“Your best self is the same as your worst self” (w/ Heather Havrilesky)

Summary

Podcast Summary: "Your Best Self is the Same as Your Worst Self" (w/ Heather Havrilesky)
How to Be a Better Human – Hosted by Chris Duffy
Release Date: June 9, 2025

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Introduction to Heather Havrilesky

In this episode, comedian Chris Duffy welcomes Heather Havrilesky, a celebrated writer known for her memoir Foreverland, and her advice columns Ask Polly and Ask Molly. Heather delves into the intricacies of being authentic, embracing the messiness of the human experience, and navigating the challenges of self-expression in both personal and public spheres.

Embracing Authenticity and Complexity

Heather emphasizes the importance of being honest with oneself and others, highlighting that authenticity often involves embracing contradictions and imperfections. She reflects on her own journey, acknowledging periods of insecurity and self-doubt that led her to a deeper understanding of herself.

"We wouldn't always make sense. But that messiness and that complexity, that's exactly what today's guest, Heather Haverlesky, is all about."
— Chris Duffy [00:00]

Personal Journey and Self-Awareness

Heather shares her personal transformation, moving from a self-described "sociopathic streak" in her younger years to a more self-aware and introspective individual. She discusses the impact of major life changes, such as marriage and motherhood, on her identity and writing.

"I recognized that I was very insecure, a little narcissistic. I had a lot of different problems. I was definitely a drinker. I wasn't necessarily completely over the top with any of these things. I just didn't know what was going on, and I didn't know who I was."
— Heather Havrilesky [06:20]

The Role of Humor in Self-Expression

Both Heather and Chris explore how humor serves as a coping mechanism and a tool for honest self-reflection. Heather explains that her ability to joke about herself is crucial to her writing process, allowing her to present a more relatable and authentic persona.

"You can't really make a good joke about yourself unless it's true. Right. No one laughs when you're like, I am so put together and I have my life on track."
— Chris Duffy [08:45]

"I wouldn't want to write an advice column where I didn't mock myself, make fun of myself, joke about things. It would be excruciating for me."
— Heather Havrilesky [09:21]

Balancing Public Persona and Private Self

Heather discusses the challenges of maintaining authenticity while engaging in self-branding, especially in the age of social media and public scrutiny. She criticizes the pressure to conform to a singular brand identity, advocating instead for embracing one's multifaceted nature.

"We cannot be tempted to turn ourselves into brands because we're hollowing ourselves out. The more you bring your full self to anything you do, the happier that thing will make you and the more satisfying and the more brilliant the thing will be."
— Heather Havrilesky [14:35]

Writing Process and Finding an Authentic Voice

The conversation delves into Heather's writing process, emphasizing the importance of capturing genuine emotions and experiences. She describes her method of writing first drafts based on raw emotions and later refining them without losing their authentic essence.

"What I want to recommend is fast processing. Fast."
— Heather Havrilesky [29:52]

"That is what I'm living for when I'm reading people's work."
— Chris Duffy [31:36]

Critique of Self-Improvement Culture

Heather offers a critical perspective on the self-improvement industry, arguing that it often induces shame and anxiety by promoting an unattainable standard of constant personal growth. She advocates for accepting oneself as a complex mix of strengths and flaws.

"Self care is bullshit. You know, every day you should, you know, whatever, but everything is a balance, okay?"
— Heather Havrilesky [40:55]

"Creative people have very naturally ambitious. Creative people have a lot of struggles for a very good reason. Because you can't be Zen and be ambitious at the same time. You actually have to be bothered by things."
— Heather Havrilesky [45:15]

Advice for Aspiring Writers

Heather provides guidance for new writers striving to find their unique voice. She encourages embracing influences from favorite authors without imitating them, trusting one's creative instincts, and allowing authenticity to guide the writing process.

"You trust them to run with the ball, you know? And then when you trust yourself, when you see that, it teaches you to trust yourself to run with the ball when you're feeling it."
— Heather Havrilesky [38:19]

"If you want, like, how do you know something's done? How do you get to the place where you're not over, you know, second guessing yourself?"
— Heather Havrilesky [26:58]

Conclusion: Embracing the Full Self

The episode concludes with Heather reinforcing the message that true happiness and fulfillment come from embracing all aspects of oneself—the light and the dark, the ambitious and the flawed. She emphasizes the importance of authenticity over striving for an idealized version of oneself.

"We cannot be tempted to turn ourselves into brands because we're hollowing ourselves out. The more you bring your full self to anything you do, the happier that thing will make you and the more satisfying and the more brilliant the thing will be."
— Heather Havrilesky [14:35]

Heather's insights encourage listeners to accept their complexities and contradictions, fostering a more genuine and fulfilling approach to personal growth and self-expression.

