Willing to Be Lucky

Arriving in NYC before the Internet

Glynnis MacNicol
10 min readApr 1, 2014


In the last few years I’ve gotten in the habit of telling people I moved to New York before the Internet. That when I first arrived here in the late nineties, I was immediately advised by those in the know to linger in front of the Village Voice offices on Astor Place every Tuesday night and wait for the rumbling newspaper trucks to deliver that week’s issue, so I could get to the back-page apartment listings before they hit the newsstands and subsequently make a run to the nearest pay phone. (It would be a few years before those same in-the-know people would begin whispering the word “craigslist”).

In other words, not that long ago—let’s call it before Facebook, so really less than a decade. We knew a little less, and moved a little slower, and life (or at least your ability to meet up with friends on any given night with the precision of a heat-seeking missile) was left slightly more to chance. So perhaps it’s not entirely surprising that when I started out, I was more willing to let the chips fall where they may than I might have been had I come along ten years later.

I sometimes wonder if luck may be weirdly harder to come by these days when so much of the world is discoverable without actually moving.

I sometimes wonder if luck may be weirdly harder to come by these days when so much of the world is discoverable without actually moving, when gut instinct often feels as though it’s been replaced by SEO results, or Klout score ratings, or Facebook profiles, or Instagram accounts. Not that I don’t enjoy these things also, or that I pine for the days before Seamless (I don’t), it’s just that I think it may be more difficult to rely on timing and opportunity as a way to get by when nearly every new lifestyle development is geared toward scheduling our lives in an increasingly streamlined fashion. We know so much all the time and we have come to depend so heavily on that access to knowledge, if not our own then the group’s, that we don’t spend any great time not-knowing. These days, not-knowing actually requires a determined effort. And yet there is so much power and opportunity to be had in the not knowing.

And yet that’s what I did and what I still try to do to a certain extent, and perhaps just being aware that it’s possible to not plan and to still be okay may be an antidote to the endlessly agonizing career guidance and “how to network” posts I come across with such frequency.

Almost everyone has a waiter or waitressing story to tell, or they should. When your income depends entirely on tips (I don’t know what the rules are now, but when I was doing it, the base pay for servers was something like two dollars per hour), you very quickly learn to become an expert in human nature. Either that, or you go hungry.

One Oscar-winning actor, had been coming in for so long he’d have his mail delivered to the bar when he was out of town, or call in his Super Bowl picks from far-off film locations.

It is common knowledge among those who have held server jobs in New York that there is a lot of money to be made in restaurants. (That Lena Dunham’s character in Girls remains a barista instead of angling for a job on the floor of a restaurant, where she might have made four times the money in one-fifth the time, has always been some signifier to me that Dunham’s New York City street savvy suffers some blind spots.)

I had a couple of server jobs early on, but the restaurant I worked in the longest was an old-school New York bar located in the heart of Greenwich Village, famous in its time for being frequented by abstract expressionist painters like Jackson Pollock, beat poets, and later Bob Dylan. During my stint, it was a locus for neighborhood locals who treated it as a second home: NYU students; artists; musicians; a few business types; remnants of what remained of the blue-collar population below Fourteenth Street, once the mainstay of the city; and movie stars who liked to be treated like normal people. Some customers, including one Oscar-winning actor, had been coming in for so long they’d have their mail delivered to the bar when they were out of town, or call in their Super Bowl picks from far-off film locations. Some had individual drink prices. It was the sort of place that still honored the three-drink buy-back, but where the customer was never right—a fact widely acknowledged by the surfeit of regulars and often a surprising discovery for the less familiar crowds that tended to swarm in on a Saturday night.

Tom Wolfe once described it as the cénacle des cénacles—forever translated to me by those in the know as the “circle that connects all the circles.” And while Wolfe was referring to the painters that congregated there in the fifties, it always seemed like an apt description to me of what it was like to be in a place where it frequently felt like the whole world, with its endless opportunities, was being showcased nightly in the form of paying customers. The staff turnover was so low that getting scheduled permanently on a Wednesday- or Thursday-night shift—coveted because the customers were all regulars, low maintenance, reliable tippers, and went home by midnight—was the server equivalent of landing a rent-controlled apartment with high ceilings. And almost as rare. People did not leave this job any more than the regulars changed their nightly drink order.

It was arguably the best server job to be had in the city, the kind you might find in movies or novels but rarely come across in real life; the sort of experience that provides both a lifetime of lessons and an endless supply of the sort of stories we tell ourselves in order to live. And the reason I landed it is that I overheard someone at a café in Soho talking about how much money a person could make there.

I’d recently been fired from a short-lived gig in a Nolita bistro, after the owner discovered I was a Virgo and felt this was incompatible with her Aries.

