Chicago, 2017.

I head up the elevator to the third floor, out of breath walking from my parking spot two blocks away. Once the elevator door opens, I’m on. Despite the 6:45 A.M. bags that live under my eyes until the second pint of coffee is finished, I am alert as I can be. Entering the sales floor, I am greeted by the familiar sight of rows and rows of desks with multiple monitors and phones on each one. Eighty yards of desks stretch five-wide along the rectangular, completely open, cubicle-free room. Music booms through a high-end sound system and monitors featuring live sports from around the world hang from every rafter in the repurposed freight train station.

The far end of the floor is occupied by the customer reps. These are the chosen ones; well-groomed with nice, guaranteed salaries. In the front of the room are the trackers; they keep track of the location of all the precious cargo and make a modest hourly wage with no benefits. I sit in the middle of it all with the carrier reps, also known as freight brokers.

My job is to connect long distance truckers with freight that our customers need moved from one place to another. Once I’ve covered my draw, a 10.5% commission is paid to me for the difference between what our customers pay us and what we pay the truckers. If our customer pays us $3,000 to move a load of aluminum cans from Winston-Salem to St. Louis, and I move it for $2,000, I earn a cool hundred bucks. The guy that sits at the end of my row, Edward, is working on completing his GED online and makes $250k a year. He once took me to a Bulls game where we sat three rows behind the home bench; he spent the entire game booking freight from his phone and screaming at truckers on his other phone. I doubled my quarterly bonus by fading the home team that night. Edward most certainly made more money than I did over the course of that game.

There are lots of characters that I interact with every day at the brokerage. “Moe” is the man who trained me here. He looks like he is 45, not his actual age of 31. The contours of Moe’s face are worn in. The wrinkles etched around his eyes give him the look of an experienced seaman who’s spent years in the sun performing less-than-fun manual labor. Short, black hair streaked with thick patches of gray cover his head. His neckline is untrimmed. Moe’s facial hair is always more than a five o’clock shadow, but less than what you could call a beard. All this combined with his bloodshot, brown eyes give the impression that he is always operating on 2 hours of sleep.

“Let’s move some freight!” Moe yells from his desk with a raspy voice that sounded twice as old as it is, like a pack-a-day smoker who attended a concert the night before. He isn’t a tall man, maybe 5’9, and he certainly doesn’t weigh much either. His lacking physical stature melts away once his massive personality becomes apparent.

Sometimes referred to as “Dr. Fun,” Moe carries a reputation. There are stories of the old days at the brokerage where he would work the entire day in just a pair of boxer shorts, twirling his shirt over his head and bouncing to the beat of whatever music happened to be playing (his artist of choice was Cher).

The more experienced brokers at the firm know to turn down his invitations to hang out after work on weekdays. Those with less experience would shuffle in the next morning ten minutes late and massively hungover. Moe is one of those guys who has a roll of hundred-dollar bills in his pocket and won’t let you pay for anything, but if he buys it, he expects you to drink it. His guests are always welcome to crash at his massive, three-bedroom Wrigleyville apartment. When they show up for work in the same clothes that they left with the day before, the office knows that Moe has claimed another victim.

A digital deli counter on the wall reads “3,” representing the number of times in 2017 that the constant flow of coffee and NOS energy drinks caused him to shit his pants at his desk. It is May 18th.

The details of the job are complicated, but the general idea is pretty simple. Freight brokers work with their co-workers to move all the freight on the board for a given day. They also compete with their co-workers to book the most lucrative loads and earn as much as they can. The job requires multiple computer screens, phone lines, and sources of caffeine to keep up with the ever-changing trends and circumstances of the business.

A good portion of the day is spent yelling at truck drivers and dispatchers for being late or, more often, completely flaking out on an important load. It sounds sketchy, but my company earns $500 million in sales per year and is one of the largest privately owns logistics firms in the country.

The job is messy, which is exactly why companies look to freight brokerages, also known as third-party logistics firms, to handle the headache of transporting goods from one place to another. The freight I move is limited to businesses that patronize my employer. For the most part, my day consists of moving corn starch, large paper rolls, medical supplies, glass bottles, aluminum cans, lawn mowers, steel coils, lumber, recycled car batteries, paint, and frozen potatoes. Occasionally, we get something cool as an ad-hoc load. For example, I moved a decommissioned jet engine that had been converted into a museum exhibit. It made me about thirty bucks.

