Across a certain swath of the Internet, where people discuss existential crises over G-chat and link one another reading material to soothe the general hurt of being alive in 2018, Heather Havrilesky is a big name.

As the author of the beloved Ask Polly column in New York magazine’s The Cut, Havrilesky has become the anxiety whisperer for a host of very modern people—particularly women in their 20s and 30s—with very modern problems: Acute feelings of emotional instability, professional insecurity, and general unmooredness springing from our culture of perpetual striving. As Polly, she answers questions like “How can I make art when so many people expect such greatness from me?” and “How do I start over now that I know how damaged I am?” and addresses problems like “I quit my job to have a baby—and then I had a miscarriage” or “I work too much and I’m miserable.”

The common threads of anger, emptiness, loneliness, inferiority, and feeling unloved are heavy topics for any writer to take on, let alone when they’re attached to real people. Havrilesky’s responses are genuinely understanding, giving every person the right to the feelings they’re feeling while also serving serious tough love, forcing not only the questioner but anyone reading the response to stop and consider their mode of existence and its implications. She makes it clear—and here her background as a cultural critic serves her well—that our emotions do not exist in a vacuum. With nuggets of relatable wisdom woven in every column, Havrilesky feels like one of the few people writing today who fundamentally understands the real morass of being “a person in the world” today—which was, in fact, the title of her first book of essays, compiled from the column.

Changing tacks, Havrilesky’s new book, What If This Were Enough?, draws from the same personal place but refocuses on cultural essays, some new and some repurposed from her other writings, including her seven years as a TV critic for Salon. Examining bits of our microculture—Disney trips with her kids, Mad Men and peak TV, Fifty Shades of Grey—she considers how the things we consume, and the means by which we consume them, have led us to a culture of insecurity in which we are all constantly projecting lives of perfection while actually experiencing anything but—something she admits to feeling herself. Insightful, intelligent, and with trademark honesty, the book (and Havrilesky through it) seems to want to grant us all permission to feel deserving of, and happy with, our lots in life—or at least to not make them into something they’re not.

I spoke to Havrilesky in New York about the book and this modern conundrum of too-many-feelings, and how writing for both has led her to a greater confidence and ownership of her career, work, and self.

—Mickie Meinhardt for Guernica

Guernica: Let’s start at the beginning—a very good place to start. What was the genesis of the book?

Heather Havrilesky: At first I thought it was more natural to go for just personal essays, but my editor, who also edited How To Be A Person In The World, said, “I really feel like you’ve been doing cultural essays for a long time and it’s the part of you that a lot of people haven’t seen as much.” There were pieces I’d already written that I’d knew I wanted to build out and make full-size chapters.

But then Trump was elected. And as I started building these essays out, everything had these Donald Trump bookends, which were just as heavy as you can imagine them being. So I wrote all this crap and had to take it out and was kind of spinning my wheels for a few months.

Guernica: This was in 2016 or so? 2017?

Havrilesky: The end of 2016. And with the new year I turned a corner. I really didn’t want to write something that was flatly a criticism of the culture. I really wanted to look back and say, all these things add up to a moment of paralysis that we’re facing right now, culturally. But I also wanted to look forward to find out what our path is out of this predicament, as individuals and as a community. How do we learn to reconnect with each other? And part of that was a personal question for me.

Guernica: Were you trying to avoid prescription?

Havrilesky: Or being reductive. Any time you’re talking about our culture, how all of these insane disparate pieces of it fit together, you always run that risk. But a lot of great literature is filled with extremely simple themes that reoccur in everything that’s ever been written. At some point you just have to yield to that. In the writing, I did ask myself if the themes I was teasing out of this material were exotic enough, new enough, relevant enough. That’s a very common paranoia for a woman to have. Because we’re so often experienced and encountered as, “Oh, I’ve heard this before.”

Guernica: There is an element of advice-giving in the book. Does it feel like that’s is now your style, unavoidably? Does the Polly voice seep into other writing, or do you actively lean into it?

Havrilesky: I don’t go looking for it. You could say that Polly is slipping into my other writing, but those impulses predate the advice column by a lot. Even my first job as a cartoonist—that stuff was heartfelt, a little more prescriptive than perhaps it should have been.

I think when you’re firing on all pistons you conjure the full range of what you’re capable of as a person in your writing. When I started writing, there were a lot of restrictions on how free a woman could get on the page. I had a lot of paranoia about doing it wrong and how much could I say about myself and get away with because everyone believed that girls are boring—that really was the feeling I had. It was the ‘90s. Now, I think that I’ve indulged myself a lot in my career and I’ve been lucky to get away with it. I guess my feeling is that if you’re sharp and you’re a little bit funny you can get away with a lot of shit. So I’ve used that to my advantage.

Guernica: How so?

Havrilesky: When you’re entertaining people you have a lot more leeway. I definitely see myself always as part entertainer. I hope that didn’t sound too pretentious.

Guernica: Not at all.

Havrilesky: Part of it is where we are as a culture—I almost feel like it’s my duty to talk seriously about my work instead of undercutting it the way I have my entire career. Now it’s time for me to fucking own it.

