Paper route at 10 years old until I was 14 or so. I bought a PS2 and my first computer with that money.

Then I worked part time at a pizza joint until I was 19, just as a cook. I sometimes did opening shifts on weekends but not often. By Grade 11 / 17 years old I only attended high school until lunch break for my last two years there (I exploited a few specific classes, had 52 out of 100 credits in my first year alone) and then started work by noon and working until 7pm. A lot of my friends worked there too so they'd do 4pm - 7pm after school, just the supper rush.