I listen to my stuff fairly often, even though by the time I've finished producing, I've already heard it a million times.

However once I've decided it's ready to stop tweaking it, I usually listen a little less critically.
I'm actually pretty satisfied with what I create, even if I recognise how terrible the production quality is, or how repetitive the beat is in this particular section, etc.
Sometimes I just listen to old pieces simply for pleasure. That's a huge part of my motivation for writing music; it's the chance to specially tailor music to suit my listening preferences.
Listening to a finished piece as if it came from another artist is a huge reward.

Of course, if I go back more than about 2 years ago, I can't bear to listen to the poor quality... It's too cringeworthy to enjoy.

Also having other people around while listening to my music instantly makes me more critical of what I've done. It's mostly a general 'fear of failure' or 'what if they don't like it' thing, but it can make me really uncomfortable when I'm listening to my own music in the company of others.