Failing at Everything in the Greatest City on Earth - I Love New York and It Likes Me Okay - Is Everyone Hanging Out Without Me? (And Other Concerns) - Mindy Kaling

Is Everyone Hanging Out Without Me? (And Other Concerns) - Mindy Kaling (2011)

I Love New York and It Likes Me Okay

Failing at Everything in the Greatest City on Earth

IWAS HESITANT to write this essay because, of course, I would rather you guys think I’m some kind of wide-eyed wunderkind who just kind of floated into my job at The Office without even trying. I want you to picture me as a cute little anime character that popped out from behind a mushroom or something and landed in Hollywood. But writing about my struggles was actually really fun. Besides, who wants to read about success, anyway? Successful serial murderers, maybe.

Usually I didn't bother with homework and used an essay writing service


Not to sound braggy or anything, but I kind of killed it in college. You know that saying “big fish in a small pond”? At Dartmouth College, I was freakin’ Jaws in a community swimming pool. I wrote plays, I acted, I sang, I was the student newspaper cartoonist. All this, of course, was less a function of my talent than of the school’s being in rural New Hampshire, where the only option for real entertainment was driving one and a half hours to Manchester, on the off chance the Capitol Steps were touring there.

After beer pong, floating in an inner tube down the Connecticut River, fraternity hazing rituals, building effigies and burning them down in the center of our quad, a cappella, and driving to Montreal for strip clubs, student-run theatrical productions placed a strong seventh in terms of what was fun to do on campus. We had a captive audience with low standards, which was a recipe for smashing success and the reason for the inflated sense of self I have to this very day. If you’re a kid who was not especially a star in your high school, I recommend going to a college in the middle of nowhere. I got all the attention I could ever have wanted. If I had gone to NYU, right now I’d be the funniest paralegal in a law firm in Boston.

I got even more confidence from having a steadfast companion in my best friend, Brenda. A few words about Brenda. Bren is the shit. In college, she was the star of every play at Dartmouth from her freshman fall on. She looked the way a Manhattan socialite should look: perfect posture, gazelle-like, with a sheet of dark blond hair. Girls always worried she was going to steal their boyfriends, but she never did. (I didn’t understand that at all. It’s college! Steal some boyfriends, for God’s sake!) Bren and I befriended each other early on, became inseparable through a shared sense of humor, a trove of nonsensical private jokes, and had the same enemies within the Drama Department. We clung to each other with blind loyalty, like Lord Voldemort and his snake, Nagini. I, of course, was Nagini. If you messed with one of us, you knew you messed with both of us, and Voldemort was going to cast a murder spell on you, or Nagini was going to chomp on your jugular. It was such a good, dramatic time. Bren was the kind of best friend I dreamed about having when I was a little kid. I never knew you could have someone in your life who was pretty much on the same page about essentially everything.

In theater, Bren would play Beatrice or Medea or Eliza Doolittle, while I wrote well-attended comedy one-acts and occasionally played Medea’s little buddy or something. I felt like a big celebrity on campus. Well, the kind of celebrity you could conceivably be at Dartmouth if you weren’t a jock or a sorority girl, who were the real celebrities. My fame was akin to that of, say, Camilla Parker Bowles.

In 2010, Bren was my date to the Emmys. People thought she was on Mad Men and I was her publicist.

Our other best friend, Jocelyn, whom we met through our singing group, was more or less the one directly responsible for making the traditional college experience really fun. She was less competitive and intense, and from Hawaii, so she was very comfortable being naked, which was new to us and intimidating. She, along with our other friend Christina, made us go berry picking and get our faces painted for football games, and she’d host dinners in our shared dorm dining room. Jocelyn is willowy and half-Asian, and while fitting the bill technically for a model, has no interest in modeling. She’s just that cool. Me, on the other hand, whenever I lose, like, five pounds, I basically start considering if I should “try out” modeling. When the three of us walked down the street together, I looked like the Indian girl who kept them “real.” I don’t care. After all these years with friends who are five ten or taller, I have come to carry myself with the confidence of a tall person. It’s all in the head. It works out.

Jocelyn and Brenda being really adorable at something I don’t remember being invited to.

So I left college feeling like a successful, awesome, tall person. Then, in July of 2001, the three of us moved to New York.


The job I most wanted in the world was to be a writer on Late Night with Conan O’Brien. I can’t believe that was two Conan shows ago. It seems like yesterday.

I’d been an intern at Late Night three years before and was famously one of the worst interns the program had ever seen. The reason I was bad was because I treated my internship as a free ticket to watch my hero perform live on stage every day, and not as a way to help the show run smoothly by doing errands. My boss, the script coordinator, greatly disliked me. Not only because I was bad at my job, but because hating everything was one of her personality traits. You know those people who legitimize their sarcastic, negative personalities by saying proudly they are “lifelong New Yorkers”? She was one of those. Her favorite catchphrase was “Are you on crack?” On my last day, she shook my hand limply and said a terse “Bye” without looking away from her J.Crew catalogue.

