.

The cost of doing business goes up every year. Software costs more. CE/CPE costs more. You know my thoughts on education: you get what you pay for. Insurance costs more. Rent costs more. If your rates stay flat while your expenses rise, you’re effectively giving yourself a pay cut.

That’s not sustainable.

If We’re Going to Talk About Pricing, Let’s Actually Talk About It

If we’re going to move past mythology and into reality, we should talk about how fees are structured.

There are generally three models. Each has its place. If you’ve ever sat through one of my classes, I usually say something to the effect, “I’m not here to tell you you’re doing this wrong; this is my perspective.” - the same applies here. At the end of the day, you do you.

Hourly Billing

The old standby. Track your time. Bill your time.

It’s transparent. It’s simple. It also penalizes you for becoming efficient. The better you get, the faster you work, and the less you earn.

I still use hourly billing when the scope is genuinely unpredictable. If a case is such a mess that I can’t reasonably estimate the time involved until I’m knee-deep in it, hourly may be appropriate. But I try to move off it as soon as the scope becomes clear. It can still have its place, but it's few and far between for me.

Flat Fee (Fixed Fee)

This is where I live for most engagements.

You assess the complexity. You quote a price. That’s the price.

The client knows the cost up front. You know what the engagement is worth. And if you complete the work efficiently, you’re not penalized for competence.

A straightforward installment agreement is not the same as an OIC with five years of unfiled returns and an active levy. Price them accordingly.

Value-Based Pricing

This is the more advanced model.

You price based on the value of the outcome to the client rather than the time involved.

If you negotiate an Offer in Compromise that resolves $200,000 in tax debt for $15,000, the value to that client is life-changing. Pricing solely by hours in that context may not reflect the true impact of your work.

Value-based pricing requires confidence, clarity of scope, and strong communication. I use elements of it in representation cases where the financial stakes are significant.

Subscription Pricing

This has evolved into a model I have embraced for certain engagements. For X dollars per month, the client receives a menu of services. I have several representation engagements right now that are on this model. The client knows what they are paying, and I know that, as long as the case is active, I will be paid.

All of these pricing methods have a place in the modern tax practice.

What I Actually Charge

Since everyone wants data points but few people are willing to share them, here are mine.

These are general ranges. Your experience, overhead, and positioning may differ. I’m not telling you what to charge. I’m giving you information so you can make informed decisions.

Tax Preparation

Individual returns: $750 and up based on complexity.

Business entity returns: $1,500 and up, sometimes significantly up, depending on entity type and bookkeeping condition.

Now, are some returns much less than this? Yes, but that is not the norm; I’d be lying if I said there were not exceptions from time to time. That’s one of the advantages of owning your own practice.

Representation Work

This is where it can be all over the place. But as a general rule, I do not get an 8821 or 2848 for less than $1,000. Most of my representation engagements are subscription-based at $995 a month.

As representation can range from a simple installment agreement to a full-blown examination with multiple items, I have been known to use different pricing methods.

Also, if you are handling a non-filer case, this is a representation case. I know some on social media will disagree with me (and have before), but this is still a representation case. Always look at the transcripts and for the love of all things holy:

1. Only file the years you are required to file.

2. Avoid conflicts of interest with married couples

3. Review the transcripts (yeah, it’s important to say that again)

If those numbers feel high, that’s okay. They are not designed to compete with the lowest-cost provider in the market. They reflect the experience, risk management, and depth of representation I bring to the table.

If those numbers feel uncomfortable because they’re higher than what you charge, that may be worth examining.

But if you’re reading this and thinking, “Wow, I could never charge that,” then yes, you could. You don’t have to change overnight. This is all a process, and none of us has magic solutions. Trial and error.

If you’re thinking “That’s unconscionable,” I’ll politely refer you to Williams v. Walker-Thomas Furniture Co., 350 F.2d 445 (D.C. Cir. 1965), and let you look up the legal definition.

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Stop Apologizing for Your Prices

This is where the real issue sits.

Too many practitioners feel guilty about charging appropriately.

You invested years in getting your license. You maintain continuing education. You carry professional liability insurance. You interact with the IRS, which, as we all know, can be administratively challenging (who says I can’t be diplomatic from time to time). You manage clients who are anxious, overwhelmed, and sometimes not entirely forthcoming.

You carry significant responsibility.

Charging a professional fee for professional work is not something you need to apologize for.

If a client does not want to pay your rate, that’s fine. There is a segment of the market that competes on price. You don’t have to.

The Real Reason This Conversation Matters

The secrecy around pricing doesn’t protect the profession. It distorts it.

New practitioners undercharge because they have no benchmarks. Experienced practitioners hesitate to raise rates because they lack context. Firms become overworked because they are priced below capacity.

When practitioners are chronically underpriced, they are chronically overextended. And when they are overextended, quality suffers. You cannot do your best work when you are exhausted and working 80 hours a week.

Transparency does not mean uniformity. It does not mean coordination. It does not mean setting industry-wide rates.

It means professionals sharing information so each of us can independently determine what our work is worth.

That’s not collusion. That’s professional maturity.

So the next time someone asks what you charge for an installment agreement, you don’t need to invoke federal antitrust law.

You can simply answer the question.

We could all use a little more clarity and a little less secrecy in this profession.

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Why the CE You Choose Matters More Than the Credits You Earn

Every year, sometime around October or November, the same scramble happens. Tax professionals across the country start counting their CE credits, realize they are short, and grab whatever is cheapest and fastest to hit the requirement before the deadline.

Click through the slides. Pass the quiz. Get the certificate. Move on.

Here is the problem with that approach: the quality of your continuing education directly affects the quality of your practice. And if you are being honest with yourself, you already know that.

Compliance Is Not Competence

You can maintain your license and still be a bad practitioner. CE/CPE requirements are a floor, not a ceiling. Meeting the minimum keeps you credentialed. It does not keep you competent. This is where I get to mention my favorite section of Circular 230, §10.35, which talks about competence.

That last line is the key. You can become competent through studying and consulting experts. But you have to actually do it.

The tax code changes. Court opinions reshape how we interpret existing law. IRS procedures evolve. The tools we use to serve clients get more powerful and more complex every year.

If your education strategy is to take the same last-minute classes to check a box and call it done, you might rethink it. You might not feel it yet. But your clients will.

I think about this in terms of what I do not know. I have been doing this long enough to understand where my gaps are. I know the areas of tax law where I am strong and the areas where I need to either learn more or know when to refer out. That self-awareness did not come from checking boxes. It came from intentionally pursuing education that pushed me outside my comfort zone. For example, I know absolutely nothing about clergy taxation. It isn’t my market. With that said, I have on my list a good CE class on the topic because I still like to have a basic idea of it, so I can speak intelligently.

What Good Education Actually Looks Like

The best continuing education I have taken has a few things in common.

It is taught by practitioners, not just presenters. When I am learning about IRS representation procedures or practice management, I want to hear from someone who has actually done the work. Someone who can tell me not just what the IRM says, but what happens when the IRS does not follow it. Someone who has sat across from a Revenue Officer and can tell me what actually works versus what sounds good in a textbook. In other words, I’m not attending to hear some funny story that is completely irrelevant.

It goes deep, not wide. A one-hour course on “Quick Updates” is fine for general awareness, but it does not make you better at anything specific. The courses that changed my practice were the ones that spent many hours or classes on a single topic. Depth is what builds expertise. Breadth is what fills a credit requirement.

It challenges what you think you already know. The most valuable CE experience is the one where you realize you have been doing something wrong, or at least not optimally. That moment of “wait, I did not know that” is worth more than a hundred hours of content you already understood.

