Well, as a kid I had every plan to become a Lawyer. I discovered theatre in Jr. High and that ended the practical ideas right there. I went through college imagining that I would occasionally be an aide in a Special Ed. classroom or similar program to help pay the rent but mostly I would wander the earth traveling from acting job to acting job.
I started working in retail (after an extremely brief stint with a citizens action group and one summer spent working as a seasonal travel agent).
A few years later I got back into theatre, that started nudging into time I was spending bored out of my mind behind a cash register so I quit my day job.
That started the period I affectionately refer to as my "whirligig". That is a word I picked up from an astrology column of all places. ("Don't feel bad for the barista with an MA. Don't worry when you see that young lawyer selling shoes, they are probably both whirligigging. That is the act of going through life, gathering up everything, seeing what fits and discarding everything that doesn't.) During that time I was a temp, a writer for the local arts paper, a calendar editor for the paper, sold ads for a theatre company, worked for the local IATSE and rediscovered stage managing. I fear for the day I will have to explain that period on a resume.
Eventually my whirligig made one thing very clear. I don't like working outside of theatre.
I've been very fortunate in that I've been able to stage manage for almost every company in town and I have finally found one that is willing to pay me full-time to pursue my calling.
So..I guess I had 2 careers and a little 30's crisis between them? You make the call.