No one's perfect, so don't strive for perfection. ...Well, Mr. Rogers possibly was, but aside from him. perfect isn't a thing that actually happens.
Weigh the possible outcomes against each other and see if it's a gamble you can take. If a thing seems really, really stupid, but the outcome could help you or someone else, sometimes it's worth risking. Or sometimes all you learn is "how not to do xyz"
Also having friends around to help makes some of those mistakes safer to make.