Very unusual story but I left my first developer job 2 years after college to try to start a business in an unrelated field. The business is alive, but not doing well and I'm tired out and need to return to the work force.
I've been job hunting for a remote developer role for about 5 months now and have been getting rejection after rejection. HR / recruiting always thinks I don't have enough experience (even for entry level) but whenever the interview involves another technical person they usually see the potential in me.
I have a portfolio, I have my own website, I love doing side projects (web apps + apis). I can easily spend 15 - 30 hours a week on them and have worked on them for over 4 years now. I even have a bachelors in CS for whatever that's worth.
I write cover letters. I put a lot of effort into improving them based on feedback / what lands a interview. I basically conduct AB testing. I've tweaked my resume many a times.
I've tried startups thinking the business experience would help.
I've tried medium - large companies thinking they'd be more open to mentoring new-ish devs.
I don't have much of a network to connect with, and I come from a rural state with little tech.
I'm not expecting the world and would be perfectly happy with a junior role.
Has anyone else been in similar shoes, and if so how did you escape it?
Like really hard?
Just asking.
My first guess is that you're facing a triple bang situation
Everyone in a hiring situation hates you because you are young, semi successful, had the audacity to try your own thing, had the temerity to think you could escape and were therefore better than everyone else so now they need you to suffer -- along with a few other dynamics.
Are you specifically looking for junior and entry roles? I would. If you end up being too good then just get promoted early or bounce if it's too late.
I'd look at startups, fast growing and maturing startups like Stripe and post-public startups, and all the typical stuff applies when trying to get a job.
Also look at dev-adjacent jobs like tech support dev evangelist, tam, etc. The not-strictly support ones will be more open to proactive people with skills outside of just coding and complete unquestioning obedience.
5 months is a good amount of time but getting hired after just three would be a miracle. 6 months closer to normal. A year before we know you're doing something wrong.