My entrance in this circus in Toronto was as a musician. They needed a bass player for one of their monthly cabarets.
Once I had my foot in the door, I found that lots of people were happy to teach me some tricks climbing silks, juggling, fire spinning (I practiced but not with anything lit on fire), and of course a bit of clowning. If you can find a circus, you could probably work your way in on your service experience and storytelling. The weirder you are the more likely they are to warm up to you, in my experience.
The line between the community and the performers was very thin, so I got to meet a lot of other people that did it part time. A lot of those people worked in tech as well, and the first time I installed Ubuntu it was because one of those people helped me out.
It was a bit of a rough lifestyle, though, as work tends to blend right into partying. Those who kept it up were known to be pretty tough. Sketchy the clown (who ran for mayor of Toronto) was also known for walking himself to the hospital after being shot in the chest half a dozen times. He was visiting NYC for a tech conference back in the 90s (he showed me the scars).