There’s Always Something To Do

But That Doesn’t Mean You Should Do It

I am writing this from a quiet hotel bar with an espresso martini in hand. It is one of the few drinks that I enjoy, and it is hard to find a good one. The best one I have ever had is at Pesto’s in Chandler, AZ. If you are in the Phoenix area, check it out. Great food, great service.

Sitting here writing this, I am thinking about travel and work, and how the two always seem to overlap.

The truth is simple. I do not really have hobbies. Work is my hobby. Tax and tech. Tech and tax.

Even when I am not at my desk, I am still tied to a phone or a laptop. I tell myself a change of scenery is rest, but it is not. Working from a hotel bar is still working. Sitting in a coffee shop still counts as working. If my mind is on clients, tasks, or the next deadline, the location does not matter. I am still on the clock.

When you run a business, there is always something you could be doing. Always. The list never ends, and neither does the guilt of not optimizing your time. Any time I try to read, listen to an audiobook, or do something fun, something in my mind whispers that I should be doing something productive.

For years, I blamed this on a lack of discipline. I thought I needed better systems. Eventually I realized the truth. This is not a structure issue. It is a guilt issue. I believed rest had to be justified. That it had to come after everything else was finished.

But nothing is ever finished.

So I am committed to trying something different. Resting and unplugging are part of the process, not a distraction from it. Here is the plan.

The Rule of 3

Each morning, I pick three things that have to get done. Not ten. Not everything. Just three. It creates focus instead of pressure.

The Shutdown Ritual

At the end of the day, I take a few minutes to close things out:

• What did I finish

• What is still on my mind

• What are tomorrow’s top three

• Close the laptop or shut down the desktop

• Clear a small part of my desk

• Say: “Today’s work is complete.”

It gives the day an actual ending. (Credit to Cal Newport for this idea.)

The Later List

When something pops into my head with urgency, I am putting it on a list called “Later.” Capturing it is often enough to calm the pressure to do it right now.

Working From Home

I am very pro remote work. I like my space, my setup, my freedom. I have no desire to go back to an office most days. But working from home creates a different challenge. When work and life share the same rooms, the lines blur. You can finish dinner and sit back down at the laptop without even thinking about it. You can check your phone before you get out of bed and start the day already working.

Remote work is not the problem. The problem is how easy it becomes to work constantly without realizing it. So I have had to build structure to keep my home from becoming an endless extension of my office.

The People Who Criticize Remote Work

I have also noticed that the people who object to remote work tend to have a hard time trusting their teams. Their arguments are almost never about productivity. They are about control. They value proximity over actual leadership. High performers do well anywhere. Low performers struggle anywhere. An office does not fix that difference. It only hides it.

Scheduling Time That Is Not Work

Because I do not naturally have many hobbies, I am actively scheduling time for the things I want more of. Reading. Writing. Coffee without a laptop. Trips. Empty space on the calendar that is not there to be filled.

Rest Is Not Earned

This one has taken the most effort. Rest does not come after everything is finished. Rest is needed so I can continue doing anything. My upcoming trip to Europe will be the first vacation I have taken without bringing work with me. No laptop. Minimal email. No webinars. No Zooms. I have never traveled without a laptop and enough gadgets to make any techie jealous. This time will be different, a minimalist approach. Some peace and unplugging.

The Detractors

Whenever you start protecting your time, someone will notice. The “must be nice” people. The ones who benefited quietly from your constant availability. The ones who question your commitment the moment you begin honoring your limits.

Their reaction is not about your rest. It is about the roles they expected you to play. Their discomfort belongs to them, not to you. “It must be nice” is their way of saying, “I do not know how to do that for myself.”

The Realization

A few days ago, I realized that even though I am proud of not being chained to a desk, I am still chained to work. A laptop in a different room is still a chain. A buzzing phone is still a chain. A mind that keeps working long after the day is over is the tightest chain of all.

Remote work can feel like freedom, but it is not freedom if you never step away.

I want something different. I want rest, hobbies, slow mornings, evenings where the laptop stays closed, and trips that do not involve answering emails.

There will always be more work to do. That is the nature of this work. What can change is the idea that I owe all of myself to it. I do not want rest to be something I reach only when I am exhausted. I want it to be part of my life before exhaustion makes the decisions for me. Too many people work and then die without ever having lived.

To hell with this notion that you grind until 65 or 70 and then retire. I’d rather take mini-retirements and enjoy things now.

If this sounds familiar, then you may be ready for a different rhythm, too. Not a life without work. A life not swallowed by it. A life where rest is allowed, not earned.

That is the life I am trying to build. And if you are trying to build it too, you are in good company. How are you working toward this?

A few things I am looking forward to:

December 2025:

December 2nd to December 4th - NATP Taxcon - I’ll be teaching two classes. Responding to IRS notices with confidence & Reasonable Cause and Penalty Abatements.

December 5th is the fifth anniversary of Tom Talks Taxes, from 10 AM to 3 PM Central. Register here. Tom has been a mentor to many of us and continues to set the standard for excellence in our field. I am especially excited for the morning mixer with fellow Substack writers and the Q&A panel. It is going to be a great event.

December 9th - I’ll be teaching ethics for NATP from 10-12 PM (Central) - Register here

December 29th - NATP - Creating Your Firm’s WISP with Confidence Online Workshop - This will be from 1 PM to 4:30 PM (Central). Once registration is live, I will share the link.

2026:

Exciting things planned. Stay tuned!