Some Writing Advice

What I had to learn, and wish I knew before

Freddie DeBoer is one of my favorite writers for a variety of reasons, but I particularly enjoy his frankness. If you’re a young writer just starting out or someone who wants to transition into the field, his pieces must be read. Few are going to be more honest with you about what it takes to be a writer or what awaits you. In some sense, I have little to add.

But I figured, since I don’t do much of it here, I’d pass along some thoughts on how the sausage gets made. If you’re new to reading me, I’ve been writing for a living since 2011. I’ve worked inside newsrooms and outside of them. I’ve published books. I’ve hit many career goals but still seek to hit many more. Until I was 18, I had no interest in becoming a professional writer or a journalist. All I really wanted to do was play baseball. My parents are both avid readers but never worked in any writing field. There was no family business for me to enter, no one to pave the way in terms of jobs or internships. As a 21-year-old, on a whim, I sent an email to the editor of the Brooklyn Rail, a free arts and culture publication I liked, and said I wanted to write for them. Graduating college into an awful recession, I figured I’d teach high school for a living and try to hustle up writing gigs on the side since I realized, by that point, writing was all I really wanted to do. I spent my college years compulsively writing novels that would never be published. I contributed essays and acidic satire to the alternative college newspaper. I hardly did any journalism because the idea of speaking to strangers filled me with dread.

What I did have, by the time I turned 21, was ambition. It was red-hot—equally useful and debilitating. There’s a certain curse to ambition. If you have enough of it, it will be the rocket fuel that gets you through near-endless bouts of rejection and failure. I’ve rarely been recruited or “poached” to write for anyone professionally. It wasn’t until my early thirties, I’d say, when editors began approaching me, quasi-consistently, with subjects to write on, jobs to take, or books to write. And even then, I still pitch far more than I ever get approached for anything. In many writer origin stories, there’s the benevolent mentor or professor or author who begins to open doors for the young writer, who deems the writer a worthy protégé. Joe McGinniss submitting Less Than Zero, a novel written by his student at Bennington, for publication, etc. There was none of that for me.

Ambition can torture you. Only in the last few years did I let certain anxieties go—of not being good enough, of not measuring up. In my twenties, I would ride the subway out from Sheepshead Bay, where I lived, and into Manhattan with this perpetual mix of excitement and mild fury. Sure, I was doing this, but why I wasn’t I publishing there or there? Why hadn’t I been anointed something or other? Ego is dangerous. I still have plenty of it, but you can’t allow it to consume you. You will become, steadily, more miserable.

Some advice:

Be Polite, But Be Aggressive

If you are anything like me, you might be a shy person. You may even dislike making eye contact. You may not want to “bother” an editor with an idea. Understandable. But to get anywhere, you will have to engineer yourself to not be shy. It’s a shame that so many of these fields reward the overeager, the “go-getters,” the compulsive networkers. Still, you have to put yourself out there. You have to keep trying. If an editor rejects your idea, wait a couple of days and pitch another idea. Or don’t wait that long. Someone says no to you and come back with something else. The worst that happens is they say no again.

For the record, it’s always better to pitch an idea than a completed article. Only in fiction, do you want to finish the work beforehand. Don’t shop a novel if you haven’t finished it yet.

You have to learn that failure is part of the business. Absolute failure. You must will yourself, psychologically, to not care about failure. Perhaps, in this regard, being an amateur baseball player prepared me for this. Baseball, more than any sport, is a game of failure. In the Major Leagues, you can win a batting title getting hits in only 32% of your plate appearances. If you fail to reach base 60% of the time, you’re on the way to the Hall of Fame. Unlike baseball, you lose nothing by trying and failing in the world of writing. There is no batting average. No one keeps score. My success rate, in terms of pitches and getting anything published, likely hovers below 20%. I’ve been rebuffed by too many agents and editors to count.

I got nothing by waiting around. If you’re unsatisfied with your current station, you’ll have to turn yourself into a battering ram to get somewhere else. There’s no other way.

But be nice! Do not burn bridges with editors, even if you disagree with them. Don’t alienate agents or anyone else in the business. Always thank people for considering your ideas or your work. Treat people like you would want to be treated. Always respond to emails. Always hit your deadlines.

Be Reliable

Beyond Freddie, another writer I very much admire is Will Leitch. Will, Freddie, and I all write more, day-to-day, than most people. In them, I find kindred spirits; we are people with healthy compulsions. We all have fun doing this stuff and wouldn’t want to do anything else. A little while back, Will imparted a very good lesson that I think all writers early in their careers should take to heart: be reliable. Be the person who follows directions. Be the person who takes the deadline seriously. Be the person who produces when they say they are going to produce. The writing world, the media world, the world of the arts—all of them have their flakes. You’ll get further just by being the person who can be counted on. This is a very boring but real lesson.

