What do you know now that you wish you had known at twenty?

Why this question works

This is a friendly way to ask for wisdom. It does not ask your grandparent to judge their life or list mistakes. It asks them to picture a particular young person, themselves at twenty, and think about what would have helped. Most people feel real tenderness toward that younger self, and it shows in the answer.

The age matters. Twenty is specific enough to bring back a real time: where they lived, what they were worried about, what they thought the future held. The answer usually comes from the gap between those worries and how things actually turned out. You will often hear that the thing they feared did not matter much, and that something they took for granted mattered most. For a grandchild in their teens or twenties this is as close as it gets to a letter from the future, written by someone who loves them.

How to ask it

Ask it around a milestone: a graduation, a twentieth birthday, the first move away from home. If a photo exists of your grandparent at about that age, bring it out and ask them to tell you about the person in the picture before you ask the question itself.

Keep your tone curious and warm, never heavy. If they start with a joke, such as "buy land" or "wear sunscreen," enjoy it and then ask what else. The deeper answer tends to come second. Let them take their time, and do not argue with what they say, even if it is about something you are doing right now. You asked for their experience, and it is a gift either way.

Other ways to word it

• What would you tell your twenty-year-old self?
• What took you far too long to figure out?
• What did you worry about at my age that turned out fine?
• What do you understand now that you could not have understood back then?

Follow-up ideas

• What were you like at twenty?
• What were you most sure about, and were you right?
• What did you spend too much time worrying over?
• What do you wish you had done more of?
• Who tried to tell you, and why did you not listen?
• When did you finally learn it?
• Would your younger self have believed you?

An example answer

This is an invented example, written to show the kind of detail to listen for. Your grandma’s answer will be her own.

"That nobody is watching you as closely as you think. At twenty I was sure the whole town had an opinion about my hair, my shoes and whether I laughed too loudly. I turned down a chance to sing a solo at church because I was afraid of what people would say if my voice cracked. I still think about that solo."

"It took me until about forty to understand that everybody else was busy worrying about their own hair and their own shoes. All that energy I spent being careful, I could have spent singing. I would also tell that girl that the friends who are easy to be around are the ones to keep, and that she should learn to drive sooner. But mostly I would tell her to take the solo. If your voice cracks, people clap anyway. I have seen it happen."

What to write down

Start with a few lines about who your grandparent was at twenty: where they lived, what they did and what they worried about. Then write the lesson in their exact words. Add the story of how and when they learned it. If they offer more than one, number them. This page is worth copying for every grandchild as they reach that age.

A question like this one has its own page in the life lessons chapter of the Tell Me Your Story journals for grandparents. It reads beautifully in handwriting, like a note from one twenty-year-old to another across the years.

See the Tell Me Your Story, Grandpa journal or the Tell Me Your Story, Grandma journal. For more ideas, read questions to ask your grandparents or browse advice and life lessons questions.