Genuine question, sorry if it's dumb -
How do you work when there's something on the line? I find I freeze, and it's just so much more difficult to properly organize myself to produce something I'm proud of. But you've been to conventions, and you sell your work, so I'm assuming you feel pressure at least *sometimes.* do you work with it? Around it?
Hey Tymbul, it's not a dumb question, it's actually a really good one. I can only answer it to the best of my own abilities, in regards to my own art and practice, so mileage may vary.
This feeling of something being is "on the line" was what burned me out hard in 2019/20. I'd been making and sharing art for decades and all the while my thoughts took the shape of, "it has to be GOOD, it has to SAY something, it needs to hit X and Y requirement to be worthy" etc. Wherever that habit of pressuring myself came from, it wasn't helpful. I would glare at the blank page and curse every sketch I made because it (and by extension, myself) wasn't ever good enough.
I knew something had to change, so I changed. I began trying to make art with no pressure. Instead of pushing myself I let my foot off the brake. I changed the way I talked to myself about art. "I'm going to make this as good as I can. And if I can't, there's always next painting." I began starting a piece with fast, easy, not-precious stuff--random paint smears, doodles, gesture sketches. The pressure was off when all I had to do was start with trash and play around. If it just wasn't working and I had to scrap it or start over, oh well, it was just trash. I still run into this pressure today, though. Growth ain't linear and all that. Old habits die hard. I have to snap myself out of it with a feral screeching JUST THROW PAINT ON IT RRRRRRRRGH and I can usually let up on the brakes enough to get it going. It's a journey.
I like to think of this in terms of dog training. If you punch your dog and yell at it, that dog is going to have fear and doubt and won't be a healthy dog capable of performing the tasks you ask of it. But if you use positive reinforcement, they develop confidence and become dependable and sturdy. If you sit down to make art and every time its a barrage of IT HAS TO BE GOOD! YOU HAVE TO BE PROUD OF IT! EVERY NEW PIECE HAS TO BE BETTER! IF IT ISN'T YOU'LL BE A FAILURE! WHY AREN'T YOU DRAWING YET then man, that dog is cowering in the corner, it is not going to sit or fetch or anything. What if instead you said, "Okay! Time to make something. Let's do warm-ups and thumbnails to prepare so I'm ready to jump in. I am open to surprising myself by making something I'm excited about, but I won't beat myself up if today isn't that day. I know by doing this I'm practicing and getting better, it is never a waste." You are much more likely to Do a Thing if that thing feels good to do. That's just being an animal, man. Positive feedback.
To be honest, though, I still haven't found a successful way to make commissions less like pulling teeth. My method of art-making is to fuck around and find out and that's not a conducive method for a comm, which usually has a ton more expectation and strict parameters and my nemesis: Should-Look-Like. I am good at some things, I am not good at comms. Progress is not linear. I am still learning. My efforts to let up on the brakes made it so the car was a lot harder to control... for better or worse.
Hope this helps. Mostly, my advice is to find out how making art can feel good to you and then make a ton of it. Make more art than you think you should. It gets easier. And don't punch your dog.