Learned to take risks with words.
I'm an extremely risk-averse person. That's partly why I hate flying--because of that 1 in a gazillion risk that something would go bad. I don't like karaoke, non-veggie sushi, or running across the street before the light changes. I probably won't ever get LASIK (although I'm blind as a bat) because I'm not cool with the risks. I'm shy, too, which really boils down to not liking conversational chances with unfamiliar people. You could say that I've worked very hard in life to insulate myself from risk and uncertainty. (Can we all say: CONTROL. FREAK.)
Except writing is all about risks, right? It's two-fold:
1) Writing itself is risk-taking. You might not finish your project. Whatever you're writing might actually suck. As you write, the choices you make (subject matter, style, tone, voice, characterization) can be risky. They might work, they might not. You might fail, whatever your definition of failing is. Yet you try it anyway and see how it all turns out.
2) Writing for publication is full of even more risks. You might get rejected, from agents to editors. You might get bad reviews. Your books may or may not sell. A writer has control over very few things in the publishing process. If it's a road to publication, then writer isn't in a car but one of those soapbox derby thingies, coasting towards the finish line and hoping that it doesn't run out of steam or end up in a ditch.
I think the risk involved is wonderful and liberating. Risk means uncertainty, but it also means possibility. I'm so happy that I'm up for the gamble, after all.