Put yourself out there and give yourself permission to suck. That’s not to say you should try to suck, but you have to give yourself permission to allow for the possibility of sucking. Without sucking, you’re never going to find your boundaries, and you’ll never push through those boundaries. That’s all it is. Constantly bumping into walls you do not think you can climb and then climbing until you get over them. There’s no mystery to it, no magic. It’s about dedication and constantly trying to improve.
This is a bit of a Catch-22. In order to give yourself permission to suck, you have to have made a consistent fool of yourself in the past (probably not intentionally), and somehow pulled yourself through without sacrificing too many of your core values. That experience, over and over, teaches you that you can survive failure and gives you the confidence to get near it again, on a bigger scale perhaps.
We should talk about how to bootstrap confidence in surviving failure. Maybe this is why awkwardness in youth is a valuable period… I spent so many years falling short of my own expectations of myself that I learned that it’s possible to stay true to values even when you’re failing, and that has given me the confidence I need to stay focused even when circumstances are going contrary to my goals.
How else can you learn these things?