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Notable Quotes:

• "Polly is like that, too. You know, I just, like, go on too long. I mean, I think that the main thing for me is just, is there momentum? Does it feel like it's getting bogged down like a book, like a heavy book? Or does it feel like there's something important to say here."
  — Heather Havrilesky [32:29]

• "The funniest moments come from not trying to make a joke, but it just, like, it exists because you're being honest."
  — Chris Duffy [30:53]

This episode provides a profound exploration of authenticity, personal growth, and the balance between public personas and private selves, offering valuable insights for anyone striving to be a better human.

Transcript

[Chris Duffy]

Hi, TED podcast listeners. It's Elise Hu here from TED Talks Daily. Thanks for making our podcast part of your routine. We really appreciate it and we want to make your favorite TED podcasts even better. We put together a quick survey and we'd love to hear from you. It only takes a few minutes, but it helps us shape our shows and get to know you, our listeners, way better. Head to the episode description to find the link. Thank you again for listening and for taking the time to help our shows. You're listening to how to Be a Better Human. I am your host, Chris Duffy. What would it mean if you were totally honest with yourself and other people about who you are and what it is that you want? Well, for one thing, I feel certain that it would mean for me and for probably you, too, that we would be contradictory and messy and complex and we wouldn't always make sense. But that messiness and that complexity, that's exactly what today's guest, Heather Haverlesky, is all about. She's one of my favorite writers. She is hilarious and sharp and so often beautifully eloquent about what it means to be human. Whether Heather is writing a memoir about her marriage called Foreverland, or writing one of her two advice columns, Ask Polly or Ask Molly, she is always pushing for people to be more. More themselves, more honest, more fearless, more messy sometimes. So today on the show, we're going to talk about a big, huge question that every single one of us has to navigate every single day of our lives. How do you be you? To get started, Here's a clip where Heather is talking about the kinds of letters she gets from people asking for advice.

[Heather Haverlesky]

I really love answering letters from people who are in their 20s, early 30s, partially because it's such a terrible time, honestly, even though you come out of college, you know, high school, or come out of your youth having had a lot of structure, a lot of very rigorous expectations of your behavior. Theoretically, in many cases, when you enter into your 20s and it's up to you, the sudden loss of structure and someone telling you what to do and people saying, this is how the real world works and this is how life works, can induce this kind of sense of vertigo. And I mean, my own experience, months after landing in San Francisco, felt like I was a complete failure. I think a lot of people in their 20s and 30s put pressure on themselves to hit certain marks at certain times, to be a success overnight. There's a lot of pressure by the culture to be a phenom, to be a precocious 20 under 20, 30 under 3040 under 40 My first book came out when I was 40. I had some early successes, but I did a lot of flailing year after year after year. And I think my main advice for young people is just do not take those years so personally. Do not take them so seriously. You have a lot of time to figure things out and you have many times to start over and you have a million mistakes to make from now until the time you're dead.

[Chris Duffy]

Whether you are 22 or 92. I feel certain that there is going to be something in this conversation with Heather today that provokes you. Hopefully provokes you to think deeply about who you are and who you want to be. So let's get into it. Banking with Capital One helps you keep more money in your wallet with no fees or minimums on checking accounts and no overdraft fees. Just ask the Capital One bank guy. It's pretty much all he talks about in a good way. He'd also tell you that this podcast is his favorite podcast too. Ah, really? Thanks Capital One Bank Guy. What's in your wallet? Term supply See capital1.com Bank Capital One NA Member FDIC G' Day America It's.

[Heather Haverlesky]

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[Heather Haverlesky]

Hi, I'm Heather Haverlesky. I'm the author of four books, most recently Foreverland on the divine tedium of marriage. I write the advice column Ask Polly, which is on Substack, and I also write a newsletter called Ask Molly, which is written by Polly's evil twin.

[Chris Duffy]

I think of you sometimes in some ways as like the poet laureate of being yourself. Like, you're allowed to be who you are, and you don't have to feel ashamed of that. I feel like that comes up a lot in your writing, and you write about it so beautifully, both about your own personal experience, but in responding to people who are genuinely struggling and really suffering from trying to be someone who they're not.

[Heather Haverlesky]

