How to write an advice letter for future generations

Here's a question worth sitting with: how much of the advice you received growing up do you actually remember?

Not the generic stuff. Not "work hard" or "be kind" or "save your money." You've heard those a thousand times from a thousand people and they've blurred into background noise. I mean the advice that changed how you think. The stuff that stuck with you because of who said it and how they said it.

If you're like most people, the advice you remember came wrapped in a story. Your dad didn't say "be honest." He told you about the time he lied about something small and it snowballed into something that nearly cost him a friendship. Your grandmother didn't say "marry someone kind." She told you about the winter your grandfather drove forty-five minutes in a snowstorm to bring soup to a neighbor he barely knew, and how she decided right then that she'd picked the right one.

That's the difference between advice that gets filed away and advice that gets carried. And if you're thinking about writing an advice letter to your children, your grandchildren, or family members you may never meet, that difference matters more than anything.

Why most advice letters end up in a drawer

Let's be honest about something: most advice is ignored. Not because it's bad advice, but because it arrives the wrong way.

Think about the last time someone told you what to do. Even if they were right, your first instinct was probably to resist. That's human nature. We don't like being told. We like discovering things for ourselves, and we trust the people who help us do that more than the people who hand us conclusions.

An advice letter that reads like a list of commandments — "Always be honest," "Never give up," "Follow your passion" — is easy to write and easy to forget. It sounds like a greeting card. It could have come from anyone.

An advice letter that reads like a human being talking about what they actually lived through? That's something else entirely. That earns a kind of authority that no amount of bold-font wisdom ever will.

The difference isn't what you say. It's whether you've earned the right to say it. And you earn that right by being honest about how you learned the lesson, usually the hard way.

How to write advice that someone will actually listen to

Here's the simplest test for whether a piece of advice belongs in your letter: can you attach a story to it?

If your advice is "Always be honest," that's a bumper sticker. Anyone can say it. But if you write this:

I lied to your grandmother about the dent in her car for three weeks. I told myself I was waiting for the right moment, but really I was just scared. The guilt ate at me worse than anything she could have said. I couldn't sleep. I snapped at people for no reason. When I finally told her, she was upset for about ten minutes and then we moved on. That's when I figured out that honesty isn't about being virtuous. It's about not wanting to carry the weight.

Now you've given someone a reason to believe you. They can feel the three weeks of dread. They can picture the confession and the relief. They're not just hearing advice — they're living your experience alongside you, and that's what makes it stick.

This is what separates a meaningful legacy letter from a well-intentioned but forgettable one. The specifics are the whole game.

A few more examples of the difference:

Generic: "Money isn't everything." Real: "I took a job that paid twice what I was making, and within six months I was miserable. I'd come home too drained to play with you kids, too stressed to be present on weekends. Your mom finally said, 'We were happier when we were broke,' and she was right. I quit that job three weeks later. We ate a lot of rice and beans that year, and it was one of the best years of my life."

Generic: "Don't be afraid to fail." Real: "I failed the bar exam the first time I took it. I told almost nobody. I was so ashamed I considered switching careers entirely. What got me through was your grandfather calling me and saying, 'Good. Now you know what failing feels like and you know it won't kill you.' He was right. It didn't kill me. I passed on the second try, and more importantly, I stopped being so terrified of getting things wrong."

See the pattern? The advice itself isn't revolutionary. But the story behind it — the shame, the rice and beans, the grandfather's phone call — that's what gives it weight.

The kinds of advice worth writing down

Not every piece of wisdom you've collected belongs in a letter. Some lessons are too situational, too dependent on circumstances that won't exist in twenty years. The advice worth writing down tends to fall into a few categories.

What you've learned about relationships

This is probably the most valuable territory an advice letter can cover, because nobody figures out relationships without getting hurt. Write about what you've learned about love — the romantic kind, the family kind, the friendship kind. Write about the relationship you almost lost and what saved it. Write about the friend you did lose, and what you wish you'd done differently.

Your children and grandchildren are going to fall in love with the wrong person at least once. They're going to have a fight with someone they care about and consider walking away. They're going to wonder whether a relationship is worth the work. Your stories won't prevent any of that, but they might make the pain feel less lonely when it happens.

What you've learned about work and purpose

Not career advice in the "here's how to get promoted" sense. That stuff dates fast. What lasts is the deeper layer: how you figured out what kind of work made you feel alive. The jobs you hated and why. The moment you realized you'd been chasing someone else's definition of success.

If you spent years doing something that didn't matter to you before finding something that did, say so. If you never found the work you loved but made peace with that and found meaning elsewhere, that's worth writing about too. Not every life lesson about work ends with "and then I found my calling." Some of them end with "and then I learned that a job is just a job, and that's okay."

