This birthday feels strange. Saying the number out loud—44—feels older than I imagine myself to be most days. But I also know that growing older is a privilege denied to many, and I don’t want to take that for granted. Plus, I can always lie and say I’m 35 and remind everyone my older sister is, well, older. (She’s really not, she’s actually eight years younger.)
I’ll spare you the birth story I’ll soon hear from my mother, right on cue, as I do every year. But truthfully, I never get tired of hearing it, the story of how we almost died, and how the doctor said I might not be normal. The joke’s on him, none of us are.
I’ve always been what people call an old soul. For most of my life, I’ve felt more comfortable around people older than me, because they tend to be more authentic and more willing to say what they think. That kind of honesty is something I value above almost anything else. In a world full of performative noise, we need more authenticity
Normally in “Josh & Taxes” I write about two of my favorite subjects: tech and taxes. But today is my birthday, and I thought we’d make it all about me instead.
Here are 44 truths I’ve learned so far. Some are small, some are big, but together they tell the story of what I’ve learned along the way. And if you find any of these useful, let me know. I’d love to hear which ones resonate with you.
Some of you reading this are very likely responsible for some of these truths.
Coffee is essential. The ritual, the quiet grind, the smell, the first sip is, as important as the caffeine. Starbucks can be great sometimes (local independent coffee shops are my favorite), but nothing beats the ritual of making it yourself. (I love my Jura.) I prefer a cappuccino with oat milk.
The right pair of glasses changes everything. Not just how you see the world, but how you see yourself walking through it. If you don’t wear glasses, sunglasses!
Dogs (or cats, birds, etc.) don’t just wake you up early, they remind you why you wake up at all. Kirby has taught me that love isn’t always convenient, but it’s always worth it.
Clutter eats your focus. A messy desk or inbox doesn’t just look chaotic, it feels like static in your brain. Order clears the way for creativity.
Writing connects deeper than scrolling. A thoughtful article can linger with someone for years. A viral tweet disappears into the abyss.
Never underestimate simplicity. Style doesn’t have to be complicated. Uniforms simplify decisions and keep you focused on what matters. For example, a simple black v-neck shirt.
Technology should serve you, not the other way around. If your phone or apps are running your life, it’s time to rethink the setup. I say this, I know this, but like the rest of us, I struggle with it.
A good book in hand beats a thousand tabs open. You can’t skim your way to wisdom. Pages invite presence in a way screens rarely do.
The right bag matters. It’s not about price, it’s about carrying something that makes you feel capable and collected. It can be a backpack, tote, messenger, etc. (Or a giant Birkin if you’re so inclined.)
Quiet luxury is better than loud logos. Confidence whispers. It doesn’t need a monogram or a giant billboard that screams “Look at me!”.
The tax code is complicated, but kindness is simple. And kindness is not the same as being nice. Nice avoids conflict. Kindness tells the truth, even when it’s uncomfortable, and does what helps rather than what flatters.
Celebrate milestones with things that last. A nice pen, glasses, or a watch are more than objects; they’re markers of growth.
Deadlines create movement, but intention creates meaning. You need both: one to finish, one to feel proud.
Social media drains more often than it fuels. Logging off feels less like leaving and more like plugging back into real life.
Every city has its soundtrack and vibe. For Montreal, it’s Leonard Cohen and an old world charm that is also modern with exquisite culture. For Seattle, it’s rain and a certain hesitance to talk to others all while being cool and relaxed. For Dallas, it’s the hum of traffic, friendliness (both real and fake), and being home.
Your environment matters. The right chair, desk, and lighting aren’t luxuries; they’re the foundation of your health and brainpower. I am a person that has to change my environment from time to time. I love to work from different locations. (Coffee shops, WeWork, library, airport lounges) Being in one place too long makes me feel trapped.
Find clothes that feel like you. When your clothes fit you, not the other way around, the world feels easier. I prefer to never wear a suit. That wasn’t always the case, but needing one feels like a bygone era.
Solving IRS problems changes lives. What appears to be paperwork is often someone’s freedom. It provides fulfillment but shouldn’t provide arrogance. We aren’t paid to judge the client, we are paid to help them.
Progress beats perfection. Whether it’s finishing a math course 20 years later, decluttering your office, or working out, done is always better than stuck.
Your accent is part of your story, not your ceiling. People don’t care how you sound when your message matters. I still hate my accent but it is unlikely to change.
Good tech doesn’t excuse bad service. No one wants to feel like a number. Yes, I schedule all of my appointments and do not take unscheduled phone calls but when someone is talking to me they have my complete attention.