It's interesting. I think I've just had a lot of different experiences with being my complete self and being half of myself and being a third of myself. I started out in the world as someone who was a little bit less in tune with other people's needs a little bit. I mean, I used to say I had a kind of a sociopathic streak to my behavior when I was really young. You know, it's a defense mechanism that you sometimes have if you are determined to have a kind of bluster and swagger when you're young. I wrote a cartoon when I was 25 for one of the first websites online. And my whole thing was being kind of an asshole. My cartoon was about my co workers. They loved it. They were all assholes. I rode that horse until it died. And then I had to reassess. And I had a bad kind of late 20s, early 30s, kind of come to Jesus, oh my God, I make everyone mad, no one likes me moment. I recognized that I was very insecure, a little narcissistic. I had a lot of different problems. I was definitely a drinker. I wasn't necessarily completely over the top with any of these things. I just didn't know what was going on, and I didn't know who I was. And so I spent years rebuilding. Then I had kids, which incites its own kind of crisis of identity. I struggled a lot with mom friends, kid playgroups, the social scenes formed from that. My kids chose that I didn't choose. I mean, that was hellish for me. I lived in the suburbs, and Now I just, four years ago, moved to North Carolina from LA lived in LA for 23 years. So I'm undergoing this whole new transformation, adjustment to Southern culture, adjustment to much more polite, much less extroverted culture. I have been through the wringer. I've tried everything, I've failed at everything. And I am not really that naturally good at that many things. So that's at the heart of the whole column. It's just about the joys and terrors of being humbled over and over again.

[Chris Duffy]

Yeah, I think so much of what you're talking about too is at the core for me of like a good sense of humor. And I think, like, you are so funny and you have such a great sense of humor that I think sometimes when you've broken out into the broader world, people don't fully appreciate that you have a sense of humor. And it leads to people misinterpreting your work in a way. You can't really make a good joke about yourself unless it's true. Right. No one laughs when you're like, I am so put together and I have my life on track. That's just not funny. But I think being able to look at yourself with clear eyes and then make a joke about it, that's to me, at the core of a really good sense of humor.

[Heather Haverlesky]

Well, I mean, I wouldn't want to write an advice column where I didn't mock myself, make fun of myself, joke about things. It would be excruciating for me. I mean, in some ways my, my sense of humor helps me in everything I do. I don't think that I would still be interested in writing Ask Polly if I couldn't swear and insult myself and go on tangents and do a lot of messed up stuff. You know, in terms of my personal writing, I don't know if it's. Part of it is that Polly is sort of serious a lot of the time and earnest a lot of the time. And so people confuse that with my tongue in cheek writing. They just were. They assume that I'm in earnest, saying, for example, everyone hates their husbands. It must be so, you know, as opposed to just love and hate are things that exist hand in hand. Being an artist includes hating yourself. And trying to create things is necessarily a battle of good and evil at some level. And day to day, kind of trivial choices you make can feel heavily moralistic and moral and, you know, feel like giant moral failures. I take a lot of artistic license, I veer around a lot. I work hard to sort of drill down into the core weirdness of my being in order to do any of the stuff that I do. And when I stop doing that, when I feel like I'm just, what do people want? I gotta give them the product that they signed up for. And, you know, that's when I really lose the magic. And so I. I think because I have to do that myself in order to produce work. It's easy to give people a lot of advice about when you're speaking from your core self, you know, you are naturally being your best self. And also your best self is the same as your worst self. They are the same person.

[Chris Duffy]

It's been interesting to see some of the, like, public reaction, especially to your book, which I loved from. I thought was so funny and so great. And you wrote about marriage and relationships in a way that was so truthful. And I had never read before, but it's interesting to see that. I think people were. They didn't always want to acknowledge that you could be joking or funny. And there was this very moralistic tone around some of the parts of the book, like what you said of, like, writing about, like, sometimes you're going to hate your husband, which to me is like, I can't think of a more innocuous and true statement than if you're in a long relationship with someone, there will be times where you're like, like, oh, my God, this person.

[Heather Haverlesky]

Yeah.

[Chris Duffy]

And yet, I think because it was coming from you, that was, like, almost, like, shocking. People, like, clutch their pearls about that kind of an idea.

[Heather Haverlesky]

Definitely. People who had read my stuff for many years were sort of like, no, no, you don't understand. She writes. This is how she writes. Yeah. I never really figured out what it was, what kind of preconceptions people were bringing to the table. I mean, for sure, women talking about marriage don't have a ton of leeway. Women have less leeway in talking about almost anything. After the book came out, I beat that drum a lot. And I'm an outspoken feminist. Always have been, always will be. So that's pretty natural. Honestly, part of what I love about what I do is challenging these kinds of, like, ways that people want to pigeonhole you and sort of pushing the new, apparently new notion that each individual can be a lot of different, contradictory things. And it's much healthier to embrace a lot of the contradictions in who you are. And it's more fun to bring your whole self to everything you do. I mean, I started Ask Molly, my other newsletter, written by Polly's evil twin, partially because there's so much room for experimentation with creative Projects and with your identity. I mean, it sounds like hopelessly 2025 to say that. I'm confused by the fact that people, that they feel like a brand, they have to be a brand, and the brand has to give one thing. I do understand the temptation. It's hard not to worry about confusing people because when you confuse people, like, you do end up not selling that many books, right? Like, you know, I'm very proud of my. My book Foreverland, but it didn't sell that well. People, I think were like, a marriage, is it. Are you talking about happiness? Are you talking about hating your husband? Why aren't you divorced? Why isn't this a divorce memoir? I mean, but I still feel like it's. One of the most powerful messages I have to share is that we cannot be tempted to turn ourselves into brands because we're hollowing ourselves out. The more you bring your full self to anything you do, the happier that thing will make you and the more satisfying and the more brilliant the thing will be.

