10 questions to answer in your legacy document

Most people who sit down to write a legacy document get stuck in the first five minutes. Not because they have nothing to say, but because they have too much. A whole life is staring back at them from the blank page, and the question "what should I include in my legacy document?" feels about as helpful as "tell me everything."

So here's a different approach. Instead of trying to capture everything at once, answer ten specific questions. Not all in one sitting. Maybe one a week, or one whenever the mood strikes. Each question opens a door into a different part of your life, and together they build something your family will actually want to read — not a formal document that sounds like it was written by someone else, but a real picture of who you are.

These are legacy document questions that work because they're specific enough to get you writing but open enough to let you be honest. Treat them like conversation starters with someone you love, because that's exactly what they are.

1. What do you believe in, and where did those beliefs come from?

Not the polished version. Not the values you'd list on a job application. The real ones — the convictions that actually shape your decisions when nobody's watching.

Maybe you believe in showing up, even when it's inconvenient, because your mother showed up for you every single time and you didn't realize how rare that was until you were thirty. Maybe you believe in being careful with money because you watched your parents fight about it at the kitchen table when they thought you were asleep.

Your values didn't arrive in a vacuum. They were forged by specific moments, specific people, specific failures. When you trace them back to their origins, you give your family something more useful than a list of principles. You give them the story behind the principles, and that's what makes the difference between advice they'll nod at and wisdom they'll carry.

If you want a deeper look at how to connect your values to your personal history, this guide on including memories and values in your legacy document walks through the process in detail.

2. What's the hardest thing you've been through, and what did it teach you?

This is the question most people skip, and it's the one that matters most.

Nobody learns anything useful from a story where the hero had it all figured out from the beginning. Your family doesn't need you to be infallible. They need to know that you were once in the same kind of pain they might face someday — and that you found your way through it.

Maybe it was a divorce, a job loss, a health scare, or the death of someone who left a hole that never fully closed. Whatever it was, write about what it actually felt like in the middle of it. Not the cleaned-up retrospective, but the confusion and the fear and the way you weren't sure things would be okay.

Then write about what changed afterward. Not in a "everything happens for a reason" way, but honestly. What did you learn about yourself? What did you stop taking for granted? What would you tell someone standing at the beginning of that same road?

That kind of honesty is a gift. It tells your family: you're allowed to struggle, and struggling doesn't mean you've failed.

3. What do you hope for the people you love?

Be careful with this one. The temptation is to project — to write a list of things you wish you'd accomplished and hand them off as aspirations for your kids or grandkids. That's not a hope. That's an assignment.

Real hopes are looser than that. Maybe you hope your daughter finds work that makes her forget what time it is. Maybe you hope your son learns to ask for help before he's drowning, something you never figured out yourself. Maybe you hope your partner eventually gets that trip to Italy, the one you kept postponing for one reasonable reason after another.

Write about what you actually want for their lives, not what would look good. And if your hopes for them have changed over time — if you used to care about their grades and now you just want them to be kind — say that too. The shift tells them something important about what you learned along the way.

4. What's a story from your life that your family has never heard?

Every family has a version of the past that gets repeated at holiday dinners. The same five stories, polished smooth from retelling. Your legacy document is the place for the other stories — the ones that didn't make the highlight reel.

The summer you worked on a fishing boat and lasted exactly eleven days. The friend you lost touch with who taught you more about loyalty than anyone since. The time you made a decision that everyone disagreed with and turned out to be right. Or the time you made a decision that everyone disagreed with and turned out to be spectacularly wrong.

These untold stories fill in the gaps. They turn you from a parent or grandparent into a full person with chapters your family never got to read. And sometimes the stories you've been holding back are the ones they need to hear most.

5. What does money actually mean to you?

Money is one of those subjects families talk around but rarely talk about. What you put in your legacy document doesn't have to be a financial plan — that's what a will is for. This is about something deeper: your relationship with money and what you want your family to understand about theirs.

Were you raised to save every penny, and did that serve you well or hold you back? Did you ever take a financial risk that changed the course of your life? Do you wish you'd been more generous, or more careful, or both at different times?

Be specific. If your best financial decision was quitting a high-paying job to do something that paid less but let you be home for dinner, say so. If your worst financial decision was buying something you couldn't afford because you wanted to prove something to someone, say that too.

Your family will make their own choices with money. But knowing how you thought about it — the mistakes and the wisdom — gives them a head start on figuring out their own relationship with it.

