The worst job I ever had

In the summer of 2015, the freelance copywriting job that had fallen into my lap and brought me back to New York was on its last legs, and I began my first large scale job search. This proved to be eye-opening.

Growing up, I didn’t really know what any of my friends’ parents did for work unless I could see them working. If they were a teacher at a school I attended, for instance, I knew they were a teacher. Entering college, I only really knew of the types of jobs my two-year-old daughter is actively learning about when flipping through the pages of a Richard Scary book.

Diagram of the only jobs.

During undergrad, my only friends who talked definitively about what they wanted to do for work after graduation were a handful of cross country teammates heading into horrible-sounding but highly lucrative finance jobs. I knew that wasn’t for me, but I also didn’t bother figuring out what sort of work might be. I was an unmotivated student at the time, focused on being a middling NCAA athlete and sporadically blogging—a lifestyle with no obvious post-college pathway to prosperity. I figured things would work out, and I got lucky. They basically did, until aforementioned copywriting job petered out.

For reasons not entirely clear to me now, after 18 months in the field, I had decided I was done with copywriting. Which is why—after already spending several years as a baffled member of the workforce—I had to learn about jobs at the same time as I applied to them.

I applied to all sorts of entry-level positions at all sorts of non-profits, which I figured out were a good way to make a difference while not making much money. I discovered fields called “public relations” and “marketing” and tossed my name in for positions with cryptic job titles. And I learned that lots of people in my position—20-somethings in possession of a liberal arts degree and no obvious pathway to steady employment—went to law school.

Lawyer. Now that’s a job I’d heard of!

A quick Google search revealed that plenty of future lawyers spend a couple of years working as something called a “paralegal,” basically an administrative assistant in a law office setting. I hopped over to my college’s career services page and found a job listing for a paralegal in the Financial District. I skimmed the job description, saw phrases like “support senior legal staff” and “no experience required” and submitted an application.

I heard back a few days later from the firm’s office admin. They invited me to come in and speak with the head of the firm the following Thursday. Sick. I was going to be a lawyer. I took the 4 train to the Atlantic Terminal Uniqlo to procure a button down shirt and non-jean pants without holes in them for my interview.

The following Friday I got gussied up and made sure to allow plenty of time to get to the office just in case the trains were messed up. I arrived about half an hour early and ducked into a nearby Dunkin’ Donuts. Then I pulled out my phone to confirm the address and names of people I’d be speaking with. Aw crap. I missed the interview by 24 hours. My legal career was toast.

It was a long shot, but I drafted an email explaining that I had gotten my wires crossed and put the interview in my calendar for the wrong day. I was sorry. Was there any chance they’d still want to meet with me?

In hindsight, I received a disconcertingly quick response: Sure. Mistakes happen. Come on up.

Damp and appreciative, I entered the lobby of a massive office building and checked in at the front desk, my temporary visitor’s name tag barely adhering to my sweated-through shirt. I walked through a turnstile, took an elevator up to the firm’s floor, and was guided to a windowless conference room where the firm’s head honcho was seated, smiling.

I remember nothing from the interview, but on the train ride home I received a congratulatory email: a job offer. Look out legal profession, there’s a new sheriff in town making $30,000 a year with no benefits!

The following week I turned up at 8:00am as requested to begin my training, and was taken to a two-person cubicle. The other person was, like me, a dude in his early 20s, but had the slicked back hair and ill-fitting suit of a much older man. This was the other paralegal. He knew everything there was to know about the place and as he attempted to get me caught up to speed on the processes of the firm, he told me he lived with his parents in the Bronx and was going to start at Fordham Law in the fall. Far from only recently learning that paralegal was a job, he had always wanted to be a lawyer, and this stop along the way was part of that plan.

The job basically entailed taking electronic record of client paperwork and submitting forms and payment to various city bureaucracies. After a few minutes of following along, I realized that the firm seemed to solely represent slum lords who were trying to make active violations and abuses go away. Somehow this fact had not registered for me at any point during the slapdash hiring process.

Documents and photographs detailing collapsed roofs, bed bug infestations, busted pipes, non-functioning stoves, and rusty water required collation. Paperwork explaining how these issues had been rectified—generally in the most half-assed way imaginable—had to be taken by courier to city agencies and courthouses.

After a lunch I spent sitting on the ground, massaging my temples, and figuring out whether I could perform the ethical gymnastics necessary to perform my duties, I was told to accompany the firm’s courier on his afternoon runs.

Wearing a bluetooth headset and glasses, he handed me several manila envelopes and we joined the hive of office workers scuttling about on the sidewalk. We stopped in a building, had to wait for a specific clerk, who traded us more paperwork for one of our folders. We waited some more. Walking around and waiting in chairs? Maybe I could muscle through a year of this then follow my weird coworker to law school at Fordham.

While we sat in a dimly lit hallway, the courier tried to sell me a cell phone plan. I told him “no thanks, I already have a cell phone.” He gave me the hard pitch: some people—like him—made use of multiple cell phones.

I got home around 6pm and fired off a resignation email.