We carry with us scars (emotional and physical), bruises, and burns - reminders of what not to do. These are helpful when encountering a risky or dangerous situation so we can properly determine a worst case scenario.
But what about when the outcome is awesome? How do we remember that? The feeling we had of accomplishment or victory isn't usually codified in some physical manifestation and so we forget the upside of laying it all on the line.
My solution? Create a way to remember the positive outcomes since they won't automatically be created for you with a scar or blemish. Write it down, draw a picture, or record your happy reaction.
Then, when you have another chance to go for it, draw down on the balance of this memory bank so that you can better determine when the reward is worth the risk.