← All letters Letters to Lucca Letter 28
Letter № 28  ·  A father, to his son

A Letter from My Friend Jake to His Son

My friend Jake Taylor's letter to his son at 18 — live by an inner scorecard, work hard when it's boring, choose integrity even when it's costly

January 7, 2026
Date
486
Words
For luccapavese@gmail.com, Age 12
To

Dear Lucca,

Every so often someone shares something so good that I have to save it for you. This is one of those. My friend Jake Taylor — a fellow investor I deeply admire, and the author of a wonderful little book called The Rebel Allocator — wrote the note below to his own son, Asher, when Asher turned 18. He texted it to me one January morning, and I asked if I could hold onto it for you. When you turn 18 yourself, I hope you’ll read it as though it were written to you, because nearly every word of it is what I’d wish for you too.

Here it is, in Jake’s words:

Asher,

Today, you turn 18.

I’m proud (and a little amused) that the kid who would occasionally cry in the garage after a tough game can now deadlift a small car.

I admire your efforts in the gym, consistent hitting off the tee, swing after swing. No audience, no highlight reels, just tiny tweaks. One of my favorite jobs is throwing you boys BP in the cage as you polish your swing. That work ethic isn’t just baseball. It’s a way of being. Every rep is a vote for the player (and person) you want to become. Habits maketh the man.

College is going to offer you a thousand scoreboards: grades, baseball, social status games. Most of them are loud, and none of them are permanent. Here’s something I’ve noticed about the .01%: they don’t really struggle with people pleasing. Not because they’re callous (they’re not), but because they don’t reshape themselves to win approval. They live by an inner scorecard, not external applause. I want that for you: calm, internal grounding that doesn’t require others’ permission for your self-worth. Creating a life that reflects your values and satisfies your soul is a rare achievement.

Protect a little solitude, too. Turn down the noise long enough to hear your own thoughts. Ask yourself the uncomfortable questions early:

What do I stand for? What am I willing to sacrifice, and what am I not? Which standards will I hold myself to? If you answer those honestly, decisions get simpler. Recognize that the world wants to hijack your dopamine and fill you with mimetic wanting. Resist.

I believe you’re destined for a special life. Anything is possible if you’re willing to pay the price of hard work—your potential is ridiculous. Aim it with intention toward greatness, whatever your definition of “greatness” may be.

Three reminders: work hard even when it’s boring, choose integrity even when it’s costly, and invest in people who inspire you to be a better person, even if the return on your investment is not immediate.

Love, Dad

— Jake Taylor, to his son Asher

I couldn’t have said it better, Lucca. So I won’t try. Just know that every line of it is true for you, too.

Love,

Dad

End of Letter 28