In July 2001 I quit my tech job of 8 years so I could take some time to de-stress and work on projects thinking I could just jump back into a job 6 months later. Of course, that timing was really bad. Since there weren't any tech jobs available, in the Fall of 2002 I decided to go back to school and get a masters. We had a few months in 2003 where I made just enough money to get by by going to the Goodwill outlet store and buying books that could be sold online for a profit - Goodwill got wise to that arbitrage and started their own online store which kind of put an end to that. Had a few contract jobs in there that lasted anywhere from 4 to 6 months, even had a summer internship (at age 40! That interview was interesting), but it wasn't until 2006 that I found something permanent again. Fortunately we had paid off our house back in 1999 otherwise it would've been even scarier.