How Writing an Advice Column Changed Heather Havrilesky’s Life

"I believe in having some acceptance that things are not within your control entirely, that things can get very dark unexpectedly and you don’t have a choice."

Willy Somma / Doubleday / The Atlantic

I have a bookmarks folder called “extremely good shit” and 25 percent of it is Ask Polly. That’s not an estimate; I crunched the numbers. Another 3 percent is non-Ask Polly articles by Heather Havrilesky.

Havrilesky is a wide-ranging writer, but she is best known for Polly, her “existential advice column” that she’s been writing since 2012, first for The Awl, then for New York magazine’s The Cut. On July 12, Polly goes print, with Havrilesky’s book How to Be a Person in the World, which is mostly made up of new columns, with a few of her greatest hits sprinkled in.

In anyone else’s hands, an existential advice column could be too navel-gazy, too repetitive, too insubstantial to actually be helpful. How to be a person in the world? There is no broader question. But Havrilesky keeps the existential tethered to the earth with stories from her life, plenty of well-placed “fuck”s, along with pop-culture references and extended Kanye West analogies.

There’s something nourishing in every column. (“We have to be self-protective but still vulnerable” is one I’ve been chewing on from the book.) But sometimes she writes things that are like opening up the fridge and finding the universe inside. You’ve come to expect that there’s going to be some sustenance in there when you open that door, and instead you get entire worlds. “Savor that precious space,” she writes, of time spent alone, working on something you care about. “That space will feel like purgatory at first, because you’ll realize that it all depends on you. That space will feel like salvation eventually, because you’ll realize that it all depends on you.”

Or sometimes you open the fridge door and a hand comes out and slaps you across the face. “YOU ARE CURRENTLY PRAYING AT THE ALTAR OF THE MOST TEDIOUS RELIGION IN THE UNIVERSE” she shouts to a woman made bitter by the rejections of men.

As Buffy the Vampire Slayer said, “The hardest thing in this world is to live in it.” As Polly says, “Uncertainty and vulnerability are your guides through this soggy life you’re living.”

I spoke with Havrilesky about her book, giving advice, and the gap between people’s fantasies and reality. Below is a lightly edited and condensed transcript of our conversation.

Julie Beck: It seems like there has been a newish interest in advice columns with Dear Sugar and yours and Dear Prudence and the like. Do you think there is a new appetite for this? Why would people would be interested in advice right now?

Heather Havrilesky: I think that a lot of things that have been traditionally defined as feminine are being outwardly acknowledged as interesting and valuable at this point. For a long time media was very male-dominated, and the tone, the level of toughness, and the things you were supposed to be interested in were all dictated by this reigning idea of what’s cool and what is not worth spending your time on. Emotional and psychological concerns have been treated as these soft things that are not serious or essential by the media, by writers, and by the general culture at large.

There’s been this slow shift in emphasis from living a primarily intellectual life without examining what motivates you towards acknowledging and recognizing the emotional currents that lie underneath our behaviors. At this exact moment culturally, I think people are a little bit obsessed with showing their true selves, and also obviously with social media, expressions of vulnerability and truth are becoming kind of a mainstream thing. TEDx talks are wildly popular. Graduation speeches go viral. I’m kind of stating the obvious, but it’s interesting that these things haven’t busted into the mainstream culture until recently, because you know, people sit and talk about their heavy heavy shit, and have done this for decades.

Beck: I think there is still a pressure on those soft things. I write a lot about psychology as a science, and I always feel a lot of pressure to make sure I do it super rigorously, cite a thousand studies, lest I be the one that's writing about the “fluffy” topics.

Havrilesky: Uh huh, yeah. I’m so suspicious of that. If you write a piece about anything emotional or psychological, there are places that will make you go through and arbitrarily attach a bunch of academic research to it, a bunch of statistics. If you scratch the surface of some of these studies, it's like “Oh yeah, fascinating, you took some college students and you gave them a questionnaire.”

Beck: Oh my gosh, it's ALL college students.

