Girlboss or Bust

Girlboss culture is now, as they say, cringe, but during the 2010s, SO MANY of us thought we were on the precipice of busting through that glass ceiling. We thought we could rise and grind, hustle our way to the life of our dreams, and as long as we loved what we did we wouldn’t work a day in our lives. Leigh Stein is also a recovering girlboss, who went into debt building an organization that supported women but left her burned all the way out.

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Transcripts may not appear in their final version and are subject to change.

I’m Nora McInerny, and this is “Terrible, Thanks for Asking.”

I am the creator and host of this podcast. I’m the author of several funny books about sad things. I’m a public speaker. I was an entrepreneur. I was a founder until I wasn’t anymore, and … for many years, I am sorry to say, I was a girlboss.

And I wasn’t alone, either. There were thousands, maybe millions of us out there, thinking that we were on the precipice of busting through that glass ceiling while leaning in, that we had as many hours in the day as Beyonce, that we could rise and grind, that we could hustle our way to the life of our dreams, that as long as we loved what we did we wouldn’t work a day in our lives.

Before I started all my own things, I got to my job in social media marketing at the crack of dawn, dropping my TEENY, TINY BABY off at daycare that cost more than 50% of my take-home pay. I BROUGHT A LAPTOP TO THE HOSPITAL WHEN MY HUSBAND WAS GETTING CHEMO. I prided myself on working not smarter, but harder. On having my phone within reach at all times. At replying to client emails with the subject line “911” … emails that were about a BANNER AD … when that same night, I would actually CALL 911, because my husband’s brain tumor was inducing seizures.

Girlboss culture is now, as they say, cringe. It’s so far out of vogue that it’s now TOXIC, and to admit you were once a willing participant in a culture that told you the best way to participate in a damaging structure was to assimilate and perpetuate everything that was wrong with it is like an admission of guilt for a crime against yourself and the rest of a culture that now seems to agree that actually, to quote the excellent podcaster Sarah Marshall of “You’re Wrong About,” it was capitalism all along!

But we didn’t know that at the time, did we? Not when we were reading Lean In and GirlBoss and painting everything we owned millennial pink and learning calligraphy and starting a side hustle and whatever else we did in the name of feminism from 2012 until whenever we stopped.

Today’s guest is also a recovering girlboss, a woman who girlbossed a little too close to the sun. Her name is Leigh Stein. And she’s not just a recovering girlboss. She’s also a writer. Being a writer is not a particularly lucrative career, unless you’re one of a very few people. I have like, five or six jobs at any given time, and I don’t even live in New York City, where it’s every expensive. 

But in New York City in the early 2010s, that’s what Leigh had to do to make it as a writer: She had to work jobs that had nothing to do with writing to support what she hoped would become a career as a writer.

Leigh Stein: I owe my career to the internet. Without the internet, I would not have a writing career. I did not get an MFA. I have a GED from New York State, but I don't have a masters in creative writing like a lot of my peers. But I've just made connections online and really found an audience for my work through the internet.

Some of the biggest online connections Leigh made came in 2012, after the presidential debate where Mitt Romney turned a staple of office supplies into a meme.

Audio of Mitt Romney from 2012 Presidential Debate, starting at :23: “And so we took a concerted effort to go out and find women who had backgrounds that could be qualified to become members of our cabinet. I went to a number of women’s groups and said, ‘Can you help us find folks?’ and they brought us whole binders full of women.”

I look back on Romney’s infamous gaffe now, a decade later, and wish I could say to 2012 Nora, “Save your outrage, sweetie pie. You have no idea what’s coming.” But at the time, that phrase — “binders full of women” – that hit the zeitgeist HARD. There was a Tumblr account, tweets, articles, opinion pieces, people dressed up as binders full of women for Halloween. 

Looking back, it’s kind of hard to “get” the joke, let alone explain it, but it was one of those examples of the internet really shaping our culture and our cultural conversations. Had you said “binders full of women” at your office in 2012, everyone would have known exactly what you were talking about. 

