Essays
The machine or the life.
Some mornings I wake up and think, what the hell did I just do?
Pick a table.
Two people joined the same company the same year with the same pay cut. One became a CEO. The other has had seven jobs in fifteen years.
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.
Thief of Joy.
When I was 27, a friend asked me point-blank how much money I made. My answer — and my reaction to her answer — taught me something I've never forgotten.
Missing someone who doesn’t exist.
My old boss texted me during the pandemic. I went back for eight months before I realized I wasn't missing the job — I was missing a version of myself that was already gone.
I'm a crazy person.
The most successful people I know don't have better habits. They have something slightly wrong with them.
Bored to death.
At some point I got really good at my job. Nobody talks about what happens after that. I was bored to death.
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.
Rock bottom.
She threw herself down a mountain at 70mph — the same mountain that nearly ended her career four years ago. She won by four hundredths of a second.
He was only 25.
The winemaker was only 25 when he took over one of California's best wineries. What he said about patience stuck with me for weeks.
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.
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.
Nobody's even trying.
Everyone says the market is saturated. But when I look around, most people aren't even doing the basics.
One question I've been dodging for years.
Every podcast host asks me 'What's next?' I always dodge the question. Here's the real answer I've been avoiding.