Topic
Work
Essays on work, and where it actually fits inside a life worth building. I used to think the important questions about work were tactical: what to make, how to sell it, how to grow. They weren't. The questions that matter now are about what work is for, what it costs to keep doing, and how to keep it from quietly becoming the thing your whole life is organized around. These essays look at work through stories and observation, not playbooks.
Just one more year.
This one decision might cost you the next decade of your life.
Illegible careers.
Everything I believe about a successful career has changed.
Try the easy version first.
Start with the easiest version, see if it works, and only add complexity if you need it.
Maybe you’re one away.
Before you decide you’re bad at something, make sure you change the conditions.
Having fun is the new moat.
AI can now replicate content, systems, and funnels in an afternoon. Here's the one advantage it can't touch, and why I'm rebuilding my second act around it.
Stop sharpening your axe.
Why the most skilled person doesn't always win, and what actually moves the needle when you're building a business from scratch.
The two-speed problem.
Criticism shows up fast. Real results show up slowly.
Your new rabbit hole.
The hardest move in learning anything new is the first one. Here's why it's never been easier to make it, and what's been actively working against you.
There’s no map for this.
Why the advice that works for them doesn’t work for you.
Just tell me when you’ll be here.
Most people communicate what's in their own head instead of what the other person needs to hear. A nurse, a boardroom, and the difference between the two.
One person away.
A sushi speakeasy that seats eight. A hidden door. A chef who changed careers at 40. One person can change everything.
Being a purple squirrel.
Eleven years ago, I watched a sales guy tape together a paper pyramid in a WeWork. What happened next taught me what 'purple squirrels' are — and why you want to be one.
Nobody's even trying.
Everyone says the market is saturated. But when I look around, most people aren't even doing the basics.
Nobody is coming to save you.
My boss told me to move to San Francisco in two weeks and fire the entire sales team. I'd never even visited the city.
Hustling your way to nowhere.
Back in 2018, I was burning out and had no idea how to get attention for a consulting business. The hustle advice almost ruined me.
The wallet that came back.
My wife lost her wallet in a NYC cab. What happened next reminded me of something I'd been taking for granted in business.
Leverage is the solopreneur cheat code.
I used to think growing a business meant adding complexity. After $10.5M as a solopreneur, I've learned the opposite.
I'll draw your dog for $350.
A woman in a tiny shop inside Fishs Eddy in NYC was selling custom dog portraits for $350. She was booked solid. Here's what she understood about business.
Reverse engineering attention in 2025.
I used to think getting attention was about great hooks. After all these years, I've landed on a completely different formula.
My complete $10M journey (all 23 steps)
My business passed $10M in total revenue. Here are all 23 steps of the journey — including the ones I'm not proud of.
AI is coming for us (here's my plan)
AI is coming for a lot of jobs. Here's the plan I'm betting my business on.
Creator vs. Operator
He's got a loyal audience, three products, and $350K in revenue. Sounds like a dream — until you hear the rest.
The great social media exodus?
Something interesting is happening online. Some of the biggest creators are quietly leaving their platforms.
Luck is mostly just math.
Luck isn't random. It's math — and the equation is simpler than most people think.
Everything, everywhere, all of the time.
A financial coach tried to be everything, everywhere, all of the time. One conversation changed how he thought about his entire business.
The hidden cost of being perfect
I spent an hour agonizing over an email subject line. Then I laughed — because I knew the truth nobody wants to admit about perfectionism.
The hidden power of being boring
A well-known marketer asked me for my biggest secret. My answer was disappointing — because there is no secret.
Start doing the obvious work
The most productive people aren't following complex systems. They're doing something much simpler that nobody wants to hear.
You are what you tolerate
The fastest way to kill your business isn't bad strategy. It's tolerating mediocrity in small, quiet ways every single day.
Stop feeling overwhelmed
Last week I looked up and realized I had too many things on my plate. One framework cleared the fog in 15 minutes.
Why successful creators are putting limits on themselves
Too much freedom can be just as paralyzing as too little. Successful creators are putting limits on themselves — on purpose.
The Question No One Asks Me
The question nobody asks me is the one that matters most. And it has nothing to do with followers or likes.
Don't Search for a Mentor
Everyone says find a mentor. Nobody tells you that searching for one is usually the wrong approach.
Avoid Single Points of Failure
One concept from my startup career has saved my solo business more than once: never rely on a single point of failure.
The 5 Phases of Solopreneurship
Every successful business grows in phases. Most solopreneurs don't realize they're stuck in phase one.
3 Big Business Lies (And the Actual Truth)
Three pieces of business advice that everyone repeats and almost nobody questions. They're all wrong.
4 Questions for Better Weekly Productivity
Four questions I ask myself every Sunday night that keep me from burning out on Monday.