I quit my very good job twice to go sailing. -In 1983 I quit for 1.5 years and sailed to Mexico. Had a great time. My ex-job paid to ship the boat back to get me to come back. Lucky me. -In 1998 I quit an exec job to sail Annapolis to Trinidad etc for 2.5 years. Carribean trip. After that I had a couple lower pressure jobs before I retired. It worked out well and I'm glad I did. But at the same time, I left a TON of money on the table by doing that second trip. I would have a lot of money to give my kids when I die if I hadn't done that, or waited even just 5 years or more.