I've realized that my level of financial safety I feel is directly tied to the amount of margin for error I have.

I'm from rural Indiana and grew up in with a comfortable but relatively low standard of living. Going out to eat was spending $3 at Wendy's. All dollar amounts any business talks about still feel mindblowingly large.

Then I got a computer science degree and got into remote freelance web development. At first it was hard, but with shared rent at like $120/month, it didn't really matter. I could keep trying until I succeeded in freelance without much risk because I had margin for error. Rent was covered in a few hours of work, and every subsequent hour built my buffer.

My rate went from $50/hr to $90/hr to recently $125/hr while still living in this low cost of living area, and my margin for error increased even further. I think I got used to this and didn't realize how much margin I had compared to many people. I realized I could live a comfortable life working only 10-20 hours of billable work a week, and combine that with regular recurring clients and there was very little need to hustle for new work. Life was pretty chill. When my first girlfriend told me that "you make more in a day than I make in a week" I didn't really know what to say. Of course we were talking about something like $900.

I never understood how people could say that $100,000 a year wasn't enough money until I moved to Chicago. I kept the same relative amount of income at around $60k working 10-20 hours a week, but my cost of living probably quadrupled. I loved it there but there was so much less margin for error. My finances started to drain and my stress increased, and I had to take more work that I struggled to complete to pay my now $1080/month rent and buy $30-$40 dinners when going out with friends. And there were people around me making much less somehow surviving. I lived like I had margin but I didn't, so I recently moved back to Indiana.

My real goal is to spend more time working on my business anyway, and hopefully if those take off it will give even more margin. But until then, freelancing a few hours a week and living cheaply gives me infinite runway and no financial stress. Sure this town has 6000 people in it and the most exciting thing to do is walk around the local park, but I once again have margin for error.

All that to say, the van dwelling people seem to be experiencing something similar, as you describe. If finances feel like quicksand, there are interesting options for ways to gain leverage, especially as a developer.

Some of the most free and wealthy (in terms of purchasing power) people I know do this. Compare the person who can't pay all the bills with $20k a month (a figure I recently heard from a real person!) with my friend also living in this town who is extremely frugal who spends $1000 a month and built up $40k in savings from a job. She is now writing novels and basically doesn't work unless a good freelance gig comes up.

Another friend moved to Lithuania and teaches part time at a college for a visa and worked remote tech support for a US company and made $60k a year and saved nearly all of it. Now he does whatever he wants.

Nomading is another way to get that same leverage. There are others if you are creative. I'm always excited to read about people doing interesting things like living in vans, because I've found there to be so many more options if you are willing to look outside the normal ways of doing things. Many are even pretty comfortable. You may not want to move to Indiana or Lithuania, but it is an option.