I'm usually ok with my painting being crap, because it looks fine on the table top.
Seeing pics of peoples master pieces sometimes makes me feel down about it, so I've mostly stopped doing that, outside incidentally.

But holy shit, every now and again I play a game and I just feel so bad about how bad my models look. I feel I've never gotten better, just slower and more effort to get to basically the same quality I've always done.
Feels bad, man.