In an old article, Jim Wendler lists 10 nuggets of wisdom. While they’re all good, #5 stands out:
5. One of the best things I ever learned in football (and this was a big turning point for me in college) was to never be afraid to fail. This paralysis keeps too many people from trying – keeps people from doing their first meet, submitting their first article, or asking out the girl you’ve had a crush on for two years.
Emphasis added.
As I’ve gotten (much) older, my fear of failure has decreased. Because yes, it caused me to miss opportunities in life, be it fun events, career opportunities, ways to improve life, or yes… that girl. 🙂
I’m sure you can look back on your own life and see how fear of failure held you back. In fact, I can still see places in my life where the little demon creeps in; I’m working on that.
This would be something to tell my younger self, and so I must tell my children – don’t be afraid to fail.
Stuff From Hsoi 
A hefty dose of Cancer has helped me in this respect. When your time is potentially cut short, you gotta do certain things while you still can, and to hell with the consequences. If you fall flat on your face? Well, hell. At least you’re still alive.
It’s all about perspective.