I'm all for taking a risk, but the benefits have to be worth it.
The most exhilarating parts of life are experienced by doing things that you've never done before - things that you're not sure are within your reach. Think of the first time you rode a bicycle. You started out wobbly, going faster than you are used to going by foot, on a device that looked precarious and had the potential for taking you to speeds (going downhill, anyways) that you considered reckless. Still, due to a bit of prompting from parents or peers, you got on and tried to master balance, steering and locomotion all at once. But oh, the feeling once you DID get it! That is one of the sweetest fruits of life - the adrenaline of success.
Some things that you might try are within your comfort level or have the risks and possible consequences carefully explained to you. Others, you have to just guess at the outcome and the consequences and decide whether you want to put in the effort of trying. It is so much easier to hang back in the shadows, claiming that to try would be too risky - even hoping to succeed would invite defeat. The longer I live and the more I see about taking risks, the more I'm convinced that calculated leaps of faith are usually worth the effort.
I see risk all around me in my life. Risk in Banana's striving for ringette greatness; my business' drive towards being a viable, profitable company; the effort I put into growing my friendships and trusting them with pieces of me that I might not have let out before; my effort at producing well-rounded kids; all of these things are risky undertakings with potential for failure and perhaps disastrous outcomes. I only need to look at the potential benefit of what even *one* of these efforts being successful would bring as far as benefits, and I know it would move than make up for any failures that might happen from all my trying.
An important learning moment came after Banana lost in the gold medal game last weekend. During the trip home, there was much moping about losing, lots of propping up of her ego (by both Jenn and me) and a few tears. At one point I posed the question to her, "Would you rather have come home with a silver medal or never have competed in the provincial tournament?" She answered how I hoped she would, and I saw (hopefully) the seed of risk-taking sprouting in a young, incredibly fertile mind.