[xpasky]

Two patterns - you don't stick with projects for long (perhaps really like freedom) and want a safety net (medical insurance). (Plus you could be a better communicator, the post you wrote turned out into not so coherent rambling halfway in, tbh.)

Unless you are willing to relocate to a saner country than the US, you need to give up one. Most commenters here advise to give up some of your freedom and stick it out somewhere, and it's a very valid advice. I just want to add that you can also consider going the opposite way - and just get a steady stream of shorter-term gigs freelancing (e.g. Upwork).

There is a lot of upsides - it's easy to work on projects completely remotely (including written only with no voice/video) which rules out any interpersonal issues; you can work on bite-sized projects which might be your cup of tea, at the same time some of the projects will turn into long term opportunities; you can actually put the best projects on your CV.

Freelancing won't give you great medical insurance. And at the beginning (with no history on the platform) it's a grind to succeed in the competition and you need to work your hourly rates up from a low base. Longer term it can pay nicely, you'll be working on a lot of different things and learn what you enjoy, and it should teach you a lot.

Derisk this experiment, try it out while you are looking for a job.

[rattray]

Yeah, I'm not sure how well it'd work out but Upwork is likely worth a try. I'm not sure if fixed rate or hourly would work out better.

It's important there, as anywhere, to approach interactions with humility.