Earlier quoted context omitted.
Start your own business, work fewer hours, and take the cut in pay. That's what I did, and I have no regrets. It's the best decision I ever made.
I stalked you a little based on that comment, and I can't figure out what it is you really do. You must be living a good life if you've got time to maintain a toy programming language ( https://github.com/kerkeslager/fur ), and you must be able to pick your work carefully if you're so passionate about GPL, which I can respect. But how do you make money? And how did you get started? I'd be concerned about losing healt…
> But how do you make money?
I do web development, mostly. I mostly ensure that I have work by undercharging for my services ($80/hour, which is pretty competitive for a Python developer with 10+ years of experience, 6ish of them in Python). I have low expenses because I live without some comforts (I live in a shared rental). I drive a 1996 Toyota Tacoma with 248K miles on it. I rock climb. It's not an extraordinary life, but it's mine and I like it.
> And how did you get started?
Parted ways on fairly good terms with my last salary job, without any real plan.
> I'd be concerned about losing health insurance or draining savings while losing the opportunity cost of employment.
Not to nitpick semantics, but you're currently paying the "opportunity costs" of employment. The opportunity costs of employment are what you lose by being employed, not the other way around.
Health insurance is literally my biggest expense, more than rent, and I'm a healthy 32 year old guy. The US is not a good place to be a human with a fallible body. What can I say, it's a risk. Plan for health insurance in your savings. Ultimately, not being in the US is probably the best idea--we're the only first world country with a third world healthcare system.
> How sure were you that your plan would work before you took the leap?
Not sure at all. It hasn't always "worked", either, I worked at a coffee shop and drove recycling to the dump for some local businesses, did landscaping, pet watching. I've never starved, never had to borrow money from friends or family. But I'm still not sure.
Your boss could lay you off tomorrow. Tomorrow's Friday, that's when they lay people off. There's certainly a risk in branching off on your own, but don't underestimate the risk of doing the same thing you've always done.
Probably you'll be okay no matter what choice you make, even if it's a mistake. It's just your finances. Your finances matter, but there are more important things.
EDIT: I'm passionate about the GPL, but can't really afford to be Richard Stallman about it. The reason I license my free software under the GPL is that I want it to push humanity forward, not get locked off in private codebases. But that's what I do on my free time, not what I do for work. I'd love to get paid to write GPL code and maybe some day I will, but most of the code I write is closed source for companies. Maybe that makes me a hypocrite--I like to think it makes me pragmatic.