Andrew Weiner is a courier in Boston.

Business yesterday wasn't dead, but it was slow. Given the fact that last Wednesday's traffic broke records, most people probably chose to stretch their holidays by another day. One of the things you learn if you've been downtown long enough is that you only waste your own time trying to make predictions. A few truths hold from year to year—December is slammed, August is dead, and the weeks before the close of the fiscal quarter or year always jam. The rest of the time, you might as well try to forecast next week's weather. But at least that came through. The rain that was falling when I fell asleep Sunday night moved on, and by noon it was sunny and 60. Perfect for a siesta.

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These two variables, weather and business, are what alternately make or break courier work. Assuming you like to loaf, what could be more chill than spending a perfect June day outside on your bike? Then again, when it's February, it's sleeting, and you're losing the battle with a bag full of rush deliveries, and there's slush in your shoes, you might think different. Especially when someone turns to you in the elevator and, whether from ham-fisted sympathy or smug disdain, says, "Hate to have your job." The same is true of the money, which averages out to be decent but often swings between feast and famine. Since almost all couriers get paid on commission, this means that even consecutive paychecks can be off by as much as a couple hundred dollars.

So, who would ever want this job? You could figure it out pretty easily by spending an hour in one of the parks where couriers congregate between jobs. (Even on a busy day, you're guaranteed at least an hour of downtime.) These spaces tend to be organized by the same logic that assigns the squares, punks, goths, stoners, and jocks their own portions of the student lounge at any high school. One set of benches usually belongs to the alpha-dogs and tough guys who ride to show how badass they think they are. They push impossibly steep gear combinations, never use helmets, wear shorts all winter. Another set holds the hipsters, rockers, skaters, and art-school kids—the new jacks. For them, riding downtown is about rocking a style and looking the part. They're inked and pierced, have the latest deck shoes, wear studded belts over cut-off work pants, ride vintage track bikes. Here and there are a couple old-school veterans, guys who were riding in the Quicksilver era, when the scene looked more like something out of the "Beat It" video. Clustered out around the periphery are the bottom feeders: the randoms and deadbeats who ride Huffies and probably couldn't get another job if they tried.

Another way to look at it is by substance intake—my friend Ted, who's been downtown for the better part of the last decade, has worked out a taxonomy dividing couriers into the species nuntius alcoholicus (drunks), nuntius morpheus (junkies), and nuntius alacritus (cokeheads and speed freaks). While there is a small straightedge contingent, most everyone is chemically dependent to some degree, even if that only means a steady intake of caffeine or nicotine. That fact says plenty about couriers, but it also speaks to the nature of the job itself. Uppers help you match the speed of rush hour. Downers dampen dread, the uneasy knowledge that no matter how good, smart, or careful you are, you take a chance every time you ride into traffic.

The last category of courier is the one I'd align myself with: people who do it to free up their time for what they care about. People in bands or in art or in thrall to various self-determined schemes of the authentic life. People like Ted, who reads Cortázar and Beckett in the elevator and by night paints hilarious icons of demi-celebrities like Don Knotts. Or people like my friend Thom, who also works as a free-lance illustrator and took the photos you'll be seeing along with these entries.

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