Writing for the Awl Was the Best Mid-Career Decision I Ever Made

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“Get that money!” is a very popular directive at the moment. Successful writers and actors and other creatives describe walking into a room and demanding a tall stack of cash and then getting it. It’s a story we love: She could’ve accepted less, but she held out for more. As Shonda Rhimes so memorably put it in a recent (great, must-read) Hollywood Reporter piece about Ellen Pompeo’s successful efforts to get paid top dollar for her role on Grey’s Anatomy, “I know for a fact that when men go into these negotiations, they go in hard and ask for the world.”

It is good to know how to go in hard and ask for the world. But every now and then, it’s also good to know when to go in soft and ask for not very much at all.

That will sound like a compromised position at first, but hear me out. When I was 40 years old, I left my full-time staff position as a TV critic for a new full-time writing job that I thought would represent a refreshing change of pace, but quickly proved to be terrible. Thankfully, a few months later, a respected magazine offered me good money to write a monthly essay, so I took a leap of faith and quit my job.

I loved the freedom that came with freelancing, and I loved the fact that, after years of watching TV around the clock, I no longer had to ponder the finer plot points of JAG or consider the intense emotional hardships of being a Real Housewife. Meanwhile, though, I had a big mortgage, two kids in day care, a stepson headed to college, two car payments, a lot of credit-card debt, and not nearly enough income to cover it all. My husband made a decent salary, but I needed to make good money, too, or we would sink further into debt.

Then about a year in, my editor stopped responding to my pitches quite so quickly. This was understandable; I didn’t have a contract and I’d heard that a lot of good writers were vying for the same coveted spot in the magazine. Determined to get my editor’s attention, I wrote entire essays and sent them in such a polished state that I was sure he couldn’t say no. Sometimes he would accept them immediately, but other times, he would ignore my incessant email reminders for two months, and then accept my essay. Or he’d wait two months, then reject it.

I learned a lot about how rats get addicted to cocaine that year. I kept hitting the same lever, hoping my editor would reply. When he said yes, it was like winning the lottery. When he ignored me, I would sink into a funk. Even though I was pitching pieces all over the place, even though I had come to see myself as a writer who deserves to get that money, in truth there weren’t that many slots that paid well for the kinds of essays that I wanted to write. I was starting to feel less like a writer and more like an all too real housewife, one who was too depressed to vacuum or do the dishes. In the mornings, I would try to write and fail. In the afternoons, I would fall into a state of despair, disheveled and despondent among the dust bunnies. In the middle of the night, I’d lie awake, adding up all of our debts. I was anxious all the time. I had no ideas. I felt old and irrelevant.

One morning on a whim, I wrote a long email to Choire Sicha at the Awl, asking if I could write for them more regularly — maybe a TV column, or maybe an advice column. Maybe I could write both? (It was a very wishy-washy pitch; I don’t recommend this approach.) Reading this email now, it’s obvious that I wanted him to hire me and pay me a salary, even though I was pretty sure they didn’t have the money to do that. Carrie Frye, who was the managing editor of the Awl at the time, wrote back to say that they were interested and were discussing it. The following week, Choire emailed to say they were still talking it over. I probably pestered them more, but I never heard back after that.

Four months later, feeling even more desperate, I went crawling back to Choire. I sent him an email, subject line “existential advice column.” “That’s what I should be writing for the Awl. Come on. Just pay me a tiny bit and it’s yours! $150 a week? Just enough so that my husband doesn’t roll his eyes and spit whenever he hears the word ‘awl.’”

Choire wrote back with one word: “DONE.”

To outside observers, this would look like a pretty terrible move. Here was a writer with 15 years of experience writing for big publications, begging for what amounted to a part-time job making $7,800 a year.

