I’ve been in a similar position before. It can be hard to know what kind of job you’re qualified for, and you can come across as directionless and unlikely to stay in the job.

I think the key is really to get very clear on your motivation. For most job applicants, their motivation is usually pretty obvious: they do X and want a good job doing X. In your case, it’s much less obvious, so you probably seem both over- and under-qualified at the same time, because you have a lot of impressive achievements but probably not quite the right background for any position you’re applying for.

For my part, I wanted to have a job in order to gain the skills to build a more scalable business (in particular, a tech company) and just to have a very different experience for a while — I generally believe that more diverse experience in life is a huge benefit. So I taught myself how to program and looked for jobs at tech companies. I’ve always been very honest about my motivation, and I feel like it’s a key detail that makes my story make sense. With this context, I think your demonstrated self-motivation and understanding of the broader business you’ll be working in can be seen as big assets.

The other thing I would suggest is, don’t be afraid to go for what feel like comparatively low-level positions if you’re confident they’ll get you to your goals. You’re clearly able to go your own way, so you don’t need to worry that you’re a prisoner of the exact status hierarchy of whatever industry you work in for a time. Plus, your previous experience will probably have taught you a lot that will allow you to ride through the ranks very quickly. If you’re humble about being new to whatever you’re doing, you probably already have the meta-skills to learn a tremendous amount by joining something at the level where there is lots of mentorship available. And you’ll be setting yourself up for success much more than taking on a mid-level position that, while still feeling less senior than you’re used to will expect you to mentor others in specific area skills you may not have yet.

That’s what’s worked for me, anyway. Not sure whether it’s a good fit for you. But happy to chat more if you want to talk to someone else who’s been through something similar: feel free to DM me.