On following your instincts

You write two Substacks, Ask Polly, an advice column which explores creative desires, interpersonal relationship conflict, obsessions, regret and intimacy, and Ask Molly, written by Polly’s evil twin. In a recent post, you answered to someone who doesn’t know what they want. How do you choose what letter to ansewer? Is this pure instinct or do you have a selection process?

I just read my mail and go with my gut. My selection is always pretty random and depends on which issues I’ve been turning around in my mind at the time. Some days I have trouble choosing between two or three amazingly precise, entertaining, thoughtful letters, and other days I feel like I’m awash in a sea of the same repeating problems. The two most common letters are “I hate my job and I’m lonely, how do I fix this?” and “I’ve been dating the same person for two years but I have some doubts, how do I decide whether to stay or go?” Luckily I was in both of those situations many times so I have a lot of empathy for how impossible it feels to land there. I also remember believing that every emotional decision could be made using logic and reason, a conviction that can keep you mired in tangled intellectual knots, which typically only brings more anxiety and despair. So it feels good to dive back into even the most common problems and encourage the letter writer to trust their deepest desires and instincts for a change.

As a Substack writer, you have more freedom to express yourself independently and authentically. And when I think of your voice, it feels generous and empathetic. Spontaneous and playful. Yet unflinchingly honest and shameless. How did you cultivate such a distinct voice, especially while writing for outlets like Salon, The Daily and other publications? Did you ever feel creatively constrained?

Every publication has its own particular constraints. I had columns at Salon and Bookforum, wrote essays for the New York Times Magazine, had a Mad Man recap cartoon that ran in The New Yorker online, and freelanced for everything from The Baffler to O Magazine. Even when an editor hires you specifically for your voice, that voice is often muted or polished or amplified or silenced along the way, depending on the overarching imperatives of the publication in question. These days I’m much more relaxed about the end product, but in the old days I was driven mad by the tiniest edits, viewing every change as another sacrifice, another compromise. I don’t recommend this attitude, because if you’re nitpicking about small things, that makes it much more challenging to go to bat for the big things that you truly do care about.

How would you advise journalists to maintain their integrity while navigating the demands of commissioned work?

Freelancing is so absurdly hard, even in the best of times. A lot of commissioned pieces are honestly like being asked to complete a very specific theme paper: We want you to argue X and support your argument with Y and Z. Establishing a rapport with a smart editor is a big part of the job. If you trust your editor and they trust you, suddenly you have some room to get weird and take leaps, but you also have a collaborator who’s throwing out their own ideas and helping you avoid major mistakes. With books, that trust is even more important. I’ve been lucky to stumble on great editors many times over. Being a recalcitrant asshole, I often didn’t know that’s what I’d stumbled on for a while, but I figured it out eventually and was duly grateful.

I’m curious about your early career. At Duke (where we both studied), I noticed a lot of talented peers set their art aside after graduating. They went off to become doctors, consultants, lawyers, academics, finance bros…life got in the way. Nor did I see professors encourage a realistic path to becoming an artist or a writer. How did you build your life to keep writing at its center?

I had the same experience. In my senior year, I took a truly great essay writing class taught by Christina Askounis that made me realize how much I enjoyed writing. But I didn’t see it as a viable career, and there weren’t a lot of resources for creative students back then. And like you, I didn’t realize that the students around me were going to graduate and immediately pursue professional careers in finance, law, and consulting. I think I was fundamentally confused back then about how most of the people around me grew up, namely with money and a lot of pressure to make more of it. My dad was a professor at Duke but my parents were basically misfits. Then I followed my boyfriend to San Francisco, got dumped, and found a new roommate who happened to be in film school. Suddenly I went from panicking about whether or not I should take the LSAT to imagining more interesting possibilities for the first time.

It sounds like being surrounded by someone like minded freed you to think more expansively and creatively. How did you manage to financially support yourself? How did you manage to financially support yourself?

My parents never sent me money. I always had to work full-time, first as a temp, then as an administrative assistant, then as basically a typist. When the dot com boom happened in San Francisco in 1995, I had the enormous luck of being hired by Suck, the first daily website on the internet. That sounds like a lie but it really was the first website to update daily. I was hired as a glorified copy editor but I was given a throwaway column called “Filler” and I collaborated with the illustrator on staff to create cartoons that made fun of SF hipsters, online culture, and my coworkers, who were nerdy know-it-alls like me. Filler was very, very popular among the tiny community of people who were online in 1996, and I soon felt like a very large predatory fish in a very small fishbowl. It was great!

Speeding up a bit, your book Foreverland felt like a super honest portrayal of marriage. Falling and staying in love, against all the irritating parts that come along with prolonged intimacy. However both your book and the chapter excerpt in the New York Times sparked controversy, with some critics interpreting your story as “divorce papers” or labeling you a “husband-hater.” This was years ago, but what were the lasting impacts of sharing personal experiences, then being misunderstood?

Being misunderstood was such a fundamental part of my writing career from the very beginning. I wrote a pretty strange TV column for Salon starting in 2003 and many of that publication’s readers truly hated it and me. I prided myself on never taking these things too personally for years. I think after Ask Polly moved from The Awl to New York Magazine, I probably got a little soft and spoiled, such that the widespread casual misreading of Foreverland truly pissed me off. Here I had written what I considered a very romantic and loving depiction of my marriage, and because I happened to agree to excerpt the one chapter of the book that’s about anger, I became known as that woman who hates her husband.