Leigh Stein: So in 2014, a freelance writer in Toronto named Anna Fitzpatrick started a private Facebook group called Binders Full of Women Writers.  And it was invite-only for other women writers.  And she thought 20 people would join. She imagined it being small and invite-only. Within three months, there were 30,000 members. And I was one of them. And this Facebook group consumed my life.

The group was set to secret on Facebook, meaning you couldn’t find it in a search. You needed to be added by a current member to join the group. 

I was never added to that group because I was working in marketing in Minneapolis and had given up on freelance writing when my boyfriend-turned-husband got sick. But I watched it all from a distance. #Binders trended on Twitter, and there was an article in Vogue about the Binders group. I didn't know anyone who could even be in the group to invite me, so from the outside, it sounded just like a No Boys Allowed utopia meant to help women build their careers.

And for Leigh — who was on the inside — it was even better than it looked.

Leigh Stein: I was checking this group like morning, noon and night. I was seeing all these famous writers I admired saying hello and introducing themselves. It just seemed like a really fun, fruitful place to network, make connections, reconnect with people you hadn't heard from in a while, find agents. It was like a hotbed of connection and community. So I went on vacation with my boyfriend at the time, and when I got home from vacation, I was, like, really jetlagged. And I just had the idea, like, "What if we put on a show in the barn? What if we had a conference?" And so I just wrote a post in the Facebook group like, "What if we had a conference? Who would help me?" And I'd never planned a conference before. 

But oh well! The environment within the Binders group was so positive, so hopeful, that a conference — a huge endeavor even for someone who does it professionally — seemed very possibile. 

So with the blessing of the original founder, Anna Fitzpatrick, Leigh and a fellow writer named Lux Alptraum make a Kickstarter to fund the conference. 

And Lux encourages Leigh to go big. To think BIG.

Leigh Stein: We had levels for buying tickets or getting a T-shirt. She said, "Let's put sponsorship levels like $2,500, $5,000, and $10,000." And I was like, no way, like, who who would click that? And she was like, "Let's just put it on the Kickstarter." And, you know, she kept saying, like, "This is a normal thing that, like, conferences get sponsors." I thought she was insane. And I remember sitting at my kitchen counter and getting a notification that someone named Lane Shakespeare had given us $10,000. And I thought it was a joke, because who's named Lane Shakespeare? And I looked and he worked at MailChimp. And then I looked on Twitter, and another woman who worked at MailChimp had just started following me on Twitter. And I DMd her, and I said, "We just got this donation. Is this real or is this a joke?" And she said, "Yeah, he's the head of sponsorships. We're sponsoring the conference." And I just started crying, like, I want to cry telling the story. It was just like, just putting that kind of money behind us when we were so new. It was an incredible feeling.

In just 3 days, they reach 25 percent of their goal of $40,000.

By a week, they’re at 40 percent.

And at 20 days, they’ve reached 100 percent of their goal, and then some.

Leigh Stein: [00:02:28] So about 100 people commented on the Facebook thread and volunteered to help me. Within three months, I had a co-founder. We raised $50,000 on Kickstarter for our first conference in New York City, and my co-founder said, "I think we should be a 501c3 nonprofit." And before I knew it, I was executive director of a 501c3 nonprofit organization called Out of the Binders. [00:02:52][23.4]

Leigh Stein: [00:02:56] Anna Fitzpatrick, the original founder, gave us her blessing to take over the Facebook group under the umbrella of the nonprofit, and we started doing conferences twice a year — in New York every fall, in L.A. every spring. About 450 writers came to the L.A. event, which was more Hollywood-focused, and about 550 writers came to the New York event, which was more media- and book publishing-focused. And our goal from the start was really to kind of correct gender imbalances that we saw in the media industry and in Hollywood. [00:03:27][31.3]

The conferences were called BinderCon, and they specifically catered to women and gender-variant writers trying to navigate a very patriarchal media industry. Today, men account for about two-thirds of media credits and bylines. And The Columbia Journalism Review found that in 2018, 73% of editors at America’s top English-language outlets were men.

