Sometimes you need to get out there and do something that might be regarded as stupid. I’m not saying to do things that are overtly risky, of course.
Risk isn’t a binary thing though. There are things that you know will end poorly — if you jump of a building you’re not going to be long for the world since the result is rather a foregone conclusion. There are things where the lack of risk, and potential reward, are just as skewed to the other side of the picture.
Neither of those are fun.
There are plenty of situations you can get yourself into that are firmly in the middle. You can take precautions to not make the hurt too bad if things don’t go your way… but even then you’ll have the opportunity to have a good story afterward.
A good example might be my motorcycle trips. One ended in tears — in Labrador. Another ended with a bent front wheel. A couple others ended with no damage and good memories. Is there risk in taking a motorcycle trip? Yes. More than a car, certainly. Does that mean that you shouldn’t do it? No. You take precautions, then you hit the road.
But that’s only one specific thing. This isn’t about motorcycling.
This is about doing things where the outcome is you might get hurt. But you might be better off in the end. Maybe any outcome is better than stasis?
Go out on that date. Take a vacation. Buy the speakers you long for. You can’t take it with you. Don’t be stupid, but don’t be dumb either.