By Laura Van Slyke and Jeff Bernstein


Every aspiring journalist knows the dream: the Columbia degree, weekend jaunts in Central Park between celebrity interviews, hunkering down in a Harlem Brownstone with a hot cup of joe in hand while revising that line of a NY Times Piece. Jessica Henriquez has lived it for the last five years. We caught up with Jessica to learn more about her journey as a writer, her creative process and hard fought lessons as a freelancer and essayist.


Jessica is teaching a online Personal Essay Class at the Pad starting Tues. June 6. If writing brutally honest essays for top tier publications like Salon or O Magazine is your thing, you should check it out.


1. Tell us about your background.


You know those obnoxious people who say things like: I’ve always been a writer, or I’ve been writing since I could hold a pencil?  Well, I am one of those obnoxious people. On my bookshelf, I have a dozen thick journals that hold every single one of my secrets, heartbreaks, and pages of the agonizingly boring analysis I’ve made about the world since I was 6. I didn’t pursue journalism or creative writing in college. In fact, I studied to be an Elementary school teacher until I realized that I wasn’t especially fond of other people’s children. 


I broke into the publishing world like a teenager breaks into a neighbors vacant beach house: clumsily and quickly. Many people have this assumption that you need to start at the bottom and work your way to the top and for many people–this strategy works. Unfortunately (or fortunately), I was too impatient for that. One of the first cold pitches I ever sent out was to an editor at Vanity Fair (about a luxury hotel in Big Sur that housed guests on one end of the property and employees on the other side). Within 36 hours she sent me a response! It was a no. And because I was so young and naive and ambitious, I didn’t let that “no” stop me.


I simply went down my list and sold the story to CondeNast Traveler – a more appropriate place for a story like that. Rejection is a good thing. Don’t fear it. Embrace it. There are a dozen reasons an editor rejects a pitch and it doesn’t mean you’re a worthless writer who should have listened to her mother and gotten a real job. No means not right now. No means revise. No means cut words. No means find another angle. No means find the right publication.


2. Any tips for appealing to A-list editors?


The best way to appeal to ALL editors is this: have a great story and be easy to work with. It sounds simple, but it takes a bit of effort. In the beginning of my career, I wrote EVERYTHING on spec (meaning – I wrote the entire piece un-commissioned and unsolicited and hoped the editor liked it enough to buy it). That was really motivating for me because if I put in the time and energy to find sources and interview them and write up a 1500 word article, you better believe I wasn’t going to stop until somebody bought it. Another thing to remember is that the writing world is actually REALLY small. If you have one contact that can introduce you to another, that can make a world of difference.


The last thing you want is to end up in the slush pile (the general submissions inbox for a magazine or news outlet). If you have one human person to send it to directly then you are WAY ahead of the game.


3. Do you process things that are difficult to talk about in your essays? For instance, is your NY Times Modern Love essay an example of that? 


That essay was a true labor of love (from living it, writing it and editing it with Dan Jones). There are so many things that personal essays should never be (cliche, naval gazing, written for revenge!), but one thing that all successful essays have in common is that they reveal something to the writer and the reader. Joan Didion has this quote that I love: “I write entirely to find out what I’m thinking, what I’m looking at, what I see and what it means. What I want and what I fear.” Writing has always been a way for me to ask a question about myself or the world or an emotion I don’t yet understand and hopefully by the end of my piece, something has been revealed to me as well as the reader.


An essay doesn’t need to end with a pretty little bow, but it does need to come to some conclusion.


4. Tell us about the your experience as an MFA Candidate at Columbia.


For two years, I was able to dedicate my life to writing down all of the stories that had only ever lived in my head and reading five books a week; it was in so many ways every artist’s dream. I studied with brilliant minds like Hilton Als and Margo Jefferson and Paul Beatty and Rob Spillman and so many others who were generous with advice and encouragement. One bit of advice that sticks out to me is something I was told by the memoirist/novelist/biographer Benjamin Taylor, “A writer is never more exposed than when he/she is writing dialogue.”


This is so true! You know when you read bad dialogue because it is clunky and leaves you feeling uncomfortable and thinking NO ONE SPEAKS THAT WAY! We all have conversations and overhear conversations every day. Yet, so much bad dialogue exists in writing. Take a small notebook with you everywhere you go (or use your iPhone notes app), and write down bits of conversation that stand out to you. Write down that thing a pilot said over the loud speaker that made everyone on the plane laugh. Write down the things children say. Write down how your waiter introduces himself to the table. All of these will be valuable to you when you write a character. 


5. You have such admirable willingness to share your life with readers in pieces like your O Magazine essay. One of the most harrowing things for writers about the personal essay is, well, how personal it is. Has the vulnerability of exposing yourself to your audience ever been difficult for you? What advice do you have for aspiring writers hoping to overcome that barrier?


I’m actually a very private person, ironically. There are secrets and shame that I wouldn’t share with someone in my day-to-day life but you could easily read about it online or in a magazine. It is hard to put your personal life on the page because while it does something beautiful like inviting a reader into your world to connect with your pain or experience, it also invites readers in who will judge, analyze, shame and speculate. I had no idea that I was wasting so much money on couple’s therapy when the people with all of the answers on how to have a happy marriage were trolling the online comments section!


