I thought it'd be fun to create a list of jobs that people loved, enjoyed, or had fun with throughout their lives. Could be a good source of information for people to look into when they are entertaining Semi-retirement or even just something to do when they are FI.
I was a tour guide in a cave as a teenager. It was great; I spent a lot of time hanging around with other tour guides waiting for tourists to show up, and the tourists were generally nice people who asked basic questions. Very carefree and low stress. Also low pay, I made minimum wage with a rare tip.
I was also a part time tutor for a tutoring franchise; you taught their curriculum to the kids that came in. It was pretty easy, although some of the kids, on their bad days, were handfuls, but the sessions were only 1 hour long per kid, you had 2-3 kids per hour. It was very part time, I think the most you could work was 2 3-hour shifts each day in the summer, it paid something like $10-12 an hour.
Also here is a CBS article about 8 jobs that most people think would be fun, but really probably aren't:
Advertising Account Executive
Public Relations Officer
Commercial Airline Pilot