But in retrospect, it was the best career decision I ever made. Because the Awl was the perfect place for me. I knew I needed a weekly deadline to break out of the deep, dark hole I was in. But I also knew that I loved writing for Carrie and Choire. I had freelanced for them before, and their attitude was always The Weirder The Better. From the start, I discovered that I could make my column surly or odd or sentimental, depending on my mood, and Carrie would greet it with enthusiasm, a few cuts, and zero complaints. In fact, the more I filled my advice with rage and random digressions and ALL-CAPS SWEARING, the more she seemed to like it. After Choire took over editing, I turned in 5,000 words of digressive psychobabble mixed with Kanye West lyrics, and his only feedback was “omg are you on Adderall?!?!” Another time, his only reply was: “It is astounding that they let you have children.” It was like having an enthusiastic but slightly stoned teenager for a boss — but that was exactly what I needed to learn how to love writing again.

There are times in your career when you know you’re being undervalued; you have to get that money or move on. There are times when you feel undervalued, but you’re actually hallucinating — your editor is just busy or stressed out. (This was definitely true of my editor at that respected magazine.) But there are also those rare times when you have to ask yourself what you value the most, even when it means taking less than you arguably deserve. My experience at the Awl fundamentally changed the course of my career as a writer. Even though my financial situation felt precarious, I was too wound up and self-conscious, creatively, to write anything. The only cure for it was to write for someone like Carrie or Choire or Matt Buchanan, all of whom seemed to appreciate or at least tolerate my most obnoxious creative urges. That could only happen at the kind of small, fiercely independent publication that has very little interest in the conventions embraced by larger commercial enterprises. If I had developed Ask Polly anywhere else, it wouldn’t have been the same.

When news of the Awl’s demise came out on Tuesday, Los Angeles Times reporter Matt Pearce tweeted a link to this piece called “Some Advice for Young People,” written by Choire, about avoiding trouble at work. Most of the piece focuses on trying to stay calm and accept the kinds of semi-innocent drama queens and low-level troublemakers that populate any office environment. But then Choire unexpectedly sets his crosshairs on “soulless careerists,” people “who don’t care about anything or believe in anything and they’re just using us all to get ahead at any cost.” I read that piece for the first time on Tuesday, and suddenly my whole career (and also my friendship history!) made sense to me. There are people who care way too much, about something, anything, everything — love, art, politics, ideas, music, other people. And then there are people who narrow all of that noise and commotion down to one single point of light: career success.

The people who care about nothing but career success will tell you that unpopular things are unimportant, and things that don’t pay well enough are uniformly pointless. Anyone who doesn’t reward you handsomely for your work is automatically disrespecting you. Anyone who ignores you over and over isn’t just busy, but is bad and worthless and should be punished for it. Every relationship is transactional and those who don’t see it that way are naïve. But the best things I’ve ever done in my life fly in the face of those assumptions. Most of my choices wouldn’t make sense to a soulless careerist. The way that Awl founders Choire and Alex Balk operated wouldn’t make sense to them, either. Choire and Alex and the people they hired cared a lot more than they had to. They loved what they loved with sloppy, reckless abandon and lots of extra exclamation points. They turned uncertain weirdos into great writers simply by encouraging what was already there. And they led me out of a very dark place, mid-career, by giving in to my relentless begging (even though a soulless careerist would’ve seen my begging as pathetic, a sign that I wasn’t worth bothering with). And then they gracefully let me go when I did want to get that money. Almost no one is like them.

When you find people like that, be grateful. There are times in your career when your continued survival depends on them. Sometimes, to find a way back to what you love, you have to turn your back on a world packed to the gills with soulless careerists, and look for that one strange person or that one odd publication that might give you some room to breathe and be your terrible, freakish self out in the open. You can’t repay someone for that big of a gift. But when you have a chance to emulate that kind of patience and generosity, to give back to someone else, to believe in someone else for no reason, to encourage someone to trust herself and trust her weird impulses, you seize the chance. It’s an honor to have been given a front-row seat to that kind of grace. I’m glad I groveled for it.

Order the Ask Polly book, How to Be a Person in the World, here. Got a question for Polly? Email askpolly@nymag.com. Her advice column will appears here every Wednesday.

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Writing for the Awl Was the Best Career Decision I Ever Made