If you don't have regrets in life, you're either lying to yourself or you're a sociopath. (look it up!)
What I've learned about regret is that I primarily have it when I DON'T do something.
I regret not buying more bitcoin in 2014 when I first encountered it.
I regret not moving to Europe when I was 20 years old to ski.
I regret not understanding the power of my own thoughts to create the life that I wanted until just a few years ago.
So when I think about doing something or taking a chance, I ask myself a simple question.
What will I regret more, NOT doing (this thing) or doing it and having it not turn out the way I'd like?
Whichever one I'd regret less is what I do.