Always line something else up first. If possible, also have enough money to last 3-6 months without a job - makes things a hell of a lot less stressful. We would essentially just bank any bonuses throughout the year, and it would afford us a nice nest egg in case something ever happened. However it needs to remain untouched.

It seems that everyone already answered, but I will give my perspective as well.

It’s definitely very different for each person. Some people need the money more or less. Some people suffer more in their job or less. Some people have more options or less.

I like to imagine a scale where on one side you have the reasons to leave and on another side you have the reasons to stay. And reasons to leave are multiplied by how many options you have outside.

So if your job is terrible and you’re pretty financially stable and you have a lot of options for finding other jobs then the scale would lean towards leaving. Or if your job is pretty terrible, but you’re not financially stable and you don’t have a lot of options, then the scale would be pretty equal and you’ll have to take a risk.

I am a homeless man in San Francisco because I quit a public sector job that I was not allowed to fix with my good-ass coding skills. I have no regrets.

I’ve never had trouble finding new work, so it hasn’t been too scary for me. Once I got laid off and found another job before the severance ran out but that job turned out to be a disaster and I got laid off there as well, only months later. That was definitely discouraging but a relief as well. I got right back on the horse.

However now things have changed a lot. I am much more senior and earning a lot more. Senior roles are fewer and more competitive. And the job market has been a disaster this year. It used to be that I’d get a couple of recruiter emails per week and now I can hardly get a response to any job applications I send. So yeah. At this point the financial hit terrifies me because I have a lot more at stake and I don’t know when I could get back to where I am if I left. I’m not miserable but I am unhappy as well as bored. For now I’m just dealing with it. I’m a little afraid to be “dealing with it” for the rest of my days though.

I’ve never been paid enough to really do anything but feed myself, so I’ve never had to choose between working a shitty job and being homeless. Yet.

If I ever got a job that paid me enough to afford rent, I’d definitely be less willing to bail unless it was really shitty.