OK, here’s the decision after much discussion.
I’ve ironed out the financial agreement on this marketing/sales project. There shouldn’t be any more problems going forward.
I’ve agreed to extend my teaching contract for one extra year because that gives us the best way to transition forward. And it’s officially my last teaching contract. We’ll spend the year interviewing candidates to replace me. In exchange, the contract will have adjusted terms to limit the workload so that I can work a second job. But it does mean I’m gonna be cold for a bit longer and teach more than I wanted to. I’ll do my best anyway.
So I’m going to focus on getting a solid job in software that offers: full remote/async (can work from literally anywhere in the world with no set working hours but based on performance) and good pay. Bonus points if they are based in or have a presence in Japan and have perks related to life here (for ex. Japanese lessons). If that proves too narrow of a criteria, I’ll take a fully remote gig that’s Japan-only with mostly flex time, and ensure that I don’t have class during core working hours.
I’ve got a basic app that I’ve built to automate some of my work. I’m going to continue improving my skills and flesh it out. My boss is really keen on it so there’s an opportunity to either have her become my first customer and/or get her to help build out the Japanese parts and sell it as B2C as part of our marketing (she would become an affiliate) or maybe go B2B because if it helps us it would absolutely help other schools. That part isn’t clear yet but I’ve talked about it with her and I think it’s worth a try.
I’ve got my work cut out for me, and I have a clear deadlines and goals now. It feels fantastic, and, to be cliched, I feel like a huge weight has lifted off of me.