In high school I worked as an usher/ concession stand monkey/ clean-up crew troglodyte at the local cineplex.
After graduation, I was a shop jockey at Pedulla Guitars
When that job ended, I just did a series of random woodwork/ cabinet making/ interior and exterior house painting for a couple of years. Hated it.
Once I decided to get off my ass and got accepted to college, I took 2 full time retail jobs to earn money: The 3 to 11 shift at Bradlees; and the midnight to 8 am stocker shift at Shaw's supermarket.
Oh... and the whole time this was going on, I was playing in bands. Usually losing money at it!.. but that was never really the intent...
Once in college, I took a job as an usher at the college's concert hall (where I work now.)
That moved into a stage-crew light and sound tech gig after a couple of months. That led to a lot of freelancing tech gigs. Also, a summer position as a maintenance worker at one of the city's large outdoor concert venues. Did that 3 summer's in a row.
After graduation, I took the gig as chief engineer/ tech guy on the John Lennon Songwriting Contest Promotional Tour Bus. (It only lasted 3 months... but it was a very LOOOOOOONG 3 months!)
After that: more freelancing, and some part-time/ on-call work for a local sound co. Became one of the regular engineers at a local jazz club.
Finally, I was hired back on full time by my alma mater, as a stage manager/ concert engineer for all the small recital halls.
I eventually worked my way up into being the A1 tech at the main concert hall, which is where I find myself today.