Havrilesky: The structure of a lot of those studies, it just makes me roll my eyes. I’d rather hear a philosopher or a really good writer hold forth on what they have imagined inside their tiny minds after taking too many drugs than see “We beta-tested 20 college seniors.” The use of statistics to prop up poorly-written survey language bullshit, that’s just my pet peeve. It’s not interesting.

The Herculean effort to make these really interesting and essential and very literary kinds of pursuits into something that’s somehow soft and pointless unless it’s beefed up and buttressed with all this horseshit, it just kills me. So yeah, I have strong opinions about that particular thing.

I just think if you put someone smart on a task that everyone has traditionally treated as a stupid or soft or silly thing, all of a sudden everyone changes their minds about how worthwhile that thing is. Like Alain de Botton writes these really loose kind of crazy books about a million different things. He’s a smart guy, and he's a great writer, and it’s fascinating to read his stuff on a lot of subjects. I don’t like every single thing he does, but it’s interesting how people change their opinion of whole fields based on who happens to enter that field and how they do it.

I'm a big proponent of “Do the things you love and make them as good as you want them to be”. Don’t decide what they are based on what a bunch of people who aren't doing them that well are doing. I love plowing into a field that’s not being well-tended. Move into something that doesn't look that great from the outside, do it your own way, make it your own thing, and raise the bar a little bit.

Beck: Yeah, get some of the weeds out. So the book is sort of loosely organized into these themed sections. Do you find that there are themes that recur in the letters, or that you keep coming back to?

Havrilesky: There’s the kind of “I can’t get over this thing, help me get over it.” That's definitely a theme in the letters. Sometimes people get stuck simply because they're stuck telling a story about why they’re stuck. I just read a letter from someone who said “I’m dating all these guys, it’s not working out, and I feel like these two bad boyfriends I had ruined me for everyone else and that’s why I can’t date new people.” And, well, the first thing you have to shake off is this story about these two bad boyfriends who ruined everything. Change the story into “Thank God I’m not with anyone like that anymore.” Other letters are: “Help me make this person love me more.” I don’t tend to answer those ones very often, because obviously they’re doomed. That won't solve your problem, anyway. “Help me love myself more” is the real heart of that problem.

Beck: Do you get letters that will say that explicitly or is that like the subtext?

Havrilesky: “Help me love myself more?” Sometimes. I like letters where the person either can't tell at all what's happening with them, or has discerned some patterns and understands the heart of the problem, but can't figure out how to do it.

Beck: This is mostly an existential advice column. While there is some degree of, like, Dear Prudence-y, “What do I DO, what do I actually do in this situation?” a lot more is like, “How do I get my mind right?” How do you sift through somebody's letter and figure out not just what would be the best thing to do in a situation, but how they might get their mind right?

Havrilesky: I try to think about how my thinking and feeling have shifted. A big part of it is “What kind of mind puzzle can I fix so that I’m not just throwing obstacles in my own path and fucking with myself all the time?” But the irony of that question itself is that it’s always the people who want to know how to think about something who actually need to figure out how to feel things.

There must be something evolutionarily adaptive about wearing out the same grooves in your brain over and over again. Or that just must be the way that effective animals are wired, like they don’t mind just chasing the rabbits down the holes over and over. But oftentimes if you can simply get someone to just let go of the problem and admit that it can't be solved using their brain, that's half of the struggle. I see more and more that the core root problem of a lot of these mind puzzles is a basic lack of compassion for the self.

So, for example, I was in therapy when I was about 29. And my therapist had me do this thing where I had to nurture my inner baby, like go back and be with yourself as a baby and give that baby love.

Beck: Eugh.

Havrilesky: And I told her, “That doesn’t sound like something I wanna do.” And she said, “Just try it, you'll be amazed.” And so I tried it and there was something gross to me about the whole thing. In the column, if I ever say “You’ve gotta love yourself,” I tend to edit it out. I think this language works for some people, but it’s not really how it comes at me. People who are full of self-hatred, it doesn’t fix it to say “Just love yourself!” Because it sounds absurd. Like, “No no no no no, I fucking hate myself, what are you talking about? I'm not just going to turn around, like, ‘I'm in love with myself.’” And also, “I am a darling little baby that deserves love”—that doesn't really work with me.

