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What is inside
01 Origins
What shaped them, before the rest of us knew them.
- What's a moment from your childhood that you've thought about your whole life?
- Who was the first person who really believed in you?
- What did you want to be when you grew up — and what happened?
- What was the hardest part of growing up that I don't know about?
- What did you love about your parents — and what did you have to forgive them for?
- What's something that happened when you were young that you think shaped who you became?
- Who in your childhood was your first teacher about how to live?
02 The People Who Made You
The ones who shaped them, and the ones we never got to meet.
- Who's someone in our family I should have known but never got to meet? Tell me about them.
- What's a story about your family that nobody talks about, but I should know?
- Who in your family did you wish you'd been closer to — and why didn't it happen?
- What's something one of your parents went through that you only understood much later?
- Who in your life taught you how to love — for better or worse?
- Who in your life taught you who you didn't want to become?
- What's a falling-out in our family that you wish had ended differently?
03 Love
The person they chose, the love that stayed, the loss that did not leave.
- How did you know — really know — that the person you chose was the one?
- What's something your spouse or partner did that you've never stopped being grateful for?
- What was the hardest season of your relationship, and what brought you back to each other?
- If you've lost a partner: what's the thing you wish you could tell them one more time?
- What did you learn about loving someone that nobody warned you about?
04 Work, Vocation, Sacrifice
What they did with their days, and what it cost.
- What's a job you took because you had to, and what did it teach you?
- Who at work changed how you saw yourself?
- What's a moment when you knew you were doing exactly what you were meant to do?
- What's something you accomplished that nobody really gave you credit for?
- What did you give up to do the work you did? Was it worth it?
- What's something you made — anything, however small — that you're proudest of?
- If you could go back and redo one career decision, which would it be?
05 What You Learned
The wisdom from the long way around.
- What's something you used to think you wanted that you're glad you didn't get?
- What's a fear you carried for years that turned out to be wrong?
- What's the kindest thing a stranger ever did for you?
- What's a moment you're not proud of that taught you who you wanted to be?
- What's something about your parents you only understood after you'd had your own losses?
- What's a piece of advice you got that turned out to be wrong?
- What's the question you're still trying to answer at this point in your life?
06 What You Have Held Onto
The objects, places, and traditions that carry the story.
- Is there an object in this house you'd want me to keep — and what's the story behind it?
- Is there a photograph you wish I knew the story behind?
- What's a place you'd want us to go together while there's still time?
- Is there a tradition we used to have that you wish we'd kept?
- What's something you've kept all these years that nobody knows is meaningful?
- Is there a recipe, a phrase, or a piece of family history you want me to keep alive?
- Is there anyone you want me to find and tell something to, after you're gone?
07 What You Want Me To Carry
The questions worth saving for last. The ones families regret most.
- What do you most want your grandchildren — and the great-grandchildren you may never meet — to know about you?
- What's something you've never told me that you wish you had?
- Who do you wish you could thank now, and what would you say?
- Is there anyone you wish you could forgive — or be forgiven by?
- What's a regret you've made peace with, and one you haven't?
- If you could speak to me five years from today, what would you want me to remember?
- What do you hope is true about how you'll be remembered — and what do you hope I'll know that nobody else does?
- What advice would you give me for a season of my life I haven't lived yet?
- What's something you want me to forgive myself for, after you're gone?
- What's the most important thing you want me to know — not what you've already told me, but the thing you wish I'd really hear?
How to actually use them
Do not sit someone down with a list of fifty questions. That is an interview, and it makes people close up. Ask one. Let the answer go where it wants to go. The best material almost never comes from the question you asked.
Record it if you can, even badly, on the phone in your pocket. A shaky recording of someone's actual voice is worth more in twenty years than a tidy paragraph you wrote down afterwards.
And start with the easy ones. Section seven holds the questions families most often regret not asking, but they are not where you begin.