Tonight with your 13 to 17 year old
The prompt
“What would a perfectly ordinary, good day look like for you when you're thirty?”
What to listen for
Pay attention to the texture of the answer, do they focus on work, on people around them, on a feeling like calm or freedom? That tells you what they're actually optimizing their future for, which is often different from what career path they name.
If they describe something surprisingly modest and peaceful, that's worth noting warmly, it doesn't mean they lack ambition, it means they know what "enough" feels like to them, which is a genuinely mature insight.
If they say "I don't know, I can't imagine being thirty," that's completely normal too, you can laugh about it together and try again another time with a nearer target, like next year.
What this tells you
Their picture of an ordinary day at thirty tells you what they actually want their life to feel like, not just what they think they're supposed to want.