Questions about what your parents have learned

8 questions

Ask anyone over sixty what they wish they'd known at twenty-five and you'll get an answer worth writing down. These questions are designed to surface that kind of wisdom — the kind that doesn't get said unless someone asks. They work as well over a long phone call as they do printed out and read together over coffee.

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Wisdom

01
What do you know now that you wish you'd known at 25?
Ask if their younger self would have actually believed it.
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02
What's a mistake you made that turned out to be one of the best things that happened to you?
Ask how long it took before they could see it that way.
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03
What do you see young people getting wrong that you wish they could see?
Ask if anyone ever told them the same thing when they were their age.
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04
What's the kindest thing anyone ever did for you? Did you ever get to thank them?
Ask if they've tried to pass that kindness on to someone else.
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05
If you could go back and tell your younger self one thing, what would it be?
Ask which version of them most needed to hear it.
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06
What's a hard truth you've made peace with?
Ask what helped them finally accept it.
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07
What advice did someone older give you that you ignored — and now wish you hadn't?
Ask who that was, and what would have been different if they'd listened.
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08
What's the simplest piece of wisdom you'd hand to anyone, anywhere, in any situation?
Ask where it came from — was it learned from someone, or earned the hard way?
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How to actually ask these

·Pick three or four. Trying to ask all of them in one sitting will exhaust you both. The best conversations come from one question that opens up into twenty minutes of unrelated stories.
·Don't correct or argue. If their memory of an event doesn't match yours, that's a separate conversation. Right now you're collecting their version.
·Write down what they say while it's fresh — or record it. Phones are good for this. You don't need anything fancier.
·If asking face-to-face feels like too much pressure — for either of you — consider letting our service text them one question every few days. Many people open up more easily over text than across a kitchen table.