The Best Dead-end Job I Ever Had: Bike Messenger in the Late ‘90s

by Joshua Michtom

You probably have an idea of what a bike messenger’s job is like, either based on the many media depictions of the job, from “Quicksilver” to “Premium Rush,” or on the fact that in many cities, messengers do seem perennially hurried to the point of madness. Your impression is not wrong, because most messengers work for messenger companies doing piecework — they are paid by the job — so they have an incentive to do as many jobs as possible. That was not my job.

In the late ’90s, I worked in what New York bike messengers of the time somewhat sneeringly referred to as “private service.” That means that I was attached to a single business that had enough deliveries each day that it was more economical to keep a messenger on staff at some menial wage than to pay by the piece. Messenger service riders — at least, the ones for whom the job had transcended mere employment and taken on the mantle of culture and avocation — looked askance at private service riders because we were free from the defining element in messenger culture: hustle. (One can only wonder how many ponderous undergraduate papers on the ills of capitalism were inspired by a system in which employees doing hard manual labor for 140% of minimum wage looked down on employees doing somewhat-less-hard manual labor for 120% of minimum wage.) Despite this relative lack of status, it was just about the greatest job I’ve ever done for near minimum wage with no health insurance. This was principally because of the non-monetary benefits.

First and foremost, I got to ride my bicycle all around New York for hours at a time. Obviously, not everyone would consider this a benefit, but I did. At 19, I was finally back in New York after my father dragged me kicking and screaming from Brooklyn to Portland at the age of 13. I was suffused with the late adolescent instinct toward self-invention, and my project was to become the dyed-in-the-wool, street smart New Yorker I would have already been if I’d gone to high school in Brooklyn. Add to that the teenage male sense of invincibility, and I could not have found a better job.

What’s more, despite their second-class status in the messenger world, private service riders weren’t visibly distinguishable from messenger service riders, so in a lot of circumstances, we got to be part of the larger cultural subgroup. Basically, it was a lot of random fist bumps, free beers, and impromptu races through traffic. This was a time when there were still a lot of messengers in Manhattan. There were messenger bars and messenger parties and messenger freestyle rap battles on street corners. In short, for a 19-year-old, it was heaven.

And, of course, there was the image. Outside of messengers themselves, that private service distinction didn’t mean a thing, so yo non-messengers, I was another soldier in an army of professional badasses. This gave me something I’d been sorely lacking during my awkward high school years: swagger (nobody said “swagger” yet, but that’s what it was). I could walk into the office of a modeling agency or design firm, sweat dripping from my shaved head, and actually believe (erroneously, I’m now sure) that more than a few of the attractive young women whose paths I crossed couldn’t help but let their eyes linger on my well-toned leg muscles as I walked out toward the freight elevator. (Remember: I was 19!)

The real benefits, though, were at the company where I worked. It was a small color printing lab — an anonymous four-room suite in an anonymous pre-war building on an anonymous, mostly industrial block in the West 20s (the ground floor of our building housed a strip club; in the basement there was a shooting range). In addition to the owner, there were five employees: the manager (a rock drummer in his 30s), two twenty-something helpers who worked the printers, another messenger (who worked the afternoon-evening shift), and me. I worked Monday through Friday from 8 a.m. to 1 p.m., and the workload was such that I could be in and out on deliveries maybe a dozen times during a shift, with a healthy helping of down time for studying, sleeping, or shucking and jiving with coworkers.

The best days, though, were when the owner wasn’t in. The manager, you see, had two side jobs that had some impact on our workplace. As a rock drummer, he would frequently use slow moments to design and print concert posters, which he would then ask me to put up when I was out on deliveries. The boss didn’t mind this, and neither did I. The other side job, though, only came into the office when the owner didn’t. On those days, all printing and delivery work was postponed until 11:00 a.m., and the work space was given over to a triple-beam scale and a gallon-size Ziploc bag full of weed. While the contents of the big bag were carefully transferred into multiple little bags, the two helpers and I would lounge on the couch in the break room, drinking coffee and getting very very high on complementary weed. When legitimate work commenced at eleven, I would nap for 45 minutes, then load my bag with deliveries and do all my runs in an hour. When you are 19, there is nothing bad about making $7.50 an hour for three hours of weed-smoking, coffee-drinking, and drowsing.

Of course, all good things must come to an end, and my messenger job concluded as you might expect: with a traumatic head injury. Our evening messenger got arrested one weekend, caught up in one of those sweeps that made Rudy Giuliani infamous in the outer boroughs — cops arresting all the young men on a block where weed was in the air, holding them for 47 hours. I agreed to come back to the office after my afternoon classes and do the evening deliveries. As it happened, I left my bike helmet under my seat in my first class, and when I went back to look for it after my second class, it was gone. “Oh well,” I thought. I figured I’d buy a new one the following day. “What are the chances of me falling off my bike on the one day when I don’t have a helmet?” (You see what I’m doing here? It’s called foreshadowing.)

Needless to say, I couldn’t quite get around the express bus that stopped suddenly on Madison Avenue. My bike got around it, but I caught my shoulder on the back of the bus and slammed my forehead pretty hard on the pavement. Delirious, I got up, picked up my bike, and tried to keep going, unable to figure out why the pedals wouldn’t turn. It was because I had the front wheel of the bike pressed against the side of the bus, a detail I wasn’t noticing because the head trauma had rendered me temporarily blind (really!). A man who was walking by gently guided me to the sidewalk by my shoulders, saying, “Son, I think you better sit down.” My sight came back while I was in the ambulance, which was good, because I was able to catch a clear glimpse of myself in the reflective stainless steel of an emergency room instrument tray. Knowing I had a baseball-sized welt on my forehead kept me from asking the nurse out on a date.

I stopped by work two days later to return the package I’d had with me when I had the accident. Everyone cringed: the welt was still huge, and blood was trickling down beneath my skin, pooling under my eye. The owner gave me a week’s pay and told me to call when I was ready to work again, which was good, because my head was too lumpy to fit in a helmet, and if I’d had a regular doctor, I’m sure she would have counseled against a quick return to two wheels. Three weeks later, a less physically demanding job with better pay fell into my lap, and that was the end of my messenger career.

Since then, I’ve had some other dead-end jobs: waiter, house mover, law student (ha ha). It took me another fifteen years, but I finally have a stable job with a decent salary and good health insurance. Still, I sometimes miss the messenger gig, head injury notwithstanding.

Previously:A Life in Two Decades: In Brooklyn, in Massachusetts, in Hartford, Conn.

Josh Michtom is a public defender in Hartford, Connecticut. He spends way too much of his spare time decorating his children’s school lunch bags.