Go big or go home. You only live once. Are you going to spend that life saying "I should have", only to die before you get a chance? Do it.
I had a friend die last year, suddenly, and tragically, at the age of 32. Did he get to do all the things he wanted to do before he got the axe? No. Did he die doing something he loved? Yes.
And don't be afraid. "Fear is the mind-killer." It will hold you back and you'll be saying "shoulda, coulda, woulda, didn't, can't, won't, don't". Fuck that. Do it, even if you're shitting in your pants. It makes the beer taste better afterwards.