I was digging through some old journal entries of mine. I wrote the following a while ago:
The only thing worse than a bad day
Is a great day you fuck up by doing something stupid.
I thought on this for a while. And I felt it was pretty true for a short time. And then, I started thinking on things I've done that were "stupid" to wreck a good day or a good thing, that actually ended up being positive. And you know what? I can't think of many that weren't.
"Stupid" is often a word we use when we mix bravery with hindsight. It takes a tremendous amount of guts to do something "stupid" -- because you often don't know what the hell its going to end up like, and you're taking a risk that it might end up exactly how you want.
It often doesn't. That doesn't necessarily mean it ends up bad, but often it's not what we envisioned. But that's the thing about vision: you can only see what's in front of you. And almost always, decisions that end up being "stupid" are based on what's in front of us. To berate yourself or make yourself hurt by lamenting not knowing what was going to happen is a waste of time.
Take risks. If things fail, so what? You're not dead. And if you can think back to five years ago and name a single mistake you a) still think about and b) feel now wasn't actually for the best, you're in the vast minority of people (or you're in prison).
When all else fails; when you're standing there on the edge of the high dive and wondering just why the hell you thought it was a good idea to climb up there and jump off, just remember, time is the only true currency we have in this life, and doing dumb shit is how we learn. Avoiding doing stuff is also avoiding an opportunity to learn about yourself, your environment and the people around you. Avoiding learning is the first step in ignorance.
So really, doing something risky isn't stupid at all. Not doing things is actually really stupid.