There's something unique about enjoying an activity where you leave artifacts behind. Whether doing it professionally or just as a hobby, there's nothing quite like making something yourself and adding it to the world. In searching through some of my past work to accompany the case studies for this site, however, I'm reminded of one of my least favorite aspects of design: looking at my crusty old work. I think digital designers have a particular disadvantage compared to fine artists in that they are primarily making something to solve a problem for that exact time. While the painter gets to look back at their "blue" period and recall all the tumultuous or wonderful things they were experiencing at the time, the digital problem solver has to look at something that's been solved 10 different ways since then and all of them are no doubt more clever, more usable, and probably better for the environment.
I think part of the reason for this is the nature of software and how fast things move in technology. By this time next year I will probably have learned things that don't even exist yet. Something else I'm likely a victim of is spending a lot of time in the area just after the "suck zone" of the learning curve, where you're learning a ton and getting better all the time, but that's the catch. Every next thing I do is usually much better than the last thing I did and when you scale that over a number of years, you're bound to find some uggo projects peering up from under the basement stairs. Granted, there are a few interesting ideas that stand the test of time, but in my case those are usually more fluffy marketing pieces as opposed to UI/UX efforts.
I guess the one positive I can afford myself is this: if I keep improving the design & UX of our software, I bet I can outrun the demons living in my old ideas.