Getting over the fear of exposing yourself in your writing is to really ask yourself why are you writing this and who are you writing this to? I write everything that I write because I want to connect with that reader that is 10,000 miles away who feels how I felt and truly believes that they are alone. I don’t write personal essays for the likes or the shares or for the money. I write about my experience hoping that it finds its way to that person who is in desperate need of solidarity. Reminding myself of the who and the why allows me to quiet the voices in the back of my mind.


6. Tell us about your creative process. 


I just read this great Shouts and Murmurs in the New Yorker about the writing process! My process is a little more chaotic than the one described there. I freelance full time. I’m finishing my first book. I have a 4-year-old son, and I’m training for a triathlon. We all have so many things going on in our lives that waiting for inspiration to strike is not an option. I don’t believe in writer’s block. I think it is another way to say I’m feeling scared today, or I’m feeling lazy today, or I’m feeling hungover today. Writing is my job. If I were a baker, I couldn’t show up and claim baker’s block. Do your job. Mix the ingredients together, whip icing, kneed things, (I have never baked in my life – is that clear yet?) and if it tastes disgusting when you’re finished, well, then you’ve had a terrible baking day but by god you baked because you are a baker. 


As far as routine goes, I don’t need to sit in the same chair every day and drink 2.5 cups of tea first and use my lucky pen, no. I get in 4-5 hour chunk of writing while my son is at school. I write in a hotel lobby, in a coffee shop, on the subway, in my head while I’m eating lunch in the park. The idea of an office and a cubicle seems unbearably loud to me. Other people’s chatter is my white noise. I start every writing session by editing what I wrote the day before and then I pick up where I left off. I write 1500 new words every day. That is my goal and if I don’t meet it I am miserable (ask my partner, he can always tell by my mood if I’ve had a successful writing day or not).


When it comes to personal essay I always have a dozen ideas floating around in my head so I choose the one topic that I feel the most angry/saddened/confused by. I like to start with a solid emotion and write my way out of it. 


7. When you write personal essays, do you have your upcoming memoir in mind?


I think a lot of personal essayists have a book of essays in mind, especially for their first book. I do not. The memoir is called, “Autobiography of a Broken Road,” and I am telling the story of one boy’s death from the points of view of the three people who blame themselves for it. The Modern Love essay was actually the first and only thing I’ve ever published about the story. That is probably why the day it was published was so nerve-wracking for me. I had no idea how people would respond to it. I’ve written about divorce and parenting and miscarriage and illness and therapy and etc… but I’d never written about this one death that had a lasting effect it had on my family. The response was absolutely remarkable. I had 749 emails filled with positive messages and encouraging words and people willing to share their own beautiful heartbreaking stories. Every writer should have that kind of response at least once in their career because it was such a solid reminder of why I write.


8. What’s your biggest piece of advice for aspiring writers trying to get an editor’s attention?


Know the story you’re trying to tell.  The first agent I ever met with was Lisa Bankoff (Ann Patchett’s agent) . This was years ago and we sat down and she asked me what my book was about. My answer took nine minutes and left ME breathless and left her bored. She didn’t sign me (obviously). Instead, she gave me her card and said, “let me know when you know what your book is about.” Do not send an editor 1,000 words describing what your story is about. Get it down to 2 sentences.


Know your audience. You probably wouldn’t pitch the same exact story to Teen Vogue that you would pitch to Harper’s Bazaar. Each publication is different and their readership is unique and accustomed to a certain voice. Read the magazines and the columns you are trying to write for, know what topics they steer away from and what subjects they’ve already covered. Know your publication: If you’re writing a personal essay about a sister who sets up her newly heartbroken brother on a date with his soulmate, make sure the publication you’re pitching hasn’t run a story even remotely similar to yours.


Also, if your essay is 3,000 words long and the section you are pitching to only runs essays between 1500-1700 words, then you’d better start cutting. 


9. Your essays is that they always have great hooks. How do you find them?


Back to the earlier question about the best advice I was given in my MFA – the amazing writer Mitchell Jackson told me that a personal essay should start naturally, like a conversation you would have with a stranger in a bar.


You are trying to lure your reader in with how interesting or enticing or unique you are or your story is. Your first line should be something you would actually say out loud to another human being, something that shows us who you are and why we should be listening to you. Writing is very much like having a conversation, you always want to be anticipating what your reader is wondering, what information they want next. 


10. What can students expect to learn from your class?


There was a controversial New Yorker article recently published: The Personal Essay Boom is Over. One thing that students can expect from my class is proof that this article is false. Personal essays are still valuable, but the social climate is requiring us to raise the bar higher than it has been in recent years. There is no more room in our heads or souls to read click-bait cliché. It’s time for the personal essay to go back to its roots: powerful words with a purpose.


In this class I will help you find a way to write what is personal to you AND still universally valuable. What does your story offer to the world? Together, we will write the story you need to tell while maintaining your dignity, your truth and we will leave your reader with something to think about. Remember, I have been freelancing for the past 10 years! Chances are, I know an editor & the submission guidelines for the publications you’re trying to break into. I’ve made all of the mistakes so that you don’t have to. 


Thanks so much, Jessica! You gave us so much excellent advice. We can’t wait for your class.


Dream of getting paid for writing? Check out Jessica’s Online Personal Essay Class starting Tues. 6/6.


In the meantime, check out some of Jessica’s amazing pieces:
NY Times: Keeping A Family Together After Divorce and The Accident That No One Talked About
Salon: Why Waiting Till Marriage Is A Bad Idea
O Magazine: Getting Back With Your Ex