It creates community. Some of the most impactful learning I have done was not during the lecture. It was during the breaks, the hallway conversations, the post-session discussions with other practitioners who are working through the same problems I am. But please do not be the person who follows the instructor into the bathroom to ask questions. I’ve heard stories and then also experienced it.

You may not get hours for it. Some of the best education I have received is not something that adds hours to my PTIN account. Yes, get your required hours, but truly focus on learning.

High School Dropout

I do not talk about this often, but it matters here.

I dropped out of high school when I was 15. I hated school. I did not think I was learning anything useful. The irony is that the same school system I walked away from had hired me. I was doing all of their IT work. The kid who did not want to sit in a classroom was building and maintaining the technology that kept the classrooms running, and getting pulled out of class to fix issues when things broke.

I got my GED. I spent the next 20+ years in IT, building systems, managing infrastructure, and solving problems. I was good at it. I built a career out of it without a traditional education path.

And then I pivoted into tax.

I am now an Enrolled Agent. A Certified Tax Resolution Specialist. An NTPI Fellow. Certified Real Estate Tax Strategist. Cybersecurity and Microsoft certifications. I teach continuing education courses. I have been quoted in Forbes, CNBC, and others. I have a tax firm that serves clients nationwide. (Oh yeah, I do have an associate's degree and am close to a bachelor's, which I am working on. Not because it will make me more money, but I want the piece of paper. Kinda like an Hermes Birkin, I don’t need it, but…..)

I am telling you this not to brag. I am telling you this because every meaningful credential I hold, every skill that matters in my practice, every bit of expertise that my clients rely on came from education I chose. Not education that was assigned to me. Not education I sat through because someone told me I had to. Education I pursued because I recognized a gap in what I knew and decided to close it.

That is the difference between checking a box and actually learning. But I also came to realize that letters after your name don’t really matter. You can have all kinds of letters after your name, and most people will not know what they mean. People really only care that you can help them and solve their problems.

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The Person Who Hated School Now Teaches

There is something almost absurd about the fact that a high school dropout teaches continuing education classes to CPAs and Enrolled Agents. I am aware of the irony. But it actually proves the point.

Formal education did not work for me at 15. It was not that I could not learn. It was that nobody had connected what I was being taught to anything I cared about or could use. The moment learning became practical, became connected to real problems I was trying to solve, I could not get enough of it.

That is exactly how I think about CE now. The courses that changed my career were the ones where I could immediately see how the material applied to a client sitting in my office. The ones where I walked out and did something different the next day. The ones that made me a better practitioner, not just a more credentialed one.

If you are treating CE like I treated high school, going through the motions because someone says you have to, you are wasting your time and your money. Find the education that connects to the work you actually do.

Specialization Requires Specialized Education

Let me get specific, because I think this matters.

If you are telling clients you can handle cryptocurrency taxation and your entire crypto education is a one-hour webinar you took two years ago, you are doing your clients a disservice. The same goes for any specialty area: international, estate planning, representation, and state and local tax. If you hold yourself out as competent in an area, your education should back that up.

Digital assets are a perfect example of why this matters. The landscape changes constantly. DeFi, staking, airdrops, NFTs, etc. The IRS is actively increasing enforcement in this space. The rules are complex, the guidance is often sparse, and the consequences of getting it wrong are real for your clients.

My friend and colleague Matt Metras is one of the foremost cryptocurrency tax experts in the profession. He is an Enrolled Agent, the owner of MDM Financial Services, and has been teaching cryptocurrency taxation for years. He is a contributing writer for Think Outside the Tax Box, moderates the r/cryptotaxation subreddit, and runs the “Bitcoin & Cryptocurrency Tax Info” Facebook group. When it comes to crypto tax education, Matt is the real deal.

Matt has a digital asset roundtable that I want to put on your radar.

What I appreciate about Matt’s approach is that he does not just teach you the rules that exist today. He teaches you how to think about transactions where the guidance has not yet caught up. In the crypto space, that happens constantly. Practitioners regularly encounter situations with no direct IRS authority, and knowing how to apply existing code sections to novel fact patterns is a skill that will serve you well beyond cryptocurrency.

Roundtable Programs

If you have clients with crypto holdings and you are not actively building your knowledge in this area, you are either turning away work or handling it without the expertise it demands. Neither option serves your clients well. Matt’s roundtable is a practical way to close that gap.

There are other excellent roundtables available covering general tax and international tax. I attended Matt's roundtable yesterday and walked away rethinking how I approach my entire process for clients who have cryptocurrency.

These programs are all part of The Gorczynski Group's offerings available to Tax Professionals. Tom Gorczynski consistently makes the tax pro community better. A few years ago, I joined his Inner Circle program, and it has been the single most important thing I have done in my practice. I attribute much of my success to this program.

Invest in Yourself Like You Tell Your Clients to Invest in Their Business

We tell our clients all the time to invest in their business. Upgrade your systems. Hire good people. Do not cut corners on things that matter.

We should take our own advice.

Good education costs money. It takes time away from billable work. It sometimes means traveling or blocking out full days during busy periods. I understand all of that. But the return on investment is real.

I can point to specific client outcomes that were better because I invested in learning something I did not know before. Specific cases where knowing a procedure or a strategy made the difference between a good result and a bad one. That is not an expense. That is an investment with compounding returns.

A Challenge

Look at your CE/CPE plan for this year. Not just the credits you need, but the actual courses you are planning to take. What do you want to learn? What do you need to learn?

Ask yourself: am I choosing these because they are easy and cheap, or because they will actually make me better at what I do?

If the answer is the former, change the plan. Find one course this year that genuinely stretches you. One program that goes deep on a topic you have been avoiding or do not feel confident in. One instructor who is a practitioner doing the work, not just presenting slides about it.

Your clients deserve a practitioner who is constantly getting better. You deserve to be one.

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I worked from home off and on for years. On paper, it was the dream. No commute. No overhead. I have a dedicated room with a door that closes and a setup that would make any remote worker excited.

And I was slowly losing my mind.

Not in a dramatic way. In the quiet, creeping way where you realize at 3 pm that you’ve been “about to start” something since 10 am. Where the kitchen is fifteen feet away and your fourth snack of the morning has somehow become lunch. Where you sit down at your desk and your brain registers “home” instead of “work” and just... checks out.

So I got an office.

Then I got another one. And another one. I’ve had probably half a dozen offices over the last few years. The first one was too far. One sounded like someone was running a televangelist studio next door. (they were) One just didn’t feel right in a way I still can’t explain, which is a very ADHD reason to leave a perfectly functional space.

I’m telling you this upfront because I don’t want to sell you some clean story where I signed a lease, hung my art on the wall, and everything magically clicked. That’s not how it went. Finding the right office is its own whole project. But here’s the thing, for me: even the bad offices were better than working from home. Every single one of them.

The ADHD Tax on Working From Home

I have ADHD. I’ve talked about this before. It’s not a cute personality quirk or a content strategy. It’s a real thing that shapes how I work every day, and if you have it too, you already know exactly what I’m about to say.

Working from home with ADHD is playing the game on hard mode with the controller upside down. At least for me, but I have friends who have ADHD and work well from home.

Every environment sends signals to your brain. Your office chair says “work.” Your couch says, “Nap.” Your kitchen says, “There’s chocolate in there.” When your workspace is ten feet from all those things, your brain gets hit with mixed signals all day long. ADHD brains are already terrible at filtering signals on a good day.

Structure isn’t optional for me. It’s the entire operating system. I need to get in the car, drive somewhere, and sit down in a place where my brain goes, “Okay, this is the workplace.” That commute isn’t wasted time. It’s a boot sequence. But it can’t be a long drive. My brain needs a loading screen between “home mode” and “work mode,” and a five-minute drive is apparently the minimum viable time for it.