Leigh Stein:  We were also thinking like, what's holding women back? Is it psychological? So we had a workshop taught by a therapist on dealing with rejection. So we were asking ourselves these questions like, is it that women need the connections? Is it that, you know, there's sexism? Is it psychological? Is it the realities of being a parent and child care? We had many panels on writing as mothers. So we were coming at the problem from multiple angles. 

Starting a new project is always such a thrill. Always. As a person with ADHD, there’s nothing better than the dopamine rush of a new ANYTHING, but a new project? Oh boy. When every idea feels fresh and exciting? When every step feels like a substantial step forward? That honeymoon period where work really does NOT feel like work? Where the dopamine and the serotonin are just flooding through your sweet little brain? Where your productivity is just through the roof? I don’t know, that’s hard to beat. 

Leigh Stein: The energy of starting something is incredible, because you only start something once. I have this vivid memory of reading Lean In, and there's a part in the book where she said, “If someone asks you to get on board the rocket ship, you don't ask which seat you're going to have on the ship. You just get on board.” And that was the energy and the feeling I had at the time when I was launching something, because I only was able to build this conference and this organization because I had so many people on board the ship with me. And when I said I needed help, all these women, like, raised their hand and said like, “I can volunteer for that. I know someone who knows how to do this. I know someone who has space at NYU, like, let me email her.” And that's how we made it. And that energy still feels so exciting to me, even though the culture has turned against girlboss mentality and hustle culture. There's a part of me that is, like, nostalgic for that energy. 

Nora McInerny: The energy of possibility and the energy of people just being excited – and specifically women being excited to work together on something where you don't know what it's going to end up being. And the funny thing about that passage jumping out to you, Leigh, is that you ended up being in the front seat. 

Leigh Stein: [laughs] I was in the front seat. Yeah, yeah, I was flying the rocket ship. You know that line about building the plane as you fly it, it was like that. 

Nora McInerny: Yeah. So when you're in that and when things are good, describe to me how that feels and what the energy is like. 

Leigh Stein: It's such a rush for an overachiever to then achieve the things and be in the thick of it. Like, our very first conference. We rented space at the NYU Law School, and they have this, like, beautiful room with these, like, lush carpets and these oil paintings on the wall. And we had our first keynote conversation between Jill Abramson, who had been the female executive editor of The New York Times, and Emily Bell, from the Columbia Journalism School. And  We're sitting in the room, and there's all these women having lunch, and I'm like, “I built this, I built this.” And then Emily Bell says, like, “We're at a women's empowerment conference and we're surrounded by oil paintings of, like, dead white men.” And it was so funny, but it felt like a real cultural turning point moment that, like, we were the future. These guys were the past, and we were part of the future, and we were making it together. 

Leigh Stein: It felt good to be recognized for what I was building, and even at the very first conference, this woman came up to me and she was like, “Are you going to franchise this? Because I'm in Canada and like, we can have a Canadian franchise.” We have people in cities around the country saying, “Can we franchise this?” And I was like, “Whoa, I just started this thing!” So that was a little overwhelming, but also a tribute to my success that people were already looking at what I was doing and saying, “Can I do this too? Can I do this with you? Can I do my own version of this? How can I get involved?” So there was, like, a contagious energy. I'll never forget that like one of my, you know, original intentions with the conference was, like, we were trying to get all the data about what was holding back and what was holding back women from writing and publishing careers. And one of the organizations that was doing a lot of work at that time was Vida, and they were literally counting bylines in major magazines — how many men were published this year, how many women were published — and then they would publish these pie charts. And the pie charts were shocking. And in 2014, Harper's Magazine was one of the worst in terms of gender balance. And so I thought to myself, “We need to get an editor from Harper's Magazine to come to our conference and take pitches from women, because if they are getting enough submissions from women, I can surely correct that by giving them some pitches.” And I remember doing internet research and figuring out who are the editors at Harper's. I interviewed a couple of women and neither of them could come, and there were no other women I could ask at the magazine. And then the male editor in chief said, “I will come.” And so he was the one man we allowed at the conference because I thought I would make that exception. That made sense. But I just was really like, I felt really good about like my strategy and that this guy said, like, “I see what you're doing. It's important. I'm going to spend my Sunday afternoon in this room in the same room where the oil paintings were on the wall and take pitches.” So I always had a very pragmatic approach to: What's the problem and how do we fix the problem? The point wasn't to get together and just …  it wasn't like a consciousness raising session from the ‘60s or ‘70s, like, just to get together and vent. It was really like: What are the problems? What are the challenges? What are the barriers and what are the ways to work around them? 