[Chris Duffy]

You know, I think it feels really in line with the arguments and the points that, you know, I think you make so persuasively across a lot of your work about being all of the complicated mess of yourself and not feeling ashamed of that. But people sometimes feel like, especially because there's this, like, what are we putting out publicly? And how will I build my career and my friends and people want this thing from me. I have to have a thing. And yet you don't want friends who are that. That flat. But we think that we should be that flat.

[Heather Haverlesky]

That's absolutely true. And I think that people are confused. I mean, people in general who do things that are public facing are, you know, you know, reasonably bewildered by how to manage. To manage that universe, to manage the contradictions between private and public. It's just everyone's kind of learning on their feet, right? Like, we're. We're all sort of watching everyone do a lot of different levels of marketing of themselves. And even, you know, people who don't have anything to sell are almost marketing themselves. And. And I think that it's very natural to see someone doing it in a way that you would not like to do yourself. It's not that smart to do things that you don't feel great doing. You know, I just remember when Foreverland came out, I got on a podcast and it turned out to be video. And it's like, hold on a second. You know, I'm running to the bathroom, I've got like, gray roots in my hair. I mean, all of your fears and insecurities, right, are triggered by this particular moment in self marketing and self branding. It's very difficult to be a peaceful, self branded human being.

[Chris Duffy]

This is certainly what I struggle the most with personally right now in, like, my own work, is that I really love. Like, I love having conversations through the podcast, I love writing essays, and I love performing live comedy. I love those things. But they all require me to do this other thing that I don't like, I'm not very good at objectively, I'm pretty bad at. And that makes me kind of go crazy, which is the post short clips or get people to come to a show, but also entertain them in between that stuff. And it's like, that's the thing that makes me be like, maybe I should just do a completely different career. But then the thing is, I love the other parts that I do.

[Heather Haverlesky]

I think it's good to resist a lot of the dumb imperatives that are foisted on you. If you gave in, if you surrendered to it. The angle is just find the thing that you can tolerate. Like, find something that you want to create that's only loosely related to what you're promoting. You know what I mean? Like, if it's pancakes, you know, something small and weird is good. I mean, you know, we talked about being misunderstood, but I think that it's important also to understand as a person, whether we're talking about branding or just socializing, people understand you better than you think they do. The people who love you love you more than you think they do. The people who you think hate you care a lot less than you think they do. They're just not invested. And what's important is when you choose something that you find exciting. You serve everybody. You turn off the people who don't give a shit anyway. You know, you turn on the people who care and want the purest, highest level of hit of your thing that they can possibly get. You know, Molly has been very nurturing to my soul and almost keeps Polly afloat just by allowing for a place for me to be ridiculous. At some times, though, I feel like I need to remember that Polly is also Molly. And Poly always was Molly, like from the very beginning. And that's how Poly got popular in the first place. And Polly doesn't need to always be service oriented. Poly can also just be fun.

[Chris Duffy]

I think this is also 100% in line with what we're talking about in the sense that, like, you could reduce the work that you do with Ask Polly and Ask Molly into their advice columns. But honestly, for me, as a fan of them, as someone who reads them and really enjoys them and gets a lot of meaning out of them, to me, the least thing that they are is advice columns. They're so not just about someone writes in with a problem and you give them a solution. They're these big essays on life and meaning and culture and your own experience. Like, they're not, like, I was wondering, how do I invite people to my wedding? And then someone. And then you write back, like, well, you should try, like, a heavy cardstock and put it in an envelope with a nice personal signature. Like, that's an advice column. You know, yours are much bigger than that. And yet I understand how it's really hard to say, like, this is, like, a humorous but also quite earnest at times, like, meaningful column that uses as a launching place, like, someone's real problem. You can't communicate that. And yet that's what people like about work is the complicated nuance. Ness of it.

