To me taking risks is more about putting yourself out there in a way you've always wanted to, but never thought you could. Like Improv. I'm currently in my second session of improv classes and every week it is scary to me. I'm a girl who loves a plan. I like to know what's coming. Now the only thing I know on Sundays is that I have no clue what will happen during the 3 1/2 hours I'm in that room. It's scary as all get out. I'm intimidated and have to give myself a pep talk every week that I will suck and to just face it. But then, most days you get at least one good laugh. And that sticks. You hold onto it dearly and it feeds the hunger for more. Even now, 6 hours after class ended, I would love to be in that room again trying more 185 jokes.
I think that's the great thing about risk, no matter what I find it rewarding. If it pays off it is a much greater feeling of reward than something you didn't have to try at. And if you fail at the risk, well, at least you were brave enough to try.