I think compassion for the self makes more sense. It’s like, I feel for myself, I’m going to give myself a break. Instead of persecuting myself, I’m going to say, “You know what, you're worthy, you deserve to be here, you don’t deserve to be persecuted day after day.” I think the reigning wisdom of our culture is that we all deserve to be punished and we’re all bad at heart. And I think that couldn't be less accurate.

Compassion for yourself means acknowledging that you, at your core, are someone with pretty pure intentions who just wants very simple things. And when you start to recognize that about yourself and when you start to give yourself the very simple things that you want, including feelings, suddenly all these mind puzzles begin to just seem like a lot of noise that you busy yourself with.

Beck: There was a column, which is included in the book, where this woman writes, “I know what the truth of a relationship is.” And then in response to that you said, “Sometimes when someone writes something that straightforward, it's the least true thing in the entire letter.” And it reminded me of this quote—sorry, sometimes I just process things through a decoupage mess of quotes—but it's from a Jesse Ball book, and it says:

I believe in discovering the love that exists and then trying to understand it. Not to invent a love and try to make it exist, but to find what does exist, and then to see what it is.

It seems like people in the letters are doing a lot of the former, inventing stuff and trying to make it exist, and then you're trying to find what does exist and see what it is. I mean, is that what it feels like, to try to read the letters?

Havrilesky: Absolutely, definitely. Yeah. That’s really smart. More and more, the longer I do this, I notice how much there’s this illusion that people have, especially with love, that they can control what happens next. It’s like they’re playing a video game, and if they play everything the right way, they can affect the outcome. It's like, you meet someone, you decide this person is the person who is going to make everything right, who's going to be your partner forever and ever, and you're never going to have to solve this problem again. And then once you’re locked into that idea, it's like you’re playing a video game.

It’s hard not to develop that idea that you can control the people around you. When you’re young, you suddenly realize that when you're not interested, other people like you. I was literally just speaking to my 7-year-old, and she said when she wants to play, her big sister doesn’t want to play, but when she doesn't want to play, that's when her big sister wants to play with her. It makes her crazy. It's like when you’re dating someone and you suddenly realize they're losing interest, if you start acting like you're losing interest—Ding! They're back in the ring with you. So it’s hard not to believe you can manipulate your circumstances in various ways, because you can. It's just, you're not going to get what you want doing that, you know?

It’s true even of family relationships, friendships… As long as you’re trying to get the things you need from people, as long as you're trying to work the right levers, you’re not going to have satisfying relationships. Like what you said, you simply see what’s there. I find myself looking at these letters in such a new way lately where I just see people pushing levers and pushing buttons, and you just can't be happy going down that route. The happy route is, in fact, much more accepting and passive in some ways. You don’t have to do anything.

When you have compassion for yourself, you recognize yourself as worthy, you don't walk out the door thinking, “I am a bad person who has to manipulate other people in order to get what I need because no one’s going to love me if I just sit here, doing nothing.” And the truth is that people love a person who has enough compassion for themselves to do nothing, to just exist. People love that. That’s the most attractive way you could possibly be, is just to be someone who knows how to feel and exist and feel worthy without doing somersaults.

Beck: You said “the way you've been thinking about the letters lately”—has the way that you've approached these things evolved?

Havrilesky: It's almost like there's evolution and then there’s just weather. And then there’s just the various pressures on my life that change and my perspectives that have changed. Overall, writing the column has forced me to evolve as a person dramatically, which has been amazing. Just applying my brain to something that feels like it is actually moving in a positive direction, to move people in a direction that their lives might get better, has just made my experience of my life a million times better. It’s not that my circumstances improved drastically. I had everything I wanted when I started writing the column, everything was great, but my experience of what I have has changed drastically since 2012. I’m a lot happier than I was four years ago. So it's been a very worthwhile thing to focus my energies on.