If you don’t have ADHD, this probably sounds dramatic. If you do, you stopped reading to go get a snack and just came back. Welcome back. I get it.

The people who say “just use a timer” or “try the Pomodoro technique” aren’t wrong. Those tools help. But they’re duct tape on a structural problem. I’d rather spend my willpower on client work than on convincing myself to stay in my chair for one more hour when the couch is right there, calling my name, being all comfortable and stuff.

The Real Cost Calculation

Here’s where most people stop thinking: office space costs money, working from home is free. Math done. Case closed.

Except that math is wrong because it only counts the obvious costs.

What does it cost you when a project takes three hours instead of one because you couldn’t lock in? What does it cost when you push a deadline because your discipline evaporated on a Thursday afternoon? What’s the dollar value of spending your entire day fighting your environment instead of, you know, actually doing work?

I can’t put an exact number on that. But I can tell you I get more done in six focused hours at my office than I ever did in nine or ten at home. That’s not motivational poster talk. That’s what actually happened and continues to happen.

Yes, the office costs real money.

But here’s how I think about it: the office isn’t an expense. It’s infrastructure. Same category as your tax software, your secure portal (You are using one of those, aren’t you?), your practice management system. You don’t run those on the free tier and hope for the best. You invest in the tools that make the work possible. For some of us, a physical office is one of those tools.

Run the numbers for yourself. Be honest about what your actual output looks like at home versus somewhere with built-in structure. If there’s a real gap, the office might be the cheapest productivity upgrade you’ll ever make.

Your Clients Don’t Care Where You Sit

Here’s the thing that took me way too long to figure out: not a single client has ever asked to see my office. Not one. In all the years I’ve been doing this.

My clients are everywhere. California, New York, Florida are scattered across the country. They found me online, hired me remotely, and have never set foot in any of the physical spaces I’ve occupied. They don’t care if I’m working from a corner office or a closet with good Wi-Fi. They care that I know what I’m doing and that their problem gets solved.

I used to think having an office was partly about professionalism. Giving clients a place to meet. In practice? I’ve had maybe a handful of in-person meetings in the last few years. Everything else is Zoom, phone, secure portals, and email. That’s what a modern tax practice looks like. I wouldn’t change that for the world. I love it.

So here’s the part that might surprise you: I got the office for me, not for them. The office is about my productivity and my focus. The clients just see the output. Faster responses, tighter work product, deadlines that actually get met. They have no idea those improvements came from me driving to a different building. They don’t need to know. They just need results.

If you’re on the fence about an office because you think your clients need it, they probably don’t. If you’re on the fence because you think you need it, pay attention to that. Those are two very different questions.

Your Staff Deserves the Same Honesty

Everything I just said about clients applies to the people you work with, too.

There’s a certain type of firm owner who insists everyone sit in the office because they don’t trust their team to work remotely. You’ve heard it. “I need to see them working.” “How do I know they’re not just watching Netflix?” “People slack off when nobody’s watching.”

I’m going to be blunt here: if I can’t trust you to do your job without me hovering over your shoulder, I don’t want to work with you. That’s it. That’s the whole policy.

The problem in that scenario isn’t remote work. It’s a hiring problem. Or a management problem. Or a trust problem. Dragging people into an office doesn’t fix any of those things. It just adds a commute to an already broken situation.

I need an office. That’s my thing. But the people I work with? I expect them to manage their own environment and their own output. Some people are great at home. Some people need a coffee shop. Some people do their best work at 6 am in their pajamas. Fantastic. I don’t care where or when the work happens. I care that it happens, that it’s right, and that deadlines get met.

If you’re building a firm, you have to be open to what works best for the people around you. Your structure needs aren’t everyone’s structure needs. The person who’s brilliant at representation work might do her best thinking from a kitchen table in sweatpants. That’s not a problem. That’s the whole point of running a modern practice. Hire good people, set clear expectations, and evaluate the output. Not the optics.

The practitioners who build their firms around control rather than trust are going to struggle to hire and retain good people. The talent pool in this profession is already shallow. Shrinking it further because you won’t let someone work from home is a choice. It’s just not a good one.

Boundaries Are a Real Problem

The hardest part of working from home wasn’t focus. It was boundaries.

When your office is in your house, you’re never fully “at work,” and you’re never fully “at home.” You’re always this weird in-between version of both. The laptop is right there. The client portal is one click away. That email came in at 8 pm, and you could just knock it out real quick. You won’t, though. Except you will. Because it’s right there. And now it’s 9:30, and you’re deep in a collections case in your living room while your spouse gives you a look.

It goes both ways, too. Sometimes “work from home” quietly becomes “live at work.” Sometimes it becomes “do two loads of laundry while pretending to work.” Both of those are boundary failures, and they’ll eat your practice alive.

I tried all the hacks. Dedicated room with a door, a thick door to help block our noise. Strict work hours. “I’m closing the laptop at 6 pm,” I said that so many times. The laptop was open by 6:15 approximately every single day.

An office gives me a hard edge. I’m there, I’m working. I leave, I’m done.

If your boundaries at home are solid, keep doing what you’re doing. But if you’re being honest with yourself and those boundaries are more aspirational than actual, that’s worth sitting with for a minute.

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The Part Nobody Talks About

Working from home can be lonely. There, I said it.

Tax work is already isolating. Most of us are solo practitioners or tiny firms. We spend our days reading transcripts, drafting responses, and staring at tax software. Add physical isolation to professional isolation, and it gets heavy.

Going to an office, even a small one, puts you back in the world. You see other humans. You get coffee from somewhere that isn’t your own kitchen. You exist as a professional who put on real shoes today. That sounds like a small thing. It’s really not.

So, What Should You Do?

I’m not going to tell you that everyone needs an office. That would be dishonest, and it would contradict everything I just said about trusting people to know what works for them.

But I’ll tell you what I tell myself: know what you actually need, not what looks good on a spreadsheet.

If you have ADHD, or if you struggle with focus and boundaries, the office might not be a luxury. It might be what makes your practice actually work. If your clients are remote anyway, you don’t need to justify the office as a client-facing expense. Justify it as what it is: a tool that makes you better at your job.

If you’re thinking about it, try it for three months. Find something small and affordable. Don’t sign a five-year lease. Just test it. Track your output. Be honest about the results. And if the first space isn’t right, try another one. I’m on office number six or so. The search is part of the process.

And if someone on your team does their best work from home, let them. Build your practice around results, not around where the chairs are.

I’m not going back to working from home. But I’m also not going to pretend that what works for me should be the rule for everyone else. Figure out what you need. Be honest about it. Build around that. Everything is trial and error.

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Now I want to hear from you.

Where are you working right now? Home office? Rented space? Kitchen table? Coworking spot? The back seat of your car between client meetings? (No judgment.)

Drop a comment and tell me about your setup. What works, what doesn’t, and what you’d change if you could. Bonus points if you include a photo.

I’m planning something fun for a future post: a showcase of tax pro workspaces. The good, the bad, and the “I can’t believe I’m running a practice from here.” If you’d be open to having your space featured, let me know. I think we can all learn something from how other practitioners have figured this out.

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But here’s what I am going to tell you: my political opinions have no business in a client meeting. And neither do yours.

The §530A / Trump Accounts Problem

Trump Accounts are here. Created under the One Big Beautiful Bill Act (OB3), they’re a new type of tax-advantaged savings account for children under 18. Kids born after 12/31/2024 and before 1/1/2029 are eligible for a $1,000 seed contribution from the Treasury. Families can contribute up to $5,000 per year. Employers can kick in up to $2,500 per employee annually as a tax-free benefit. The funds get invested in limited but sound options.

They ran a Super Bowl ad for these things. Half a million families have already filed Form 4547 to open one. This is not a niche product. This is something your clients are going to ask you about.

