Not counting times when I was a full-time student, the longest I've gone without working was a year--the last three months of my first pregnancy, and the first nine months after my daughter was born. But I've not had a lot of traditional employment--I was a nanny for a long time, then a childcare provider in my own home, and most recently a freelance writer-editor, also at home. The last time I had a job like most people define a job, I was 17-18 and worked at Toys R Us for 2 months and then a record store for a year.
The one who buggers a fire burns his penis
-anonymous graffiti in the basilica at Pompeii
I've also had a habit of acting bizarre in the workplace in the past (in a goofy way). It's the one place where I was able to entertain others. Unfortunately, I lost jobs for expressing my off-the-wall ideas. But unfortunately, it's in a conforming work setting where I feel energized doing it.
And when I wasn't acting off-the-wall, I was cursing people out or slacking off because the work environment was uncomfortable.
Ever since I've started working, I've never been unemployed.
"When a resolute young fellow steps up the great bully, the world, and takes him boldly by the beard, he is often surprised to find that it comes off in his hand, and that it was only tied on to scare away the timid adventurers." - Ralph Waldo Emerson
Well, unless you count being unemployed while I was a full-time college student, I've only been unemployed for two months since I was 16. That time *sucked*, and I was full of anxiety. Right now, I'm looking at almost two weeks next month that I'll be unemployed between being a grad student and having a final job interview with a company I really hope to work for.