When you spend hours of your day, working on a piece that you really want to make, and you're actually decently happy with the result, but end up overwriting the original document with a rough sketch of another WIP...
This shot was a picture I made for Sonic X Shadow Generations: One Step Forward, and Falling Back.
I was pretty happy with how it turned out, since it's one of the few pictures I've done with real improvement since my first time really drawing Sonic or Shadow, which was... over a year--to two years ago? Don't remember how long it's been, but anyway, I was happy with this.
Then, opening Photoshop to sketch some more, I noticed the document for it, wasn't listed in my 'Recents,' and was confused, until I saw the title for it, was listed, but with a different WIP sketch, instead. So, I ended up overwriting the previous save of the document of this finished shot of Shadow and Maria, without knowing it. So that document doesn't exist anymore, and I'm so mad about it!
It literally drained whatever motivation I had to draw... Like- COME ON!!! All that work!