This is in the vein of "starving artist." A starving artist makes sense. How did it happen to a software developer? "Starving" is not much of an exaggeration. I have most certainly been eating less since late 2020, in part to save money. So far, this seems to be on the healthy side, but still.
Why am I writing this? I'm reminded of a potential client I wrote back and forth with. She said she was making $50 / hour, and she was always busy, but she had no money. My expenses are tiny. I was so flummoxed by that, that I concluded that she must be crazy.
Just about everyone has peaks and valleys of ability. I suspect the higher the peaks, the deeper the valleys. I'm likely mildly insane in a number of ways, and I am most certainly dysfunctional in a number of ways. It may be useful to explain how it came to this. I probably should have asked her how she wound up in that position. Thus, I explain how I wound up in mine.
Looked at one way, the main problem, or at least the start of the problem, is that I am a genetically hard-wired night owl. When I first worked 9 - 5 for most of 1997 - 2002, I gained 60 pounds. Once I stopped working 9 - 5, the weight came off fairly quickly.
A certain political category natters on about discrimination (and has the resources to use it as a devastating weapon). They talk about categories of people who need "affirmative action." If you want to experience discrimination, try being a night owl.
I got laid off during the Dot Com Bust in 2002. I didn't attempt a 9 - 5 job again for many years, and that attempt was a predictable disaster.
There exist nighttime technical jobs, and I've gotten very close to getting a few over the years. One problem is those jobs are somewhat off my core expertise. I got through two phone interviews and was flown to Amazon Web Services to interview in 2010. I applied for that job because it was 3pm - 11pm. But it was a Linux sysadmin job, not a development job. At the time, I was a decent sysadmin, but only as a side-effect of development. I've never had the sysadmin title. The questions in-person became several times harder. Also, I pretty much demanded an interview as late in the day as possible, but 1pm is still very early for me when I just flew across the country and then have to be awake hours earlier to be ready. I was tired. It's hard to say whether being in top shape would have mattered. I still remember questions that I could have answered if I were more awake.
Feeding back into the night owl thing, I'm a Myers-Briggs INTJ, and I am an extreme "I" (introvert); I almost peg the scale on "I." That means that dealing with people in most circumstances is tiring. Add to that interviews that are too early for me. Going through that process takes a lot of energy, and as close as I got, I eventually decided it wasn't worth the energy drain. The process failed cost-benefit analysis.
Along a similar vein, I've done customer support before, but with very, very technical customers. I can't stand the syrupy mush of "Oh, I'm so sorry that you're having that problem. I will help you with that." That killed another attempt.
I talked for a few minutes to a DARPA LifeLog (Facebook) recruiter at his request. I politiely cut him off a few minutes into his spiel to give him my spiel. To his credit, he tried to figure out a way to solve the "King of the Night Owls" problem, but he couldn't. He said he would take a day or two to look into it, and he contacted me a day or two later to say he couldn't figure a solution.
Years ago, I gave my spiel to a recruiter, and his genius idea was that the job description said "flexible hours" and "work from home," so let's get you in there and show them how great you are and then we can negotiate. I was almost immediately miserable and figure I was working at 50% capacity, if even. The joke was that after a month, when the recruiters would be paid, the boss wanted to keep me. He asked what it would take to keep me for two years to make paying the recruiters worth it. At that moment, I wasn't sure about another 2 days, let alone 2 years, and I wound up quitting roughly 2 days later to make sure the recruiters weren't paid. I was too furious at them. Ideally this needs more details, but perhaps later.
A few months later, another interview went splendidly. As best I can tell, I wasn't hired because the guy who was supposed to be my boss was fired that day, and I fell through the cracks. It was a 2pm interview, and it was 30 miles away in downtown Atlanta, so I was awake enough. I of course got stuck in traffic on the way home. Overall, it was an exhausting process, and too much to go through for no result.
So I gave up on the job recruiter / "real job" path. I've been attempting freelancing ever since. My biggest problem is communicating about money. The sales part is of course difficult, but it became much more difficult after I set myself up to get burned on money over and over again.
I've had a steady (but always-part-time) project since 2016. One point being that if I can get through a few payments, it will last. That project was more-or-less paying the bills until my client's second child was a few months into fetal development. (Last I heard, the child is doing fine. He's beyond a toddler now.)
A related cause is one of the feedback loops I've got myself in. I started gently pushing people away who weren't helping me figure this money problem out. Thus, I have isolated myself, and I feel yet farther away from people generally. This makes it yet harder to deal with strangers in ways that are already stressful. I seek apprentices to try to solve this problem. I have two active apprentices right now. They may wind up helping me solve this. We'll see.