I have done quite a bit of painting and caulking for a guy who's not in the profession. I despise both with a passion, though, especially caulking, and I have never once been satisfied with a single paint or caulk job I've done. I feel like I'm the embodiment of "be bad at this for a long time," although I'm objectively probably halfway decent at it.

That is to say I think Ira Glass' quote of "You've just gotta fight your way through" to get where you want to be seems especially meaningful in the context of something like painting, where most everyone _can_ do it (or writing / storytelling in Ira's case), but very few are actually good at it.