Greetings. Thank you for sharing so vulnerably and honestly.
I’m going to offer you some advice that won’t answer your immediate question, but hopefully will answer a bigger one.
Nobody has explained my inner turmoil for 2 decades as good as you just have above–and I desperately wish I had been able to explain it to the right people back when I was your age.
Here’s what I can tell you: the “discipline” you seek comes less from what it is that you’re doing, but more from developing a ROUTINE which allows you the peace of mind to not get lost in your (obviously powerful) ability to fantasize about all the other things you have the capacity to excel at.
For some people - probably quite a few here in this forum - doing something with your hands is not merely “more interesting”, but actually a method of survival. If I didn’t have the ability to regularly escape my thinking mind by creating something with my hands, I wouldn’t be here today. I would have self-cancelled long ago.
I have to leave for work so I’ll have to be a bit brief. It’s not what you do, it’s that you design your day so that you maintain a state of peace as you transition into what you’re doing. For me, getting in my little car and going to the same outdoor cafe and with only pencil and watercolors saved my life - it created a momentum that propelled me past the all-destroying tsunami of “what should I be doing with my life” thoughts.
I would say keep life as simple as you can while you begin to start putting the magnifying glass of routine and sequence to the paper of your time and burning in some growth in your skills and competence. Make it more complex only after you’ve got a SOLID rhythm of doing something every day that brings value in the marketplace. You don’t necessarily need to “live out in the country” but just recognize what the secret utility of it is for you (apart from the fact that nature is grounding, healing, and nourishing, and anchoring).
And a bit about your original question:
I would cap-off the seasonal job thing at around age 32–UNLESS you’ve got a couple years of hard evidence by that point that it is a viable way to earn a good living and you can integrate it into a bigger plan. I didn’t want a family at age 25, but now I’m 41 and lonely+broke because I didn’t take the steps early on to realistically project how my professional choices now would impact my financial future.
Anyway good luck. It IS possible to live outside “the system”…but you have to commit to being somewhat systematic in your experiments in doing so.