It was a typical hot, humid July day in Chicago when I laid down and watched in horror as a pickup truck rolled over my bicycle. The truck had run into me. The both of us had run into a blind corner at the same time, and a chromium death machine being much stronger than a normal-sized human, the truck won. I was horrified over my throbbing ankle, of course, but I was able to let that go. My ankle would heal. It wouldn’t heal WELL, mind you, but it would stop hurting eventually. My bicycle, on the other hand, wasn’t going to miraculously straighten itself back out. The entire thing was so bent that even though it was unrideable, I wasn’t able to remove the wheels from the frame. Hell, the wheel itself was fucked up beyond all recognition. My horror was a result of the fact that the bicycle couldn’t be rescued, and that I would have to buy another one. Bicycles cost money, which I didn’t have, and getting one that was affordable meant losing business time.
The truck driver replaced the bike. As for my ankle, well, I let nature do its job with it. I never went to the hospital, missed only one day of work, and spent the next six weeks basically walking it off. At the time, I was working a volunteer job as the barista at my spiritual community’s Thursday night sketch comedy show, and I was in fact limping to it 20 minutes later. To this day, whenever the subject is broached around my Minister, she still responds using the same four words: “That’s crazy. You’re crazy.”
Maybe so, but a 45-hour-$160-per-week job doesn’t leave much of a choice. I was working as a bicycle messenger – messengers are very rarely referred to as couriers – and it was hell on a bicycle. Which was incredible, because until I was doing that, hell was the one thing I never thought I could experience on a bicycle. Now, in fairness, the hours weren’t bad, despite 45-hour weeks. But the pay was dreadful and the job in itself was extremely dangerous. The typical threats from cars apply, but that’s a part of bicycling, so I’m going to write them off. Walkers are also dangerous, but that’s not because they’re in the way. They’re dangerous because so many of them make a conscious choice to put themselves in your way in order to physically assault you. Road conditions and weather can add extra threats. The three years I spent running packages back and forth were all in Chicago, which means a few of those things were magnified. I had to endure the worst weather the city could throw at me, and traverse roads that could have torn the treads from a Panzer (Lake Street, ahem).
After my career in the media crashed, I went into a messenger service with the intent to take a job for a few months while I got back on my feet. I ended up doing that job for three years, and it left me with a set of back problems, laden with debt, and with a set of Hollywood-driven stereotypes written on my head that effectively made me unemployable. There was no form of skill growth on the job, no chance at promotion, and the fact that almost all messengers are independent contractors left me ineligible for many safety net benefits which could have helped me back on my feet. After a year and a half of holding out, with my financial reputation in tatters, I bit the bullet and moved back home.
Anyway. When I first walked into my messenger service’s office to tell them I was there, they gave me a test. I had lived in Chicago for less than a year, so they wanted to see if I knew which streets were on which numbers. After passing, I was given the job and a company cell phone and told to show up in The Loop the next morning and call the office. There was no meeting at the office every morning for a meeting or assignments, and no exact location as to where I should be when I called the office. As always, I developed a few routines. When I made my morning call into the office, it was usually from the Merchandise Mart, although I would be hanging around Madison and Clark come payday because my bank was there. My service quickly figured out where my spots were, but that didn’t make much of a difference. My service would give me long-distance runs first if they decided that was necessary. Those were rare, though; most of my packages were grabbed and dropped right in The Loop, or around the Magnificent Mile.
There are no pre-assigned packages in messing. At least, there weren’t any at my service. I picked up and dropped off according to when packages came in and where I was in relation to both the pickup point and other messengers at my service. Some messengers can make around 40 runs per day, but since my service was so small, 20 was considered excellent. That would almost be a mercy, but we got paid on commission. And contrary to the widespread Hollywood myth, messengers don’t receive tips. I was given a handful of tips in my three years, mostly by people who didn’t interact with messengers on a daily basis. The regular clients that I got to know fairly well were secretaries and receptionists and mailroom clerks. They’re the ones accepting and signing for packages, and they’re not going to offer tips from their own pockets. They see messengers all the time, after all.
If it happened to be a busy day, time was never an issue. I mean that in the sense that any package I picked up would get dropped off in whatever order was the most convenient to me. Yes, I tried to drop off the hourlong packages sooner than the two-hour packages, but when you’re carrying six packages and five of them are all in a seven block radius while the eighth is at the Hancock Center, those five are getting unloaded first unless the one going to the Hancock is a Top Priority package. And the times don’t account for things like rush hour traffic, weather, or sign-in routines. And those things do affect a messenger’s performance. A lot of pedestrians asked me whether I preferred doing my work in the rain or the snow, and they were all surprised when I said I preferred the snow. But the reason was pretty simple: In snow, clients and pedestrians are a lot more forgiving. They know a package can turn up late. But they also think rain is the same condition as a sunny day, except you’re wet. They couldn’t grasp that wet clothes add weight to the bicycle and that your brakes don’t cause nearly as much friction in rain.