Guernica: Especially because that self-deprecating culture is not as present anymore. Of course it still exists, but people are now saying, “No, you—we—don’t have to do that anymore.”

Havrilesky: Oh, it was so mandatory. But we were also just so afraid of appearing earnest. It was the worst thing you could be.

Right before I met my husband, I was getting to know this guy online and said something kind of unguarded in a note to him. And he said, “Oh god, be anything but earnest, I hate earnestness.” But I wasn’t going to couch myself. I’ve always been kind of religious about this, even when participating in the self-deprecating culture of that moment. I was not going to package every pure thing I felt in some gloomy, bullshit pose just because it was unpalatable to some other person.

Guernica: Well, that’s so much what this book is about—endorsing earnest living, in a way.

Havrilesky: There was a time when this book would not have been well received at all. Analyzing a bunch of culture and then asking what it means, practically, for our emotions and our shared experience of living. It could be easily misconstrued as a kind of Goop-level of feeling good about something that should remain dry and intellectual. All writing is about emotion, really, and believing that the tone needs to be perfectly dry in order for it to be serious is outdated. It’s the mentality of human beings who are afraid of themselves. And afraid of the changes in the air.

Guernica: You have a lot of emotion in your writing, and a lot of it’s personal. I wondered if you find it almost easier or more freeing to be that emotional and open, rather than to check it.

Havrilesky: I think I’m taking advantage of the fact that I’m not that afraid of exposing myself anymore. I don’t want to produce things that don’t serve their purpose or do the job that I want them to do, but I don’t feel worried about being misunderstood at this point in my life, which is reasonably a new development. I didn’t necessarily understand myself that well when I was 40. Part of that is writing this advice column and having to dig to get to something real in myself and in the letter. But also, as a writer, there are different ways that you hide—you put on a funky hat or some lipstick. Good writers are acutely aware of how they’re perceived, or at least they have an idea of how to come across in a positive way. And there’s something amazing about hitting this strange juncture where, because I’ve used myself as a bad example in so many advice columns, there’s nowhere to hide anymore. And the others kinds of writing I do are improving as a result, because everyone already knows who I am, or they can find out.

Also, I preach the religion of understanding that you’re not that different from anyone else. And no matter how crazy you think the world inside your head is, it probably matches the world inside the heads of everyone you’re passing on the street every day. And when you reveal that self without a lot of ego packaging around it, people receive it in a very pure way. I’m sure it’s repellant to a lot of people. But to me, I love when someone digs for something real and finds a way to present it so it’s interesting and there are ideas in the mix.

Guernica: What do you think you project? Or, what’s your red hat and your lipstick that you use to hide behind?

Havrilesky: What do I dress my bad stuff up with?

Guernica: Yes.

Havrilesky: Humor is always a natural go-to for me. Being a critic is a strange thing, because a little piece of it is always like, “See how smart I am?” And that’s not a current urge in my work at all, which feels more like an experiment. I’m able to write about personal things right now in a way that feels more playful and in some ways a little more aggressive than it has in a long time. I should be more aware of what my tricks are but I guess I just feel like I don’t. It’s easier to see them in other people.

Guernica: Well, you’re too close to your own writing. And that’s what good editors are for.

Havrilesky: I’m pretty self-indulgent right now. But it’s a great feeling when you haven’t been there in awhile. Because I’m having a good time. To be productive and have fun with it feels so good.

Guernica: I want to call it being confident rather than being self-indulgent. I don’t think that’s fair to you.

Havrilesky: I guess I haven’t sloughed off that knee-jerk self-deprecation yet! But that’s definitely a piece of my personality. Self-deprecation is probably my red lipstick, actually. Recently, my husband and I were talking about that as a piece of who we are, because I said, ‘I don’t know whether to aim for a place where I can say, boldly, that I’m great, I’m good at writing, I’m good at writing an advice column.” There’s a war within myself about confidently and without apology speaking in glowing terms about my own work. I don’t like it, but I’m very conflicted because I feel women should take up space and own the quality of what they do. I spent my whole career not owning it. And I’m ready to stand up for it. But I also don’t think that I can do so without making fun of myself.

Guernica: It doesn’t feel natural to brag, though usually it’s not bragging, it’s just speaking to the level of your accomplishments. But we’re taught to call that bragging. It’s a female problem.

Havrilesky: I do really love my own humiliating stories. I revel in them. I love other people’s humiliating stories. It fits in with the theme of the book—we live in a culture that really wants you to seem like you’ve never been humbled, or that you don’t take it seriously when you are. That you’re just on an easy upward path to victory. And that’s what sells and that’s how you stay in power, and that’s how you know people in power. I’ve never been good at that, and find it hard to connect to people who are good at that.

Guernica: It doesn’t feel natural.

Havrilesky: No. Of course, I’m attracted to the ability to seamlessly glide through the world as if you’re meant to be there. I just cannot fucking imagine I was meant to be anywhere. I grew up believing really strongly that the world belonged to someone else. Definitely not a girl.

