Your thing doesn't have to be perfect the first time...or the 17th

Interview with New York Times writer Jada Yuan

You’ve probably never heard of “Jada Yuan,” but you’ve heard of the people she’s interviewed: Steven Spielberg, Taylor Swift, Mindy Kaling, Stevie Nicks, to name a few. But who she knows is not what makes Jada interesting – it’s how she writes; she is one of my favorite writers.

(editor's note from Jan 10, 2018: When I interviewed Jada in 2016 she was the Contributing Editor for New York Magazine. Today, The New York Times announced her as their new 52 Places Travel Writer. In a week Jada will travel the world and write about it for The New York Times. Can you imagine how many writers dream of this job? How many amazing writers applied for this job? Jada's interview carries even more weight for me today, because now it is not just a story about my favorite writer, it's a story about what it takes to become the kind of artist who is offered The Impossible Dream Job. Congratulations, Jada!)

Jada is a storyteller – and I want to find out how she got so good at her craft.  

I discovered her skill a year ago while doing research about Taylor Swift for an article. I’d read dozens of articles about Taylor by the time I got to Jada’s piece, but hers felt instantly different. It was the first article that made me feel like I was in the room, sitting on the “burnt-orange velvet sofa” with Taylor Swift, in a “sprawling two-story penthouse” surrounded by “jewel tones” and a “rosewood Steinway grand piano.”

If, as Joan Didion says, “writing nonfiction is…like sculpture, a matter of shaping the research into the finished thing,” then Jada is a sculptress who paints her clay once it’s been fired.

In the Taylor Swift piece, Jada could have simply listed what Taylor was wearing that day (it was an article for Vogue, after all) by writing something like ‘Taylor was wearing a dress by rvn.” Instead, she paints a scene, and lets us decide what it means:

“…when I ask Swift who made her black knit tank dress, she has no idea…Swift turns to me for help. ‘I don’t know—do I have a tag in there?’ she asks, lifting up her fluffy fair hair and leaning her back toward me. rvn, the tag reads. ‘My stylist put it in my closet,’ she says, burying her face in her hands.”

When I read this I’m not thinking about clothes at all. I’m thinking about what it must be like to sit on a burnt orange sofa with someone who has clothes magically appear in her closet. I’m wondering what it’s like to live a life where having a reporter on your burnt orange sofa is so normal and comfortable that you lean your neck to let her check your tag. To this day I still think about the phrase "fluffy hair" - it's part of a collection I have: words that sound like music. 

The more I read of Jada’s work (a variety, from pop culture reviews to exonerated prisoners), the more I see that this is what she does; she doesn’t assume something is interesting because it’s well known or sounds click-worthy. She looks for more. It feels like she doesn’t want to waste your time, like she doesn’t write for a paycheck alone – like she wants to make sure she says something, like she wants to give you something for your time.

In short, she’s an artist, though she might not call herself that.  

I call Jada for an interview a few months after falling in love with her writing. She answers the phone and I reiterate all of the above, telling her how much I appreciate her as an artist; she responds with an incredulous “Really?” in a voice that rings with kindness and the soft tones of the kind of introvert you can find me talking to for hours in the corner of a hotel ballroom when I’m supposed to be “networking.”

Her “Really?” is cradled by an unassuming lilt. Her disbelief in her own artistry is not a request for praise, nor a testament to someone who doesn’t know her worth. It’s feels like the first smell of jasmine on a summer night in Florida; the revelation that someone in her late thirties can work on a craft for years and still be surprised by a compliment, or may not totally see herself as an artist. There's a part of me that wants to feel sad, that a woman like Jada should always feel like an artist - but the truth is, I find it a relief. It feels new to know that you don’t always have to feel like an artist to make art.

I answer Jada's “Really?” with a resounding and happy “Yes.” and she explains her incredulity a little more: “It’s weird being like a journalistic non-fiction writer. I’m in it, but I’m not really in’s not like being a novelist and it’s just you on a page.” I recognize this comparison in my stomach – the ‘I can’t draw so I’m not an artist.’ The ‘I’m not creative because I write non-fiction.’ The ‘the true creators are those who create something out of nothing. I am not a real creator. I am not creative. I am not an artist.’