The conferences were selling out, and in the Facebook group, women were making connections and building their careers. They were sharing resources — even making a list of couches available for any member to crash on in cities they may visit one day. 

And the good moments — like getting the executive editor of Harper’s in person to account for the disparities at their publication, or rubbing elbows with Jill Abramson — they’re really good.

Leigh Stein: Another high moment was for our L.A. conference, one of our organizers, Jesse, her mentor at WGA, which is the Writers Guild of America, was Robin Schiff, who wrote “Romy and Michele's High School Reunion.” And I said, like, “Do you think Robin can get us Lisa Kudrow?” And she was like, “I will ask.” And she did. And so we had Robin and Lisa Kudrow in conversation about “Romy and Michele’s High School” Reunion and working in Hollywood. And it was just like … I just couldn't believe that I was a part of making this happen because it's like it's almost like, you're like, “How could I be in the same room with these people?” There was just great energy, and we were powered on volunteer labor. I wasn't getting paid, my co-founder wasn't getting paid. My organizing team wasn't getting paid.

[Record scratch sound.] 

Audio slows down to repeat Leigh saying over and over: “I wasn’t getting paid, my co-founder wasn’t getting paid, my organizing team wasn’t getting paid.” 

We’ll be right back.

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Leigh is doing all of this work — organizing two conferences a year that are bringing in decently sized sponsorships and that feature top authors and media industry leaders — and she’s barely getting paid for it. 

It’s easy for Leigh to rationalize this at first, because the work feels SO GOOD, so worthwhile. Women were coming out of BinderCon with book deals and freelance work and business contracts. Leigh felt good knowing that she was helping marginalized writers find success. 

Leigh Stein: We really tried to make the conference intersectional and accessible. We had a really innovative scholarship program. We not only awarded scholarship tickets, we also gave writers travel and child care stipends so they could be there in person. We had a VIP party, and we invited all the scholarship recipients to the VIP party, and you couldn't tell who was who. So if you paid a lot of money for your ticket or you got a free ticket, you got to mingle together and make connections. 

But positive vibes don’t pay the bills. That is not a currency that you can send to your cable company, pay your water bill with. Your rent cannot be paid in exposure or vibes. So while Leigh is running Out of the Binders full time and organizing twice-yearly conferences, she’s also working outside jobs to try to pay her bills. 

Leigh Stein: We just weren't making enough money on the conferences to pay a staff. And even me. We couldn't even pay a staff of one. So my co-founder and I received stipends for our work organizing the conferences, and that started at $2,500 for the first conference. And the most I ever made in a year was $12,500. Like … this wasn't my full time job. I was still hustling, so I had like three other side gigs. That's how I was surviving. And none of my staff, like, my staff were like the best. And none of them said, like, "I can't keep doing this for free anymore." No one ever said that to me. They were all in it, because it was like a meaningful volunteer project for them. They wanted to be a part of it, and they chose to support me. And that means so much to me. But it was me burning out. I wasn't able to keep doing this for so little money. And everyone support- I mean, there was no arguing. No one was like, "Leigh shouldn't get paid." No one ever said that. It was just, like, crunching the numbers to make it work. The other problem is that I just didn't value my own labor. I never made a lot of money. I'd always been hustling and scraping by, so I didn't have a sense of my own value — not even of my time, but, like, of my work. 