6. What do you know about love that you didn't know at twenty?

Twenty-year-olds think love is about finding the right person. Fifty-year-olds know love is about becoming the right person, slowly, imperfectly, and with a lot of wrong turns along the way.

Whatever your age, you've learned things about love and relationships that younger versions of you would have dismissed. Write those things down. Not as advice carved in stone, but as observations from someone who's been paying attention.

Maybe you learned that the flashy stuff fades and what's left is whether you can stand in the kitchen together after a hard day and still want to be there. Maybe you learned that forgiveness isn't a one-time event but a daily practice. Maybe you learned something about loneliness, about what it means to love someone and still feel alone, and what it took to bridge that gap.

This is the kind of truth that can only come from experience. Your family might not be ready to hear it now. But one day they'll come back to this section, and the words will land differently than they did the first time.

7. What traditions matter to you, and what's the story behind them?

Sunday dinners. Birthday pancakes. The way your family always opens one gift on Christmas Eve. Every family has rituals, and most of them started for reasons nobody remembers anymore.

If you know the origin story, write it down. If your grandmother started making tamales every December because it was the one thing that reminded her of home after she moved across the country, that's not just a recipe — it's a lifeline to who your family is and where they came from.

And if you have traditions you'd like to see continue, say so. Not as a mandate, but as an invitation. "I hope you keep doing this, and here's why it mattered to me." That gives your family permission to carry it forward, adapt it, or create something new from it — all of which honor the original spirit.

8. What would you do differently if you could start over?

This is the question that separates a legacy document from a highlight reel.

Everyone has regrets. The honest ones, not the kind you mention in job interviews ("I work too hard!"), but the real ones that sit in the back of your mind. The years you spent angry at someone for something that doesn't matter anymore. The relationship you let fade because reaching out felt too vulnerable. The dream you set aside for practical reasons and never picked back up.

You don't have to wallow. But naming your regrets — clearly, without self-pity — does something remarkable. It gives your family permission to make different choices. It says: I wasn't perfect, and I don't expect you to be either. But here's what I'd change, and maybe you can learn from that.

For more on approaching this kind of honest self-reflection in your writing, this piece on writing a meaningful legacy letter has some useful guidance.

9. What brings you peace?

Not happiness — peace. They're different. Happiness is the burst you get from good news or a great meal. Peace is the quiet hum underneath, the thing that keeps you steady when the surface gets rough.

Maybe it's your morning routine. Coffee before the house wakes up, watching light fill the kitchen. Maybe it's gardening, or fishing, or the twenty minutes you spend in the car after pulling into the driveway but before going inside. Maybe it's a particular kind of prayer, or a walk through a neighborhood you've known for decades, or the feeling of a dog's head resting on your lap.

Write about what peace looks like for you. Not because your family will replicate your routines, but because they'll understand you better. And in their own difficult moments, they might remember that you found stillness in small places, and go looking for their own.

10. What do you want your family to know about who you really are?

This is the open-ended one. The question beneath all the other questions.

Because here's the thing about families: you can live with someone for forty years and still not know certain parts of them. Not the secret parts, necessarily, but the private ones. The fears they never mentioned. The ambitions they set aside. The version of themselves they imagined becoming before life rearranged the plan.

Your legacy document is the place to close that gap. To say the things that are true but that you never found the right moment to say. Maybe it's "I was always a little afraid I wasn't enough for you." Maybe it's "The proudest moment of my life had nothing to do with work." Maybe it's something you can only say in writing because saying it face-to-face would make you cry, and you've never been comfortable with that.

Whatever it is, write it. Your family will be glad you did.

You don't have to answer all ten today

If reading through these questions stirred something up, good. That's what they're supposed to do. But you don't need to sit down and power through all ten in an afternoon. Pick the one that pulls at you. Write for twenty minutes. Come back next week and pick another.

A legacy document built one honest answer at a time will always be more meaningful than one written in a marathon session where you tried to cover everything and ended up saying nothing real. The goal isn't to produce a perfect document. The goal is to leave behind something true.

If you're wondering how all of this connects to a bigger picture — how a document like this can bring comfort to the people you leave behind — this piece on how legacy documents bring peace of mind is worth a read.

And if you want to go deeper on the values side, writing a legacy letter of values and beliefs covers how to turn your principles into something your family can hold onto.

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.