[Heather Haverlesky]

Yeah. I mean, in the beginning, I called it an existential advice column. I love that. I probably need to call it that in general, whenever asked everywhere. But there are times when I fall down the rabbit hole of writing about what's wrong with culture right now. And then what's wrong with the way people do things? Or, you know, what's wrong with the way people text or how passive people are, how avoidant they can be, how, you know, anxious that they can be over so many things, myself included. I'm very anxious about a lot of dumb things, but sometimes I forget that, like, I'm partially giving people a kind of optimism mixed with cynicism about having to go out and endure other human beings and to endure just the stupidity of the culture, you know, which is so oppressive. I mean, I would say that, like, the. The core Ask Pauli reader is always surprisingly smart and. And alienated from mainstream culture in a way that I don't. I don't think of it that way. I think its appeal is a little wider than that. Kind of like, alternative grumpy person in a cave. But, you know, the grumpy person in the cave exists in a lot of us. There's not a lot of culture that caters to that grumpy person in the cave. You know what I mean? Like, you. When you're grumpy in your cave and you go to your phone and you say, like, I need something to just get me through this. The combination of just apocalyptic dread and poptimistic nightmare realm, you know, I need something that's not those two things, you know, that's not hysteria, that's not realistic. Fear over the future. There are days when you just want like the Internet to sound more like a smart friend who's like, yeah, don't worry, of course you're going crazy. It's normal. I've been trying to think of what my next book should be and I just keep coming back to like, the world's on fire. Why shouldn't you be? Because, you know, occasionally I'm like, just write a book about something that's the maximum shallow that you could possibly write. You know, like, stop trying to write literature and just write the stupidest, most insane thing. That just sounds fun, you know? I mean, I do think we're in a moment of like, where do we find the fun under these conditions?

[Chris Duffy]

We're going to find more fun with Heather right after these Podcast Ads this show is sponsored by the Superhero Leadership Podcast. What can we learn about leadership from a real life superhero? On the Superhero Leadership Podcast, Marvel's former CEO Peter Cuneo shares the lessons that helped him turn companies around and inspire teams to thrive. Each week he's joined by leaders from business, media and more people who lead with resilience, purpose and vision. Together, they explore Peter's 32 leadership practical insights for becoming the kind of leader others want to follow. If you're curious about growing your impact and leading with intention, this podcast is for you. Search Superhero Leadership available wherever you get your podcasts. This episode is sponsored by BetterHelp's podcast Mind if We Talk? How do we cope with grief and loss? It's something that we're all going to have to face one day, and despite this being a universal experience, it's not something that we're taught to address. That's why BetterHelp teamed up with licensed therapist Hae Soo Jo to create Mind if We Talk, a new podcast that demystifies what therapy is really about. In each episode, you'll hear guests talk about common struggles that we all face, like living with grief, anxiety, managing anger, and more. Then he soo breaks it all down with a fellow mental health professional to give you actionable tips that you can apply to your own life. For me, one of the most important parts of therapy has been just learning some strategies and techniques that I can try out to see what works. And what's cool about this podcast is you get to hear mental health professionals talking it through with each other and sharing some of the tips that they would maybe suggest in a given situation. Mind if We Talk Is here to remind you that whatever you're going through, you're never alone. Listen and subscribe wherever you get your podcasts. This episode is sponsored by BetterHelp. You know, something that we don't talk about enough, especially among men, is just how heavy and how difficult life can feel. Sometimes there's this pressure to always have it together, to perform, to provide, to be the one who fixes things. And yet, over 6 million men in the US experience depression each year, often without realizing it and without getting support. But here's the truth. Real strength. Real masculinity. It's not about bottling things up. It's about knowing when to reach out. Therapy does not have to just be for crisis moments. It can help you to build positive coping skills. It can help you to learn how to set boundaries and most importantly, to become a version of yourself that you feel proud of every day. Now, I know that in person therapy is not accessible to everyone. That's what I do. I love it. I found it so helpful. But if that's not accessible to you, either because you can't find someone in your area or it's too expensive, BetterHelp could be a great option for you. As the largest online therapy provider in the world, BetterHelp can provide access to mental health professional with a diverse variety of expertise. Talk it out with BetterHelp, our listeners get 10% off their first month at betterhelp.com human that's BetterHelp. H-E-L-P.com human and we are back. So Heather, when you're writing and you're drawing on personal experience, you're at least giving the impression of someone who figures things out by writing. So how do you find the difference between a first draft that is for you versus a draft that's going to work for other people and you don't want to revise it too much and lose the searching and the quality of messiness that other people can relate to. How do you find that balance in your writing?

[Heather Haverlesky]

I'm going to make it sound too easy, but it's also really hard. Sometimes the best things I write honestly, I start at the beginning and I just follow my whims and they go to the end and I'm like, yes, I did. You know, I'm just on. I'm just in the zone and I just have it. The best AskPoly columns were all written in that way. The best Ask Mollys are like that, although Askamali is slightly more go back, fix the joke you know, I mean, when you're writing jokes, Ask Polly is not like, it's not precision work, right? But Ask Molly is sort of everything's got to be funny for Ask Molly. I'm sure you struggle with this when you're trying to be funny, right? It's kind of crazy because funny people are also very moody. It's like, what are we doing to ourselves? Right? How many times do you sit down and you're like, I'm gonna be funny today and you can do it.

