The Sunday Rumpus Interview: Heather Havrilesky


I want Heather Havrilesky to be my best friend. Probably a lot of people do: in her popular advice column, “Ask Polly,” she comes off as the rarest kind of comrade—the kind that isn’t afraid to get down there into the rough stuff with you, even when she has to tell you things that are hard to hear. She’s particularly skilled at addressing the amorphous anxieties of the relentlessly success- and happiness-oriented inhabitants of the 21st century, which tend to boil down to various versions of “Am I doing this right?” Her answers are delightfully meandering, hilariously conversational essays that are both insightful and inspiring.

Her new book, How to Be a Person in the World (Doubleday), combines new questions and answers with some “Ask Polly” classics. Before she took on the mantle of her guidance-dispensing alter ego (first at The Awl, and now at New York magazine’s “The Cut”), she was Salon’s TV critic for seven years, wrote a memoir (Disaster Preparedness), and contributed to the New Yorker, the New York Times Magazine, and All Things Considered, among other media.

I called Heather at her home outside Los Angeles, where we were only occasionally interrupted by one of her dogs begging for “all the treats.”


The Rumpus: You pitched “Ask Polly” as an “existential advice column.” Where did that come from?

Heather Havrilesky: Basically, I knew that I didn’t want to write an advice column that was just very concrete little problems like, “my cousin is pissing me off, my husband keeps leaving, my mother-in-law is staying with us for two weeks, what do I do.” I wanted it to be more focused on big questions of existence. Specifically people having existential crises. What that feels like, how to crawl out of it, what is the meaning of life. I really wanted it to be a high-minded philosophical thing. My idea was that I’d read thinkers every week, great philosophers. I’d drop them on the populace each week after I’d read volumes and volumes.

But as it turns out, it’s kind of evolved. It turned out to be much more of a psychological rambling hodgepodge than that. The thing that has held true is that people do write to me with big-picture questions—they describe how they are having a problem and how it affects different areas of their life. I get a lot of letters from people where they describe their entire lives. They say, “Here are all the things, I have a lot of good things, and I feel terrible.” That’s one of my favorite kinds of letters to get, because I relate to that and I understand it. And it is an existential crisis to feel terrible even though everything is in place, or things seem to be moving in the right direction at the very least. So yeah, in some ways I fell far short from my very grandiose goals, and it other ways it’s become exactly what I wanted it to become.

It was a very pragmatic approach that came out of total desperation. I wasn’t writing. I was very lost because I was writing these big pieces for the New York Times Magazine. I knew that I needed to write something that I knew how to write, that I didn’t have to read a book or watch TV to write it and that it would just flow. I knew I had to write something that would be easy for me, and I knew that I could write advice because I’ve been doing it on my blog for eleven years at this point. So it was like, “Oh look, Heather, duh, you’ve been doing this for ten years for free, how about selling it somewhere and making a small amount of money? That way you have to meet a deadline and feel that you’ve accomplished something.” It was sort of a way of push the pedal, get the pellet. I needed that transaction in my life, a little steady gig. My writing got freed up, I figured out how to write again. All of my writing has improved since I started writing the column.

Rumpus: I used to read “Dear Sugar,” and I really loved Cheryl Strayed’s columns. I don’t mean to suggest that you are the same, but when you started writing the column, I started thinking of you as the new Dear Sugar, because you also have very thoughtful and often very personal answers that go into very raw and difficult places. It’s also become accepted as a very literary form of writing.

9780385540391Havrilesky: Cheryl Strayed is really interesting. She’s very sure of herself, confident, a very healthy enlightened person. I am much more of a wreck that she is. I think both have a lot of wisdom to share, but her style is different because I think she’s had her shit together for much longer than I have, frankly. For example, I wouldn’t dream of camping alone under any circumstances. I’m a chickenshit. Our biology is different. I would not walk that far. Without Cheetos.

Also, she lost her mother, she had this tumultuous early life. I was very reckless and crazy around the same time. When she was walking through the wilderness, I was drinking way too much and vomiting on the sidewalk. I really admire her, and I loved that column, I wish she would keep writing it. She’s the most direct inspiration to “Ask Polly” by far.

But that said, we’re pretty different, too. Which is pretty obvious. I could never do it the way she does it. I come from a very “yeah I’m right down there with you” perspective. And I don’t think that’s a superior perspective—I don’t think that what I do is any better than what she does. What she does, she does better than anyone. I just think we’re different writers.

Rumpus: You say you were drinking a lot—she was doing drugs and stuff too.

