It's 2am and I can't sleep again, so I might as well put down what I'm thinking about.
I've tried to define what art is a lot of times in my life and the definition that I'm currently using is 'anything that can be iterated upon'. I've been able to think about my work very clearly with this new definition. I'm now understanding where exactly I can call something finished, instead of going overboard with it. For example I could shelf this blog for a day and come back to it, re-read it, and improve upon it, but I know that it's probably going to serve the same function as a one-pass write-up. The quality won't improve very much and will have wasted a lot of time.
Once you get what you want out of a drawing, then any more work you put into it is, honestly, wasted time. If your aim is to go for a very detailed drawing then sure, it will require several iterations. But as I come to understand what I'm looking for in every drawing I see that most don't have to be very detailed at all. There's a time and place for iterating, mostly if you're doing something professionally or for your portfolio. Otherwise you always want to be working on something different.
Sometimes (actually all the time) I shelf a project and come back to it in a few months and iterate, but I only do that because I know that I'm not good enough to do it right the first time. It's a way for me to artifically enhance the quality of my work by creating it over a long period of time. What's better to do is put it out there, crappy as it is, and if you want to come back to it later you can call it a repaint, recolor, or whatever you like.
I won't hide from how bad I am anymore.
Template88
You are too attached to your works if you feel this way. Each piece is just a step, it can be forward,nowhere or backward, it's up to you to decide what direction you go but each individual piece is unimportant. What might be important is the destination you choose.