“He who hesitates is poor,” goes the saying, and at that moment, still in my first year in New York, I happened to be very poor. It was the middle of summer, the worst time to get a service job in a city that emptied out in July and August, and I’d recently been fired from a short-lived gig in a Nolita bistro, where I poured glasses of wine and prepped salads, after the owner discovered I was a Virgo and felt this was incompatible with her Aries. “It cannot possibly work,” I recall her saying as she handed me my hourly wage in cash and saw me to the door. I remember very clearly that I had exactly fifty dollars to my name, in cash (one thing you learn from being truly broke is that money is relative—that fifty dollars felt like an absolute fortune to me as it was the only thing between me and . . . I wasn’t sure, but I learned how to make it stretch in an effort to keep whatever it was as far away as possible). I was subsisting on a large bag of lentils I had bought for two dollars at the corner bodega and cooked a cup at a time in the pot I’d purchased at a dollar store when I’d first moved in. I had ten days to come up with rent.

In my heart, I suspected the man I’d overheard had been exaggerating. The staggering amount of money he’d mentioned seem so far-fetched to me at the time that part of me assumed he’d been telling a story, not relaying a fact. But I went anyway, immediately walking the fifteen blocks and grateful I was wearing black so the sweat stains I was incurring from the raging July heat wouldn’t be too apparent when I arrived.

I think if I hadn’t been so desperate, I might have been more nervous. The place, an old tavern with wood-paneled walls and rows of back booths, appeared completely empty when I arrived, and the door banged as I came in, like a cannon announcing my arrival. It was cool inside, an immediate relief from the blazing sidewalks, but also very dark even though it was high noon. It took me a few minutes to make out the soaring, intricately carved bar that lined one wall and then, slowly, the bartender behind it. I felt like I’d been called onto a stage alone to account for myself to an audience I couldn’t see. But I stood my ground, asked to see the manager, declared I was looking for a job, and, when asked, assured them that absolutely I had waited tables before (I hadn’t, but at that point, it was figure it out or go hungry, and I concluded it was better to get my foot in the door than not—this remains true to this day). I agreed to come back the next morning to train. On the way home, I bought myself a two-dollar egg sandwich at the Sidewalk Café on Avenue A.

I don’t remember what I learned during that Saturday morning training session, just that I spent the day in the state of extreme anxiety, suffering that feeling of deep ineptitude that a new job almost always brings on. But I had showed up, and when, at five p.m., one of the staff called in sick thirty minutes before the Saturday-night shift, I offered to fill in.

That night is a blur. (In fact, it ended up being eleven hours of such nonstop chaos that even after all these years, I am still prone to nightmares about it.) Actually, it felt like going to war, if war were conducted in a small restaurant in the middle of New York City that served five-dollar martinis and deep-fried bacon atop hamburgers. What I remember most clearly is that I spent the entire time running—from the customers to the bar to get drinks, from the bar to the kitchen window to get food, from the table to the service station to find water glasses, to clear ashtrays, to place orders, to clear dishes. And then back again. And then again. There was no busboy to help and no break until the bar closed at four a.m. I wrote everything down everyone ordered, most of which didn’t make sense to me and then sounded out drink names at the top of my lungs to the bartenders, always requesting the drink “neat” when I’d forgotten, or didn’t know to ask, whether the customer wanted ice (easy enough to deliver it on the side if need be). When I was wrong, I learned quickly to apologize to the bartenders who wielded all power (benevolently, it must be said, as many of them are still close friends) and discovered the power of the word “sure” when it came to customers (Them, accusingly: “I ordered that with ice.” Me, calmly: “Sure.”) I learned not to sweat the details (Was there garlic in the chicken marsala? I had no idea and no time to run the twenty feet to find someone who could tell me. Better to say yes like I meant it and have them order something else than take the time to find out).

I could tell what sort of tipper a person would be before they were ten feet past the door.

But mostly I learned to learn on the run, and also to know that I could do so, a talent that served me well many years later when I leapt into the blog world. I also learned to pay attention. which is something that has served me in every job I’ve held since. People will tell you who they are, Maya Angelou once said, and this may never be more true than in a restaurant, partly because food and drink are such basic human motivators and partly because, as I said before, when you work for tips, you become extra attuned to signals that let you know what sort of tip you can expect. In the restaurant, this meant that more often than not I could tell what sort of tipper a person would be before they were ten feet past the door: the way they banged open the door, the way they made eye contact, what drink they ordered (Jameson on the rocks meant twenty percent, Stoli with Coke meant 15 percent tops). In my later careers, it has often meant knowing when (and when not) to ask certain questions of interview subjects, or employers, or employees. Or how to gauge from a distance the intentions of people who are approaching me. Or even how best to enter a room while picking up on the small gestures that can tell you so much about the other people entering it: what they might want or be afraid of letting you know they want.

The next morning, four hours after I’d returned home reeking of cigarette smoke, having spent seventeen hours on my feet, I came back for my second training session. And then, when the same server remained out that night, I stayed on again to work the Sunday-evening shift. By the time I finally got back home at three a.m. the next morning, covered in dried mayonnaise with revoltingly swollen ankles, I’d made my rent for the next two months, landed a regular schedule, including the Saturday-night shift, and found a way to not just stay in New York, but live here.

Glynnis MacNicol is a writer and co-founder of TheLi.st. This is an excerpt from her essay, “Willing To Be Lucky,” from The 10 Habits of Highly Successful Women on Amazon Kindle.



Glynnis MacNicol

Glynnis MacNicol is a writer and author of the memoir NO ONE TELLS YOU THIS (Simon & Schuster, 2018).