And this is where it gets uncomfortable for some of us, because they’re literally called “Trump Accounts.”

I’ve already watched this play out in real time. Tax professionals on social media fall into two camps. One group refuses to acknowledge that these accounts exist or dismisses them outright because of the name on the label, or feels like this “isn’t a tax matter”. The other group is cheerleading them as the greatest financial innovation since the Roth IRA because of who signed the bill. Both groups are letting politics drive their professional judgment and failing their clients.

Politicians Have Been Doing This Forever

Before anyone clutches their pearls over the branding, let’s take a step back and acknowledge something: politicians have been putting their names on tax provisions for decades. This is not new.

The Roth IRA? Named after Senator William Roth, a Republican from Delaware, who sponsored the legislation as part of the Taxpayer Relief Act of 1997. Before that, the Kemp-Roth Tax Cut of 1981 was named after Representative Jack Kemp and the same Senator Roth. The Coverdell Education Savings Account was originally called the Education IRA until Congress renamed it after Senator Paul Coverdell, a Georgia Republican, following his death in 2000. We don’t call them “Section 530 education accounts.” We call them Coverdells.

Nobody refused to recommend a Roth IRA because they didn’t vote for William Roth. Nobody steered clients away from a Coverdell ESA because they disagreed with Paul Coverdell’s politics. The provisions were evaluated on their merits, explained to clients based on their financial situations, and utilized when appropriate.

Trump Accounts should be no different. The name on the label doesn’t change the tax code. §530A works the way it works regardless of how you feel about the person whose name is on it.

But Let’s Be Honest, the Name Hits Different

I get it. The Roth IRA is named after a senator most people outside of Delaware had never heard of. “Coverdell” sounds like it could be a mutual fund family. “Trump” carries a little more cultural weight than those names did.

If the exact same provision had been signed by a different president and called “Child Investment Accounts” or “American Future Savings Plans,” most of the controversy would evaporate overnight. The mechanics would be identical. The tax treatment would be identical. The planning opportunities would be identical.

But they’re not called that. They’re called Trump Accounts. And that name is doing something to practitioners that should concern all of us.

I’ve seen posts from colleagues who flat-out said they won’t discuss these accounts with clients. A tax professional, refusing to inform a client about a legitimate, legally enacted savings vehicle because they don’t like the name. That’s not a political stance. That’s a failure of professional responsibility.

I’ve also seen practitioners pushing these accounts aggressively on every client who walks through the door, not because they’ve done the analysis to determine whether it’s the right vehicle for that specific client’s situation, but because they want to be seen as supportive of the administration. That’s not advice. That’s salesmanship wrapped in a political flag.

“That’s Not Our Job”

I’ve also heard another excuse from practitioners who don’t want to touch Trump Accounts: “That’s an investment advisor conversation, not a tax conversation.”

No. It isn’t. Or at least, it’s not exclusively one.

This reminds me of the BOI (Beneficial Ownership Information) days. I miss those days, when some people screamed it was the unauthorized practice of law, and we shouldn’t do it. By the way, I’m still waiting on a citation on that, and no one has provided it.

Form 4547 is an IRS form. It gets filed with a tax return. The election to open a Trump Account is made through the tax filing process. This is literally part of our world. Yes, people can also go online to the TrumpAccounts.gov website and fill out the form, but most clients expect their tax professional to tell them about it.

We talk about IRAs with clients all the time. We discuss Roth conversions. We walk clients through the tax implications of 529 contributions. We help them understand how employer retirement plan contributions affect their returns. Nobody says “that’s an investment advisor issue” when a client asks whether they should do a Roth conversion. We explain the tax consequences and let the investment advisor handle the portfolio allocation. That’s how this works.

Trump Accounts are no different. The investment decisions, which index fund to choose, how it fits into an overall portfolio, sure, that’s investment advisor territory. But the form, the contribution limits, the tax treatment, the comparison to other tax-advantaged accounts? That’s us. That’s what we do.

If you’re a tax professional and a client with a newborn asks you about Trump Accounts, telling them to “talk to their financial advisor” without providing any guidance on the tax implications is a disservice. You don’t have to manage the account. You do have to know how it works and be able to explain it.

What Your Client Actually Needs to Hear

Your clients with kids under 18, and especially those with newborns or children born since 2025, need to know that these accounts exist. They need to understand the contribution limits, the investment restrictions, the tax treatment on distributions, how they compare to 529 plans and custodial accounts, and whether the account makes sense for their specific financial situation.

Some of your clients are going to walk in excited about Trump Accounts because they love the president. They don’t need you to validate their politics. They need you to walk them through whether a 529 plan might be a better fit if the goal is education funding, since 529s often come with state tax benefits that Trump Accounts don’t offer.

Some of your clients are going to walk in hostile toward Trump Accounts because they can’t stand the president. They don’t need you to commiserate. They need you to explain that leaving a $1,000 government contribution on the table because you don’t like the name on the account is not a sound financial decision when you have a newborn.

In both cases, the conversation should sound exactly the same: “Here’s what the law says. Here’s how it applies to your situation. Here are the pros and cons compared to other options. What questions do you have?”

That’s it. No editorial. No commentary on the administration. No eye rolls. No cheerleading.

It’s Not Just Online

I teach continuing education classes. Recently, I briefly mentioned Trump Accounts during a presentation. Briefly. The comments section lit up like I’d thrown a grenade into the room. Not questions about contribution limits or how they compare to 529 plans. Political commentary. From tax professionals. In a CE class.

And I got off easy. Another instructor I know almost had to eject someone from their class over it. A continuing education class for tax professionals, where an attendee got so heated over the mere mention of a legally enacted tax provision that they nearly had to be kicked out.

Think about that for a second. We are the people our clients rely on to be calm, objective, and knowledgeable. We are the professionals who are supposed to cut through the noise and deliver clear guidance. And we can’t even sit through a CE class without losing our composure over the name on a financial account?

We should be better than this. We have to be better than this.

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The Social Media Trap

I want to talk specifically about what I’ve seen on practitioner social media, because it’s been ugly.

Professional Facebook groups and forums that are supposed to be about tax practice have turned into political battlegrounds over these accounts. Practitioners calling colleagues idiots for recommending them. Other practitioners calling colleagues unpatriotic for questioning them. Threads that start with a legitimate technical question about contribution limits devolve into political arguments within three replies.

If you’re a practitioner and your professional social media presence includes political hot takes about Trump Accounts, understand that your clients can see that. Prospective clients can see that. And roughly half of them are going to conclude that you can’t be objective about their financial situation.

You might be fine with that. I’m not going to tell you how to run your business. But don’t pretend you’re not making a choice about who you’re willing to serve.

It Goes Both Ways

I want to be clear that this isn’t aimed at one side of the political spectrum. I’ve seen failures in both directions.

I’ve seen practitioners who automatically enroll clients unless they opt out, because they want to promote the program. I’ve seen practitioners who oppose the administration steer clients away from a legitimate $1,000 government contribution because they couldn’t stomach the branding.

Both of those are wrong. Both of those put politics ahead of the client’s financial interest. And both of those should make you uncomfortable if you take professional standards seriously.

The Practical Takeaway

Here’s what I’d suggest:

Get educated on Trump Accounts. Read Notice 2025-68. Understand Form 4547. Read Tom Talks Taxes’ article on it. Know how these accounts compare to 529 plans, Coverdell ESAs, custodial accounts, and Roth IRAs for minors. Understand what happens when the child turns 18.

Then, when your client asks, and they will ask, give them the facts. All of them. Without editorializing. Let them make an informed decision based on their financial situation, not based on your feelings about who’s in the White House.