On the outside, Leigh looked like she had it made. She was a published author, twice over! She was running a well-known nonprofit with an online community of almost 30,000 members. She got to hang out with Lisa Kudrow and the executive editor of The New York Times! 

But twelve thousand dollars when you’re living in New York City is … I’m not an economist, but I don’t think it’s enough. And one of the clearest ways to show just how much this “dream job” was ruining Leigh is to talk about the dollars.

Leigh Stein: In 2016, I clocked 859 hours. And that year I made a little more. I made more than $2,500. But when I did the math, I made $14 an hour. 

Nora McInerny: [sighs] This is supposed to be a side hustle. 

Leigh Stein:  Right, and  it did feel like a windfall. So our L.A. conference never made money. Our New York conference made money. So the New York conference paid for the L.A. conference. And I would get paid once a year at the end of the year after the New York conference. By the end, the most I had made was $12,500. That check would come in like a windfall at the end of the year. I would pay off the credit card debt I had accumulated during the preceding months, and then I would send all that money to the IRS, because I couldn't afford to make my quarterly tax payments. I was not paying quarterly, I couldn't afford it. And I would use that BinderCon money to pay the IRS every year. I was privileged to live with my boyfriend, so had an apartment I lived in in Brooklyn. And I was either on Medicaid or I was on his insurance during the time that I was doing this. But I wasn't making enough money to cover all my expenses, and so I started going into credit card debt and started borrowing money. And I had been working on my third book, which was a memoir. So in the back of my mind, I was like, “I’ll sell my memoir for a lot of money. And this credit card debt will just be temporary, because once I get that big book deal, I'll be able to pay off my credit card debt.” I did end up selling the book for $20,000, paid in three installments over two years. So we're talking about, like, a $5,000 windfall of cash in 2015. But that wasn't obviously the book deal that I dreamed of. I was ashamed of being in debt, so I wasn't telling my co-founder the extent to which things were getting bad. And meanwhile, she and I were taking lunches with, like, potential sponsors and putting together these decks for them of what $40,000 would get them, what $50,000 would get them. 

As she takes these lunches with potential sponsors, Leigh takes notes in her work diary. It’s in this same work diary that she’s also keeping track of her personal expenditures. Leigh has actually made one of these pages public – we’ll link to it in our show notes. 

On one side of the page, you can see Leigh tracking her credit card debt, taxes owed, and other money she’s borrowed from friends and family. On the other side, she’s taken notes about a major media company who has just offered a $40,000 sponsorship for the next BinderCon.

Leigh Stein: And just these two pages juxtaposed together, like, just sum up what it was like. I would put on my best outfit and I would go to these meetings and make the pitch. And the pitch was always, you know, you're always asking for tens of thousands of dollars, and you have to tell them how it will make their brand look good, how they will get visibility for being on the right side of history, on the right side of social justice for supporting your cause. And I knew none of that money would come to me, you know? Yeah, I got burnt out on the game, on the hustle. I realized: I'm the executive director. This is what my job is. My job is not to organize the conferences. My job is to ask rich people for money. And I hated doing that. And so it was just this surreal juxtaposition between writing down in my work diary, tallying my debt — that made me feel more in control, to write it down. I'm someone who wants to know what it is. It would make me more anxious not to know. So I had to write it down, and I think I was tracking it over every month how I was doing better or worse. I also owe taxes, because this is all freelance. I wasn't getting a salary, so I also owed taxes. I read something from Cheryl Strayed where she talked about how much credit card [debt] she got into to write “Wild.” And for some reason, I took that as, like, an inspiring story and said to myself like, “Yeah, if that's what you got to do, that's what you've got to do.” Like, if you have to go into debt for your art, like, look at Cheryl Strayed. What a great example of, like, a happy ending to that story. [laughs]

Leigh is in trouble, but she doesn’t feel like she can stop. And she doesn’t want to stop, either. She loves putting on the conferences, even if she isn’t being paid fairly for her services. She feels like she’s making a difference in the world. 

