I am not an expert in any of this. These are the subjects I have kept returning to since 2003, usually because I was working something out in public. Each section links to what I wrote at the time.
Building things that last
The long game, and why I keep choosing it over the quick exit.
- Long term view vs the quick flip
- What gets measured, gets improved
- The bus lesson
- Building something great? 3 types of folks not needed
- What are you optimizing for?
Equanimity
Stoicism, mostly. Holding outcomes loosely. This is the thread that has held up best over twenty years.
- Good thing, bad thing, who knows
- The philosopher: Epictetus
- Ego and humility
- Why failure and misfortune is "good"
- Thriving during uncertainty
- No drama
How people actually learn
Skeptical of school, curious about everything else.
- A modern way to look at education
- Education should be changed
- Investing in yourself via long term travel
- Expanding your creative capacity
- Getting unstuck
Community over extraction
Why BootsnAll was a forum before it was a business, and what that taught me.
- Passionate communities
- Thinking about indie travel
- We invented professional blogging ;)
- Why is this free?
Family
The part that turned out to matter most.
- How to be present with young children
- Challenges of being a single dad
- Summertime with son
- First thoughts on having momo twins
- What matters in the end?
What I am learning now
Agent-native tools, regenerative agriculture, and what AI does to a twenty-year-old travel business. Less written down yet. See what I am working on and the recent flight log.