School & learning
Did you go to college? What did that decision mean for the rest of your life?
Why this question matters
This question cuts to the heart of how one decision can ripple through decades. Some parents will describe college as the making of them — intellectually, socially, professionally. Others will talk about the roads not taken, the debt carried, or how they built a life without those credentials. The answer reveals their relationship with education, opportunity, and the stories they tell themselves about their own choices.
If they pause, try this
Ask what they'd say to a younger person facing the same choice now.
What people often remember when asked this
- 01
The parent who went and calls it transformative — ask what specific moment or person there changed them, and whether they think that growth could have happened elsewhere.
- 02
The parent who didn't go and built something anyway — explore what they learned instead, and whether they ever felt that absence as a limitation or a freedom.
- 03
The parent who went reluctantly or dropped out — dig into what that experience taught them about following expectations versus following instincts.
A small tip for the conversation
If they brush off the question with "it worked out fine," ask them to imagine advising their younger self facing that same choice again — sometimes the real feelings emerge when they're thinking about someone else.
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