I left a job I had started immediately after college and had been at just under 3 years. We built and sold software. I figured I needed to branch out and not get stuck at one company.

Left and went to a company that sold insurance (i.e. not software). My boss was a psychopath and expected everyone to be in the office 8-12 and 1-5. No exception.

I lasted 5 months before I scheduled a resignation email to send at 5:30PM on a Friday, telling them I wouldn’t be at work on Monday. Went back to the first company and stayed another 9 years. Just resigned from that company last week (really unhappy with post-acquisition re-org) with nothing lined up. We’ll see if regret follows…