I have strong opinions about plenty of things. When I’m sitting across from a client, the only opinion that matters is my professional one. And my professional opinion is always going to be based on what the law says and what’s best for the person in front of me. That’s literally what I am paid to do.

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The tax code doesn’t care about your politics. Your clients shouldn’t have to either.

If you read cases from the Tax Court, you already know Judge Mark V. Holmes. He’s been on the bench since 2003, he clerked for the legendary Judge Kozinski, and he’s written some of the most memorable opinions in the court’s recent history, from the Michael Jackson estate valuation to micro-captive insurance in Avrahami. He writes opinions like a storyteller, not a bureaucrat, and that alone makes his work worth reading.

His latest, Clinco v. Commissioner, T.C. Memo. 2026-16, is vintage Holmes. It involves an attorney who ran a restaurant, self-prepared his own returns, underreported over $2.2 million in gross receipts, cited DOGE to challenge the IRS’s analysis, and, through his counsel, submitted a brief so riddled with fabricated case citations that Holmes compared it to something “cooked up by AI.”

The food metaphors are intentional. The taxpayer ran a restaurant. And Holmes clearly had fun with them.

The Facts

Peter Clinco was a Los Angeles attorney whose practice focused on real-estate leasing and representing small businesses. He was also an entrepreneur who spent 25–30 hours a week running MedCafe Westwood, LLC, a restaurant and bar near UCLA with approximately 60 employees. It was a family operation: Clinco’s brother Michael held a 33.4% ownership stake through 2014, and a third brother, David, served as manager and bookkeeper. In 2015, Clinco converted MedCafe into a single-member LLC.

MedCafe didn’t record tips — employees received them directly at the end of each shift, including cash from customers, and were responsible for their own tip reporting. Clinco estimated that 90% of MedCafe’s income came from credit card payments and 10% from cash.

Here’s where it gets interesting: Clinco prepared his own 2015 Forms 1065 and 1040. The joint return with his wife wasn’t filed until September 2018 — over two years late. On his Schedule C for MedCafe, he reported gross receipts exceeding $1.6 million but claimed expenses, producing a net loss of approximately $400,000.

He also claimed $56,798 in depreciation deductions on Schedule E for two rental properties in Pasadena that he said were placed in service in May 2015. No purchase invoices. No closing statements. No records establishing depreciable basis or placed-in-service dates.

The Audit

Revenue Agent Yi Liu began the examination in 2019. Clinco was already seriously ill, and much of the communication ran through his accountant. When the RA discovered a discrepancy between reported gross receipts and audited credit-card-sales-to-cash ratios, she summoned bank records and conducted a bank deposits analysis across eight accounts at Chase and City National Bank.

She also pulled third-party Information Return Processing (IRP) data, Forms 1099-MISC and 1099-K, from UCLA, First Data Reporting, American Express, and Grubhub. Using those records, plus Clinco’s own admission that roughly 10% of revenue was cash, the RA reconstructed MedCafe’s gross receipts at approximately $2.29 million, well above what was reported on the return.

After an $82,000 concession for substantiated capital contributions, the Commissioner asserted that Clinco had underreported gross revenue by about $2.2 million.

Within months of receiving the notice of deficiency, Clinco passed away. His wife, C.M. Barone-Clinco, continued the case as successor in interest.

The Procedural Challenge: “Where’s the Wet Signature?”

Before getting to the merits, Clinco’s attorney, Abraham Wagner, challenged the validity of the Notice of Deficiency because it lacked a “wet” signature from an IRS employee. The notice bore the name of David H. Okuda, the technical services territory manager, followed by initials indicating a delegated signing official. Wagner argued that “critical requirements like a signature must be followed for a Notice of Deficiency to be valid.”

Holmes wasn’t convinced. He pointed to IRM provisions that provide multiple acceptable methods for signing notices, including delegation, typed names, and electronic images. But he went further: the caselaw doesn’t even require a signature at all. Citing Tavano v. Commissioner, 986 F.2d 1389 (11th Cir. 1993) and Urban v. Commissioner, 964 F.2d 888 (9th Cir. 1992), Holmes noted this question “has been settled since before World War II,” pointing all the way back to Commissioner v. Oswego Falls Corp., 71 F.2d 673 (2d Cir. 1934).

The AI Problem

Then Holmes turned to the citations in Wagner’s brief, and the opinion shifted from routine to remarkable.

Wagner cited four cases to support his signature argument. Three of them don’t exist.

Holmes, in his signature style, wrote that the argument’s persuasiveness “collapses like an overmixed soufflé when one looks at the citations used to prop it up.” He went case by case:

“Cacchillo v. Commissioner, 130 T.C. 132 (2008)” — doesn’t exist. Page 132 in volume 130 of the Tax Court Reports falls within Porter v. Commissioner, 130 T.C. 115 (2008), a case about §6015(f) relief — completely unrelated.

“Miller v. Commissioner, 57 T.C. 440 (1971)” — doesn’t exist as cited. Page 440 in volume 57 is within Winfield Manufacturing Co. v. Renegotiation Board, 57 T.C. 439 (1971), which doesn’t mention a notice of deficiency at all.

“Tefel v. Commissioner, 118 T.C. 324 (2002)” — no such case. Page 324 of volume 118 is a paragraph in Hillman v. Commissioner, 118 T.C. 323 (2002), a case about S corporation management fees.

Here’s what makes it worse: the Commissioner catalogued all of this in his answering brief. Wagner’s response? He “chose not to clarify their origins in his reply.” He even listed “Cacchillo” again in his table of authorities.

Holmes then delivered the line:

“The bouillabaisse of case names, reporter citations, and legal propositions suggests something cooked up by AI.”

He cited a string of federal cases condemning fabricated citations, quoted Chief Justice Roberts’s 2023 Year-End Report advice to lawyers who cite nonexistent cases “Always a bad idea” and noted that while the Tax Court doesn’t have a direct equivalent to Federal Rule of Civil Procedure 11(b), lawyers appearing before the court must follow Model Rule 3.3(a)(1), which bans knowingly making false statements of law.

Then came the footnote that every practitioner should read. Holmes acknowledged it wasn’t entirely clear from the record whether Wagner actually used generative AI. He allowed that “a bit of embarrassment for failure to citecheck, failure to ‘fess up, and (if it occurred) use of AI to write a section of the brief is enough for now.” But he added:

“Tax Court has not done so. Yet.“

That single-word sentence is a warning shot. And in a characteristically Holmes touch, he even acknowledged that judges aren’t immune: “And, one must confess, even judges have contributed to this stew,” citing a Bloomberg Law article about judicial AI blunders.

The Substantive Holdings

Beyond the AI fireworks, the opinion addresses issues that come up constantly in IRS representation work.

Unreported Income and the Bank Deposits Method

The IRS reconstructed Clinco’s income through bank deposit analysis and IRP data, standard tools when a taxpayer’s books don’t match reality. Clinco raised three arguments:

First, he claimed the Commissioner didn’t sufficiently identify the sources of unreported income. The court found the Forms 1099 were identified through IRP data, and the cash estimate came from Clinco’s own statements; there was nothing arbitrary about it.

Second, he argued that over $385,000 in deposits were personal capital contributions misclassified as income. The RA had already reviewed this and conceded $82,242.18 in verified contributions before trial. Clinco offered no evidence of additional contributions beyond an email, and the court held that “the existence of some substantiated deposits does not support a finding of other unsubstantiated deposits.”

Third, and this one is notable. Clinco cited the Department of Government Efficiency (DOGE), arguing that DOGE “has found errors in some IRS records” and that the Commissioner’s analysis was therefore “likely faulty.” Holmes dismissed this as “entirely speculative,” noting Clinco offered “no substantive evidence” for the claim.

Clinco also argued that MedCafe “never made a profit and had in fact been in bankruptcy.” The Court’s response: “Even money-losing businesses, however, can have unreported income.”