But it’s a little like being at Duke and not knowing where I was. The internet and the world have changed rapidly over the past few years. No one can expect to be understood, and bold creative moves, humor, and sharp critiques are all a liability. Everything pure and honest you could possibly create will be used against you on the internet. So what’s the solution? Doing whatever the fuck you want. But that was always the solution.

I’m a show-off and I enjoy attention, which helps. But I’ve had long stretches of feeling overexposed and ashamed, too. It’s very hard to strike the perfect balance between self-protection and self-expression, particularly at this moment in human history. I think writing an advice column has helped me a lot, because when young people ask me how to navigate the world as sensitive, smart, creative people, I remember the fundamentals: You have to cultivate faith in yourself, even when you’re not feeling it. You have to trust that when you love something, other people will love it, too. And you have to get into the habit of writing exactly what you find interesting and exciting. For me, that means finding something weird or funny or dark and running with it. I have to follow my whims in order to make new discoveries and connections. Building that active-brainstorming muscle every day will improve your writing immeasurably. Taking that leap of faith every day will also build your faith in yourself. It’s frightening, but it’s fun.

Standing at the edge of the cliff never really gets easier, of course. You’re always a little afraid. You don’t know if you’re going to pull it off this time. And sometimes you don’t! But daring to start, to take the leap, to fall, is everything. You have to fall to fly.

How has your writing affected your marriage and motherhood?

My writing has made me a much better wife and mother, quite honestly, because writing humbles me every single day. Writing is like starting over, from scratch, every morning. You wake up every morning and you recreate your entire world from nothing all over again. Feeling humbled is good when you have teenagers. You need to meet kids where they are, and feel where they are. That’s 90 percent of the job.

And thankfully, my husband and my kids are very supportive of my writing. Bill has never said to me, “Don’t write that.” If he thinks something is funny, he’s all for it, even if it’s about him. I’ve never met anyone who cares less what other people think. He truly doesn’t worry about it for a second.

Which authors do you feel inspired by?

I just finished Miranda July’s novel All Fours and I love it so much. It’s so funny and strange and perfect, I can’t list the number of times it made me smile or laugh or reflect on my own weird path over the past few years. July is a great writer, and she’s absolutely shameless. Her novel reminds me that it’s possible to show your whole self to the world without apology.

Your advice column is expressive but also seems like service-based work. How do you nurture your creative side outside of writing for Ask Polly?

I created Ask Molly in part because I needed a place to follow my most obnoxious impulses. Having that outlet has been a real gift. I would also say that making pottery, taking voice lessons, running, and playing poker also support my writing in ways I couldn’t have anticipated. For years I made the mistake of believing that I should be writing eight hours a day. Now I realize that I wasn’t actually writing, I was staring at my screen and becoming overwhelmed by dread every single afternoon. So I give myself much less time to write and much more time to get out into the world and do things now. I’m not always as productive as I was before, but I think the quality of my ideas has improved a lot.

It’s hard to feel inspired when you force yourself to do too much every single day, and you don’t have any variety in your life. Right now I’m all about variety. I want to know a wide range of people and be engaged with a lot of different kinds of activities. I also really love being out of my element. Just learning to enjoy making pottery around other people took a long time for me. I was too anxious about my failures to relax and have fun. But now I love it, and that’s made me much more open to trying all kinds of new hobbies that I would never have dreamed I’d enjoy.

You often weave in the benefits of meditation, running and exercise for sanity/well-beingin your columns. How does movement influence your creative practice?

I don’t think clearly unless I’m exercising regularly. I don’t know if I’d still have a writing career if I hadn’t bought a treadmill desk in 2018. My neck and back started to hurt around the clock from sitting all day, and the treadmill changed that immediately. My attention span is much longer now and I enjoy writing so much more. I’ve also been running long-distance over the past two years, and the uptick in my optimism is hard to even express. If I’m running four or five days a week, I feel cheerful. If I take more than two days off, my good attitude starts to crumble. Not everyone is like this, and thank God for that, because we’d all be punching each other in the face if so.

You’ve talked/written about moving from Southern California closer to family in North Carolina. How important is living within a creative community to you? And what does your community now look like?

I loved living in LA for many years, but my husband and I were both ready for a change. North Carolina has really exceeded my expectations in every way. I love the weather, I love the people, I love the fact that it takes ten minutes in the car to see most of my friends. But I also love driving here. The roads are smooth, the trees are tall and beautiful, the seasons are incredible. And I love being close to my family. I wasn’t sure how that would go, honestly, but it’s been great. My mother, brother, and sister all live here, and we see each other at least once a week.

I’ve always been kind of a creative recluse and have rarely been focused on creative communities, outside of the ones I found on Twitter back when Twitter was fun and interesting. I had a lot of writer friends in LA, but our conversations tended to circle around the same repeating frustrations, fears, and ambitions. I have a writing group in North Carolina, but I don’t think of that community as more important to my writing than my other communities–my various friend groups, my pottery acquaintances, my neighbors, my voice teacher, my therapist, my poker buddies. All of these connections have enriched my life and energized me in ways that feed my creative work.

I don’t think there were less opportunities to connect with people in LA. I just think I had fallen into a major rut. Moving across the country in the wake of Covid was the shock therapy I needed to start over and break out of my comfort zone. I can see now that I was pretty bored for years, and that made me anxious. I needed to try new things and meet completely new kinds of people. Nothing is better for your creative life than hurling yourself into new environments with an open mind. So even though we tend to think of creative communities as important for support and feedback, something as arbitrary as a book group, a dance class, or a sewing club can be just as generative and vital to your creative energy.