Better Sorry Than Safe

"Most are afraid of living, not dying."
Playing it safe was never a motto of The Chemical Buddha. He wasn't afraid to embarrass himself because he was all about enjoying the now. Although he encountered people who seemed obsessed with playing it safe and doing whatever it took to keep from being made fun of. And while The Chemical Buddha was sometimes laughed at for his exploits, he found the rewards of going (and getting) after what he wanted far outweighed any potential fall from grace. (Besides, if he actually fell from grace he didn't have far to fall.) For example, no matter how many drinks he had thrown in his face, The Chemical Buddha would ask every woman in the bar if she wanted to fuck until he found one that said, "Yes." The reward of sex far outweighed any shame or ridicule he might have felt. Plus, the fact he was really, really drunk, insured he didn't feel much of anything.
How does playing it safe in your life keep you from getting what you want?
Would you rather look like a fool and get what you want or look reasonable and not get it?