That’s a one-sentence lesson that some taxpayers and their representatives need to hear. A business can lose money and still have unreported gross receipts. Those are not mutually exclusive concepts.

Depreciation Without Substantiation

Clinco claimed $56,798 in depreciation for two Pasadena properties — an apartment building (claimed basis of $1.8 million) and a single-family home (claimed basis of $700,000). He filed Forms 4562 reporting both as placed in service in May 2015. But he provided no purchase invoices, no closing statements, no records establishing basis or placed-in-service dates.

His argument? He claimed the same depreciation on his 2017 return, and the IRS never questioned it.

Holmes cited §§167(a) and 6001, along with Cluck v. Commissioner, 105 T.C. 324 (1995): taxpayers must prove depreciable basis, cost, and useful life with adequate records. His conclusion: “Whether Clinco claimed the depreciation in a later tax year is no proof he was entitled to the depreciation for 2015.”

Each tax year stands on its own. The IRS not challenging something previously does not establish entitlement. This comes up constantly in representation work, and it’s always worth reminding clients.

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What This Means for Practitioners

There are two big takeaways from Clinco, and they happen to sit at the intersection of IRS representation and technology.

On the representation side: This case is a textbook example of why records matter. Bank deposit analysis, 1099-K matching, cash percentage estimates — the IRS has tools to reconstruct income when taxpayers can’t substantiate what they reported. If you’re representing a client with a Schedule C business and the books are thin, get ahead of it. Pull transcripts. Review the IRP data before the IRS does. And make sure your client understands that “the business lost money” is not a defense against unreported gross receipts.

On depreciation, the lesson is equally fundamental: document everything. Basis, placed-in-service dates, useful life calculations. If you can’t prove it, you can’t deduct it.

And the DOGE argument? It’s tempting to think recent headlines give you ammunition in Tax Court. They don’t, at least not without substantive evidence tied to the specific case. Speculation doesn’t carry the day.

On the technology side: We’ve seen federal courts sanction attorneys for AI-generated citations since Mata v. Avianca in 2023. But Clinco is, as far as I’m aware, the first time a Tax Court judge has explicitly called out likely AI hallucinations in a brief filed in that court. And Holmes made sure we know this isn’t the end of the conversation, “Tax Court has not done so. Yet.”

If you’re using AI tools in your practice, you should be; they’re powerful, and you have to verify every single output. Every case citation. Every code section reference. Every regulatory cite. AI is a research assistant, not a research replacement. The moment you file something you didn’t independently verify, you own it. And if it turns out to be fabricated, you’re the one standing in front of a judge explaining why you cited a case that doesn’t exist.

What makes Wagner’s situation worse is that he had a second chance. The Commissioner identified the fake citations in his answering brief. Wagner could have addressed it, corrected the record, taken responsibility. Instead, he said nothing and cited “Cacchillo” again. That’s the kind of thing judges remember.

This isn’t theoretical anymore. It’s happening in Tax Court.

Clinco v. Commissioner, T.C. Memo. 2026-16 (Judge Holmes). Decision to be entered under Rule 155.

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When a new client comes to me with a tax problem, they usually start with a story.

“I got a scary letter.”
“I think the IRS made a mistake.”
“My old preparer messed everything up.”
“I haven’t filed in years, but I’m not sure which ones.”

All of those stories might be true. Some of them usually are. But before I give advice, before I talk strategy, before I promise anything, I do the same thing every single time.

I pull the transcripts.

Because IRS transcripts tell the story. And they tell it better than memory, emails, or a stack of unopened notices ever will.

Why Transcripts Matter More Than What the Client Thinks Happened

Clients rarely have the full picture. That is not a criticism. The tax system is complicated, IRS notices are confusing, and problems often build quietly over the years.

Transcripts show what actually happened.

They tell you:

• What returns were filed and when

• What the IRS processed versus what the client submitted

• What payments were posted and how they were applied

• When penalties and interest were assessed

• Whether the IRS believes a return is missing

• Whether enforcement has already started

Without transcripts, you are guessing. With transcripts, you are diagnosing.

And tax problems should always be diagnosed before they are treated.

The Core Transcripts That Tell the Story

Not all transcripts serve the same purpose. When evaluating a tax problem, these are the ones that matter most.

Account Transcript
This is the backbone. It shows assessments, balances, penalties, interest, payments, and enforcement activity. If there is a lien filing, levy action, or adjustment, it will appear here.

Record of Account Transcript
This combines the account transcript with return data. It is especially helpful when something does not add up, and you need context.

Return Transcript
This shows what the IRS processed, which is not always what the taxpayer intended to file. That distinction matters more than most people realize.

Wage and Income Transcript
This reflects third-party reporting. W-2s, 1099s, K-1s, brokerage statements, and payment processor reporting. For non-filers and audit cases, this transcript is critical.

Each transcript answers a different question. Together, they tell the full story.

Non-Filers: Where Transcripts Become Essential

For non-filers, transcripts are not just helpful. They are essential.

When someone says, “I haven’t filed in years,” the next question is not how many years they believe are missing. It is how many years the IRS expects returns for.

Those numbers are often very different.

Transcripts tell you:

• Which years the IRS believes are unfiled

• Whether the IRS has already taken action

• Whether the taxpayer still has an opportunity to file voluntarily

Did the IRS Prepare a Substitute for Return?

A Substitute for Return, or SFR, is when the IRS prepares a return using third-party information such as W-2s and 1099s.

SFRs are almost always unfavorable to the taxpayer.

They typically:

• Omit deductions

• Omit credits

• Use the least favorable filing status

• Create inflated balances

The account transcript will show whether an SFR has been prepared. That single fact often determines the strategy.

If an SFR exists, the goal is usually to replace it with a properly filed return.
If no SFR exists, timing and filing order become far more important.

Without transcripts, you do not know which situation you are in.

Wage and Income Transcripts as the Non-Filer Blueprint

For non-filers, the wage and income transcript is the roadmap.

It shows exactly what the IRS already knows. Employers. Banks. Brokerages. Payment platforms.

When preparing delinquent returns, you are not guessing at income. You are reconciling to what the IRS already has on file.

Filing without this information is risky. If the IRS has more data than the taxpayer does, the return is likely to be challenged.

The IRS Six-Year Filing Requirement and Why It Matters

Another critical reason transcripts come first is the IRS policy on how many years must be brought into compliance.

The IRS generally requires the last six years of tax returns to be filed before it will consider a taxpayer compliant and eligible for most resolution options.

This policy is outlined in IRS Policy Statement 5–133, which governs delinquent return investigations.

This does not mean the IRS can only assess six years. It means that, as a matter of administrative policy, six years is usually the minimum required to move forward.

But here is the key point:

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You cannot determine which six years are required without reviewing the transcripts.

Transcripts show:

• Which years the IRS expects returns for

• Whether earlier years were assessed through SFRs

• Whether certain years fall outside of practical enforcement

• Whether filing an older year could create new problems

Blindly filing 'everything' without transcript review can be a serious mistake, one that's difficult to undo. Strategic compliance starts with knowing exactly what the IRS is asking for.

“I Don’t Know What I Elected” and the ENMOD Transcript

Another common issue involves uncertainty around entity elections.

Clients will often say:
“I think we elected S corporation status, but I’m not sure.”
“I had an LLC years ago and don’t know how it was taxed.”
“My old tax pro handled all of that.”

The ENMOD transcript answers this.

The ENMOD transcript provides entity-level information, including:

• Entity classification

• Filing requirements

• Certain elections

• Account status with the IRS

If you do not know how the IRS currently classifies an entity, you cannot confidently file returns, amend prior years, or correct past mistakes.