“It’s weird,” Jada continues,” I’ve never really thought of myself as a creative person…someone in the arts, but sort of on the periphery…I think that’s also what journalists are: we’re always on the outside looking in.”

But it’s what Jada sees when she’s looking in that makes her an artist to me.

I tell her how I feel about her piece on the exonerated prisoners, a piece you could argue she wasn’t “in” at all, since she chose to let the prisoners tell their own stories. But I find her artistry in the very choice she makes tell their stories in their own voice, and in the details she doesn’t edit out, like in Jeffrey Deskovic’s retelling of his experience on the day he was released from prison, after 16 years, for a crime he didn’t commit. See if you can spot my favorite detail, or better yet, choose your own: 

“In the morning, when they opened my cell, they told me they were transferring me. I knew that that meant I was going to court…the guards wanted to put the handcuffs and the chains and all the manacles on me. And I asked them, ‘What are you doing all that for?’ That’s when they told me, ‘Well, the judge might change his mind.’ They brought me to the holding area in the courthouse in White Plains. Doubts start coming into my mind. They gave me this brown-bag lunch, which had like an apple and terrible sandwiches in it. One of them was just a dry cheese sandwich and the other was like a bologna sandwich and you could tell that things had been made early that morning so the bread was soggy. I initially put the thing aside. But as more time is going by, I start thinking, Well, damn, I might need this, actually. I might be going back to the prison afterwards, and by the time I get there, lunch is long since over. So I ate the damn sandwiches.”

I tell Jada how many writers might cut the description of the sandwich, how it could seem like an irrelevant or boring detail. To me, the sandwich is everything.

I think about the kind of interviewer it takes to get a well-told story like this, to make someone feel relaxed enough to remember the sandwich, to feel valued enough to repeat it.

Jada is an artist because she recognizes the literary in the mundane. Jada is an artist because she doesn’t cut the soggy sandwich.

She is creative. She is good. And she’s been working at it for a long time. She wrote her first book in middle school: “I wrote a book in 6th grade…[with] vivid scenes in a haunted house, and a character named Fatso Bratso.” The book was 40 pages, and much of it took place in Nantucket, which Jada laughs about when she remembers she’d never actually been but had always read about Nantucket: “I was an indoor kid in New Mexico, and it’s really hot and desert-y…so all I did was read.”

But despite all the reading, writing, and imagining, Jada didn’t plan on a writing career, the same way someone who grows up swinging on swings doesn’t think about making swings a full time career. Reading and writing were simply forms of play – ways to stay cool in the desert.

Jada won creative writing contests and wrote poems throughout the rest of her schooling, but writing is not the career path she envisioned. Non-fiction “stories” of a different kind caught her attention; after high school she majored in History at Yale University where she was assigned a writing tutor, Fred.

Jada saw Fred a lot in college because, as she explains, he’s someone you'd see “anytime you had a paper and you were struggling to figure it out,” and by her own admission, that happened to her a lot: “I had five hours until deadline and I hadn’t written anything; I would go in and he’d be like, ‘wow I’m really worried for you.'"

I can't help but start to imagine that voice in my head as my own personal "Fred" - wow I'm really worried for you you haven't finished your book yet. Wow I'm really worried for you what are you doing with your time. Wow I'm really worried for you why is this taking so long?

And yet, Fred sees something in Jada’s procrastinated writing. “At some point he mentioned that he thought I should take this non-fiction writing course.” Jada takes both of his writing classes and joined the magazine he ran at Yale called The New Journal, where she is immersed in an intensive writing environment: “everything went through 18 rounds of edits.”

Eighteen rounds of edits. Eighteen rounds of edits. Eighteen rounds of edits. Would it annoy you if I repeat that eighteen times? I kind of want to. But I won't. You get it, I know. EIGHTEEN! Ok. That was the last one. I promise. It's just I can't help but be obsessed with this idea of editing. Editing is painful the first time, let alone the seventeenth. And yet I think it's what makes an artist good. But what I feel like they don't tell you is that when you're in edit number fifteen you feel like I AM THE WORST AND I AM NOT AN ARTIST AND I'M OBVIOUSLY A TERRIBLE WRITER SO REALLY I SHOULD STOP NOW. I feel like it's those who can keep going in that space who get really good. The goal perhaps not to stop the voice, but to simply make it to eighteen despite it. And then, to do the really brave and impossible thing: start again with edit one. 

