Forty Lessons at Forty

I recently turned forty, which is the age where you go from being an older young person to a younger old person.

I tend to do all my existential angst-ing in the final year ahead of a decade milestone. I stressed throughout my twenty-ninth year under the tyranny of thirty before I crossed that threshold.

Ditto for this one.

I’ve been calling myself a “forty-year old man” for the last twelve months, so it feels totally normal now.

The truth is, I was much more disappointed with my life at 29 than at 39.

At 29, I had founded and shut down one startup and struggling to land my first product job. I had gotten out of a toxic relationship and frustrated with dating. I had pay out an unfair settlement to a copyright troll so I was not in a strong financial position.

My ambition back then was more generic: start a unicorn company, lead a team of hundreds of people, get profiled in major media outlets, see eight figures in my bank account, be with someone beautiful and alluring.

As I turn forty, I’ve found myself accepting the way I do things, the choices I’ve made, the pursuitsI enjoy, and the flaws I carry. I’m not fighting who I am as much.

My ambitions are more specific:

• Continue growing my coaching business, now focused on thought partnership to solo founders and conflict repair for cofounders.
• Be the best husband I can be to my brilliant, beautiful, and sometimes gremlin-like wife, raise my daughter to be curious, brave, and kind.
• Share ideas and stories that move people and make their lives better.

I feel really good for my age.

I’m healthy, my blood tests are all positive minus genetically high cholesterol (statins here we come). I completed a fully weighted Murph in 55:32. Not remarkable for a competitive Crossfitter, but not something I could have completed five years ago.

As a rough halfway marker in life, forty felt like a good time for personal reflection. Here are forty life lessons I’ve learned with some personal commentary on each one, grouped into seasons based on vibes.

Spring

1. Control is sublinear: effort grows much faster than influence
 Uber & Doordash have lowered the floor and raised the ceiling

2. Having too much political savvy can be a golden prison
 Leaving FB was easier with a Meets Most

3. The stuff that hurts you less than others becomes your strategic advantage
 AAPI + ADHD = I’m used to being an outlier

4. Without causal thinking, good intentions gets you cobra farms
 Gumball Capital, Lunar Accel, and every activist cause

5. Creating optionality but never making commitments is a waste of energy
 True for pivot hell and your special someone

6. Being delusional can remove the stress that keeps you from doing your best
 Every gymnastics season and startup required it, most creative projects too

7. The incremental value of the credentials falls off rapidly
 Chasing more badges for their own sake (PIF, TED, IC6) becomes less appealing

8. You can’t perform at your best without high quality recovery
 Sleep, naps, and breaks are an essential part of my process

9. Most conflicts are about interpretation, not facts
 Until you can see what they see, you’ll never agree on what should be

10. Gut feel only develops when you actually follow it.
 All my big decisions (startups, Amanda, house, Ashton) were gut moves

Summer

11. Everything worth doing takes longer and hurts more than you expect
 I’ve been trying to get a book deal for almost 10 years

12. Your biggest payday is usually adjacent to what you worked hard at
 50 Cent made more on Vitamin Water than all his records. Tony and others.

13. True expertise is being able to solve and explain problems on the spot
 True in gymnastics, music, and anything with immediate feedback

14. Media-free walks and commutes = better thoughts
 It’s too easy to listen to something all the time. Try silence.

15. Addiction is when fewer and fewer things can satisfy you.
 Many sources of joy = a good life

16. It’s never too late to start over
 Don’t fall into the trap of sunk costs

17. Sometimes the best system is a constantly changing one
 A novelty seeking brain needs rotating tactics

18. Leadership is disappointing people at a rate they can tolerate.
 Whether you’re a PM, CEO, or parent — people always more than you can give.

19. It’s never really about the dishes.
 The surface fight is almost always a stand-in for the harder conversation.

Autumn

20. The one moat AI can’t cross is a life actually lived.
 People will always connect better with real humans who have stories to share.

21. Breakthrough tech always brings unforeseen risks — and benefits.
 Accelerationists and doomers are both wrong. It’s always a mixed bag.

22. Always ask: am I solving the right problem?
 The biggest waste is work that doesn’t ladder to anything you actually care about.

23. Giving everything while asking for nothing is selfish martyrdom.
 I was not being generous by hiding my needs. I found the courage to ask.

24. Raising a kid is the most masculine thing a man can do
 Sorry not sorry to all the non-fathers out there

25. Your tolerance for damage declines much faster than your ability to perform.
 I can still output 90%, but I bounce back at like 50%

26. Getting older means an ever-growing list of things you need to function.
 Eye mask. Supplements. Mouth guard. The right pillow. Skin care. The list grows.

27. Wisdom is knowing what you like and not caring what you’re missing.
 FOMO is for people who haven’t decided what they actually want.

28. Attention is love
 Someone who consistently gives you full attention? Keeper.

29. You can’t skip the bad drafts.
 Good writing / product / art lives on the other side of bad stuff. No shortcuts.

30. It’s fine to keep listening to the same old music.
 The 2010’s are just going to be my decade forever.

Winter

31. Friendship becomes a calendar event or it’s a concept.
 My most consistent touchpoints are recurring invites.

32. Editing and revisions is what makes writing / products / art good.
 The myth of the fully formed piece is just that.

33. Winning at 40 is having great days, often.
 Hard work with people you like and respect on stuff that matters.

34. True partnership is knowing your person’s sore spots, and how to soothe them.
 Most of love is what you do when things get hard.

35. Handling yourself when your child is upset is a skill
 Nobody is unflappable, and everyone can learn to regulate better.

36. The repair is the relationship
 It’s not about being perfect. It’s about being good at making up.

37. Your parents become your teenagers in your late thirties.
 More stubborn. Full of wild ideas. Ready to party. Need extra supervision.

38. The best educator is natural consequences
 Whether kids and clients, sometimes you gotta learn through experience!

39. Being healthy is mostly learning to love boring stuff
 Foods without sugar, salt, and fat. Zone 2 cardio.

40. Going faster isn’t always better
 Learned at a meditation retreat, applies to most things.