Assumptions here can create years of compounding errors. Transcripts replace assumptions with facts. ENMOD transcripts require calling the IRS and having them faxed to you. You can read more about them in this article from Tom Talks Taxes.

Collection Statute Expiration Dates and Tolling

The collection statute expiration date, the CSED, is another reason transcripts must come first.

In most cases, the IRS has ten years from the date of assessment to collect a tax debt. Once that statute expires, the balance is no longer legally collectible.

But that ten-year clock does not always run cleanly.

Certain actions toll the statute. You cannot reliably identify those without reviewing the transcript.

Common tolling events include:

• Bankruptcy filings

• Offers in compromise

• Collection due process hearings

• Certain installment agreement activity

• Time spent outside the United States

• Military deferments

Clients rarely remember these events accurately. Some do not realize they affect the statute at all.

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Why CSED Analysis Changes Strategy

Two taxpayers can owe the same amount and require completely different strategies based solely on statute timing.

If a CSED is approaching, aggressive collection alternatives may not make sense. Sometimes compliance and patience are the best strategy.

If the statute has been significantly tolled, waiting may be the worst option.

CSED timing affects decisions about:

• Offers in compromise

• Installment agreements

• Appeals

• Delay strategies

You cannot responsibly advise on any of this without knowing exactly where the statute stands.

Why This Should Always Be Step One

I still see practitioners draft letters, make phone calls, and promise outcomes before pulling transcripts.

That approach leads to bad advice and broken expectations.

Transcripts cost nothing but time. They save enormous amounts of it later. You should be charging for this. Present the client with a report, lay out their options, and offer an engagement for representation if you want to take the case. The diagnostic work has value; price it that way.

If you do tax representation work, transcripts are not optional. They are foundational.

The Bottom Line

Every tax problem has a timeline, a paper trail, and a legal endpoint.

The IRS tracks all of it.

Transcripts are how you see it.

Before advice.
Before strategy.
Before solutions.

Pull the transcripts.

They tell you what happened, and what can still happen.

If you want to learn more about transcripts, this class, taught by Clarice Landreth for Compass Tax Educators, is very good.

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TL;DR

TikTok’s January 2026 privacy policy update explicitly confirms the collection of sensitive user data, including mental health diagnoses, citizenship status, and precise GPS location, while significantly weakening the promise to notify users of government data requests. This shift exposes users to greater surveillance risks, particularly regarding immigration enforcement and political dissent, as the platform removes safeguards that previously alerted users to legal inquiries. Although much of this language is a forced transparency measure to comply with new state laws like the Texas TDPSA, it formalizes the tracking of deeply personal traits that were previously only inferred. To protect themselves, users must aggressively opt out of targeted advertising, revoke location and contact permissions, and exercise their legal right to limit sensitive data use through direct privacy requests

January 2026 brought more than just a new year; it ushered in a new era of explicit data vulnerability for TikTok users across the U.S.

While headlines focused on the geopolitical restructuring of the new “TikTok U.S. Data Security” (USDS) entity, the fine print of the platform’s updated privacy policy tells a deeper, more concerning story. It is a story with implications for your citizenship data, sexual orientation, mental health, and physical location.

Why TikTok’s New Privacy Policy Matters More Than Ever

TikTok’s January 22, 2026 Privacy Policy update does more than signal compliance with U.S. laws, it introduces broader permissions to collect and share user data with government entities.

The “Mental Health Diagnosis” Clause

Perhaps the most shocking addition is the explicit collection of “mental or physical health diagnosis” data. Previously, health data was a vague category. Now, the policy clarifies that if you discuss depression, anxiety, or other conditions in your content, captions, or even private messages, TikTok can categorize this as “sensitive personal information.”

• The Risk: This isn’t just about ads. In an era where data brokers sell mental health profiles, having your “diagnosis” formally logged by a social media giant creates a permanent digital record of your medical history, one that isn’t protected by HIPAA.

Broadened Government Sharing

A particularly troubling clause now reads:

“We may disclose any of the Information We Collect to respond to subpoenas, court orders, legal process, law enforcement requests, legal claims, or government inquiries...”

What changed? Previously, TikTok’s policy generally committed to notifying users of legal data requests unless prohibited by law. That safeguard has been significantly weakened. The new language suggests data disclosures may happen without your knowledge, provided it isn’t explicitly forbidden by law to do so.

With immigration enforcement and political dissent remaining hot-button issues, this removal of “standard notice” opens the door for agencies to access user data for civil or administrative matters (like deportation hearings) without the user ever getting a chance to challenge the request.

The prior concern with TikTok was that data was being shared with the Chinese government. Now the concern shifts to how easily the U.S. government can obtain this data. This echoes the Snowden revelations. In the current climate, the concern shifts from foreign espionage to domestic surveillance: how easily can U.S. agencies now access this data for civil or administrative use?

The Geolocation Update: “Precise” vs. “Approximate”

A major technical shift in the 2026 update is how TikTok handles where you are.

What They Were Doing Before:

Previously, TikTok collected “approximate” location data. Even if you denied GPS permissions, they inferred your general location (city/district level) using your IP address and SIM card information. This is why you still saw local ads even with GPS off.

What Changed in 2026:

The new policy explicitly allows for the collection of “Precise Location” data.

• This uses GPS signals to pinpoint your exact coordinates (within a few meters).

• The Good News: This is technically an “opt-in” feature for U.S. users. It is off by default, but you may see pop-ups aggressively asking you to turn it on for “better local content.”

• The Bad News: The policy language is vague on whether they can cross-reference this new, precise data with older historical data to build a retrospective map of your movements.

Reality Check: Transparency vs. New Surveillance

It is important to read this update with nuance. Is TikTok suddenly becoming “evil” in 2026, or were they always doing this?

The “Transparency” Defense

Much of this scary new language—specifically the lists of “immigration status,” “sexual orientation,” and “biometric data”, is likely a response to strict new U.S. state privacy laws (like the Texas TDPSA and California CPRA).

• These laws force companies to explicitly list every category of data they might collect.

• In Reality: TikTok was almost certainly already analyzing your content for these traits (via algorithms that tag you as “LGBTQ+ interested” or “Immigration content interested”).

• The Difference: They are now admitting it in writing. While the practice isn’t new, the admission confirms our long-held suspicions: the algorithm watches what you watch to determine who you are.

Possibility of Censorship

Some concerns exist that the U.S. government could use censorship to prevent certain content on TikTok, as a means to control information and frame narratives. Some users have reported seeing fewer protest videos and information concerning the unprecedented events in Minnesota. While this could likely be due to algorithmic changes, it leaves the door open to 'shadowbanning' inconvenient narratives during times of unrest. While the mechanism for such control is currently unproven, it is now possible.

How to Regain Control: Step-by-Step Opt-Out Guide

Here’s how you can limit what TikTok collects and uses, based on its latest settings.

Turn Off Personalized/Targeted Ads

This limits TikTok’s ability to use your off-app activity (what you buy or search for elsewhere) to target you.

• Steps (iOS/Android):

  1. Open TikTok → Tap Profile (bottom-right).

  2. Tap Menu ☰ → Settings and privacy.

  3. Select Ads (sometimes labeled Ads and data).

  4. Targeted ads (and targeted ads outside of TikTok) → Toggle OFF.

• Deep Clean:

  • Still in the Ads menu, tap Clear off Tik-Tok data & also Disconnect advertisers. This wipes the data they have already collected from third parties and stops targeted ads with your off Tik-Tok data

Download Your Data

TikTok allows you to request a full export of your activity, including “inferred interests”—what the algorithm thinks you like.

• Steps:

  1. Profile → Menu ☰ → Settings and privacy.

  2. Tap Account → Download your data.

  3. Choose format (TXT or JSON are best for readability) → Tap Request data.

• Note: It may take a few days to process. When it arrives, look for the “Ads Interests” file to see exactly how you are being categorized.

