General Education

How to Become a Professional Writer, as Explained by the Funniest Writer We Know

How to Become a Professional Writer, as Explained by the Funniest Writer We Know
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Ben Robinson August 7, 2019

“I wake up at 10:30, which is honestly reason enough to become a writer as far as I’m concerned.”

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Jennifer Wright writes books. Jennifer Wright writes articles, for Harper's Bazaar and other publications. In all of those things, Jennifer Wright is very, very funny.

The political Editor at Large is also very funny when she talks about her path to becoming a professional writer, which began during her college years at St. John's College—not after, which she will tell you (and told me) was crucial. Her journey involved a lot of pitching, many rough rejections, a few lucky breaks, and wearing an eyepatch while serving shots in a pirate-themed bar in Greenwich Village.

We also covered a ton about how to write a book and get it sold. The writing part is almost the simplest—and Jennifer provided a ton of insight into how pitch book ideas, where to find an agent, and how the entire, often convoluted process works, from marketing, to auctions, to first-read contracts. That, and how she uses Twitter.

"Then, I wrote a book about fashion accessories and trends throughout history that killed people."

What is your job title?

Author. I've written four nonfiction history books, Get Well Soon, It Ended Badly, Killer Fashion and the upcoming Dead Girl's Guide to Dating.

Where do you work?

I am the Political Editor at Large for Harper's Bazaar. I write for numerous other publications, including the New York Times, the New York Post, the Washington Post, Glamour, Cosmopolitan, Popular Mechanics and many more.

How did you build a freelance writing career?

I started writing a column for my college newspaper and realized that I really liked doing it. I knew it was something I would feel comfortable doing on a regular basis and wondered if there was any way to get paid for it. I looked into local publications and began writing for a magazine called What's Up Annapolis. Then I began reaching out to publications that I was reading online, and sending them ideas for articles I'd like to write for them. I started getting picked up by a few.

By the time I graduated, I was at least able to say, "I've written for publications and been published—here's where I've done that." I graduated in 2008, which was right in the middle of the recession.

So, things did not immediately translate into a job at Vogue as I was hoping they might. But they did mean that when I started pitching smaller publications around New York, I could get a few little, maybe 200 word assignments, at places like City Magazine and Gotham.

"You could write a piece about how teenagers only listen to bird calls now, not music, and the New York Times would follow up with a trend piece about it in the next week."

At the time, I was working as a shot girl in a pirate-themed bar, which was terrible. I was supposed to wear an eyepatch. Have you ever tried to serve a tray of shots with an eyepatch on? You have no depth perception. I'm pretty sure that place had more spills than anywhere in the world. But it paid very well, and left my days free to write, pitch places, and beg editors to let me write for them.

Some editors did not like my writing at all. One told me that I would need to pursue far more serious journalism if I was expecting to write for a website the caliber of So, I spent my first year-and-a-half in New York doing that.

I edited a woman's blog called "Ask Melissa" by a very nice woman who really wanted to have a famous blog, but didn't really want to write a blog. It was a weird time cobbling together as many tiny jobs as I could and waiting to see if something would take off. I remember going home over Christmas break and bursting into tears, asking my family if I could come home for a while to figure out what I was doing. They said, "absolutely not, go back to New York." That was a wise decision on their part.

Then I got a job as a deputy editor at a website that Elizabeth Spiers was starting, called The Gloss. I worked there for three years and eventually became the editor. We got up to something like 2 million pageviews a month and had a lot of fun for a while. I left and worked at the Observer for a little while, and then I got a book deal.

I sold my first book and worked on it pretty steadily for a year while writing for the New York Post. Then I got a second book deal and spent another year working on it. After, I did a smaller third book, and another, smaller fourth book—both are illustrated, so they didn't require my entire life to write them. After the 2016 election, I started writing more about politics, including at Harper's Bazaar.

Let's say I have an idea for a book—where do you recommend going from there?

First of all, you need to find an agent. A lot of people say you can go to Publisher's Weekly and pick from the lists of agents. I don't recommend that. Go to the acknowledgments section of any book you really like and feel is similar to the book you want to write, and see who that author's agent is. It'll probably be the third person they thank, right under their parents.

Then, write, maybe, the first three chapters of your book so you have something to send agents. Let's say it's on cool historical women. You'd write three sample chapters, each on a cool historical woman you love. Next, you'll email this agent, explaining who you are and what your book idea is. Hopefully they will say, "Wow this sounds really interesting. Show me what you've got."

So, you'll send them your sample chapters. If they like it, they'll probably say that you need to come up with a 50 page proposal to send around to publishing houses. This will include your sample chapters, what books yours is similar to (hopefully all of which are amazing best-sellers), and who you see as your market. If this is a book on historical women, let's say the market could be young women who enjoy watching Drunk History.

"There's probably always a part of me that sees edits on my work and thinks 'You fool, my work is perfect, how dare you try to edit me?'"

You can find statistics on how large this audience is and stretch your imagination to anyone else you feel your book would appeal to. It's also good to have connections to publications that you think would review your book or interview you when it comes out.

Your agent will shop your proposal around and hopefully, at least one publishing house will want it. If it goes really, really well, more than one will want it and there will be an auction to determine who gets your book. As I was disappointed to find, an auction doesn't mean you get to sit in a room and watch people furiously fight over your book. It's conducted through your agent.

What's hard about writing for a living?

There's probably always a part of me that sees edits on my work and thinks "You fool, my work is perfect, how dare you try to edit me?" I don't have much of an issue putting those feelings aside, but they're always there.

I have acquaintances who haven't been very good at turning writing into a career and they give into those feelings much more than I do. There is an amount of egotism in every writer. Otherwise, they wouldn't think their ideas were important enough to be published in the first place.