The online community aspect of the nonprofit, on the other hand …

Leigh Stein: My proudest moments were at the conferences. It was just like the best energy if you were there. But the Facebook community was filled with drama and conflict. And we only ran the main Facebook community, which had grown from 30,000 to 40,000 members. There were also over 200 subgroups – subgroups for moms, subgroups for women of color, subgroups for LGBTQIA identifying people. Then there were subgroups based on genre: short story writers, memoirists, journalists, Jewish humor writers. I mean, you name a classification, someone could make a subgroup for them. And there was no way that I or my organization could run over 200 subgroups. We only ran the main group. But inevitably, whenever there was conflict in a subgroup, I would get tagged to intervene. So I felt like the mom. And my co-founder would say, "We are not the police of the internet. This is not our job." But again and again, there was a sense of: Someone's feelings would get hurt, someone would get outraged, and they would look around and say, like, "Who can I tell? Who is the authority to tell?" And because I was the face of this organization, it looked like I was the boss, that I was the mom, that I was the caretaker, that I was the mediator that would settle these conflicts. And that took up so much of my time. Even trying to disentangle myself from this, so that I didn't have to be involved, took up my nights, took up my weekends. Every holiday weekend, for some reason, everyone would be more on Facebook than ever before. I have memories of spending Easter Sunday in a conflict. I have memories of being at 4th of July on a boat to see the fireworks, trying to get reception so I could deal with a Facebook controversy. And that really took a toll on my mental health. So it wasn't the conferences that burned me out. It was the 24/7 job of being a moderator of one of these Facebook communities. And I wasn't alone. I had other people helping me, and volunteers, and they did really good jobs. But the work was relentless, and it was punishing, and it was not satisfying at all. Because no matter how you tried to resolve something, how you tried to communicate, there's always going to be one party or more parties that were disappointed in how you handled it, that would have done it differently. Everyone thought they could do my job better than me, but of course, no one wanted my job. 

Nora McInerny: I think a cornerstone of girlbossing is that it looks so good, right? It appears to have all of the trappings of what you might imagine success is. And you're also meant to be hustling without showing any of the actual struggle, right? Without showing your work the way your fifth grade math teacher insisted that you do. 

Leigh Stein: Yeah! Right. Because my whole conference had arisen from this private Facebook group, and the point of the private Facebook group was that it was a place you could go to for support. But the more influential I became as the leader of this organization, the fewer places I had to go for actual support. I had friends, but I lost the best part about the group, which was getting support from your peers, because I was no longer the peer. I was kind of the … I was the leader of the group. And so I couldn't turn to the group for support the way I once did. I had to appear high-functioning.

Eventually, the job comes for Leigh’s physical health, too.

Nora McInerny: What are some of the moments that indicate to you that this is untenable, or that this is going sideways, or that things are starting to sour for you? 

