September 24, 2023

Financing the Flaneur: Discovering New York Through @Postmates

From September to January, I was an editorial intern at a literary non-profit in Manhattan. I had just finished my master’s degree and was trying to transition away from academia, so an internship in New York felt like the most logical choice. I interned three days a week, and had two other jobs when I wasn’t in the office.

One of these jobs was in a coffee shop in midtown, initially for three days a week. As my hours dwindled and it became increasingly clear that the coffee shop was going to close down, I started working as a courier for Postmates. Postmates is an iPhone/Android App, and more or less works according to the same logic as apps like Uber and Lyft. People order food, groceries, and other miscellaneous items via the app, couriers in the area are alerted with a prompt to either accept or decline this “job.” The app takes 20% of what they charge the user. Payment depends mostly on proximity: the further away a job is, the more money it pays. Couriers also received tips for their errands, which were usually somewhere between 30-50% of total money made; generally 15-20% of the cost of the actual bill. On busy evenings, I was able to make around 13-15$. On less busy days, particularly during the idle hours between lunch and dinner, I would sometimes go an hour without receiving a notification for a job.


Postmates couriers can either drive, ride a bicycle, or walk. I chose to walk partially because I love walking, but also because I lacked a bike. The flaneur, if he (he, because he is invariably a male) exists at all outside of literature, is a probably member of landed gentry, of the leisure class. I didn’t have the luxury of wandering around for hours on end, so I had to find a way to monetize my penchant for traveling on foot. Given the unpredictability of the app, I probably wouldn’t recommend it as a full time job, but it was a great way of getting paid for essentially seeing the city. I mostly did Postmates in the evenings, especially after the internship. This was miserable when it was raining and I needed the money for rent, but otherwise it was fun. The majority of the jobs were usually in SoHo, Greenwich Village, and occasionally, Chelsea. I learned exactly how far $6 was worth; some people lived literally 90 seconds away from where they were delivering. Doubtless, I delivered to a fair amount of people with disabilities; grocery delivery apps were initially made with this population in mind. Doubtless, too, I delivered to people with unseen maladies, disabilities not immediately evident. During the day time, the West Village was extremely popular, for whatever reason. It was also the most depressing place to make deliveries to. At least a quarter of all of my day-time West Village excursions were for alcohol, often hard alcohol. More often than not, a morose, prematurely aging woman would open the door and the reek of furniture permanently embedded with cigarette smoke would ease its way into the hallway. I imagined they wouldn’t be getting their security deposit back, but given the location of their apartment and quality of the hard alcohol they were buying at 3 p.m., I doubt they cared much.

Given my tenure as a barista in a very slow and ultimately generous coffee shop, I had just discovered the joy (and utility) of caffeine. That is to say, before arriving in New York, I could count on one hand the amount of times I had tried coffee. On days (mostly weekends) where I didn’t have work in the morning, I would leave my Washington Heights apartment at around 7 or 8, grab a coffee too large for my own good, put an audiobook that I downloaded from Youtube earlier that day, and manically parade around the city. Most of the time, I probably looked more like a fuguer than a flaneur, less a stroller and more a fevered, competitive fast walker. Walking quickly also staved off the cold – I hadn’t bought any clothes since leaving California a year and a half earlier. On days where I planned on doing 6+ hours of walking, I would bring a sandwich in Tupperware, and sit on a set of set of stairs when the constant smell of restaurants was too much to bear. I was occasionally met with strange glances, either because of my preferred dinner location or because of the admittedly strange contents of my sandwich. The economic incentive to walk as quickly as possible probably took a bit out of the joy of walking, but it did mean that the more I walked, the more money I made.

I learned to navigate the supposed center of the universe pretty well in a short amount of time. I delivered to students and families, to the ultra-rich and to those who seriously debated whether or not it was worth spending 5-6 extra dollars on Shake Shack. Some people treated me poorly, others were both friendly and grateful. I found little correlation between a person’s disposition and how much they tipped: to be sure, the former mattered much more than the latter. I once delivered $90 worth of Thai food to a teenager in a $2 million penthouse in midtown. I was hoping his tip would make my week, but I was mistaken. I made friends, both with strangers on the streets and people who worked at the restaurants I visited. Workers at Milk Bar would give me overpriced snacks for free, on account of being a fellow service-worker. I would shamelessly take as many free samples as I could carry from overpriced Juice stores. The most popular order was a taco salad from by CHLOE on Bleeker street, a comfort-food styled vegan restaurant. The second most popular was probably Shake Shack. I learned where the cleanest public bathrooms were; Best Buy on 14th street was generally where I answered nature’s call if by CHLOE was particularly busy. In and outside of restaurants, I met a fair amount of people. I met a Mexican-American who learned Arabic through owning a falafel shop, I had a spirited discussion over the merits of Vietnamese Banh Mi sandwiches with an architecture grad student from Minneapolis. With a bit of research beforehand, I was able to trace out where Irish pockets were situated at the beginning of the 20th century. Lost late at night in the East Village, I met a girl from Georgia working as a nanny and waitress while trying to establish her sci-fi theater troupe. I exchanged banter with friendly doormen, and was told to go through the “Poor door” by others. I met a homeless man who asked me for half my sandwich, only to have him laugh and tell me never mind when I told him what kind it was. On Christmas Eve, I provided technological advice over the phone for a father ordering a point-and-shoot camera for his kid through the app. I delivered dog food. Too much dog food. I generally avoided the stranger orders; orders from sex shops were more common that I would have thought.

Walking for 4-5 hours a day intensified the sort of encounters that a person can only encounter in a large, dense city. It was a condensing mechanism, a way of continually finding myself in conversations with strangers that were unique if only for the sake of their specificity. It’s a tired trope, but the city is indeed a palimpsest. More often than not, history was felt in its absence. I’m not living in New York at the moment, but in South California, a place notoriously inhospitable to the walker on account of poor public transportation, suburban sprawl, and urban development after the advent of the car. Everything is painfully spread out. I imagine I’ll be back in a walkable city soon, and when I am, hopefully Postmates is for fun instead of income. In any case, for anybody without friends in a big city, it’s an enjoyable way to spend weekends.

by Jeremy Klemin

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