Havrilesky: Her rising and falling at the time was just kind of amazing. She hit a lower depth and climbed to a higher height. I just think she’s braver than I am, honestly. I’m saying this from a place of total humility. I’m not comparing, I was a wreck back then—there are lot of similarities. But then also, her nature is so kind of sure—she changed her name after she cheated on her husband. I just think she’s a really interesting artist in person. I’ve met her a few times; she’s pretty amazing. I’m in awe of Cheryl Strayed. I think she’s fucking great. Let me be super clear. I wish she was still writing that column. I would read it every time, because every time I read that column, it made me cry.

Rumpus: With yours, something I notice, maybe 75 percent of your columns really resonate personally with me, to the point that I think you must be reading my mind. We’re the same age so maybe that’s not so surprising. But often I think, what’s going on, how does she know this stuff? So what do you think you’re tapping into? Is it that we’re all these frightened blobs of jelly inside and we’re all afraid to show it?

Havrilesky: Whatever your circumstances happen to be, I’m sure we’re very similar. If you met me, you’d say, yeah, she’s not that different from me When I meet twentysomethings who are like, “Oh my god, my whole life is a wreck,” I relate to them. I don’t feel like some kind of a special guru. So yeah, honestly, it’s strange that every column starts from me relating to the mess. I feel it and I remember it, because chances are that I had a sensation like the letter writer did a few days before. So I guess what I’m saying is, the longer I do this, the more I feel that the essential nature of most people is incredibly conflicted. I mean, when you say to people, “Yeah, everything in my life is in place but I still have ways of torturing myself about these things,” that stuff doesn’t change based on your circumstances. But I think what does change is, you get to a point where you look around and say, “I have all the elements I need to be happy, and yet…”

I am happy now, definitely. I feel happiness every day, very palpably. Sometime after my second kid, I had a decent career, I had done a lot of things, my husband I get along great, my kids are awesome, I have a pretty relaxing life, and I just thought, “I have everything I need, and I still have this terrible noise in my head. I don’t know how to relax, I don’t know how to go on vacation and have a good time. I don’t know how to feel where I am.”

I remember looking at pictures of my kids one day. I was just staring at this Christmas card, and I was like, “I cannot believe this is my life.” Someone outside, if you looked at this, you would say, holy shit how did she do this, you know? But I also thought, “Why don’t I feel this enough? I don’t feel this enough.”

I had to really figure out how to be more connected to my actual life. And it wasn’t something like, oh just meditate for twenty minutes a day. It has to be more rigorous than that. I think that the message is that everyone—especially smart people who live in their heads a lot—we struggle with how to feel our feelings. And also how to feel good, how to feel satisfaction in our accomplishments. You know when people say to you, “Wow, you wrote that article that’s so great!” Or, “You got published, that’s amazing,” and you just think, yeah, whatever, small beans, who cares.

Rumpus: Totally.

Havrilesky: That’s the way I was about every accomplishment, I’d be like, I really want to take this in, and I’d just sit there. Like uhhh, I can’t feel it. And now, when I write a good column, I sit there and go, “Oh yeah, I wrote this great column.” I really savor the things I do now in a different way.

Rumpus: You have to train yourself to do that, I think.

Havrilesky: Oh yeah. And you have to remind yourself. You need a little bit of peace of mind just to get a place where you can say, “This is important to me. I’m going to take some time and do this today. Instead of just, “Here I am again, busy busy, hurry hurry, what did you do to justify your existence today, Heather?”

Rumpus: You touch on a lot of themes about the unseen expectations of the culture around us, which says you’ve got to be successful and you’re always looking at the next thing—that’s the way we’re supposed to be happy versus how we actually are happy.

Havrilesky: I do think that having the illusion of forward motion is useful in the way that coming home to a house that feels comfortable is useful. It’s a nice backdrop. It’s not the meat of a life by any stretch of the imagination… It’s a natural thing to do, constantly be striving for more. These things are helpful but they aren’t everything. So if you make them everything, you feel this void. One tempting thing these days is to be very popular, have a lot of followers, get a lot of likes, check back to see who says you’re great. That’s a totally natural urge. Social media is in many ways is a natural human thing that’s great for writers especially. The isolation that I used to feel is gone in large part thanks to Twitter. I love Twitter. But if you find yourself going back to that place and looking for a pat on the head every few minutes, it says something about—it’s like a drug obviously. It’s an easy way to give yourself something. I get into ruts where I’m very indulgent, or I’m just like, “I just want to eat a lot and have like three beers,” where I’m just focused on on rewards, rewards, rewards. It’s nice, but it can’t be everything or you just feel like you’re falling apart. There’s no center.