[Chris Duffy]

Oh, well, I was gonna say very often the first part, very rarely the second part where I'm like, I'm gonna be funny, but then successfully doing it almost never. Oh, it never works. Then I'm like, I end up writing the saddest or most serious thing or the most boring thing I've ever thought of. Very hard to get into that.

[Heather Haverlesky]

Like, sometimes if I'm trying to be funny or I'm trying to write something that's worthwhile, and I just veer in the total opposite direction and just go negative, just dark. It can be funny too. Like you let some beast out and then you can. You have to follow what you have inside. You have to follow your soul. You know, you can't just force yourself to be one thing or another. But I was gonna say that when you put funny stuff down, it's, you know, it's the start of something funny. You pick it up again, make it a little funnier. I mean, that's how I used to write my cartoons. Put it down, pick it up, write another joke, put it down. But I would say, though, that if you want, like, how do you know something's done? How do you get to the place where you're not over, you know, second guessing yourself? I feel like sometimes you just write bad drafts of things and then forget them. And then one day you get up and, you know, you're in the right mood and you're like, maybe I'll write about that thing that I tried to write about before. And then you've got it. The second chapter of Foreverland is about going to Europe with my soon to be husband and just hating him, hating him the whole time. And just, we're about to get engaged and I've like, I've never been less into this person. And now I'm about to get engaged, which was just a weird moment in time. It was just like I had high expectations of Europe, I had high expectations of getting engaged. I. You know, I just wanted everything to be magic. And of course, everything Was shit because I wanted too much. But I tried to write that experience so many times. I think I wrote. Actually wrote bad versions of it maybe five times. And then one morning, I was like, I'm gonna try to write that. That's just a funny story. I'm gonna write it. I think I sent it to Corey Siga at the New York Times, and I said, this is a crazy piece. I don't know if you'll like it. He was my editor at the all and hired me to write Ask Paulie in the first place. He's so great. And he was like, oh, I don't want to change that many things. I want it to be just like this. And I was like, yes. You know, that's the magic that you love. But it took a lot of work to get to. You do have to do the drudgery, the just tedious, terrible work to land. I mean, every now and then you're just like, ah, I'm just on fire today. I can write about anything, and it'll be great. And half the time you're like, oops, that wasn't actually that great. But I hit publish before I knew that. And other times you're like, wow, I just had the magic. But generally speaking, especially stories that are yours, like, from your past, it takes a lot of, like, processing that out. But fast processing. That's what I want to recommend. Fast.

[Chris Duffy]

Yeah.

[Heather Haverlesky]

You know what I mean? Like, get it down, move on, come back.

[Chris Duffy]

I mean, think especially, like, with a true story from your own life. Almost always the best way is the way that you would tell it if you were telling it to someone who was in person.

[Heather Haverlesky]

Exactly.

[Chris Duffy]

That does require, like, you have to have the story, but you also have to not, like, overwork it and get it overly complicated.

[Heather Haverlesky]

That's exactly right. And if you're that kind of person who enjoys entertaining people, live and in person. Right. If your favorite thing that most human beings never let you do. Damn them. Is talk forever about your thing, you know? And so, like, how do you tell a story conversationally? Like, let some storytellers tell a damn story. I love it when people go long. But anyway, if you're that kind of person, it is like talking, and it's sort of like, essentially writing becomes building your relationship with the page so that the page is a good friend that you tell everything to.

[Chris Duffy]

Yeah, yeah.

[Heather Haverlesky]

And you. You try to enter that state as much as you possibly can.

[Chris Duffy]

I think, like, the funniest moments come from not trying to make a joke, but it just, like, it exists because you're being honest or you're just having a natural reaction, and that ends up being the funniest moment in a Ask Polly column. Somewhat recently, there was a moment where, like, you were writing and then you paused and you said, like, I'm. Right now. I'm sitting next to Bill in bed. And I paused because I liked what I was writing so much that I wanted to, like, push this over into another day. I just, like, thought that was so funny and so perfect, but it's because it was like a very truly honest. Like, this is this thing where I wanted to sit with your letter for a little bit longer. And here's where I am right now. We have a spotlight. And I think whatever that moment is in people's writing where you get to see them, that's always the most. For me, that's what I live for when I'm reading people's work.

[Heather Haverlesky]

Yeah, that's true for me, too. I need to remember that, because I forget that that's part of my job sometimes. The more off the cuff you can be, I don't know, There are a lot of worrying impulses with writing, right? You just. There you can have these heavy things that you're carrying around. Like, I'm a great writer. I'm really great, so I gotta be more literary more, whatever that is. And then you read, you know, Nabokov or whoever, and you're like, jesus. These people were just casual, actually. I mean, sure, they had a beautiful way with words. They also put in, you know, Moby Dick, the sperm whale. You know, I'm obsessed with whales. So I'm just going to tell you about whales for a while.

