So You Want to Be a Chicago Bicycle Messenger?

Industry veterans offer tips on breaking into the biz

By John Greenfield

[This article also appears in MOMENTUM magazine, www.momentumplanet.com.]

It’s hard out there for a courier. Business is down in Chicago due to the sluggish economy, and building security is tighter than ever in the wake of 9/11. And of course there’s always traffic dangers and weather challenges.

But for long-time messengers the work is its own reward. “Riding a bike and being free is the best part of the job,” says Andre Gordon, warming up at Cal’s Liquors, a courier hangout at 400 S. Wells, after a day working in cold December rain. Steve Kuntsler, Gordon’s co-worker at Dynamex, agrees. “I like not being stuck in an office all day,” says Kuntsler. “There’s no one over your shoulder cracking the whip.”

With dozens of companies and hundreds of riders, Chicago has one of the largest bike messenger populations in North America and couriers play a key role in greasing the wheels of commerce. “If every messenger stopped working one day the Central Business District would cease to function,” Gordon says.

Receiving orders by two-way radio, couriers crisscross the Loop, picking up and dropping off packages at office towers and loading docks. Most are paid commission, usually 50% of the delivery charge, which varies according to the urgency, distance and weight of the delivery.

Mark Hirsch with Faster Messenger

Although it’s been a slow winter, if you’re interested in checking out the lows and highs of the job, this spring might be a decent time to give it a spin. “March and April is a good time to get hired because it’s tax season,” says Scott Sons, a dispatcher at Arrow Messenger Service.

Arrow’s one of a handful of companies, including Standard, Chicago Messenger, Apex and Chicago Messenger Service, which hire newbies. “We sometimes prefer people with no experience because then we get to train people to do the job the way we want it done,” says Sons. Before applying for a courier job, he recommends wannabe couriers study a map of the Central Business District (between Division, Halsted, Roosevelt and Lake Michigan) and ride around downtown for an afternoon to get the lay of the land.

Marshall Arnold, who dispatches for Dynamex (which doesn’t hire rookies) adds that anyone who wants to messenger should learn basic repairs. “You’re not going to make any money if you’re going to a bike shop every time you get a flat,” he says. Arnold also recommends applying to companies where the bikers are employees, not independent contractors, because the latter are required to pay their own social security taxes and are not covered by workers’ comp.

Once you’re ready to apply, try hitting up local messengers for leads on who’s hiring, says courier Josh Korby. During the daytime you can often find them “standing by” in the outdoor plaza or basement food court of the Jim Thompson Center, 100 W. Randolph, AKA the “Tom-Tom.” After work, Cal’s and the Blue Frog Bar & Grill, 676 N. LaSalle, are popular, especially on Friday payday.

Korby’s an “owner-rider” with 4 Star Courier Collective, a cooperatively run messenger company where everyone bikes as well as dispatches. “A good messenger always shows up on time or early, and always ‘10-4’s all work, no matter how challenging,” he says.

He recommends being agreeable and polite at all times – especially with the building security guards who sometimes delay couriers by demanding they drop their bags at the front desk, leave an ID and sign into the building log. “If you’re too pushy that goes against you sometimes,” he says. “A smile goes a long way.”

Julian Benitez with U.S. Messenger

Korby says it’s important to put some thought into what to wear while working so you can stay reasonably comfortable in nasty weather. He recommends a wool base layer and waterproof jacket and pants for cold and wet conditions. “I spare no expense for gloves and socks,” he says. “If your feet get wet that’s one thing, but if they get cold that’s a problem.”

It’s also key to invest in a comfortable, waterproof messenger bag that will keep the packages dry, says Korby. “It makes such a difference,” he says. He uses a Shag Bag, made in Milwaukee, and also recommends Chicago-made W.I.G. bags, as well as bags by Freight, Seagull, RE-Load and Bailey Works.

As for your vehicle, Korby recommends a single-speed road bike, either fixed-gear or freewheel, as lightweight, cost-effective and low-maintenance, although he prefers fixed since freewheels sometimes freeze up during the winter. “A fixed-gear with a hand brake and full fenders is your best year-round bike, the most miles for your money,” he says.

But aren’t hand brakes on fixies considered un-cool? “There’s a certain machismo to riding brake-less, but a front brake is a good thing to have because it allows you to stop with both wheels,” Korby says. “There used to be a stigma to having a brake, but nowadays I don’t think anyone would make fun of you – at least not to your face.”