Three years ago, I finally got my neurological disorder correctly diagnosed. It’s not cured, but I finally understand my triggers and can manage my symptoms. (I can discuss details in a comment below if people want, but this post is already too long.)
I’m trying to re-enter the software industry now, but I’m feeling a little lost. Providing work references is hard when you haven’t been in the field for five years, and everyone remembers you as the guy who was checked out all the time. I still have recruiters reaching out to me, but they always assume I have 10+ continuous years of experience, which I really do not, and none of those interviews have lead to job offers.
Where do I go from here? What places are likely to be open to a candidate that superficially looks overqualified, but comes with a dozen red flags?
Does it make sense to try to reset my career by going for a master’s degree? Should I double down on my (zero revenue so far) side projects until I have a respectable portfolio to share? Should I dive into open source contributions in hopes of getting references I can use for job applications? Or should I skip all that and aggressively apply to jobs now?
I still love programming. I believe that I’m good at it, when I’m not fighting other problems at the same time. If I’m going to work a 9-to-5 job, there really isn’t anything else I want to do.
Frankly, with the job market the way it is right now, you can probably find a job as-is. Just don't expect a big name or interesting work.
> Once upon a time, I earned a degree in software engineering from a major university, and for the next seven years I worked a string of jobs in Silicon Valley. (Not really FAANG companies, but still names you would recognize.)
This is still good experience! The technologies may have changed a bit, but a lot of the dynamics are timeless, and even if you didn't enjoy it at the time you can bring more experience than a fresh graduate.
> Providing work references is hard when you haven’t been in the field for five years, and everyone remembers you as the guy who was checked out all the time.
Get in touch with your references, meet up with them, tell them what happened, see if you can agree on a few positive aspects that they are comfortable vouching for. It's possible that they had a different perception, or things seem better in hindsight. It may be that they really cannot be used as a reference at all, but it's worth trying and at least you'll know. Yes, it will be a bit awkward, but it's what you need to do to build a network. In any case, using references is pretty rare these days, so this isn't a bit deal.
> What places are likely to be open to a candidate that superficially looks overqualified, but comes with a dozen red flags? > Does it make sense to try to reset my career by going for a master’s degree? > Should I double down on my (zero revenue so far) side projects until I have a respectable portfolio to share?
You should put in some work to put together a clear story and resume about your skills, experience, and side projects. You may find it useful to work with a career coach on this, since your situation is complicated, but salvageable.
Something like:
Career objective: Re-enter the tech industry after career break due to medical issues which have now been resolved.
2018-2021: Worked on x, y, z personal projects, which kept me current with a, b, c technologies while taking a career break.
2016-2018: Company C, project x, y, x
2013-2016: Company B, project x, y, x
2011-2013: Company A, project x, y, x
You cannot and should not try to "reset" this, ignore it, hide it, etc. People can find things via google, linkedin, background checks, asking around. You just need to come up with a clear story and own it, focus on the good things, admit the mistakes, share what you learnt along the way and can bring to the table.
Good luck!