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'Ask Polly' Advice Columnist Heather Havrilesky On How To Survive 2018

"What If This Were Enough?" author and professional advice-giver Heather Havrilesky tells us how to make it through the present doom-filled moment.

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Oct 29 2018, 5:01pm

Heather Havrilesky. Photo of author by Willy Somma

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The morning we talk, Heather Havrilesky has woken up from a nightmare in which her middle school–aged daughters were in college, having a party in a dorm room, but she hadn’t been invited. Then she saw delicious sandwiches everywhere, which she would have loved to have if she hadn’t already eaten. Then, she looked around the room and there were all these college students—oh, wait, it was full of 40-somethings, too.

“I asked my daughter why she didn’t invite me, and she said, ‘These are all young people.’

I said, ‘What about these people my age?’ and she told me they were five years younger than me. She didn’t invite anyone over 43—like people above [that age] don’t matter anymore. I woke up feeling left out and irrelevant, which is just bizarre, because my conscious mind is not in this place!” she laughs.

Havrilesky is the woman behind The Cut's advice column, Ask Polly, and she’s telling me this anecdote to illustrate how she’s “on the same rollercoaster as everyone else,” which is one of the reasons the column has become one of the most popular of its kind in a relatively recent wave of feminist, witty, no-nonsense advice-giving. Her advice often advocates for radical self-acceptance and honesty, delivering truthfulness peppered with swearing and pop culture references, whether she’s responding to someone who’s grappling with a dying parent or a recent graduate who’s crumbling under societal expectations of greatness.

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We were meant to be meeting at a Mexican cantina in her Los Angeles neighborhood, which I’d daydreamed about extensively—as well as attending a reading of hers with Ann Friedman—but life had other ideas. Instead, we’re having to Skype for our interview coinciding with the launch of her new book, What if This Were Enough? But it’s okay: Havrilesky talks thoughtfully and is generous with her time, and is as funny as I expected as she moves between her treadmill desk (“a little bit obnoxious,” she says of the contraption) and her sofa.


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Though I try to stay on topic, it’s hard not to ask Havrilesky for advice, a problem I share with many others on the internet: She says people often want her to DM them advice, as opposed to printing her answer. It has to be an automatic no, she says: “It’s nice to feel wanted, but it’s also impossible to serve at every term.”

What if This Were Enough? is a collection of essays about how we got here, and more specifically, about America’s moral decline viewed through the lens of popular culture (though, given that the rest of the world consumes American culture and that we’re all in this dumpster fire together, it will be of interest to readers everywhere). She dissects the culture the country has been metabolizing for the past decades, and the consumerist messages we receive day in and day out on social media (which are, of course, no longer framed as brands selling us products, but instead about us being brands, and actual brands being lifestyles). One of Havrilesky's greatest hits was her 2016 Cut essay “It’s Never Been Harder to Be Young,” an extended version of which is included here and focuses on the “popularity contest” life and work have become.

Despite the saturation of books about the present, What If This Were Enough? feels cathartic in the style of Good and Mad, Rebecca Traister’s treatise on the political power of women’s anger. Havrilesky's book is hilarious and pulls no punches, and its cohesiveness feels fresh. Here, Don Draper (who could, better than anyone, “evoke the terrifying state of having it all but needing more”); Tony Soprano; Fifty Shades; Shirley Jackson’s books; Marie Kondo’s neurotic decluttering; the foodie movement; and modern obsessions with survival fantasies all belong together—they’re parts of the same Rubik’s cube.

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The pleasure of the book is that what brings all the pieces together are several short personal essays, including one about a toxic relationship and another on how awful going to certain parties can feel. Bringing more of herself into her writing has made it better, she argues. “ You can be so caught up in your own genre that you believe, My writing is only supposed to do this one thing. You’re not taking some leap into some ‘soft’ art simply by bringing human concerns into your writing. Human concerns should be in all writing.”

Havrilesky has written cultural criticism for 15 years, including stints as a regular contributor to the New York Times Magazine, book critic for Bookforum, and seven years as Salon’s TV critic. She started writing the Ask Polly column six years ago for The Awl before moving to The Cut (though she’d started writing advice in 2001 for the webzine Suck.com and later on her blog). Ask Polly was conceived as an existential column, and that’s feeling quite literal lately.

"There are things that come up in life that you can’t just navigate around. You have to go straight through them."

She reflects on the collective feeling of doom: “There is a bleakness to the letters now that did not exist in 2012; it’s completely a world apart. There are decades where you feel like everything looks apocalyptic.” In the spring of 2017, it got to her, too. She started to order survival supplies online, and it helped to face those feelings in a more direct, practical way. “I almost had to confront the idea that an apocalypse could happen. Suddenly, the bleakness transcended just, Everything is terrible, and moved into, When things get worse, what do we do—and I have two kids, how am I going to handle that? [Maybe] we all have to kind of go to that reality. By the same token, you can’t walk around saying ‘the world is ending’ every day.”

Her message is to tune into everything. “There’s nothing honorable about flipping out. I think that’s a missed cue of the current moment,” she says. “I don’t mean forcing the bad things into a happy little shape. I mean more instead of holding them at arm’s length, allowing them in and dealing with that reality—which is sort of ordering the fucking water purification pills—but then letting in the good things too, and living in the reality of today. We don’t necessarily need to reinforce in each other the sense of panic and darkness, it’s kind of acknowledged now, and it’s not denial to still want to be happy and connect with other people. We’re animals, and we’re going to fucking try to survive, it’s not dishonorable to want to enjoy the time you have.”

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Havrilesky likes these kinds of heavy questions. Her overall approach is to dive into a letter and let it go once she’s done: “My relationship to the letters is hard to describe. They’re this weird part of my life that’s a constant. I feel connected to the people who write to me. I care often more than I want to, but then I also try very hard to set it aside—otherwise, I’d go nuts.”

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Some letter-writers stick in her mind. Others, she knows she can’t help. “Ask Polly gives you the illusion that there’s a solution to a lot of things, and that’s mostly because I choose letters where there is somewhat of a direction.” It’s instructive, she says, to know that sometimes there is no external solution. “There are things that come up in life that you can’t just navigate around. You have to go straight through them, and that experience has probably influenced the way that I answer questions. Particularly with psychological issues and emotional issues, a lot of us want to just seem healthy while we remain unhealthy.”

She says she sees it all the time: the people who face things and move through them come out differently on the other side to those who just “find a life hack around something that they’re carrying around—and always will, you know!” All of her advice happens to crystallize to this. “As you get older, you can tell that the people who do that work and face that reality are the the calmest, most centered, happiest people you know. So it’s easy to recommend that process, even though it’s grueling when you’re in the middle of it.”

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