Before I became a bike messenger, I put in four years of mind-numbingly monotonous office drudgery. I was a receptionist and fair-weather commuter cyclist who deeply envied messengers. Loafing lackadaisically at my desk all day in uncomfortable boring office garb, trying to sound like I cared when I answered the phone or talked business, checking my email at any available opportunity, discussing American Idol and the caloric content of my lunch with co-workers I mostly hated: no matter how well it paid, after four years of this, I’d had enough. I was starting to feel like Bill Murray in Groundhog Day.

I had friends who were messengers. I heard the stories of wipeouts and car crashes and biking in the ice and snow. I knew the pay was crap and you were tired as hell by the end of the day. But still, the best part of my day was my bike ride to and from work. It had gotten to the point at the office where I knew what everyone was going to say and do before they did, and so it wasn’t all that difficult for me to work up the nerve to give my notice.

Nobody in the office could really understand why I would quit a well-paying reception job in order to exert myself outdoors all day in downtown traffic for less money, or why I’d choose to even associate with smelly, low-life couriers. But they wished me well, and everyone I knew told me repeatedly to be careful.

My first day was February 26th, a Monday, around 8 am. It was cold (I think around 5 Celsius) and rainy, so I wore several layers under a rain jacket and rain pants. I soon realized I’d overdressed. When you’re riding around all day, you keep pretty warm. You need to worry more about your hands and your feet than anything else. Nobody wears rain pants — if you have fenders, you’re pretty much covered — it’s not really all that bad if your knees and tops of your thighs get wet. Plus, rain pants don’t have a back pocket, which everyone uses to carry their lock around as they ride.

There are all kinds of practical considerations like these that make your life as a messenger easier, some so much that they’re a kind of unofficial messenger uniform. Kryptonite mini U-lock in the back pocket is one. (it’s worth the $50, considering how much you’re using the thing and how durable it is.) There’s also the ubiquitous messenger bag slung over the shoulder. Swinging it around and un-velcroing the flap that covers it becomes an unconscious motion when you do it a hundred times a day. Another, consideration is a key on an elastic around your wrist for ease of locking and unlocking swiftly, because that’s another thing you will be doing a hundred times a day. You always need to have a pen, and you’ll discover that retractable ballpoint pens are best because they’re: a) retractable, so no stupid lid to worry about fumbling with and no pen getting all over you and your clothes; and b) ballpoint, so if your manifest gets wet, the ink won’t run, and you can still mostly write on it. Always carry a pump, tire levers, and an inner tube in case you get a flat, and a map in case you get lost. A multi-tool and an adjustable wrench also often come in handy. Granola bars or energy bars of some kind are a godsend, particularly on busy days when you don’t have even a minute to stop but you need to shove food in your face quickly before you run out of energy. In fact, it’s best to carry as much food as you possibly can, because the food downtown mostly sucks and/or is expensive.

Another discovery will hit you rather quickly upon becoming a messenger: you are an eating machine. Especially when you first start, you will probably eat about twice as much as you normally do. It is so awesome. When you are a girl, and especially when you work in an office with a bunch of women who are constantly on diets and are – out of hunger and guilt – willy-nilly projecting their body image and food values onto everyone else in the office, the sudden realization that you can eat 6 chocolate chip cookies at a time if you damn well want to and not feel horrible pangs of guilt and self-loathing after doing so because you know it all got burned off when you delivered that Super-Hot package to City Hall, is a thing of joy and beauty forever. The novelty has yet to wear off for me. I doubt it ever will.

I spent the first half of my first day shadowing my friend who got me the job. Training was pretty simple. At the company I work for, jobs come in on your BlackBerry. You write them down on the manifest. When you pick something up, change its status to “picked up” on the BlackBerry. When you deliver it, enter into the BlackBerry that you dropped it off. Get a signature from the person you delivered it to. In essence, all I do all day is try to learn and perfect the intricacies of picking stuff up from one place, and dropping it at another place before the time it’s due.

Back to the first day: we were riding around in the rain, and I was learning the ropes. It was just before lunchtime when I skidded out on Cordova and Burrard and bailed. There are these metal dividers on the road at that intersection, and my back wheel slipped out on one when I cornered too hard and fast. I landed on my knee, hand, and chin. I ripped open the knee of the rain pants, and got a big scrape on my chin (you can still see the scar). Anyway, the beneficial part of my wipeout was that when I told other couriers about it, they all knew exactly the place I’d fallen. “Oh, right in front of 200 Burrard? The metal part on the road? Yeah, I wiped out there too,” I heard from more than a couple of messengers.