In 2010 I moved to a bigger house, and it was very palpable that I had everything I ever wanted—and it wasn’t like I was swimming in money. I actually left my stable job that year. I had a book coming out that didn’t sell like crazy. A lot other things that I would hope would kind of explode didn’t, and I was just living a regular existence in the suburbs of LA. But I looked around this house and I thought, “There are so many things that need to be fixed in this house, but I can’t afford to fix them. This house needs to be cleaned a lot but I don’t have time to clean it.” So I just found myself very disgusted about my smudgy windows. I had a one-and-a-half-year-old who was really good at sitting down in the middle of the room and just peeing on the floor. And she would laugh and splash her pee with her hands…

At one point I was cutting raw chicken in the kitchen, my husband was out of town. My four-year-old came in and said her sister’s doing something very bad. And I walked in with my hands covered in raw chicken—I couldn’t touch anything—and my younger daughter was smearing shit on the armchair. I’m little bit like “germy germy germ,” and I was like—ahh! I couldn’t touch her. You’re just in this apocalyptic scenario suddenly.

At that point I was like, “I’m gonna have to learn how to look through a smudgy window and be happy, because my windows are always going to be smudgy.” I wrote this essay about dirty laundry for Aeon magazine that’s all about just accepting the incredible mess around you and just living in the mess, instead of always having a brain that says, “This must be fixed for you to be happy.” Maybe ideally you’ll vacuum the room and then you’ll feel slightly better. But in general, if you’re looking for smudges on the window, you’re gonna see smudges on the window. It’s actually a much better skill to savor the moment in spite of smudges, or with the smudges, than it is to learn how to clean the smudges off the window.

Rumpus: That kind of ties into your advice that if you’re going to be an artist, you’re going to have to accept feelings or circumstances that you don’t really like, and sit with them, and explore them.

Havrilesky: Yes, absolutely. I find the less that I scold myself for the things I naturally do and the person I naturally am—including an angry person, a frustrated person, an impatient person—the less that I treat that as an anomaly, a pathology, as something that needs to get fixed, not only the more creative and free I am, but the more things flow out of me in a positive way. The more I savor the moment, the more I feel l alive. We’re very much instructed to squelch, or cover up, or sweep the darkness under the rug—like you’ve got to overcome this darkness in order to proceed. For me personally, I find that bringing that darkness into everyday life makes it possible to proceed in a way that is much more full than just “shut that out, don’t think about it, move forward.”

And in fact, that lie that eternal progress and winning and brightness and greatness is somehow the best, best possible way to live—it’s an insidious piece of our culture. It’s an insidious piece of our victorious march to high capitalist greatness. It doesn’t necessarily bring people that much happiness… I know a lot of victorious rich people who live like they’re under siege. Because they can’t just exist. Everything needs to be fixed. And as you get older, things get even more calcified and crazier. People who aren’t rigorously looking at themselves in the mirror and thinking, “What do I really need, what is essential,” really fly off the map when they get older, because a lot of shit flies apart.

It’s not like I’m talking about a strategy that saves you from all that. It doesn’t fix everything. There’s no way to fix everything, We are in a chaotic mess of a world, and our lives are going to be chaotic messes no matter how victorious and shiny we manage to become.

Taking away that goal of shiny perfection is such a great first step. Not only just accepting that you’ll never get there, but actually learning not to want to be there. Because it’s not a there—it’s not a place. It’s just a nothing illusion that fucks with you. If you can’t make this moment better just by fixing where your head is, you’re not going to make anything better.

Rumpus: It sounds like you came to a lot of realizations through writing your column and the book. It’s obviously been a huge professional thing for you, but also a big personal thing too.

Havrilesky: It really is. It’s kind of crazy how great it’s been for my life. At the beginning I kind of resented it: “I’ll do this for a while, but the one thing I don’t want to become is someone who talks about how to fix your life forever.” I don’t want this to be to be my whole career. I still have to write book reviews, I’ve got to write cultural essays, I’ve got to write cartoons and weird things. But because this is the most satisfying work I do, because it’s made my life so much better, it’s impossible for it not to take up more space in my life. It’s great! I love this book, and I love writing that column. I can’t imagine a scenario where I wouldn’t be writing that column. Sometimes I think well if my life went to shit, it would be harder. Maybe it would be impossible to say helpful things.

Rumpus: Do you see yourself as Dear Abby, doing this thirty or forty years from now?

Havrilesky: I can’t imagine not doing it. Because every time I sit down, I feel like there are new things to explore. I’ve always been someone who could talk endlessly about big life questions. Not everyone necessarily wanted to listen. Who knows, but all I know is, I can’t see not wanting to do it. It’s so gratifying. Hearing from people with all kinds of problems and frustrations is amazing.