Being immersed in an intensive editing process at one of the best universities in the country can make Jada’s path seem deceptively straightforward: combine her early fiction writing (e.g. "Fatso Bratso"), interest in non-fiction stories (as a History major), and ivy-league-writing practice, and botta-bing-botta-boom she has found her perfect career and will be a journalistic non-fiction writer for the rest of her life! Easy peasy.

Except that’s not at all how it happens.

Jada enjoyed her time at her college magazine, but she didn't feel any grand calling towards a journalistic non-fiction career. She graduated college and returned home to New Mexico: “I didn’t really have an idea of what I wanted to do for a job. My mom was like, ‘Well, you’re not living here for the rest of your life, so we’re getting you on a plane.  You can stay with your grandparents for a couple weeks [in New York], and then you have to find an apartment and figure out your life.’”

Jada is pushed back out of the nest, into the city.

Following a vague interest in film Jada started off doing a series of unpaid script development internships in New York. She found it fun, but as she put it, “I couldn’t live without any money.” Any artist knows this song well.

So she started applying for any job she thought would pay the rent, walking her resume around New York. 

She brought her resume to New York Magazine because of one of those seemingly innocuous moments that sometimes start entire career trajectories. “I’d never read New York Magazine. I just went because my mom’s friend had it in her apartment and she said, ‘Why don’t you apply for New York Magazine?’”

Around that same time an assistant at New York Magazine had just told her boss that she needed to leave her job right away, but her boss told her that she had to find her own replacement first. Enter fresh-out-of-college Jada, resume in hand. The assistant offers Jada her job on the spot. 

But Jada got a higher paying offer that same day from another job she'd applied for at American Lawyer. Jada had done a law internship as part of her History major and was considering law school – she applied for the American Lawyer job as sort of“a waylay station before I had to go to law school…sort of about trying to be the ‘good girl’ that I thought that I needed to be, which meant that I probably ‘should’ have gone into law.”

As I'm reading this part on my eighteenth edit of this piece Bobby Lopez and Kristen Anderson-Lopez's lyrics dance into my head: "that perfect girl is gone..."

Jada remembers walking into the office at American Lawyer and realizing “I don’t want this to be my life. And no disrespect for anyone who works at American Lawyer. It was like, ‘Am I really going to be writing stories about lawyers?’ I just couldn’t do it.” I picture Jada walking out of American Lawyer with a clear cape cascading down, following her down subway stairs, the ends collecting new york grime but the windows of the subway car crackling with icicles. 

Jada chose the New York Magazine job even though it paid a lot less than the American Lawyer job (and neither paid very much). I ask her why she didn’t take the higher paying job and she explains: “Lots of people leave college and know what they want to do, but I had no idea.  It took a really long time to figure it out…I knew deep down I didn’t want to be a lawyer.”

I think about the times when I have no idea where I’m going or where I even want to go next in my career - when all I can do is move away from the things I know for sure I don’t want. But often that leaves me feeling more lost than ever, like I'm stuck in a manhole (or womanhole?) with a bunch of construction workers peering down like, eh, lets just leave her there, we have no work for her up here. 

But for Jada, the rest is a dream come true: she takes the assistant job at New York Magazine and an editor quickly notices her creative brilliance and within a few weeks she is interviewing Spielberg!



Jada spends the next four years “answering phones…filling out healthcare forms…writing contracts and paying writers.” Jada remembers: “It was definitely a drag.”

You know what's coming now right? Four years. Four years. Four years. Four years. 

Eighteen rounds of edits. Four years of filling out healthcare forms. The things that make a writer that no one ever quite tells you. 

What gets someone through those four years? For Jada it was the creative atmosphere and sense of possibility: “We were in a very creative office…[the assistants] sat right outside the editor’s offices….[and the editors] would walk out of meetings and just hand us small things to do – really tiny assignments – and those just built on each other.”

