Topic
Ambition
Essays on ambition, drive, and the difference between what you actually want and what you were taught to want. For years, I never questioned my ambition. I just wanted more: more work, more growth, more revenue, more reach. Then I started to notice the toll it was taking on me personally, and I realized I needed to figure out which parts of my drive I wanted to keep, and which I was carrying out of habit. These essays are written for anyone trying to be honest about what they actually want.
Selective editing.
The stories we make up about our heroes (and why we shouldn’t…)
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.
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.
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.
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.
The addiction to relevance.
My wife looked up from her phone in disbelief. 'Have you seen Madonna's Instagram?' The addiction to relevance is everywhere — including in our businesses.
You've changed.
A friend paused his newsletter and podcast after ten years. His reason shook me: it no longer brings him the feeling of 'aliveness.'
Your wins don't stay won.
I found a 'Salesperson of the Year' award buried under a pile of junk in my desk. Fifteen years old. Wins don't stay won.
“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.
Your parents advice is outdated.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 Their advice was 30 years out of date.
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.
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.
Ambition is overrated.
Ambition is the one virtue everyone celebrates. I'm starting to think it might be the most dangerous one.
“Someday” is a dangerous lie.
A friend is crushing it by every business metric. His SaaS just crossed a major milestone. He told me he's never been more miserable.
Don’t build a brand. Live a life.
Personal branding advice has become formulaic. We've lost sight of what it actually means to build a brand that's yours.
When is enough, enough?
In the game of business, we chase growth for growth's sake. But at some point, you have to ask: when is enough actually enough?