The Letter I'm Writing My Kids Instead of a Will

Writing a legacy letter to your children is one of the most important and most neglected things a father can do — and yet most entrepreneurial dads I know have never started one.

I have a will. It's organized, updated, handled by a good attorney. It specifies what happens to my assets, my business interests, various legal and financial matters. I'm proud of it as a document. It protects my family in the practical sense.

But a few years ago I started thinking about a different question: what happens to the relationship?

If something happened to me tomorrow, my family would be fine financially. They'd also grow up with questions I can no longer answer. About who I was. What I believed. What I was trying to build, and why. What I hope for them.

A will can't answer those questions.

The Story That Started This

My grandfather on my mother's side lived in Holland during World War II. As a young man, he had to sneak out at night to scavenge for food while under constant threat from the Nazis who occupied his town. I only know that in broad strokes. I don't know what he was afraid of. I don't know what kept him going. I don't know what he learned about people in those years.

I always assumed there would be more time to have those conversations. Until there wasn't.

Now I'll never get to ask. And I'm left with a man I admired enormously, whose life shaped mine in ways I can't fully trace, and whose inner world is permanently closed to me.

I don't want that for my son Neary.

When I started writing REBL Dad with Adam Holt, the Stewardship of Legacy chapter was the one I worked hardest on. Not financial legacy — the other kind. The legacy that lives in how your children talk about you, how they make decisions when you're not in the room, what they carry from you into their own families someday.

What We Leave Behind

We spend enormous energy building things that outlast us. Companies. Wealth. Reputations. That's what entrepreneurs do.

But most of us don't apply that same thinking to the most important legacy we'll leave: the people our children become.

We assume they'll know us by being around us. But the version of you they know is the version they see across the dinner table, at soccer games, in the everyday routines of family life. They don't see the version that existed before they were born. They don't know what you were afraid of. They don't know what you changed your mind about. They don't know the moments that shaped you.

Unless you tell them.

One of the fathers we interviewed for REBL Dad — Blake — had lost his own father under sudden, devastating circumstances and spent years afterward processing all the things he never got to say or hear. He eventually built his life's work around helping fathers write letters to their children. His insight has stayed with me:

"There's a story you're telling yourself about how much you love your children, and they're telling themselves a story about how much you love them. There's just no way the story is matching up perfectly."

Letters bridge that gap.

What Goes in the Letter

Your letter is yours. But here's what I've been working through.

First: what I believe. Not necessarily religious beliefs — foundational convictions. What I think actually leads to a good life. My kids hear fragments of this in conversation, but never assembled into one coherent thing. The letter gives them that.

Second: what I've gotten wrong. Mistakes I made that I want them to learn from. Places where I operated from fear or ego and paid for it. This is harder to write than the proud stuff, but it might be the most useful.

Third: what I hope for them. Not achievement goals — real hopes. I hope you find work that uses the best of who you are. I hope you're brave enough to build a life that's actually yours.

Fourth: what they mean to me — specifically. What they specifically brought into my life. How they changed me. The moments I hold onto. The things that made me proud that had nothing to do with achievement.

One of the most thoughtful fathers we spoke with for the book — Doug Lennick — put it in terms I think about often: "If you are serious about being a good father, you must be explicit about that goal. Then, you must let your commitment be known through behavior."

A letter is the most explicit version of that commitment I know how to make.

He also shared a principle that stuck: we are accountable to the three generations that preceded us, and responsible for the six generations that will follow us. Your kids aren't just your kids. They're the next link in a very long chain. What you teach them will outlast everything in your will.

Why This Is Hard for Entrepreneurial Dads

We're builders. Doers. Writing a letter that gets into vulnerable territory — fear, regret, love, legacy — goes against every instinct.

We're also busy. There's always a reason to put this off.

And there's a superstitious quality to it. Writing a letter to your kids in case you're not around feels like you're inviting the thing you're preparing for.

None of those are good reasons to skip it.

Your kids deserve to know who you were. Not just the dad-across-the-dinner-table version. The full version — the person who struggled and built and learned and failed and got back up. The person who loved them more than he was always good at showing.

Write it down. Give it to your attorney to keep with the will if you want. Set a reminder to update it every few years.

The will handles the assets. The letter handles the relationship.

Start the letter.

The Stewardship of Legacy is the seventh and final principle in REBL Dad — the book Adam Holt and I wrote about what it takes to be a great father and a great entrepreneur at the same time. Learn more at rebldads.com/book.

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Common questions about legacy letters for fathers:

What should a father write in a letter to his children?

A meaningful legacy letter typically includes: your core beliefs and values (what you think actually leads to a good life), your honest mistakes and what you learned from them, specific hopes for each child's future, and what they specifically meant to you — not just "I love you" but the particular moments and qualities that made you proud. The goal is to give them a complete picture of who you were, not just the role of "dad" they experienced.

Why should fathers write letters to their kids?

Because the story you tell yourself about how much you love your kids and the story they carry about how much you loved them almost never match perfectly. A letter bridges that gap explicitly — it gives your children access to the inner world they could never fully see from the outside. It also preserves your values, reasoning, and hopes in a form they can return to at different stages of their lives.

What is a legacy letter and how is it different from a will?

A will is a legal document that distributes your financial and material assets. A legacy letter (also called an ethical will or legacy letter) transmits your values, beliefs, stories, hopes, and love — the things that have no monetary value but may matter more to your children over time. The two documents complement each other: the will handles what you leave behind materially; the letter handles who you were.