Hey Ateacup - I'm a Generation Xer with kids about your age. You're triggering my parental instincts, so take this essay for what it's worth! :-D

I think it's admirable what you're doing, forging your own path. The 8-5 economy is a trainwreck, especially if you're a creative soul. I always remember people saying, a "gig" economy sucks in that you are not guaranteed a paycheck. Well, a corporate job has no guarantees either. I've seen my own job go away when a corporation moved out of state. I had no say in the matter. There ain't no guarantees, and especially with corporate USA.

I've been on the career track that you've described since I graduated college in 1992. Struggled with my own bouts of depression and anxiety because of it. As a creative soul, I kept doing it to feed my family.

However, the last couple of years, I've finally started doing creative stuff on the side that I'd been wanting to do the last 25+ years. I always loved gaming, acting, drawing, creative endeavors, but I could not find a way to monetize it. The Internet has opened things up for this new economy. So a few years ago, I finally listened to my younger self, and picked up magic as a hobby, to feed some of that creativity. Now I'm a part-time professional stage and close-up magician. I started out slow, and built success upon success, gig after gig. Now, people are hiring me that I don't even know, and it's a rush! It's like my 25-year-old self is waking up after being asleep all this time.

I sometimes lament the time lost, but I'm mostly looking to the future. In a few more years of this success as a magician, and I might be able to "retire" from my job and do full time magic and other creative stuff. Fingers crossed.

The reason I didn't do it back then was FEAR of non-conformity. That fear was instilled in me at a young age, because that's the only way that my parents and advisers knew how to go forward. I've learned much since then. So my advice: Be a dog, or whatever you want to be, and find ways to monetize that. Keep your eyes open for new things that you want to do that you can monetize as well. The Internet is all about connectivity - you can find people that want your creative spark. Cross-market yourself like you do on "# Find Me Elsewhere" at the bottom of your post. Hit all the platforms, and keep a lookout for some that haven't even been invented yet. You will eventually make it "adulting".

Good luck.