For four years she hangs on every tiny assignment, writing whatever she’s given, doing the grunt work. Waiting, hoping, writing, waiting, hoping, writing, filing, filing, writing, writing, filing, filing, filing, filing, writing, writing, writing, hoping, filing. 

So many dues being paid in the only currency accepted - diligence and difficulty.

Jada and her fellow assistants take on any writing assignment they can get on the side, building their skills, all the while longing for the next step – to be summoned out of the assistants desk and into a full time writing job.

Four years after Jada is given the assistant job, one of those full-time writing jobs opens up.

It goes to an outside hire.

This happens again and again and Jada and her fellow assistants feel crushed. “When is it our turn?” they wonder.

Then another full-time writing job opens up (a listings job in charge of chronicling upcoming events in a particular category, like sports) and this time an assistant is promoted.

That assistant isn’t Jada.

“I was so mad!” she laughs as she remembers watching her friend get the job she wanted, “I was happy for her, but she got the jail break, and I didn’t get it.”

Jada was friends with the editor who had just made the hire, and she was comfortable enough (and frustrated enough) to walk into his office and express her disappointment at not being given a chance to move forward. His response: “'I hate to tell you this but you’re never going to get that job…I’ve seen your sports listings - they’re great - but they’re like twice as long as they need to be.  We have to keep cutting them down…But you’re really good at interviewing people and you should just do that.'”

Jada's long profiles are what drew me to her. I love that her writing is not pithy, I love that she does not take shortcuts to keep up with our shortening attention spans. Her articles are what gave me the hope I needed to start this long form blog, hope that maybe people don't read long stuff simply because the writers haven't taken time to edit it eighteen times. Hope that there's still a place for words without gifs. (No shade to gifs though.)

So when the editor tells Jada the reason she isn't getting promoted is because her writing instincts lean towards detail and length, skies open up and Jada finally sees what she was always meant to do. She hugs the editor and they ride unicorns along a rug of rainbows all the way to the features office where she promptly gets a job interviewing people full time and…you already know where I’m going with this, right?

Here is what actually happens next: “I was so pissed off...I spent another year doing the editorial assistant thing.”

Another year.

But those editor’s words stayed with her. “I took it to heart.”

Jada is patient. She works hard and continues to take any writing opportunity available, even if it isn’t necessarily what she “dreams” of doing.

Another full-time position opens up at the magazine in party reporting. It’s still all about concise writing, but this time it’s also about interviewing people at least, so Jada decides to apply.

She gets the job. 

Jada spends the next few years going to elite parties, asking celebrities questions and getting quotes for the magazine. She interviews. She writes. She starts managing a whole team of freelancers and interns. She works until 4am most nights. And despite having a job that revolves around parties, her social life dissipates.  

Prince was a catalyst for the next turning point. “One of those [4am] nights, Prince had a book party that I was invited to where he was playing in an apartment, and [because of my job] I missed Prince playing a concert in an apartment, and I was like, ‘This cannot be my life anymore.  I cannot do this.’”

First world problems, amiright? But Jada isn't whining about missing one elite event because her job has her at another. The Prince Disappointment was about something else entirely. 

Jada realized the job she was doing was close and yet very far from the art she longed to do. After that night she realized, “I do not want to be the person who is telling people what to do or managing them.  I want to be the person there.  I want to be the person who is seeing things and writing about it.” It can seem like a simple revelation, even an inevitable one knowing what Jada does today - but when you're living this part of your life its all fog and these kinds of epiphanies are fresh batteries for a flashlight that's burnt out.

And like most career turning points, this one for Jada “came out of frustration.” Frustration is a prickly guide, but a guide nonetheless. 

I notice that Jada never seems to let the frustration keep her from building thousands of hours of practice in her craft. Even in the frustration, when her days and nights were consumed with managing others and doing her job, she took every opportunity to do writing assignments on the side: “I was writing every single day and every single night.” Because 10,00 hours of working on a craft on top of a day job is always oodles of fun, right? Jada tells the truth about this part of craft development: “…it was exhausting.”

And even though so many of her words are rejected, like that time she spent five hours working on a 250-word sports listing about a dedicated group of fans in Harlem and it’s cut to 30 words, she keeps trying. She keeps writing.