Be Different

Freddie, again, put it well—for God’s sake, be weird. Social media has, unfortunately, bred conformity, flattening writing and ideas. Twitter hardens the groupthink. No one wants to be the outcast and relive high school, getting shunned socially or alienating the wrong editor. It’s far easier to aggressively seek the consensus and stay there. There’s nothing worse, it seems, than being the “just asking questions” guy or the “main character” or whatever the elderly millennial hall monitors deem strange or unsightly.

Your best bet, these days especially, is to ignore them. Writing, like everything else, is a market, and if you’re desperate to keep up with one hundred other people belching out the same takes about politics and society, you’ll lose. Don’t manufacture an opinion or choose the opposite side for the simple sake of choosing it, either. Be yourself, as much as you can be, and find your own voice. Find the gaps in coverage, the gaps in existence, and fill them. It’s okay to have a writing style that is your own. Experiment with simile and metaphor. Consider rhythm. Think about what you can contribute that isn’t exactly like everything else being contributed already.

If you’re writing a novel, you do want to keep in mind what other contemporary books it might compare to—for selling it, an agent or editor wants to know your market. But write the book you want to write! You will fail, or write a lousy book, if you’re too consciously trying to imitate someone else.

Print Stuff Out

You really want to be a writer? Buy a printer. If you’ve written something you like, read it once over in the Word document or Google doc. Then print it out. You’ll be shocked by how many errors you’ll catch reading it a second time on paper. That’s how the eye works. Read with a pen and mark it up. Read it out loud to see if it flows. With fiction especially, this is a must.

Read, Read, Read—And Write

Writing instruction matters and MFAs can be helpful, particularly with finding your writing community. If you’re not getting a degree or spending any time in the classroom, the best way to get better is read more and write more. Another trite lesson, but a lot of this is like athletics. How many thousands of swings does a batting champ take in a year? How many thousands of shots does a point guard take to make the perfect jumper? You will become a better writer by reading widely. Read fiction, read nonfiction, read magazines, read newspapers. If you can’t naturally find time for reading, carve it out. Force it. Treat it like a job.

Writing is a craft. Writing is work. Writer’s block exists, but the electrician or the plumber or the nurse can’t decline work for two or three weeks if they simply aren’t feeling it. They show up anyway. If you want it badly enough, you have to show up. Some days are easier than others, as the cliché goes. I write because I love it and I write to make money. The more I write, the more money I make. I’ve written my way into the middle-class and I’d like to not fall out of it.

The more you write, the more you’ll work towards finding your voice and your style. If you’re going to be great, having a style matters. The best books and essays can’t be carried along without it. When I first became an obsessive reader and writer in my late teens, I read and wrote a lot of fiction. Much of it was not great, unconscious imitations of Ken Kesey or Don DeLillo. But I worked through it, getting to where I needed to go. I paid attention to sentences, paragraphs, and word choice. I studied flow. It took years. Read what you like and read what makes you uncomfortable. Take it all in.

Have a Back-up Plan

Writing for a living is a challenge. Freelance budgets are being slashed constantly and book advances are too low to live on. Your Substack may take years to reach any kind of sustainability. If you’ve got rent to pay, it’s very hard to make it with writing assignments, especially when you’re starting out. One unorthodox piece of advice is to leave an expensive city like New York and try to hack it elsewhere. You can pitch great ideas from rural Ohio or Georgia. I’m a native Brooklynite and still live here, so that advice, coming from me, is a little hypocritical. Instead, I’ll speak to you like you’re living in New York, San Francisco, Los Angeles, or anywhere else that charges you too much for a one-bedroom.

Have another job. My plan was to be a public school teacher. I substitute taught until I landed a poor-paying staff job at a local newspaper and decided to do that instead. It’s fine to have a day job that has nothing to do with your novel-in-progress, your essays, or your reportage. Editors don’t expect their freelancers to not be making a living elsewhere. If your job causes an ethical conflict with the project you’re doing, disclose it. Otherwise, work anywhere. Herman Melville ended up in a New York customs house. William Carlos Williams was a pediatrician. Nell Zink, one of my favorite contemporary novelists, has held every job imaginable. “Whatever I was writing at the time, I knew there was no market for it and never would be, because there’s never a market for true art, so my main concern was always to have a job that didn’t require me to write or think,” she said in one interview.

It’s nice to be independently wealthy or marry someone who is. Until then, do what you can to get by. If anything, the experience will only make your writing better.