When I arrived in New York, I didn’t even really know how to apply for the job. I had not kept in touch with anyone at Late Night, because even as a nineteen-year-old, I knew that no one wants to keep in touch with the intern. I had placed a lot of faith in Woody Allen’s belief that 80 percent of success is just showing up. I said to myself: Are you serious? 80 percent? Sure, I can just show up. Here I am, New York! Give me a job!

It turns out the other 20 percent is kind of the difficult, nebulous part.

I wrote a letter to NBC asking how I could submit sketches to be considered for Late Night. I got a letter back saying that the network could not even open an envelope that contained creative material that was not submitted by an agent. I thought the phrase “cannot even open the envelope” was a tad dramatic. NBC legal, you drama queens. This initial rejection served as NBC “negging” me, to borrow a phrase from my very favorite book, The Game. It worked. NBC became the sexy guy at the party I needed to be with. When I finally got with him, years later, sure, he was fourth place, kind of fat, balding, and a little worse for the wear, but I still got him.

Here I am, ruining my guest appearance on my hero’s talk show with dorky gesticulation. (photo credit 7.3)


I was jobless, but so were Brenda and Jocelyn. Together we rented a railroad-style apartment in Windsor Terrace, Brooklyn. The railroad apartment, for those of you who’ve never seen one, is styled after the sleek comfort of a 1930s industrial railroad car. All the rooms are connected in a line, and you have to walk through one room to get to the next. Everything about it is awful, except if you need a set for a play that takes place during the Great Depression. The only people this intimate setup worked for were three female best friends who had no secrets from one another, were comfortable (enough) being walked in on naked, and had no boyfriends (or no boyfriends who were ever invited over). Enter us!

Real estate was our first disappointment in New York: we had set our sights on trendy Williamsburg, which had plenty of chic coffee shops, cool boutiques, and cute, straight guys. I knew I wouldn’t have been able to afford those coffee shops and boutiques, or had the nerve to talk to any of those hipster guys, but I would have liked to be around them, and felt that it was plausible I could have that life. After visiting several basement-level tenements that were out of our price range, we settled for Windsor Terrace. When we moved there, Windsor Terrace was a Park Slope-adjacent mini-neighborhood that could’ve been the exterior set for much of Welcome Back, Kotter. Not grim, but not great. It was populated mostly by middle-age lesbian couples who had taken on the noble challenge of gentrifying the neighborhood.

Brenda and I shared the center bedroom and the single queen bed it would hold, and Jocelyn fashioned herself a sort of bohemian-chic burrow out of the last bedroom, which, while it was the only room with true privacy, was also the size of a handicapped bathroom. She installed a twin loft bed and hung a batik tapestry over the lofted area, where she would read books and magazines for hours. Jocelyn is the kind of person who goes into any room, sizes it up, and immediately tries to loft a bed there. To this day, she lives in an apartment with a loft bed.

This was a good arrangement because Jocelyn has hoarding tendencies, and some degree of containment was crucial. (Hoarding has pejorative connotations now, but you have to understand this was before the show Hoardersdepicted hoarders as gruesome loners with psychological problems. Joce is a hoarder of the cheerful, social, Christmas-lights-year-round variety.) Jocelyn would save stacks of six-year-old magazines because there might be a recipe in one of them for jambalaya, which she would need someday if we threw a big Mardi Gras-themed dinner. (This wasn’t crazy, because we would occasionally do things like that.) People who visited our apartment and saw her curtained lair probably assumed Jocelyn was a gypsy we had inherited as a condition of getting the apartment.

I was going through a phase where all my photos had me making a “whoo!” face.

And the stairs. Oh, the stairs. The staircase in our third-floor walk-up was the steepest, hardest, metal-est staircase I have ever encountered in my life. It was a staircase for killing someone and making it seem like an accident. Our downstairs neighbor was a toothless man, somewhere in his eighties or nineties. He lived with what seemed like two younger male relatives, with “younger” meaning in their sixties. In the dead of summer or winter they would wear those ribbed white tank tops grossly named wife beaters, which is how we knew they were rent-control tenants (if anyone wears year-round wife beaters, it is the same as saying they are enjoying the benefits of a rent-controlled apartment). They also spoke a language with one another that seemed like a hybridized version of an Eastern European language and the incomprehensible mumble of Dick Tracy henchmen. They would’ve been frightening, except they were incredibly timid and scared of us for some reason. Like when that monster in the Bugs Bunny cartoon gets scared of a mouse and runs screaming all the way back to his castle.