Her dedication is eventually noticed. She starts to get assigned mini profile pieces which turn into bigger culture pieces which eventually turn into full-length features. “It was sort of gradual,” Jada remembers, “you start voting with your feet. You do the things that you want to do and then eventually those become the things that you do.”

After years and years (and years and years and year and years) of grunt work Jada is finally doing work she completely wants to do, in a craft she cares about, and everything about it is perfect and wonderful. Right?


“The process of writing is terrible. It’s so painful.  It’s the worst thing in the world.  But the idea of writing is great, and it’s also a compulsion…it’s just the way that I am, and I can’t stop it, so I might as well go with it.”

Jada explains how her compulsion is also part of a joyous chase: “That’s the great thing about writing…you can always go over a sentence again and find a word you can cut or find a different way to say something… I do think there’s a time when you should let it go and just be happy that’s it out in the world, but the process of learning how to be a good writer, you can go to the grave working on that.”

I don’t know how we get to where we get next, but somehow our conversation about the pursuit of mastery turns into a conversation about rejection. Maybe because rejection is so good at matching the pace of ambition.

Jada tells me about a rejection that gutted her during her time party reporting: “It was right after my grandfather had died, and I was going out to parties and having to put on this thing where I’m cheerfully going up to celebrities. [One night] we were all trying to wait for Kanye West. Kanye was supposed to show up and he literally walked into the room and walked out, and we sat around and waited an hour for that to happen…[so now] I really didn’t have anything to write about for this party.”

Ever the professional, Jada looked around for another idea and spotted a well-known super model. “I went up, and I was like, ‘Hi, I’m Jada from New York Magazine.  Just a couple quick questions.’ And she agreed to it...I had this really innocuous question.  It was something like, ‘Have you ever not sat front row at a fashion show?’ And she was like, ‘That’s a really stupid question.  I can’t believe you’re asking me that.  Why are you wasting my time?’ And I held it together for another two minutes, and then I just ran off and cried, and I was like, ‘What the f--- am I doing?’”

Jada remembers the blow, how personal it felt at the time. I ask her how she feels about rejection now. “I don’t think you ever get over it…I would be surprised if there was anyone [rejection] didn’t hurt…whether it’s rejection when you’re trying to interview someone or a bad comment on an article, or no one reads the article.  I still experience it constantly…[but] it helps…[when] you can’t picture yourself doing something else.”

She also tries to remember the mantra “It’s not about me.”

We talk next about rejection’s close cousin, self-doubt. It’s “just always there,” Jada shares. I ask her a question that means a lot to me: What keeps you writing through the self-doubt? I don't realize it but I'm holding my breath waiting for her answer. I don't hold it for long because she doesn't hesitate. 

 “Guilt, probably."

I laugh one of those laughs that spray water.

“Guilt” is the last thing I expect Jada to say, and yet it feels immediately and deeply true. Guilt has kept quite a few projects alive when all I wanted to do was kill them. I wonder for a moment if this is true for anyone else. I start to imagine a new kind of Oscar acceptance speech:

I’d like to thank my manager, my agent, but this award is really dedicated to guilt! Thank you guilt for getting me out of bed to work even when I hated myself and everything I was working on. I couldn’t do it without you guilt (tears up) and, guilt, I just wanna say…(cue exit music).

Guilt gets Jada moving on a project when she feels unsure, but what gets her all the way to the finish line is knowing she’s good at what she does. Guilt can morph into confidence, excitement even.

Jada credits great people in her life for helping her build the kind of confidence that pushes projects past the breaking point: “I was able to get past a lot of [self-doubt] by having other people around me who believed in me.  It’s really sort of a fake it until you make it kind of thing, and it really helps if you have other people who see something that you can’t see yourself.”

While we can’t control who might see something in us we can be that person for someone else. I try to remember to tell the artists in my life what I see in them. We need more artists, and emerging artists need at least one person to tell them what they see  – or they will most likely stop during the crucial but very painful parts. They still stop at edit sixteen. It’s a survival mechanism. Any sane person will stop. 

Jada found ways of thinking that also helped slowly built her confidence during the editing process. She'd say to herself, “Maybe…you didn’t write it the way that you wanted to, but you got some good quotes.  So feel ok about that, and then have the confidence that you always get good quotes…and then try and work on the [other] parts...[but] concentrate on the thing that you did well.”