I was on my own after that. That’s one thing that really struck me about couriering, especially when I first started — the freedom. The only person you need to stay in regular contact with is your dispatcher. For this reason, the relationship with your dispatcher is very important. They decide which jobs you’re going to get throughout the day. In a way, aside from the hellos and thank-yous with receptionists, and the friends you make when you hang out with other couriers, your relationship with your dispatcher is the only one you have at your job. It was a complete novelty for me that the person most in charge of what I was doing could only be in contact with me via email or radio. After being under surveillance and suspicion (guilty until proven innocent) at most of the other jobs I’ve had, it was totally liberating.

I can decide the manner in which I do my job. Most companies are also pretty slack in terms of dress code. Some have uniforms, and try to enforce them as much as they can, but I don’t think any courier companies care about, say, facial piercings, hair colour or tattoos. It’s unfortunate that this aesthetic freedom comes about 10 years too late for me. Alas, at times I wish I still had the urges I did when I was 16 to pierce and tattoo everything I could. Luckily, there are some messengers who take full advantage of this freedom, especially one guy who regularly wears miniskirts, makeup, and wigs to work.

As I got to know my job, I became acquainted with the city in a totally new way. You get to know which buildings have easily accessible public bathrooms. Some companies take up several floors of a building, but only one of the floors allows courier deliveries, and it’s often not posted, so you just have to remember. Some buildings have entrances on more than one street, which makes for handy shortcuts. You start to remember the names of receptionists, the suite numbers of certain companies, and the regular deliveries you do for them. Just looking at the city skyline, you can list off the addresses of a good number of the buildings.

You begin to learn the personality and peculiarities of each building. 837 Hastings always smells like gravy for some reason. 1095 Pender has the American Consulate, so there are often political protests outside of it. 1067 Cordova only takes deliveries on one of the below-ground floors. 200 Granville can only be reached by a pedestrian overpass, or by walking through 250 Howe. 925 Georgia, also known as the Cathedral Building, has really bad radio reception. Some buildings are so well known that you only have to say the number. For instance, if you say “triple 6”, most people are going to assume you’re talking about 666 Burrard. The Marine Building, everyone knows that’s 355 Burrard. And the most familiar to messengers in Vancouver is the HSBC building on Georgia and Hornby, 885 Georgia, which is just called “eight-eight-five”. Apparently some time in the past, a portion of 885 Georgia was a public park, so when a building was placed over top of it, a section of it was still public space, now that’s the atrium in 885 Georgia . There’s a cafe there, with tables and chairs, and a piano. At lunchtime a pianist comes and plays. On Fridays, there’s a jazz trio. There’s always some kind of exhibit on display in the atrium, usually art or design. This is the closest thing to an official messenger hangout spot. There’s usually a handful of bikes locked up out front, and people sitting inside and outside. If you’re clear of jobs and waiting for your dispatcher to give you more, it is assumed that this is where you are in the meantime. It’s not only ideal because you can loiter there as much as you want, but it’s also conveniently in the centre of most deliveries you’re going to make.

Getting a job as a courier is the easiest thing ever. If you can ride a bike and are willing to do it all day in all kinds of weather, and you kind of know the layout of the city, you’re pretty much hired. It’s the not quitting once you’ve got the job that is the hard part. The persevering. Messengers count the years they’ve worked by the number of winters, and the ones who’ve been around for many years are tough. You have to be. Everyone has their own car-crash story. The Time I Got Doored. The Time I Was Hospitalized. How I Got This Gnarly Scar.

That’s the part I get asked about most. What it’s like navigating my way through city traffic all day? I don’t know what I could say that wouldn’t be obvious. Yes, it’s difficult. It’s the fundamental risk of the job. I guess I’m superstitious about the whole thing, because accidents happen all the time, and I don’t want to jinx myself by saying that it’s because I’m such a good rider that it hasn’t happened to me yet. I wear a helmet. I obey the lights. I stay attentive and on the lookout. But when it comes down to it, if somebody driving a car is being an idiot, it really has nothing to do with how good of a rider I am. You feel and know that inequality every time you get on the road: if you fuck up and run into a car, not much is going to happen to the car. Maybe you’ll scratch the paint or break a window. But if they make a mistake and crash into you, you could get seriously injured, or even die. I guess that risk is part of what makes being a messenger such a romantic notion.

What’s romantic about couriering to me is the fact that I have become so intimately acquainted with the goings-on of my city. If something’s happening downtown, chances are I’m going to be around to see it, or I’ll hear about it from other couriers. When a cruise ship lands, when there’s a hockey game, when it’s 4/20, when there’s construction, when there’s an accident, when they’re giving out free coffee at Starbucks, I’m one of the first to know. You get to see what’s inside all those buildings, and who. I am part of the transactions and relations between them all, and yet I stand separately from it, stinky and not in business attire, downtrodden yet liberated, transitory, moving from place to place. You don’t get much more urban than a messenger.