In the summer, feral cats in heat clung onto the screens of our living room, meowing mournfully until we threw a glass of water at them. When it got cold, the roaches migrated in and set up homes in every drain. Sometimes, when I got up in the middle of the night to use the bathroom, I would feel a disgusting crackly squelch under my foot, and I’d know I’d have to rinse off a roach from my heel. That was our apartment. We took the bad with the pretty good. Plus, we could afford it, Prospect Park wasn’t too far, and people already assumed we were lesbians, so we fit into the neighborhood right away. It was all good.

Until we tried to pursue our dreams.

Jocelyn accompanies me on the subway to my first-ever open mike gig.


Everything I learned about trying to get hired as a comedy writer came from the Film and Television section of the Lincoln Center Barnes and Noble. I didn’t have the money to buy many of the books there, so I spent hours sitting in the aisle, copying down sections in a loose-leaf notebook. I was not the worst offender. There were aspiring screenwriters sprawled all over the place there. They’d nurse a single coffee for hours. One kid I saw there all the time frequently brought a large pizza with him and ate the entire thing slowly while handwriting inquiry letters to literary agencies.* The only really valuable thing I learned from the Lincoln Center Barnes and Noble was that the only way I could get hired by a TV show was to write a “spec,” or sample script, of a popular current show. That’s when I started working on my first spec, a Will & Grace sample, having seen the show only a handful of times.

I went on one audition when I was in New York. I wasn’t actively pursuing acting jobs, but this one was tailor-made for me. It was an open casting call for Bombay Dreams, an Andrew Lloyd Webber-produced musical extravaganza that was transferring from London to Broadway. I was encouraged by the relative lack of actresses, aged eighteen to thirty, who sang, lived in the tristate area, and also looked Indian. Nothing gives you confidence like being a member of a small, weirdly specific, hard-to-find demographic.

The first Bombay Dreams audition was a singing audition. I auditioned with “Somewhere Out There” from An American Tail. In the audition room I saw some Indian girls, but mostly Latina girls trying to pass for Indian. The audition sign-in sheet read like it was for a production of West Side Story.

My singing audition went really well, mostly because they were relieved an actual Indian person was auditioning. On the way out, the casting assistant walked me all the way to the street, saying, “We were really so happy you made it out here.” I nodded demurely, like I had a million other auditions that week that were more exciting than this one, and left. They were so happy I made it out there? Why not just hand me my start paperwork? On the subway I started planning what I would do when I got the job. First I would go to Dean & Deluca and buy some tiny marzipan candies in the shape of fruit, an expensive treat I noticed a lot of fancy-looking older white women buying. Next I would pay for an exterminator to come to our apartment to kill the cockroaches. After that I’d take Bren and Joce out to dinner at Le Cirque, like I was a creepy Wall Street sugar daddy and they were my pretty arm candy.

I got a callback for a dance audition. I had never danced in my life and did not know what to wear. I went to a dance clothing surplus outlet in Chelsea I’d seen ads for in the PennySaver. Their stuff was discounted because it was irregular, which means the colors were weird or some buttons were off. I bought brown tights, a sleeveless pink leotard, and a white iridescent skirt that wrapped around my waist and was fastened with Velcro. I capped off the entire look with some traditional pink ballet slippers. In the communal mirror of the dressing room of that surplus store, a young Asian girl trying on ballet clothes with her mom said, “Mommy, you should dress like that,” referring to me.The mom hushed her in an Asian language. This sealed the deal. I had never felt more graceful in my life.

At the audition I looked like a fucking idiot. The other girls were all dressed in versions of what actual dancers wear: low-key black leggings, a tank top, and sneakers. I looked like the children’s birthday party performer playing Angelina Ballerina, the ballet-dancing mouse. A Kevin Federline-looking choreographer taught us an incredibly complicated Bollywood dance routine, which we then had to perform on tape. I stumbled through it like a groggy teamster who had wandered into the wrong room backstage, breathing heavily and vaguely hitting my marks. KFed stopped me before the song was done and kindly asked if I needed some water. I laughed because, as everyone knows, laughing is a great way to disguise heavy breathing. I then exited on the pretense of getting a drink, and quickly left the building. It remains the single most embarrassing performance of my life, and it’s on tape somewhere. I like to think Andrew Lloyd Webber watches it whenever he’s feeling down.

My Will & Grace spec was a disaster. In an attempt to achieve the cheeky, gay-centric tone of the show, I had written a sample so over-the-top offensively gay that it actually reads like a propaganda sketch to incite antigay sentiment.

So things were coming together nicely for me to embark on a full-fledged depression. One good thing about New York is that most people function daily while in a low-grade depression. It’s not like if you’re in Los Angeles, where everyone’s so actively working on cheerfulness and mental and physical health that if they sense you’re down, they shun you. Also, all that sunshine is a cruel joke when you’re depressed. In New York, even in your misery, you feel like you belong. But it was still hard to fail, so consistently, at everything I had once been Camilla Parker Bowles-level good at.

Brenda and I would fix that, but we didn’t know it yet.

*It is interesting to note that this Barnes and Noble no longer exists—perhaps no one was buying books there?