I’ve done this twice. When conditions and stress and the possibility of anything getting better we’re all so bad that I literally thought it would be better to

I’ve done this twice. When conditions and stress and the possibility of anything getting better we’re all so bad that I literally thought it would be better to be homeless than to keep going at work. The first time I was very young, had no savings, and no professional network. I ended up moving across the country to stay with my family while I got a new job lined up. It took me almost no time at all to get hired at what turned out to be a very good company. The second time, I had 6 months of expenses in cash and more in long-term savings of various types. For whatever reason, the way the interview dice rolled that second time it took me 8 months to get back into a solid gig, I chewed up all my cash savings, and it hurt a little more because I was counting on professional network contacts that made promises they didn’t deliver on. So, your mileage is going to vary. I was probably too ambitious in my initial searches the second time around, looking for a big boost in both salary and title. I can’t speak to how common it is, but I will say that the frequency of it is related to a few key factors: 1. How startupy the company is. How willing they are to burn people out with long, pointless hours. 2. The strength of your savings and family and friend networks. How likely are you to be actually homeless and broke vs. just unconfident because you’re sleeping on a couch and don’t have a job right now. I don’t think people do this as much at mature companies because the overall amplitude of how bad and how good things can get is smaller. Startups can have really great highs, but the lows can destroy you. The worst most established companies will do to you is slowly wear you down, so there’s often a lot of time to plan an exit and get a new gig before you flame out.