What you've learned about money

Money advice from a family member hits different than money advice from a book, because you can see the consequences in real time. If you went through a period of financial struggle, write about what it taught you. If you made a money decision you regret, explain what you were thinking at the time and what you'd do instead now.

The most useful money advice isn't usually about investment strategies or savings rates. It's about the emotional relationship with money: the fear, the security, the way it can make you do things you wouldn't normally do. That's the stuff nobody teaches in school, and it's the stuff your family needs to hear from you.

What you've learned about hard times

Everyone goes through seasons where the ground falls out. Grief, illness, job loss, divorce, failure, loneliness. You've survived some of those. Maybe all of them.

Write about what got you through. Not the platitudes — not "time heals all wounds" or "everything happens for a reason." Write about what actually helped. Maybe it was one person who showed up without being asked. Maybe it was a routine that kept you moving when you didn't want to get out of bed. Maybe it was something embarrassingly small, like a TV show that made you laugh when nothing else could.

The people who read your letter will face their own dark stretches. When they do, knowing that you went through something similar and made it to the other side won't fix anything. But it'll remind them that surviving is possible, and sometimes that's enough.

What you've learned about joy

This is the one people forget to include. We tend to focus our advice on how to avoid pain, but some of the most valuable wisdom is about how to recognize and hold onto happiness.

Write about the things that brought you the most joy and whether any of them surprised you. Write about the period of your life when you were happiest and what made it work. If you have opinions about what joy isn't — if you've learned the hard way that achievement doesn't equal happiness, or that busy doesn't equal full — say that too.

Who you're writing to (and why it matters)

An advice letter to your ten-year-old daughter reads very differently from an advice letter to grandchildren you haven't met yet. And both are worth writing.

Your children already know your voice, your mannerisms, your particular way of seeing the world. For them, an advice letter deepens a relationship that already exists. You can reference shared memories, inside jokes, specific moments. You can be direct because they know you well enough to hear it the right way. If writing to a daughter specifically, the legacy letter to my daughter guide goes deeper into that relationship.

Your grandchildren may know you, but they know a curated version — the grandparent version. An advice letter to grandchildren is your chance to show them who you were before the gray hair. The struggles you went through. The person you were at their age. Grandchildren are often hungry for this, because their parents tend to edit the story.

Nieces, nephews, and extended family might not expect a letter from you at all, which is part of what makes it powerful. Sometimes the most impactful advice comes from someone slightly outside the nuclear family, someone with enough distance to see things the parents can't.

Future family you'll never meet. This is the one that feels strange to write, but it might matter the most. Imagine your great-grandchild, fifty years from now, reading a letter from an ancestor who took the time to say: here's what I learned, here's what I got wrong, here's what I hope for you even though we'll never share a room. That letter becomes an artifact. A piece of shared wisdom that lasts across generations.

Being opinionated is a feature, not a flaw

The worst advice letters are the ones that try to be diplomatic about everything. They hedge. They qualify. They say "but of course everyone's different" after every sentence until the whole thing feels like a disclaimer.

Here's what I think: your advice letter should have an opinion. You've lived long enough to believe some things strongly. You should say them.

If you think most people spend too much time worrying about what others think, say so. If you believe that marriage is hard and worth it, say it. If you're convinced that the best thing you ever did was quit a stable job to try something risky, or that the worst decision you ever made was prioritizing career over family for a decade, put it in the letter.

Your reader doesn't have to agree with you. But they should know where you stand. People remember the advice of someone with convictions far longer than they remember the advice of someone who tried to cover all the bases.

The same principle applies to how you structure any legacy letter — the ones that sound like a real person with real beliefs are the ones that get read more than once.

Start with the lesson that cost you the most

If you're staring at a blank page wondering where to begin, start with the lesson you paid the highest price to learn. The one that came through failure or heartbreak or a decision you can't undo.

That's your opening. Not because pain is the point, but because that's where your credibility lives. Your reader will feel the weight of that story, and it'll earn you the trust to say everything that comes after it.

You don't have to write the whole letter tonight. Write the one story. The one lesson. Come back tomorrow and write another. A letter written in pieces over weeks or months is often more honest than one written in a single emotional sprint, because you'll catch different moods, different memories, different angles on the same life.

And don't worry about whether your advice is original. It doesn't need to be. "Be honest" isn't a new idea. But your version of why honesty matters, told through your specific experience, is something no one else can write. That's what makes it worth reading.

The people you love are going to face things you can't protect them from. You won't be in the room for every hard decision, every heartbreak, every crossroads. But your words can be. And the advice that's wrapped in your real, honest, imperfect story is the advice they'll actually carry with them.

When I Die Files gives you a secure, private space to write the letters that matter most — and make sure they reach the right people at the right time.