Topic
Freedom
Essays on freedom, time, and building more of your own life without blowing everything up. I left high-growth startups because I wanted my time back. What I didn't expect was how hard it would be to figure out what to do with that time once I had it. Freedom isn't just leaving a job. It's deciding what you want your days to look like, and then building the discipline and the income to protect them.
The machine is a mirror.
AI promises to free up your time, but history tells us otherwise.
Rich and broke.
The difference between looking rich and being secure isn’t what you make.
Small enough to see.
When life gets wider, paying attention to the most important people gets harder.
Freedom. Sort of.
What if the freedom you quit your job for isn’t really freedom?
Get out.
We squeezed into two bar seats on Valentine's Day without a reservation. When the bartender handed us menus, I noticed something that changed how I think about business.
Small by design.
A tiny Champagne bar in Healdsburg seats twelve people and there's always a line. They have no plans to expand. On purpose.
The case for anti-scale.
A consultant at a mastermind was doing $1.3M a year and wanted to 'scale.' The room's advice surprised him.
You'll never "find time" to rest.
My wife and I just got back from two weeks in Tokyo. The trip taught me something about rest that productivity advice never will.
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.
Lifestyle inflation kills freedom.
My friend makes $500K a year and still feels trapped. Lifestyle inflation is the silent killer of freedom.
The anti-VC playbook.
When I started, my only goal was to avoid having a boss. Then doubt crept in: am I thinking too small?
Urgent? For who?
I returned from a three-month sabbatical to 45 brain-pick requests and 100+ messages. Almost every one communicated fake urgency.
The luxury of doing less
Five years ago, shutting my laptop at 3pm would have felt like wasting time. Now I consider it the whole point.
8 Questions to Transform Your Week
Eight questions I ask myself every Friday that keep my weeks from going off the rails.
Life-Work Integration: The Road Less Traveled
Part of being a solopreneur is maintaining your sanity. Nobody talks about this enough.
How to Avoid Burnout in Work, Business and Life
On December 16th, 2018, I had a massive panic attack at my executive job. That day was one of the worst of my life — and the beginning of everything that came after.
Use Anti-Goals to Stop Doing What You Hate
Instead of setting goals for what you want to do, try setting goals for what you want to stop doing.
5 Rules for a Permissionless Life
A Twitter thread from Naval Ravikant knocked me sideways during my burnout. Five rules that changed how I think about work and freedom.