Jada does a lot of things well today, and if you don’t believe me, ask Stevie Nicks.

Three years ago, Jada was assigned a profile on Stevie. Fear gripped her as she knew so little about Stevie Nicks or her music. But Jada got right to work and started with research, letting herself be drawn to what she found most compelling. A question beings to emerge from the heaps of research that Jada grows desperate to answer: Why does Stevie Nicks mean so much to so many women?

Jada spends the next four months trying to answer that question (she has to fight to keep extending the deadline because she is so dedicated to getting it right). She finishes the piece. It reads like a song. Some of my favorite ‘lyrics:’

“Look to the shawls…”

 “ …a woman transformed, wrapped in fringed silk…fine fabric unfurling from her delicate shoulders like the banner of an advancing army, heralding not just a song but the coming of an event…”

“…those shawls have magic in them.”

Jada rarely hears back from the people she writes about, so when two weeks after it publishes she hasn’t heard any feedback from Stevie Nicks’ camp, she isn’t surprised: “In this business you really don’t expect to hear anything.”

After the article publishes Stevie Nicks plays a show nearby and Jada wants to go. She reaches out to Stevie’s assistant whom she’d gotten to know from the piece and nervously asks for tickets. Jada remembers the assistant’s response: “’Oh yeah.  Stevie loves you. Please come!’” 

Jada shows up with a friend and enjoys the show – somewhere along the way she has become one of those women Stevie means something to.

Stevie sings her songs and Jada and her friend watch the shawls. “Landslide” is up next, Jada knows, because she’d seen the show in rehearsals; Stevie dedicates “Landslide” to someone every night.  On this night, Stevie places her gloved hand over the mic and begins her dedication:

"I always kind of save this for people who I consider to be family or really my closest, closest friends…I would like to dedicate this song to a girl, a lady…Jada. She wrote the most beautiful article about me She followed me around for three days. I thought, 'She's 35 years old, she doesn't even ... ' [but] come to find out that she got it. She got something that no one who has ever written about me has ever gotten. I'll never, ever forget it. It lives in my journal."

Jada bursts into tears. Her friend grabs her phone and starts taking pictures of Jada crying and all the people around them start asking “‘What?  Is that you?  Is she talking about you?’”

“It was really…really crazy,” Jada remembers. After the show Stevie invites Jada backstage because she wants to talk to her more. “Stevie Nicks is herself a beautiful writer.  That’s why people connect with her songs.  She’s a poet.  So for her to see something in that was really special, and also to acknowledge…I put so much effort into it. I really wanted to do a good job, and I had.”

As a creative, it doesn’t get much better than that: “I was high on it for a couple weeks.”

So Jada The Writer lived happily ever after and never doubted herself or her writing again!

The End. 

Roll Credits.

I thought about actually ending this piece there. There is satisfaction in the perfect ending, maybe because real life is ongoing, messy, a continuity of plot and conflict, sometimes painfully devoid of dénouement. But at about edit seventeen I realized that the story just doesn't end there. And at least all that messy continuing is also evidence of something to be thankful for - if you’re still struggling, it means you’re still alive.

It means you’re still trying.

It means your story isn’t over yet.

And neither is Jada’s.

Self-doubt returned, even after the Stevie Nicks Moment. “Then this huge wave of self-doubt came through where I was just like, ‘That’s the highest that it’s ever going to get.  Where do I go from there? I can’t top that piece.’ And I haven’t.  I’ve written other pieces that I think are good but…”

Jada’s favorite piece of advice about the highs and lows of creative work came from a therapist who told her: “It’s about batting averages…you have to just be a baseball player and the best baseball players in the world, they strike out.  They strike out.  Every once in a while they hit a home run and that’s a great moment. But if you’re going to choose this to be your life…if you’re going to keep putting yourself out there, you can’t expect greatness every time.  But you can expect some really good satisfying moments, and you just have to keep working toward that.”

Luckily, it’s the “working toward” that Jada finds most satisfying. It doesn’t mean there aren’t still days when writing feels terrible, it just means she’s learned that somewhere on the other side is something worth the frustration.

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