1. Assistant proofreader
  2. Paperboy
  3. Babysitter
  4. Roadside weed whacker crew
  5. Sandwich cook/pizza maker/pizza delivery guy
  6. Door-to-door political canvasser
  7. Photocopy machine operator

All of these by the time I was 20, I think. The assistant proofreader job was my first paying gig, helping my dad proof the galleys of his book. I had to read the original manuscript, making sure to pronounce each punctuation mark: open quote Like this comma close quote while my dad checked the galley against what I was reading.

The paper route I got when I was about twelve, after seeing a neighbor’s home computer — a TRS-80, the first personal computer I’d ever seen — and learning that it was actually within the realm of possibility for ordinary humans to own their own computers. In short order I was able to land a delivery route in my neighborhood, for the local afternoon paper, and held that gig for about a year, which enabled me to save up about $1,200. That was still maybe $300 short of what I needed to buy the Apple ][+ I wanted, but my dad loaned me the difference and we got the computer. That’s where I learned to program, got motivated to learn algebra, perfected my typing skills, and fell in love with the possibilities of technology to transform the way we think and live, an obsession that I’ve held onto more or less continually since.

Number 4 was a summer job with the Ohio Department of Transportation, during the summer before my freshman year of college, secured with the help of a politically well-connected friend and neighbor. It paid well, and the guy in charge of our teenage crew — an ODOT lifer named Eddie who was probably within a couple years of retirement and just didn’t give a shit any more — liked to take extra-long morning, lunch, and afternoon breaks, preferably parking the truck in the shade of a tree and napping. Drivers would sometimes yell at us out their windows as they drove by, justifiably irate at the waste of their tax dollars.

Numbers 5-7 were all jobs I held during a year I took off in the middle of my college career. The pizza job was a particular high point — maybe the most fun I’d had at a paying gig I would have for another decade and a half, until I got a job at Mobile PC in 2003. It was an unusually good combination of a great working crew, fun times after shifts were over, and a job where I actually got into the “flow” of doing my job and the hours just flew by. Plus, there’s honor in making a good sandwich or a good pizza.

I was a terrible door to door canvasser. That job lasted about 3 months. After that, it was a relief to sit in the hospital’s basement copy shop, running off hundreds of copies of various executive presentations or research reports for six hours a day.