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Use Your Privacy Rights

If you are in Texas, California, Colorado, or other states with comprehensive privacy laws, you can submit a formal request to delete or limit sensitive data use by contacting TikTok. Although it remains to be seen how effective this will be. I am reminded of what the late comedian George Carlin said about rights being, in reality, privileges that can be taken away, because if they were rights, you couldn’t take them away. He had a lot more to say, but most of it would not be appropriate for this substack.

Additional Quick Privacy Wins

• Contacts Sync: Go to Settings and privacy → Privacy → Sync contacts and Facebook friends. Toggle Off, then crucially, tap “Remove previously synced contacts” to delete the data they already have.

• Location: Go to Settings and privacy → Privacy → Location Services. This will usually direct you to your phone’s OS settings. Ensure it is set to “Never”.

• Permissions: Go to your phone’s main Settings → Apps → TikTok → Revoke access to Camera/Microphone when not in use.

Beyond TikTok: The Privacy Risks of Big Social Media

TikTok isn’t unique in its data practices. Meta (Facebook, Instagram, Threads) has long monetized deeply personal user data through behavioral profiling and targeted advertising. In early 2025, the Electronic Frontier Foundation launched its “Mad at Meta” article to draw attention to how Meta tracks users across the web, even beyond its platforms, using embedded tracking pixels and app integrations.

EFF’s concern is not just that Meta gathers huge volumes of personal data, but that it monetizes this information across a surveillance advertising ecosystem, including data from non-users. Meta’s behavior has included collecting information on health topics, offline purchases, and sensitive interests through third-party sites.

EFF encourages users to Minimize what data Meta collects (by changing settings and using privacy tools), Ask for transparency and better protections (including stronger laws), and Delete any unnecessary data or accounts. While these steps are a stopgap, EFF argues that lasting protection requires robust U.S. privacy legislation.

Protecting Your Privacy Beyond Social Media: Start With Your Browser

The web browser you use plays a central role in how your data is collected. If you’re using Google Chrome, you are likely handing over enormous amounts of behavioral data by default.

Why Brave Browser Is a Better Choice

• Built-In Blocking: Brave automatically blocks third-party trackers, fingerprinting scripts, and invasive ads.

• No Data Collection: Unlike Chrome, Brave doesn’t track your browsing history or sell your data.

• Tor Integration: It offers a “Private Window with Tor” for true anonymity when needed.

• Speed: By blocking heavy tracking scripts, pages typically load 2-3x faster.

Other Privacy Tools You Should Consider

• Search Engines: Use DuckDuckGo or Startpage instead of Google to avoid search profiling.

• VPNs: Use a reputable VPN (ProtonVPN is my favorite) to mask your IP address.

• Password Managers: 1Password is what I now use and recommend. (Full review coming soon)

• Encrypted Email: Protonmail or similar types of services

• Messaging: Use Signal for end-to-end encrypted chats that collect virtually no metadata.

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Take Your Privacy Seriously

This has long been a topic of interest to me, and I look forward to sharing more information on how to maintain privacy online. The new TikTok policy is a wake-up call, but it’s also a symptom of a larger problem. The internet is structured around surveillance, and platforms from Meta to Google thrive on our unexamined digital behavior.

You can fight back. Opt out of behavioral tracking. Switch to privacy-first tools. Exercise your legal rights under state laws. And most importantly, talk about it. Privacy isn’t just a technical setting; it’s a personal act of setting boundaries.

Try it, test it, and tell someone.

Questions? Ask below.

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Why I Reclaimed My Firm’s Tech Stack to Meet the FTC Safeguards Rule

For most small accounting firms, information technology (IT) is treated as a black box. It is a necessary and significant expense outsourced to a Managed Service Provider (MSP) and rarely scrutinized until a system crashes or a client’s sensitive data is leaked.

Following a recent merger of my firm, I reached a crossroads: continue with the status quo of hands-off IT management or build a modern, distributed architecture from the ground up.

My background isn’t in IT, but I spent some time working with community financial institutions as an outsourced internal auditor. We assisted the banks with various areas of operations and one that I focused on was information technology and GLBA compliance. I saw exactly how regulatory examiners scrutinized information security practices in financial institutions.

When it came time to secure our own firm’s PII and NPI under the FTC Safeguards Rule, I realized that the standard MSP cookie-cutter approach often prioritizes their ease of management over our specific legal requirements. To ensure proper oversight, I decided it was best to dump the MSP and start from scratch.

The Risk of the Hands-Off MSP Approach

The traditional MSP model is built on volume—managing as many clients as possible with the fewest number of technicians. This often leads to three critical vulnerabilities for a financial institution like an accounting firm:

• The Visibility Gap: When you outsource your IT entirely, you lose the ability to verify that controls are actually in place. “I think we’re encrypted” is not an acceptable answer.

• Supply Chain Risk: If your MSP is breached, their master key access to your systems becomes a backdoor for attackers. For a small firm, an MSP’s vulnerability is your firm’s liability.

• The Perimeter Fallacy: Most MSPs still rely on the office firewall model. In our world of shared desks and home Wi-Fi, the perimeter no longer exists. Security must follow the user and the device.

The Auditor’s Tech Stack

In professional IT circles, Ubiquiti and Synology are sometimes viewed as prosumer rather than enterprise. However, for our firm, they are the cornerstone of our security for one reason: total visibility.

I manage a robust Ubiquiti environment in my own home, but this familiarity isn’t just a hobby; it’s an audit advantage. I don’t have to call a help desk to see if our IDS/IPS (Intrusion Detection/Prevention) is active or if a firmware patch was applied—I can see the dashboard in real-time. Similarly, the Synology NAS provides us with immutable snapshots of our Google Workspace and other data. In the event of a ransomware attack, we don’t pray that our cloud provider’s system works; we have physical possession of our backups and data.

We chose these platforms because their interfaces are transparent. We’ve traded the “black box” of an MSP for a system where I, as a partner, can personally verify every security toggle, and satisfy the oversight requirements of the Safeguards Rule.

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The Hybrid Model

Internal management doesn’t mean doing it alone. We utilize a hybrid IT model:

Oversight: I manage the day-to-day configuration and security posture.

Expert Consultants: We engage niche specialists for project-based work. JumpCloud architects to refine our Mobile Device Management (MDM) policies and networking pros to assist with network configuration.

This gives us direct access to Tier-3 engineering talent without paying the $150-$200 per-user, per-month overhead of a full-service MSP.

The Bottom Line: Cost and Conscience

The cost savings are substantial. Reclaiming our IT function has cut related spending significantly, but the real ROI is the ability to sleep at night. I found countless issues as we transitioned out of the MSPs systems, which solidified the decision to move away from them.

If you utilize an MSP, I encourage you to do an in-depth review of their practices and question them about the FTC Safeguards Rule and GLBA. You might find that your biggest liability is the company you hired to protect you in the first place.

“I didn’t know” is not a defense for firm owners. By owning our tech stack, I know that MFA is enforced via JumpCloud, I know our laptops are encrypted and up-to-date, and I know our client data is backed up. We have eliminated the “hope” factor and replaced it with verifiable certainty.

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Conclusion: Accountability Cannot Be Outsourced

This approach is not right for everyone, but oversight of your Written Information Security Plan (WISP) cannot be outsourced.

The FTC Safeguards Rule is clear: the responsibility for data protection rests squarely on the shoulders of firm leadership. While an MSP can provide the labor, they cannot provide the accountability.

In an era where a single data breach can damage a firm’s reputation, understanding your own security posture isn’t just a technical choice—it’s a fiduciary duty to clients.

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