Life After Messenger vs. 'Career Courier'

I’ve had a DVD copy of Career Courier for months and months. I’ve been waiting for the opportunity to watch this documentary about the lives of bike messengers with someone who had lived that life. The problem is, I live in Flagstaff, Arizona, which is not a bike messenger town.

So when I went to Washington DC last month for the National Bike Summit, I got my friend John Dinn to watch it with me. I stayed (crashed, really) at John’s house for a couple of nights after the Summit.

It’s a fun, funny, and bittersweet documentary. The theme of freedom is repeated many times. The people who work as bike messengers love the freedom the job gives them — in spite of the low pay, few opportunities for upward mobility, and hostile, car-oriented streets.

Clearly not the intention of filmmaker Kenton Hoppas, but for me, the film underscored the way car-centrism has taken over American cities. It makes sense that the people who choose to bike and work in this environment are the types who demand freedom in ways more compliant people can’t fathom.

Freedom is a hollow watchword in much political rhetoric. The day before I watched this film, I had been on Capitol Hill, dropping the word like a special kind of f-bomb in meetings with Congressmen and/or their staff members. I hoped the word would resonate with them; convince them to save Federal funding for cycling infrastructure.

The seemingly apolitical messengers in Career Courier don’t request freedom in the halls of Congressional office buildings. They live freedom on the streets while us play-it-safe cycling types plead and wait for politicians to give it to us.

I felt envious of the subjects of Hoppas’ film, and even more resentful of this Congress.

But that’s just me. This is the description of the film from the Career Courier Website:

Whether you are a bicycle messenger for a day or for 20 years, it's a dangerous and physically demanding job. But it is also a lot of fun. So much fun, in fact, that a few bicycle messengers start out on the job thinking that they will just messenger for a summer or two, and then find themselves still doing it 20 years later.

Hardly the preamble for a bike advocacy polemic.

John Dinn
John Dinn

My friend John was a free-range courier in DC for about two years in the 90s before becoming an in-house courier for a visa service. Later, he stopped being a courier and took an office job for a visa company — although he bike commutes four or five days per week from Kensington, Maryland to downtown DC, “if I am not being a pussy about the weather.”

As a courier, John didn’t just move documents across the city “faster that anyone in a cab.” John had made connections that helped him learn the soft side of moving paperwork through a bureaucracy. “The companies I have worked for in the visa business always appreciated the fact that I know a lot of people in the embassies.”

So, unlike the subjects of Career Courier, John found and/or chose a path out of his job as a messenger, while still satisfying his love of cycling. He stays connected to the courier community in DC, and in other large cities on the East Coast. John knows many of the couriers in the film from alleycat races in the region.

An alleycat race, if you don’t know, is an unsanctioned (usually) race in a city where cyclists race to various checkpoints, and complete tasks like a scavenger hunt. It’s basically a courier fix for an ex-courier. And John gets his fix by organizing alleycat races.

Watching the film with him, he would knowingly laugh at moments that didn’t seem significant to me, like when Ellie says, “There’s always been an obsession with the biggest bag.” Or when there was a mention of the “psychic benefits” of the job.

And he’d say the names of his friends as they appeared on the screen.

“Ha ha… Squid.

“Squid is a true courier and a true gentleman, living the courier dream!,” John told me in an e-mail.

I’ve known John for about 15 years, but I think I get him better, having seen Career Courier. The film makes no attempt to romanticize messengers or even to rehabilitate their scofflaw reputation.

I’m reminded of a quote by Abbie Hoffman:

You measure a democracy by the freedom it gives its dissidents, not the freedom it gives its assimilated conformists.

In a sense, couriers are a front line claiming city streets as equals with motor vehicles — which is my dream too, but to do it within the law, not as an adversary.

I bet most couriers wouldn’t see it that way. They’re just doing (as one courier called it) “the world’s best job.”

Career Courier is available on DVD or on demand from Amazon.


John’s latest race, the “I Gotta See A Man About A Dog” alleycat will be held this weekend in Washington, DC to benefit pit bull advocacy organizations and Dogs of the 9th Ward in New Orleans.

Two sponsors of the race are:

R.E.Load Bags, maker of the first place messenger bag

Banjo Brothers, who donated a messenger bag to be given as a prize.

Banjo Brothers Messenger Bag

Banjo Brothers bags are now available at Bike Bag Shop.


My participation in this years’ National Bike Summit was made possible by these sponsors.

Campfire Cycling Tern Flagstaff Biking Organization Bike Virginia
Post navigation