In the beginning I thought a lot about how to empower people to move on from their crappy boyfriends, their crappy girlfriends, their crappy jobs, how to encourage people to expect more from their lives, because that’s what had served me in the past. Then I got into a phase where I was amazed at how much better I felt because I was exercising a lot, and I talked a lot about your physical self and exercise.

Beck: Oh my gosh, yeah. There’s like the two concrete pieces of advice and everything else is more vague. One is therapy, and then you wrote that whole column about why you tell people to go to therapy. The other is you always say “Exercise every day,” and it always bums me out so much.

Havrilesky: I probably need to write a column that's just about why I say exercise every day.

Beck: Even my doctor will take, like, three times a week and be happy.

Havrilesky: If you’re in your 20s or 30s, three times a week is fine. Once you get past 40—I’m 46—you kind of have to aim for five times a week. The only reason I say once a day is because I have to say that to myself in order to do it 5 times a week.

I talk about it a lot in terms of people who are anxious and depressed, or working too hard because it just fixes a lot of those things. You just feel differently when you're doing exercise. So yeah, you're right, those are my two concrete things, and then the rest is just floaty philosophical madness.

Beck: Another column that I really liked, and this one is not in the book, is the one where the person was like "Are you sure?" And in there somewhere you asked, “Do you have to build a religion around your choices?” And you talked about Cheryl Strayed who seems to perhaps have done that, with changing her last name to “Strayed” after she cheated on her husband, etc. So then the converse question is: Do you have to build a religion around uncertainty? You talk about uncertainty a lot and I've written a bit about psychological research around uncertainty and how your tolerance for it, or lack thereof, is really what fuels anxiety.

Havrilesky: I think for me, raising kids would be unbearable if I couldn’t tolerate uncertainty, because you care enormously about how these little people turn out and you can’t guarantee anything and you also can’t keep them safe every second of every day. I had a baby when I was 36 and I remember my husband, he was saying “Just relax, calm down, everything will be fine.” I needed to explain to him that those kinds of words weren’t really going to work on me anymore and they were just going to make me mad. When you have an infant, your body and your brain are in this very aligned state where you're just like “My whole purpose is to make sure that little throw pillow slash human somehow survives.” It's like the most vulnerable state you can imagine.

One day, I walk in the door and my husband is stirring this pot of soup that’s boiling with one hand, and he’s got the baby across his other arm, and she's just like flying over the soup. And he’s talking to my stepson at the same time, and gesturing. This is like the first time I left the house, I think the baby was two months old, just to regain my sanity for a few minutes, and I come back into this scene. You’ve gotta understand what I’m seeing here—it's as if I cut my heart out and left it in your hand and now you're gesturing with it over a boiling pot of water.

So anyway, yeah, uncertainty. People talk about things that are heavy in the world and it’s almost like I have no choice but to say “I’m going to assume that bad things won’t befall us because I can’t survive otherwise.” But I also believe in having some acceptance that things are not within your control entirely, that things can get very dark unexpectedly and you don’t have a choice.

Lack of control, uncertainty, people get obsessed with that stuff. Any time you’re fixated on the same little puzzle, that says something. It's like, just put the puzzle down and walk away from it. The philosophical puzzles themselves can become traps if you burrow in too deeply. Smart people create cul-de-sacs in their minds over and over again.

One way out is just finding something that you know you love and doing it every day. And savoring the thing. I don’t think I knew how to savor my work until pretty recently. Even though I act like I’m just skinning the cat and trying to solve a problem in order to get a paycheck, I’m alienating myself from the means of production when I tell myself a story that I'm just trying to get a paycheck. Because actually, I love to write. And then all of a sudden when you acknowledge that, the writing gets better, your life gets better.

I think people are very divorced from understanding what they actually love in this life, I think it’s really easy to see your life as a series of problems instead of seeing it as a patchwork of things to savor. The circumstances in your life don’t change, the way you encounter those circumstances changes dramatically as you learn to feel what you feel and not fight it, and as you learn to give yourself space to be a full person and not some little mind-puzzle solver.