[Chris Duffy]

Very much the energy of, like, a third grader telling you a lot of whale facts. In some chapters, for sure.

[Heather Haverlesky]

You're just like, what? Why would I.

[Chris Duffy]

Okay. You know a lot about the whales. You're. You definitely know a lot about whales.

[Heather Haverlesky]

There's a way that those parts of Moby Dick, though, are so great, because certain writers like making you pay a little bit, because some of the prose in that book is so insanely good and so relatable. It's just like these soulful, relatable moments. It's almost like you pay the price on your knees, you know, hearing about sperm whales. Polly is like that, too. You know, I just, like, go on too long. I mean, I think that the main thing for me is just, is there momentum? Does it feel like it's getting bogged down like a book, like a heavy book? Or does it feel like there's something important to say here.

[Chris Duffy]

We're going to take a quick break for some podcast ads and I really hope one of them is whale related. I mean that would be incredible. Hopefully they were able to find a whale company that wanted to advertise. Either way though, we will be right back after this. Banking with Capital One helps you keep more money in your wallet with no fees or minimums on checking accounts and no no overdraft fees. Just ask the Capital One Bank Guy. It's pretty much all he talks about in a good way. He'd also tell you that this podcast is his favorite podcast too. Aw really? Thanks Capital One Bank Guy. What's in your wallet? Term supply See capitalone.com bank Capital One NA member FDIC got a new puppy or kitten? Congrats. But also yikes. Between crates, beds, toys, treats and those.

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[Heather Haverlesky]

I think it was just, if you read enough of someone you love, you end up through osmosis, kind of imitating them whether you want to or not. And my thing, I think, was just, I love Joan Didd and so much. I mean, like, so many cliche white women of the universe. I also really love John Updike. And I think what happened was I would just. I had been writing in journals so much that I could freely write in a conversational tone pretty early on in my career. The key with me was if I managed to write about something that I was emotionally invested in, either angry or, you know, I mean, in the old days, it was TV shows I loved a lot I could write really well about when I was a TV critic for Salon. I could write passionately, passionately about them. And something would kick in about a third of the way through the piece where I'd start sounding a little didion, like, I don't think it sounded imitative, actually, because I wasn't aiming for it. It was just part of my subconscious that. That conjured it. I personally feel like that's the ideal. It's like, you read enough books that you love and writing that you love. And I think when you read someone who's funny enough, you just. You just end up kind of like. It's not that you're imitating their style. It loosens you up. Because the funniest writers are always very loose. They're just like, you know, they go on weird tangents, and you're like, yes, yes, go on a tangent. You know, you trust them. You trust their tangents. I mean, that's like a good writer. You trust. You trust them to run with the ball, you know? And then when you trust yourself, when you see that, it teaches you to trust yourself to run with the ball when you're feeling it. So I feel like feeling it is like 90 of the battle. I mean, that makes it sound a little bit magical thinking, like. But I don't think it. That's it. It's like you put in the practice until you can feel it.

[Chris Duffy]

Yeah. I mean, for me, it started, like, when I started in comedy. It was very clear to me that I was like, if you are looking for a less funny John Mulaney, here I am. Like, I can copy him but not be as good at the thing. And then. And a few times my wife and I would, like, go to his shows. You know, I'd be, like, performing for, like, five people in a basement where I was begging people to come. And then we'd go and see, like, him tape a special at Radio City Music Hall. And he would have, like, just subjectively the same topic, but so much funnier and better. And she'd be like, well, I guess you gotta stop talking about that joke. And I'd be like, no, why did you have to do it? Why are you so good? But it was also, like you said, it was this real path of, like, oh, I see what the craft is and how you can do it in these ways. And I think it does help to be like, okay, I think that I want to be like that, but actually, I'm going to be myself. And myself might be different, and it may not be. You know, it may not be a Radio City Music hall level of comedy, but it may be something that's more me, that I won't then be like a weird carbon copy. And I don't feel like I'm a carbon copy of him anymore. But I also still don't feel like I'm as funny. Both of those are okay.

[Heather Haverlesky]

I had a little thing with Cheryl Strayed for a while where I was like. I mean, you know, I was sort of writing advice before she started writing advice, but, like, she did it in a way that was amazing. And I was like, she's great. I love her. But then, you know, I started writing advice, too, and I was like, I don't know, maybe I hate her just because it's, you know, you're competitive and you're like, I don't do it that way. I do it this way. You're just like you said, you're always gonna bring your own weird shit to the table. You're always gonna innovate. And the more you follow your own whims, I'm kind of just repeating what you said.

[Chris Duffy]

If there's one thing I love, it's someone saying back what I Said, I love that. That's truly why I do what I do.

[Heather Haverlesky]

Pod. It's a lot like therapy.

