Usually, the pain of losing is greater than the joy of winning and thus we don’t take risks that have potentially huge payoffs (financial or other).
When we adjust what we view as a failure we make it more defensible to take a risk.
Even if we lose, we're simply learning and we're no longer ashamed of that.
To be one who takes a risk is already a winning strategy. If the risk doesn’t work out, you’ve done more than most others, you took the risk. No shame in that.
I think we need to begin looking at the pain of losing as less severe than the joy of winning and begin putting more of our skin in the game.
If you risk $5,000 for a chance at $500,000 or maybe losing all that money, most people wouldn’t risk the $5,000. But a life spent taking these all-or-nothing risks (maybe except in situations of life or death) will reap far greater rewards than being the person who sits still, too afraid to take a risk.
When harm incurred is much less than a potential gained, that is a situation where you should spring to action and make your move. You have little to lose and much to gain.