Ambition
It is easy to chase a version of success you never chose. These essays explore ambition, comparison, and deciding which goals are worth your time.
24 essays · Newest first
- 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- Your parents advice is outdated.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 Their advice was 30 years out of date.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.