Systems only work if you use them. Airtable, Notion, Apple Notes, none of them matter if they sit unopened. People are accomplishing great things with just a pen and paper. Don’t be distracted by shiny objects. (I should write this on my mirror as I am 100% guilty of this.)
Boundaries are everything. In business, they protect your energy. In life, they protect your peace. Saying “no” isn’t selfish, it’s a way of saying “yes” to what actually matters. Those who get offended by your boundaries are red flags.
Trust your gut. Your instincts usually spot the truth long before your brain rationalizes it. My mother calls it her “spidey powers” and she is very good at it.
You can be friends with people you disagree with. Debate sharpens you. But if someone’s moral compass is broken, distance is wise. I could write an entire manifesto on this but I will spare you.
The better you do, the more jealousy shows up. You’ll think it won’t happen, but it will, and it feels strange, almost surreal. Don’t let it knock you off course.
Anger fades when you choose your response. It’s not about who you’re mad at, it’s about who you want to be in the room. As my husband says, no show, no audience.
Nothing works unless you do. Tools won’t save you from the effort. Disciplined and constant effort. That part is hard.
No one really has it figured out. Most people are playing a role, often afraid to show you who they really are. Influencers, especially, are too often selling a product. Realness is rare, and that’s why it matters.
Taxes are about numbers, but a good business is about people. The math may get you started, but relationships keep you going. Choose wisely and do not take every client. Not everyone is a good fit for you and vice versa. This is the absolute hardest thing when every dollar is important. It will be scary at first, but I promise you it is worth it.
Music resets your day. Sometimes the right playlist is better than caffeine. My day starts with Leonard Cohen, by noon the 90s, afternoon it becomes Cher, Tina Turner, Madonna (no stereotypes here). Evening slows down to Frank Sinatra or Rufus Wainwright.
What matters most is who and what you love. Don’t assume they know it. Tell them. Despite our best efforts, everyone will cease to exist at some point.
Travel is education in disguise. Every trip teaches you something you’ll never find in a classroom. If you look at the most closed mind, they probably haven’t left the country or even the county.
Your tools should match your season of life. The right system at 30 may not be the right system at 44 and that’s okay.
Energy management matters more than time management. Time is fixed, but energy can be guarded, shifted, and recharged.
Forgiveness is freedom. It doesn’t erase what happened but, it frees you from carrying it. A friend of mine once quipped, “There are more horses asses than there are horses.” He had some other wonderful sayings but I don’t want to have to put a NC-17 rating on my Substack.
Consistency compounds. Every rep, every page, every habit, it’s the accumulation that builds change. It compounds like interest.
True friends defend you when you aren’t in the room. If you want that, you have to offer it first. If someone is my friend, I will always defend them. I will also try to give credit where credit is due, even if I do not like someone.
Helping others helps you. Generosity isn’t just about them; it’s grounding for you. But don’t be the person who has to always post about it on social media. Privacy is a great thing.
Learning and change keep you young. Every new skill is proof you’re not done yet. Change is good. As Martha Stewart says: “When you’re through changing, you’re through.”
Gratitude changes the lens. The view might not change, but your perspective always can. We should always remember those who have helped us along the way. Most of us didn’t build or create anything 100% by ourselves, someone helped us, inspired us, mentored us.
Health is an investment, not an afterthought. Your body will remind you of this if you forget. This is probably the most important thing on this list. You could have a billion dollars but if you feel bad and can’t do anything then what do you really have?
Rest is productive. Sometimes the best way forward is a nap, a walk, or an early night. Confession: I love an afternoon nap. Even if it is only 30 minutes.
The world is full of injustice. One of my biggest flaws is a strong sense of justice. I say flaw because it can be exhausting yet I wouldn’t change it. We should remember it is possible to care about many different causes and do what you can to help those causes. We can all do something to make the world a better place.
Final Thoughts
At 44, I’ve realized life isn’t just about what you do — it’s about what you refuse to do. Boundaries, gratitude, integrity, and love will carry you farther than “hustle” ever could. Speaking of “hustle,” why is everyone so obsessed with it? If any of these truths resonate with you, I hope you’ll adopt them.
And if nothing else: buy the good coffee, wear the good glasses, adopt the good dog (or cat, bird, etc.), and take the good people with you. Enjoy.
(I’m finishing this up at my local coffee shop, Cerulean Blue, one of my favorite spots. Sinatra’s “My Way” is playing in the background, which also happens to be my favorite song.)