Aside from that, very little. I love writing. I love working from home. I love learning and researching history, and making it accessible and funny for readers. The publishing industry deals with a huge amount of writerly neurosis.

When you get to the stage of writing books, people in publishing will treat you as if you're running around their offices with a gun—everyone is insanely polite and kind and complementary. You'll read three paragraphs of praise before you get to a fourth that says "this chapter is actually very bad."

You write books that are informative but also funny. What does humor bring to history?

The classes I enjoyed most in college were about history, crazy things people did, weird events, personalities, and gossip, and I wanted to write history books about that. I tried to bring a spirit to my books so that they read like a very good friend who has researched a lot about history and is going to tell you all about it over a few drinks.

How do you choose what to write about?

Once things I've noticed about many history books is that they don't really focus on female stories. I try to write about historical topics that are somewhat gender-neutral or more skewed towards female voices.

From the start, I really wanted to come up with topics that focused on the female experience in history. The first book I wrote was about historical breakups. The second was on spread of diseases and how they affected society, which allowed me to write about Typhoid Mary and the women who started the healthcare system in New York. Then I wrote a book about fashion accessories and trends throughout history that killed people.

It was another chance to talk about an area that affected a lot of women, especially when they aren't addressed in other areas that historians that tend to cover, like war or politics, or the evolution of the stock market.

"I wake up at 10:30, which is honestly reason enough to become a writer as far as I'm concerned."

What publisher are you with?

I'm under a first read contract with MacMillan Publishers.

How does a first read contract work?

It's pretty common that if they publish your novel, they'll ask to have the first read on future novels. If they liked the second proposal your agent sends around, they'll be able to bid on that before anyone else. You can say, "No, I think we can make more money if we shop it around," but doing this can really alienate your publisher. Hopefully, you'll like the people you worked with on your first book and be satisfied enough by the bid to say, "Yeah, that sounds great. We'll take that amount."

Where did you go to school?

I went to St. John's College in Annapolis, Maryland. I graduated in 2008.

What was your favorite thing about college?

It's a great "books" school, so everyone was required to take the same reading-focused curriculum. I frankly romanticized the idea of reading all of "Plato's Dialogues" out of proportion, so it was right for me.

There was a huge emphasis on reading the classics—and learning Ancient Greek to be able to read them in their original form. It's good to read "Thucydides," if only so that when someone you don't like describes themself as an intellectual for having read him, you can scoff and say, "I know plenty of dumb people who have read 'Thucydides.'"

Looking back, are there classes you wish you had taken or could have taken?

Women's studies would've helped a lot, as I spend a lot of my time writing about female Presidential candidates and writing for women's publications. A creative writing class. A journalism class, so I would know what "TKTK" meant when my editors used it in their notes! In retrospect, I think I should've taken anything that would've actually helped with my career. Instead, I read a lot of "Thucydides."

What's your advice for students who want to go to St. John's?

The idea behind St. John's is that you'll read the great works of western literature. If you go there, you should read a lot of works by people of color and women to balance the almost entirely white male curriculum. You're going to spend at least your first year reading philosophers who will tell you that women don't have souls. Luckily, I think a lot of people can read their ideas and say, "I'm reading this from an interesting historical perspective."

What's a typical workday like for you?

I wake up at 10:30, which is honestly reason enough to become a writer as far as I'm concerned. After I get up, I generally respond to emails, and send out article ideas to publications for an hour or two. Then I go to the gym for half an hour and grab some lunch, which I eat in front of the TV. I usually finish that by about 2 p.m. and write until 6:30 p.m., at which point I make dinner for me and my husband.

Mostly, I just try to make sure I write at least 500 words every day. Some days, they come really easily and I knock off early and go to the movies. Some days, it's like pulling teeth and I end up working for a few extra hours at night after my husband goes to bed.

How did college prepare you for your job?

I think reading texts written a thousand or so years ago reminded me that people in the past weren't all that different. They were funny. They were petty. They loved dirty jokes way more than we do. I wanted to write books that exposed people to that, which lead to writing humorous history books.

What's your advice for students who want a job like yours?

Start pitching local publications now. It's not too early. If you're a teenager, you can propose pieces on youthful concerns to your local paper, and they will publish it because no one over thirty has any idea what teenagers like and we're all obsessed with trying to figure it out.

Seriously, you could write a piece about how teenagers only listen to bird calls now, not music, and the New York Times would follow up with a trend piece about it in the next week.

What do you wish you knew when you were starting out your career?

Never, ever offer to write for free. It might happen, like if a great website you want to contribute to that has no budget. But if you treat your words as though they're worth money, others will as well.

That, and at the beginning of your career, you should say "yes" to every industry event or party you're invited to—even if you're a writer and dread having to socialize so much.

What inspires you?

Reading, mostly. I'm a strong advocate of reading everything—great books, terrible books, nonfiction, fiction, the works.

Do Jackie Suzann's books qualify as terrible books? I've read "Valley of the Dolls," and everything Jackie Suzann ever wrote. They're fun to have on hand when people talk about how things were better in the good old days, because the people in those books were horrible to each other.

How important is Twitter to your field?

Well, I have to use it. Some of the places I write for include sharing my work on Twitter in their contracts. In that way I'm sort of tied to it, because they're not just paying me for the pieces I write, but to be my own publicist.

I use Twitter to post almost every article that I write, to promote my books, and post about lectures I'm speaking at that are open to the public. I also use it to make jokes and give people an indication of the content they might find in my books. I don't think anyone who's reading my Twitter is going to wander into my books and be shocked.

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