Like a giant video game, a broker’s screens flicker and change from tab to tab as they track the shifting trends of load-to-truck ratio from city to city. The best of us forecast days into the future and book loads in advance. I am not the best of us. I scramble to pick up incoming calls from truckers looking for more information on the loads we have posted online.

It should come as no surprise that this occupation attracts heteronormative men in their twenties and thirties who… let’s just say they like to party. As a freight broker, I fostered an already-growing love for sports gambling, recreational drugs, and Miller High Life. Between January 2017 and April 2018, I gained what I estimate to be forty pounds. My diet consisted of NOS energy drinks, Dunkin Donuts iced coffee, a lunch sausage and fries, Roger Federer bets, Palermo’s frozen pizza for dinner, and twelve High Lifes. I had to buy sixty beers each Monday to get through to Friday. The cashiers at Rico Fresh must have thought I owned a small bar.

As one might guess, there aren’t many women in this position. I think at my company there are four, and two of them work in satellite offices outside of Chicago. The two that I do work with are absolute freight-booking monsters. They seem to be less distracted and certainly wouldn’t accept an invitation to happy hour from Moe. My first supervisor when I graduated from the training program was named Dianne and she was the top salesperson in the entire company. She was married with two kids, had a degree in human resources, and dressed in clean, pressed, business-casual attire five days per week. Shortly after my appointment to her team, also referred to as a “pod,” she was poached by another company and left the brokerage. Even a painfully average broker like myself was approached on a near daily basis by competitors, so it wasn’t a huge surprise that our top dog left during a lunch break shortly after giving her notice.

Being a freight broker can feel slimy. Booking a trucker on a load for an undesirable price, sending him seventy miles to his pick-up location, then bouncing him for a different trucker who will pick up the load for fifty dollars less was a daily practice at the firm, and I never got used to it. Granted, truckers would do the same thing to us, which is what caused most of the screaming and telephone arguments, but I never got used to being mad at someone who was playing by the same rules.

I’d moved from Milwaukee to Chicago to pursue a lucrative career in a large city brimming with opportunity, but I found myself missing the slower-paced lifestyle of the Cream City. My drinking had reached the point of shaking, early-morning hands. My beer gut was taunted when I visited home for a wedding. I also hated my boss in a way that I didn’t realize wasn’t reserved for sitcoms and contemporary fiction.

Not long before I decided to make a change, my boss called me into his office to tell me that this was the best job I was ever going to have, to leave it would be foolish. What a crappy thing to say to somebody. He was tall, in his fifties, and balding slightly. He had blues records hanging from his wall in a pretentious way, not a cool one. This man loved the power that came with the position and would wield it whenever possible. Just a total dork would be a simpler description for the vice president of the brokerage. He would often call me into his office to shoot the shit and talk about our mutual experiences working as “creatives” before we discovered freight. He was going to be a writer, he would say. We’re not friends, I would think.

I planned an elaborate escape from Chicago and slowly began moving my belongings to a studio apartment eighty miles north, in Milwaukee. My quarterly bonus hit my bank account at noon on a Thursday in the middle of April 2018; I tendered my resignation at 12:02. It was a standard two weeks’ notice, but I was on the curb with my belongings in a matter of minutes. Although it was shocking to me at the time, I later came to learn that this hurried exit was standard procedure at many sales jobs.

The vice president caught me before I could grab my phone charger and leave the building with my head down. He pulled me into his office and lectured me about the ethical standing of somebody who would quit the day he received a bonus. Do you really think that we would’ve stiffed you on your bonus if you had quit last week? Yeah, I’m positive that’s exactly what would have happened.

I was not the greatest freight broker, but I certainly wasn’t the worst. The experience I gained at the brokerage allowed me to pick up sales jobs that paid me more than what the average college dropout was earning at the time, so for that, I am grateful. I also learned how to talk business and speak in a direct and efficient manner. Upon returning to Milwaukee, I walked directly into a job selling wine for a startup. This job sucked for its own reasons, but that is a different story. I think sales just sucks in general, hence why I am back in school to pursue a writing degree.

There are times that I look back fondly on the days of loose rules and Roger Federer wagers; I made some friends at the brokerage that I hope to have for life. I sometimes have to remind myself that I was truly miserable for a year. When I returned to Milwaukee, things began to turn around almost immediately. Sometimes learning what you don’t want is as valuable as getting what you do want.