Guernica: That’s a feeling many people have.

Havrilesky: Even though you get an education and read about people who felt that’s too, the world around you still moves forward in the same way, where the message you recieve is crystal clear: You’re marginal at best.

In all the talk of trauma that gets kicked up, there’s something missing about the way our collective mindset has changed about how much of right to a voice we have. I’ve seen it evolve online really quickly. And I really feel a change in the way that I understand what I have a right to ask for. And I feel like that’s pretty new. I’m not that young. I’ve been through this. And I thought I was a confident person, that I grew up a long time ago. Someone younger might have simply just grown up with more ownership of the universe.

Guernica: I think the ability to have confidence and ownership is a collective feeling. Because a lot of people, women, all of a sudden have realized we’re sick of not feeling that way. But you have to see a couple people do it and own it first. I think that’s a slow waking up in all of us.

Havrilesky: It’s kind of like going through therapy. It moves from this place of pain: Oh my god, I had these impoverished relationships as a child, and I’m angry about how I was raised, and upset about the mistakes I’ve made, and feel shame about how much damage is in my past. That’s where we were a few months ago, and I’m sure a lot of people still feel that way. Now, I feel like there’s a turning point, like in therapy, where you start to say “I’m feeling my feelings.” And I can walk out on the street and really see people and connect to them, and I have more power than I realize. I’m not helpless. And I’m not the same person I was when these bad things happened, yet I am still that fragile and vulnerable, and it’s good to know that, too. I am still conflicted about everything under the sun and I am a complicated human being, and these aren’t disqualifying traits. These don’t make me someone who doesn’t deserve to be in the world and connect to people, because I should be ashamed of not being a simpler, shinier thing.

Guernica: Is it hard to step away from those, and the emotions of other people’s problems, and just live your regular life with your family?

Havrilesky: It depends on the thing.  There are days I think, “Get me out of this soup of hell.” The little cultural things that just eat you alive. Most of the time, it’s not that hard. Your kids are going to be exposed to the world. At the time I wrote that Disney piece [in What If This Were Enough?] I was really torn about relenting to American pop culture and letting my kids sink into the shit of that, but I also really knew I didn’t want us to be the all-wooden-toys no-pronouns parents. There was no way I could live in that kind of purist realm. It doesn’t feel practical to me. We had idealistic intentions that fell by the wayside, but I think a lot of parents are like that.

Guernica: A lot of the issues you speak about in the book are because of social media, our phones—we ended up here because of the fake presentations that are driven by those things. Does that worry you, as a mother?

Havrilesky: Oh yeah. My daughter just started using Instagram. She’s eleven. It’s kind of a mess, like Disney. Your kids demand Disney but you think, “You shouldn’t even go near that place, it’s a bad place.” Instagram allows her to connect to things she naturally loves—she’s into fashion, she loves drawing, but she’s very private—so it’s really hard for me to say, “I won’t let you go near that.” I basically said, you have to let me look at what you’re looking at and see how you’re using it. And obviously we talked about safety. But the fact is, all the social pressures are amplified. I did say I really don’t want her to take a ton of pictures of herself. I don’t think it’s good for other people, and I don’t think it’s good for you to think that way.

I don’t know what to think about it or how to think about it. It’s like trying to describe a walk through the dark. I just think that the constructed self through social media at a young age is so fraught. I don’t know how to counter it. It’s the weird interplay of letting your kids find the world outside your door, and helping them understand it as they’re kind of horrified by it. Protecting them and giving them advice. It’s one of the most painful things to even think about. But I guess my main angle is, I just talk very honestly about myself and what I’ve been through. My husband polices the kids much more than I do. I let them kind of stumble around and find their way. So when I do talk they actually listen, and I do think they understand honesty and how important it is to feel like you can trust people. I think they have good heads on their shoulders.

It’s easy to be paranoid because I was pretty dysfunctional, and it got worse until I was like 30. But it’s the definition of dysfunctional to assume that your kids are going to be as big of a mess as you were, and I think it’s the definition of a good parent when you can realize and not feel threatened by the fact that your kids are way ahead of you. When you can see that and acknowledge it, like, “Look, you grew past me!”—it’s really amazing. Though it’s hard to recognize it and let it in and not feel inadequate in the face of it.

Guernica: Well, that’s so much of what the book is about, addressing that inadequacy.

Havrilesky: As I get older I realise how I’m wired to look for a sad moral to every story. To experience reality as a rejection; any reality can add up to a message that I’ve failed. And I think most people probably are wired that way. It’s amazing to me that these things don’t change.  I do think it’s from a nervous or neurotic personality. Though I do feel like I’m at a point where I can look at these things and see them come up and think it’s funny. And I’m having fun with it in my writing. I want to see it and use it. Because it’s still embarrassing—I’m gonna be 80 and writing about how insecure I am? Bummer. But that’s okay too, I think.

Guernica: It makes great writing.

Havrilesky: That’s what matters. Why write if you’re writing stuff you don’t like?