The thing that could REALLY add time to a delivery, though – as well as put the elitism of the white collar upper classes on full display – was getting into the buildings. There were some places which let messengers sign in and use the regular elevators like any other guest, but they were more likely to shove you into a messenger center or send you into the winding labyrinth used for freight deliveries. Some buildings were excellent about that. 311 South Wacker probably had the best messenger center in Chicago, and its cross-street neighbor, the Sears Tower, had a great one as well. The worst buildings sent messengers through the freight entrances, which not only added time but usually demanded a trip on dangerous Lower Wacker Drive as well. After you navigated the Chicago netherworld and found the address you needed, the wait for the freight elevator could add another 10 minutes. In my time as a messenger, one building (I believe it was 317 East Wacker, but the exact number escapes me) tried to make the switch from bringing messengers through the front door to bringing us through the freight entrance. That experiment was dropped after less than two months because the building’s clients complained to the management about how long basic deliveries started taking. That information was, shall I say, EXTREMELY revealing.
There’s something weird about messenger work when it comes to your relationship with cars. You yell and scream at the motorists who share the road, but that’s okay; they know you’re there. Most drivers might hate your guts, but they DO have enough awareness of the streets to keep themselves from killing you. But if you’ve worked as a messenger for a significant length of time, you’ve definitely been hit by cars. It’s considered a known and accepted risk of the job. Most of the times I got hit were pretty benign: A cut or a scrape or a bruise from a car that jammed the brakes. But more serious injuries can happen through weird and innocuous reasons – I once got doored in a narrow space and ended up in a hospital getting stitched up for a basic cut which went through to my bone. Ironically, that was the only time my bicycle survived a shot from a car. Like other messengers, I avoided going to the hospital for anything if I could, because messengers can’t afford insurance. (I still haven’t even started paying back my old medical debts from Chicago.) As mentioned, we have a cavalier attitude toward getting hurt, and that’s necessitated by the fact that we don’t have much control over how many pickups our services get. Even high-performing messengers are just scraping by, and that’s before taxes. (We always owe, because contract workers don’t get pay automatically removed from checks.) If our bicycles get damaged, we’ll usually have the driver pay for the damage.
If there’s no work coming in, we’re forced to just sit down and relax somewhere while we wait for a call from the dispatcher. Standby breaks are indefinite. We don’t know when they’ll start, we don’t know when they’ll finish, and we don’t know what we’ll get called for when we hear from the dispatcher again. Smarter messengers will carry books with them (almost everything I know about world affairs, politics, and economics is grounded in books I read on standby time) and most of us won’t bother trying to buy a lunch. (It’s not like we could afford one anyway.) The only thing we really have to go on is the time of year. In Chicago, there’s likely to be a lot more standby time in summer because more people are willing to go out and make a drop of three blocks themselves. In winter… Well, it’s Chicago. It gets cold there. There’s a lot more work in winters, and not as many people will be confusing messing for summer work, so there are fewer messengers around willing to do it. The ones who are around will dress in the works: Multiple layers underneath thick jackets, a couple of layers of pants, several socks plus plastic bags on both feet. Hats and gloves are important. Some messengers spend extra money on proper facemasks. Others go for the basic scarfs. I couldn’t afford a facemask, and when I learned how difficult it is to breathe through a scarf, I opted to let my bare face get scalded in the often-negative temperatures.
As for the money, there’s nothing good that can be said about messenger work. My paychecks maxed out at about $250 per week, and they rarely hit that ceiling. $200 was a high-earning week for me, and my average earnings were about $160 per week. All the bad weather, dangerous roads, and back problems I endured got me enough money for some groceries. There were summer weeks when my 45-hour paycheck didn’t even clear three digits. As a result, I lived in scraping poverty and squalor. My daily meals consisted of one bowl of oatmeal and one bowl of ramen noodles on more days than not, as well as whatever candies the receptionists kept on their desks. (My spiritual community held Sunday dinners after services, where I earned a reputation as the person who ate a lot. The other members of the congregation joked about it, but that Sunday meal was usually my only nutritionally substantial meal of the week.) I lived in mortal fear of my bicycle getting damaged because a broken bicycle meant a loss of both time and a substantial amount of rent money. My heat was shut off twice, and for awhile I had to steal my electricity. (The electricity is now one of the very few debts from those days I managed to pay off.) I went to HEAP in order to get my heat turned back on, which had an irony in the fact that I had to lose runs during work hours in order to get it.
I earned a little over $10,000 a year before taxes. When the IRS caught up to me, I owed close to a total of $6000 in back taxes between state and federal. My parents had to dip into their retirement savings to erase my federal debt. My debt to Illinois wasn’t paid until 2015. I tell people today that I’m pretty sure I ended up losing money working as a bike messenger.
The only thing that kept me going for as long as I did was a mortal fear of losing my meager paychecks and then dropping off the face of the Earth. Quitting jobs denies a lot of benefits, as does being an independent contractor. The end of my job came in September of 2009. My service already had clientele jumping ship, but it was about that time that the largest messenger service in Chicago started a monopolization campaign. My service closed down and I was laid off. Unfortunately, I was also afflicted with a Hollywood-induced stigma about bike messengers being anarchic slackers which probably destroyed my chances of finding gainful work somewhere else. I managed to hold out in Chicago for another year and a half, strictly through my landlord’s generosity. But between the messenger stereotype (fuck you Hollywood, fuck you very much), most of my other work experience involving commission sales, and the ruined economy, I was effectively unemployable. The safety network ran me around because I was technically not an employee as a messenger. My landlord tried to help however he could, but I was too much of a liability and my time ran out. In March of 2011, I stored everything I could save (some of which I was never able to recover) and abandoned my home.
I’ll grant that the kind of freedom I had as a bike messenger is something I’ll never have again at any decent job. But there was nothing else about messing that makes it worth the trade-off.