You know, I didn’t think I would be the best therapist. Maybe I would make a good therapist now that I’m a little more sorted out. I’m able to get my distance when I need to be cynical and terrible. My whole philosophy is, make room for all the stuff. Make room for all things you want to be. Some part of me wants to be a cynic, even now. And there are days when I need to go to that part of me, because it’s a big part of who I’ve always been. I don’t want to be 100 percent optimistic and openhearted. It’s not really what I profess is the way to be anyway. It’s not really the core of what I think it means to be a person or an artist or a writer. But there are days when I write, “Have compassion for yourself. Reach out and touch the beautiful void.” Then there are other days when I read those tweets or those columns and I think, “Ehhh, shut up lady.”

I think a lot of artists in particular and writers in particular are sensitive, really smart people who are complicated and who are very specifically tortured by the reductive nature of our culture. Those kind of people kind of need to be fifteen million things, and they need to be out of the closet about it. When you come out of the closet and you say, “I am a lot of different things,” their whole life changes, everything changes. Once you own the fact that you’re never going to be “good” in the eyes of a very reductive simplistic culture, that’s just an incredibly emancipating thing. That is salvation.

Rumpus: That’s something that comes up a lot when you’re answering these young women. You’re pointing out how sexism permeates our culture, not just inhibiting their goals but the way we’re encouraged to live through men.

Havrilesky: Yeah. The first part of my life I was really just consumed by making sure that I was a consumable good that many people would want to buy. It’s this weird conflicted thing where you’re basically making yourself as shiny and agreeable and chill and as cool and as loveable as possible. You’re emulating Jennifer Lawrence in every dimension. At the same time, once you lure someone in with that, I was just burning it to the ground every single time. I would attract people that weren’t necessarily in for all of my moods and my bad side. And then when they were dismayed by the fact that I was much more complicated than I let on, in the early days.

Women are so cobbled by the feeling that they need to be as simple as the men they are dating. In my experience, as someone who’s forty-six years old, women are extremely complicated human beings. Not to be completely binary about it, but my anecdotal experience backs that up. That’s not to say that a lot of men aren’t incredibly complicated too. But it’s a bloody shame to be reducing yourself to some lowest common denominator goal. Because it will just never work. At least for me, that was never going to be a path to success.

When you’re in a relationship with someone who wants you to fulfill one dimension, it really squelches your creative impulses. It squelches your desire. There are lot of things that just fly out the window because you don’t have access to the full force of what you have on board. That’s one of the heartbreaking things about being young. Throwing yourself at someone and wanting them to take all of the things in, and then slowly running up against the same wall over and over again. Especially it’s an issue of, have you accepted all of these things about yourself to begin with—as so few of us have.

Rumpus: And it’s not just young people. That can take a lifetime for some people.

Havrilesky: I know. It just takes a long time. It depends largely on how you grew up and what messages you got. I think about 70 percent of the messages I got growing up were amazingly positive and good for me. They made me a confident person in many ways, sure of my abilities, sure of my intelligence. Then that 30 percent can really ruin the party.

Rumpus: Your column and your book really function as that 70 percent for people who maybe only got 50 percent or less. They can read your stuff and say, “This is actually how it can be. Even if I don’t believe it right now, this is a model I can work toward.”

Havrilesky: I think that’s true. There are a lot of people who grew up in just amazingly ideal circumstances and they just expected perfection from themselves, because maybe their parents were perfect and pretty high-functioning. Their parents unknowingly laid that trip on them. It is the culture, you have to be a crazy hippie to tell your kids don’t be perfect. It’s an anomaly, it’s not the most average thing to tell kids don’t work so hard. The work itself is great, it’s just what is your goal—people don’t don’t interrogate the goal very much, especially in an affluent Western society.

If you teach your kids that everything is about getting into fucking college, how good at they going to be at appreciating the moment? Fuck you, do your fifteen hours of homework studying the fucking arbitrary stupid SATs, get into your perfect pristine school where all the other automatons are going. See if you can get a job working with the automatons.

I’m not saying these people aren’t human beings that are suffering. I just think we are not a culture that knows how to instruct people how to enjoy themselves. My main focus as a parent has become to learn how to tolerate hard work not for a goal, but to tolerate and even savor the act of working hard. But also learn how to savor the moment. Notice how hard work makes you savor the time after hard work a lot. Let’s all notice that when we’re on vacation, we’re enjoying each other company right now. We’re not just waiting for the next thing to happen. It’s hard to train kids to do that. They just want the ice cream cone.

Rumpus: How do you like that I got though this interview without mentioning that we’re both named Heather?

Havrilesky: You’re forty-six? See, that was the year that everyone fucking thought all together at the same time that they had the most original name in the world.


Author photograph © Willy Somma.

Heather Kenny is a writer, irregular blogger, and occasional cartoonist in Chicago. Recent and not-so-recent work is at More from this author →