Essays
“Future You” isn't coming to save you.
Winter Me was too cold. Spring Me wanted to enjoy the weather. Summer Me was too hot. 'Future You' isn't coming to save you.
How to revive a dead dream.
I saw people on LinkedIn announcing their 'dream job' again. Different dream than last time. The pattern is telling.
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.
Act like you’ve already won.
I was on a Zoom call agreeing to things I didn't want to agree to. Normally I'd push back. Something was off.
The money trap nobody warns you about.
She finally hit her income goal. Then she wrote to tell me she's more anxious about money than when she was broke.
Why I drink coffee at 10:47 AM on Thursdays.
Last Thursday at 10:47am, standing in a coffee shop line, it hit me: this is what freedom actually looks like.
Your parents advice is outdated.
His parents spent an entire dinner explaining why he should go back to a 'safe' job. Their advice was 30 years out of date.
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.
The corporate detox no one warned me about.
She wanted a 'behavioral hack' for the corporate-to-solopreneur transition. The real shift is much harder — and more important — than a hack.
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.
The day I 7x'd my prices (and it worked)
I went from $250/hour to $1,800/hour in one year. What happened in between rewired how I think about pricing.
The content nobody likes (but everyone remembers)
A piece I wrote about my panic attack two years ago still generates emails today. Not likes — actual emails from people saying it changed how they work.
The portfolio life experiment.
One friend spent thirty years becoming great at something he hates. Another is on her third wildly different career. The difference is instructive.
Lifestyle inflation kills freedom.
My friend makes $500K a year and still feels trapped. Lifestyle inflation is the silent killer of freedom.
I almost made a terrible mistake last week.
I almost automated the one thing that keeps me connected to my readers. I'm glad I caught myself.