Questions to ask · Childhood · for your grandpa
What did you want to be when you grew up?
Every child has an answer to this question, and almost every adult remembers theirs. A pilot, a nurse, a cowboy, a shopkeeper with a pencil behind one ear. Asking your grandpa what he wanted to be shows you the boy he was and the world he was looking at.
Why this question works
A childhood dream is a small window into a time and place. Children want to be what they can see: the engineer who waved from the train, the teacher at the front of the room, the uncle with the delivery truck. The answer tells you who the heroes were in your grandparent's corner of the world and what looked exciting from where they stood.
It also leads naturally to the life that actually happened. Some people became exactly what they planned. Most took a different road, and the story of how one turned into the other is often the story of a whole life: a family that needed help, a chance meeting, a talent nobody expected. Asked with warmth, this question lets your grandparent look back at that young dreamer with affection, and often shows that part of the dream came true in a different shape.
How to ask it
This is a good question for a relaxed moment with more than one generation present. Children love asking it, and they love being asked in return, so let it go around the table. Hearing a seven-year-old's plan often loosens a grandparent's memory of their own.
Keep it light and curious. Ask why that job, and what they imagined a day of it would be like. If the answer comes with a shrug, something like "oh, it was silly," smile and ask anyway. No childhood dream is silly. Avoid turning it into a question about what went wrong; you are asking about hope, and hope is a pleasure to describe.
Other ways to word it
- When you were little, what did you tell people you were going to be?
- Who did you look at as a child and think, I want to do that?
- What did you pretend to be when you played?
- Did your dream change as you got older?
Follow-up ideas
- Why that one? What did you like about it?
- Did you know anyone who did that work?
- What did your parents think of the idea?
- How close did you come to it?
- Is there a part of that dream in the life you ended up with?
- What would you want to be if you were starting out today?
An example answer
This is an invented example, written to show the kind of detail to listen for. Your grandpa’s answer will be his own.
"I wanted to drive a train. The tracks ran behind our school, and at ten past two every afternoon the freight came through and the engineer would lean out and wave. I thought he was the freest man alive. I used to line up kitchen chairs and make my little sister be the passenger."
"I never did drive a train. I went to work at the lumber yard at sixteen and stayed in that business for forty years. But I drove the delivery truck for the first ten, and I will tell you a secret: every time a child waved at me from a porch, I waved back like that engineer did. So maybe I got a little piece of it after all."
What to write down
Note the dream job and the reason for it, including the person who inspired it if there was one. Write down what your grandpa imagined the work would be like, and what his parents said about the idea. Then add a line about what he did go on to do, and any part of the early dream he feels came true. Keeping both halves side by side tells a small, complete story.
A question like this one has a page of its own in the Tell Me Your Story, Grandpa journal, in the chapter about school days. The pages that follow ask about first jobs and proudest work, so the journal holds both the dream and the life that grew out of it.
See the Tell Me Your Story, Grandpa journal. For more ideas, read questions to ask your grandparents or browse childhood questions.