[Chris Duffy]

Well, actually, let's talk about like the podcasting and the advice column, because one thing I think is interesting, especially about like a show called how to be a Better Human exists in this space that is like, I don't think of this as a self help show, but it is in like a self help adjacent place. At the very least. There's this idea that's kind of implicit in a lot of self help that's like, you need to change, you need to like, make yourself better. You need to like, do all this work to improve who you are. But I think that you have pushed back a lot on that idea of like, you need to be someone different and better than who you are. That in fact probably what you need to do is to be exactly who you are and to understand that and accept that more.

[Heather Haverlesky]

I always sort of flinched at the concept of living your best life, even though Oprah's awesome. I love Oprah. And obviously anything you come up with, other people are just going to kick it over and say, you know what? I hate self care. Self care is bullshit. You know, every day you should, you know, whatever, but everything is a balance, okay? Today I literally wrote a Ask Poly column where I said, we all want total control and total perfection and we all want to live forever at some level, and we're all a little self obsessed that way and we're willing to be hated at some level just to kind of honor that neurotic perfectionist inside us. But then the other side of that is just as you have to honor that inner perfectionistic neurotic, you also have to honor the grumpy bridge troll that lives inside you and also invite the chaos of other human beings into your life. You know, failing to connect with other human beings as well as you might if you just ceded some control or just surrendered to the moment, learned to surrender to the awfulness of other people a little bit more often. So I feel like I have so many self improvement impulses just poised and ready to go inside me that are just really awful. There was a time in my life where I was a little bit chubbier and I would look at myself in the mirror and I was like, I don't feel like myself. I don't feel like this is me. And it's like, that's not a good place to be. If Chubby were myself, it would be great. I'd be able to eat more snacks. I would like, it. It's just you have to be true to whatever crazy, crazy, crazy mix of beasts exists inside you. So a lot of the problem with self improvement culture is that there's an inherent shame to believing that you should always be making progress in life. There's also just an inherent anxiety about it. It's depressing to think that you're supposed to always get better because people just don't do that. People don't understand that if you're not good to yourself, especially like, if you don't learn to be good to yourself when you're younger, you grow up and have this like terrible, punishing, neurotic idea that you're supposed to keep improving and that marriages don't get better and worse and better and worse, and that relationships with people don't require all kinds of special care and attention and a lot of frustration and a lot of like, blech. One of my main purposes in life is to just tell people, once you cut out the shame of not being this idea, this fantasy idea of what you're supposed to be, you're gonna be 80 times happier. You know, you just. And it's hard because you don't want to stifle people's ambition or their dreams. I mean, dreams are a huge part of feeling happy. Dreams in and of themselves can make you bring you satisfaction even when you don't achieve them. Because it's just good to have dreams. They're part of your sort of like imagination and part of your ability to feel the possibilities in any given day. Right. So that balance between putting too much pressure on yourself, triggering your shame with your ambition, it's a hard path to walk. Creative people have very naturally ambitious. Creative people have a lot of struggles for a very good reason. Because you can't be Zen and be ambitious at the same time. You actually have to be bothered things. You have to be dark, light, optimistic, skeptical. You have to be all of it, you know, and you have to accept all of it and play with all of it to create. So I'm pretty anti self improvement. On the one hand, I'm obsessed with it, I love it. But I think that the language of self improvement is just lazy and sloppy and it presupposes a kind of like capitalism of the soul where you're optimizing your product for the masses. I mean, there's nothing worse for you than that creatively.

[Chris Duffy]

Heather Haverlesky, thank you so much for being on the show. Really, this is great.

[Heather Haverlesky]

Thank you. I had a really good time. It was fun. And I hope I can come back.

[Chris Duffy]

That is it for this episode of how to Be a Better Human. Thank you so much to today's guest, Heather Haverlesky. Her latest book is called Foreverland and she is the author of the Ask, Ask Polly and Ask Molly newsletters. I am your host, Chris Duffy and you can find more from me, including my weekly newsletter and other [e-mail] how to be a Better Human is put together by a team of geniuses constantly doing battle with their evil twins. On the TED side, we've got the radically honest Daniela Ballarazzo, Ban Chang, Michelle Quint, Chloe Shasha Brooks, Valentina Bohanini, Eleni Lott, Tanzika, Suma Nivong, Antonia Ley and Joseph De Bruyne. This episode was fact checked by Julia Dickerson and Matias Salas, who know that the only true for Everland is the truth. On the PRX side, they give audio advice that cannot be denied. Morgan Flannery, Norgill, Patrick Grant, and Jocelyn Gonzalez. Thanks again to you for listening. Without you, we are not a podcast. We're just me talking alone in my basement. Please share this episode with a person in your life who you think would love it, who you think would enjoy it. We would so appreciate you helping us to spread the the word about our show. We will be back next week with even more how to Be a Better Human. Until then, thanks again for listening and take care.

[Heather Haverlesky]

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