Do you ever worry so much that you are going to falter that you play it safe which turns out to not be in your best interest?
I have been reading a lot about design thinking where the belief is to fail as fast as you can, so you can fix whatever doesn’t work now rather than later when the stakes are high.
So think of something you are working on where you are a bit timid and tentative. Be bold in a low risk environment. Keep what works. Modify what doesn’t. Then get going again.