Sandwich Deliveries

In the fall of last year, I was asked to vacation in Cancun with a friend and her family. It sounded brilliant, but I needed some extra cash to make it happen. I decided to pick up a part-time job.

I applied to a few craigslist gigs, but what I ended up taking was a bicycle delivery position at a sandwich shop. The pay was decent, and I didn’t mind the exercise. I figured I’d make some spending money and quit before Thanksgiving.

Well, now it’s February, and I have been dedicating more and more time to the gig. To be honest, I’m not sure how I am still tackling the challenge because the job requires far more than cycling.

This is the Midwest, and we’ve had our share of freak weather. The Polar Vortex is dropping record temperatures and the snow accumulations are dangerous pothole-concealing burdens.


For example, a series of four potholes appeared on one of my well-traveled routes. They were deep enough to fit my entire foot and definitely not something thin commuter tires can handle. When it snowed, these ruts were hidden, and I accidentally took the path that crossed them.

By the time I noticed, it was too late. Sandwiched (pun intended) between moving and non-moving vehicles, I literally bounced right off of my bicycle. Somehow, I managed to land upright between two parked cars and was safe.


This is also Chicago. The streets are congested. The bike lanes are narrowed by unplowed curbs. The salt creates puddles despite a subzero chill, effectively rending my sopping snow boots useless.

It has gotten to the point where I now wear rubber boots, a balaclava and snowboarding goggles through city traffic, at an average of $3 a delivery.

Are sandwiches really that important?

They are to my general manager, who neither stopped deliveries for the turbulent autumn storm (that created a tornado in rural Illinois) or the blizzard-like winter conditions (that generate a two-inch blanket of snow over which bicycle tires have no friction).

But, let’s take a step back. Our sandwich delivery radius is less than a mile, and I’ve been cycling for two years. I have the physical and mental strength to weather these roads. The problem is other cyclists couldn’t handle it. Over half of our delivery team quit.

To cover the empty shifts, I started being scheduled on double doubles. That means both Saturday and Sunday I work 10 hours a day nonstop, in addition to my full-time job.

That’s 60+ hours a week, 7 days a week for the last month.

And yet, somehow, I still find the job enjoyable. There are little spontaneous moments that make it fun.

One time, when it was raining, I ducked under an awning to call a customer.


That’s a whole separate issue. When my phone gets any small amount of precipitation on the screen, it’s flips out and starts calling random people, pushing buttons with a mind of its own. It took me five whole minutes once just to dial a number.


So I’m standing under this awning, trying to keep my phone dry and a nice, young couple opens their door to check on me. They encourage me to stay warm and wish me luck.

I love that, and I do get a lot of endearing “Stay Warm” and “Stay Safe” farewells. There’s also a few justifying “I can’t believe you’re delivering in this weather!” remarks that make me feel appreciated.

I don’t mind the scenic freedom either. Without this job, I never would have discovered all the beautiful, traditional churches and interesting businesses in my neighborhood.

I’ve delivered to art museums, toy shops, hair salons, tattoo parlors, clothing stores, dental clinics, bars, wine shops and theaters in addition to the multitude of city apartment complexes.


That’s another challenge: apartments. Many of these old buildings are homes divided and repurposed into separate living spaces. No two buildings are ever the same.

Sometimes you deliver the front door. Sometimes it’s the side door or the alley. Sometimes you use the buzzer. Sometimes you use an intercom or have to call.  Sometimes the apartments are labelled. Sometimes they’re not. Sometimes they’re in a separate coach house beyond the gated area.

Is the first floor really on the ground level second floor, or is it the basement? Because sometimes it’s the basement. Is the garden apartment really in a garden or just on the backside of the building? If the receipt says you are floor one, but the buzzer says channel one, is that what I use?

“So, this street doesn’t jog to the east. But it does jog to the west? And it jogs a third time if you go north? But on the north jog it also splits into two different one ways streets and you’re on the east side because that’s the side with odd numbered addresses? Got it.”

I know so many detailed directions now, I can’t even believe it. Yes, odd numbered addresses are on the east and south side of the street and even ones are north and west. If an apartment is listed as 2R, the R stand for Rear. If it says 2N, the N stands for North. The same applies to F (front), E, S, and W.


It sounds wholly confusing, but you get used to it. And I’m not always out on deliveries either. Some days are slow, and I work more in the shop. Of course, those are also the days I don’t get any tips and make crap for money.

But nothing is worse than rounding the busiest intersection in the neighborhood and witnessing a grown man projectile vomit a few feet from your tires.


He literally took a step into the crosswalk, regurgitated lunch, wiped his mouth and kept right on trucking as if nothing happened. I had a perfect drive-by viewing of the entire scene. And honestly, that’s nothing compared to what our 3rd shift employees face.

Our shop is open until 4am on the weekends, which means we get a lot of drunks. A few weeks ago, some guy was letting people in through the back door. That’s super shady and totally uncool. My manager asked him to leave and the customer got so angry, he slammed his sandwich against the door window.

If employees want to escape the shop, they can drive. But that means they’ll be riding around until 4am in the city of Chicago. My neighborhood is pretty safe, but when people are murdered, it’s usually around 3 am.


If there’s any lesson in all of this, it’s that you should fully appreciate all the chaos a delivery person must go through on a daily basis. Please tip your drivers well. They work hard and deserve it.


2 responses to “Sandwich Deliveries

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