Leigh Stein: I was on my computer morning and night, and I ended up getting repetitive stress injuries in both wrists. And I, of course, went on Facebook to the Binders to talk about this. I got a bunch of advice from people. And actually this is really moving, but a woman in the binders PayPal’d me 50 bucks so I could go to CVS and buy wrist braces. So I started wearing these wrist braces. The day I got the wrist braces, I had this big opportunity to write for the New York Times, and I had sent them this essay months, months, months before and they had accepted it, but said, like, “We're really backed up. You're going to have to hold tight. We don't know when we're going to publish it.” I said that's fine. And then, of course, the day I get the wrist braces, they're like, “We have to edit this in 48 hours and it's going to print.” And I was wearing these braces and trying to type on my computer, and it was very awkward. I couldn't do it. And I was just, like, tears were streaming down my face. I was just, like, in so much despair. I mean, I did do it and I did turn it in, and it did get published. It just … iit felt like the worst of times in the best of times, you know? I'm meeting Lisa Kudrow. I'm writing for the New York Times. I'm in shooting pain. And I started drinking more, I don't think I was a daily wine drinker until this conference, where wine went from being, like, an occasional treat to being a non-negotiable thing I did every day. I had two glasses of wine every night. It was like my treat. And I would drink it while I was on Facebook. And it was kind of a way to numb out while I was scrolling as if I was just … I don’t know. In hindsight, it's like I was drinking at work. Like, I was working so many hours, and I was just drinking at the end of the day. But then it just became this bad habit where it felt like, “Oh my gosh, I'm drinking seven days a week. There's never a day when I'm not drinking.” And my wine intake, it didn't really increase, so it didn't get worse and worse sol I was drinking a bottle a night. That never happened. But I did feel like this was a pattern that I couldn't break for years. I had pain inside my ears, which I realized was jaw tension. So they made me a mouth guard for grinding my teeth, and I bit through it and, like, broke it. Then, they injected my face with muscle relaxers, which was very scary for me. I didn't do that again. 

Nora McInerny: Did your family, your boyfriend, your friends, did any of them raise their hand and say, “Leigh, this is bananas? Why are you doing this?” 

Leigh Stein: I think this work and this conference and this nonprofit, it was so all consuming that the only people I saw and talked to were the friends that got involved to help with the conference. So it really took over my life. I did have my boyfriend, now my husband, and he's always been very supportive of me, which is why we're together. I think it was hard for him to know what to say or to do. When I first had the idea to do it, I told him. He was the first person I told. And he said, “Conferences are really hard.” And I said, “Watch me.” Like, he's always a little nervous for me, and then his doubt is what is like, extremely motivating for me. Like, people could see that I was burning out and people told me to take care of myself. And I got told that metaphor about putting your oxygen mask on first. Like, I'd heard that so many times, but I felt like they were wrong, and I felt like the answer was work, and the solution to the problem was work, and I just had to keep working to solve the problem. 

Leigh is on a midnight train to massive burnout. She’s unhappy. She’s not sleeping. She’s spending all of her free time and holidays trying to moderate a massive Facebook group while racking up debt. Sounds like some big girl boss energy to me! Rise and grind, baby!

We’ll be right back.

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We’re back. And Leigh, who has been managing Facebook groups and conferences meant to connect women to more opportunities in writing is … to put it mildly … burning the hell out.

Leigh Stein: I was losing my identity as a writer, because this was taking over my life, and I was like, “Wait a second, when did I say I wanted to be an executive director of a nonprofit when I grew up?” Like, how did I get into this … by accident? Like, I said yes, but then, but I didn't think through the implications. And then this all came to a head in 2016 for the New York conference, which happened about one week before we all thought Hillary Clinton would be elected president. We were riding high getting ready for that. And there was a controversy about our attendance policy. Our attendance policy said it was for people 18 and over, meaning no children and no infants. This was extremely controversial, because some people thought that we should allow nursing infants. Some people thought we should allow children. But a lot of people in the Facebook community thought our attendance policy was wrong, and they had never come to the conference. They had never volunteered for the conference. And in my opinion, I thought, “Who should be the ones deciding the policy? It should be the people that built the conference.” And the majority of the people on my team thought we should keep the policy the way it was. The majority of these people were parents themselves, and they said they were scared to say so on Facebook. They were scared to say so on Twitter. Because they would get dragged. And I understood that. And so I had to take the fall. And I, a childless person, had to be the face of the organization, the one saying, "This is our policy." I wanted to come up with a compromise, and I wanted to come up with a solution that would please a lot of people. And this was the hardest problem I've ever had to deal with, because the community was so divided. Ultimately, I feel like it came down to a generational conflict, where the older women in the group said, "This is a professional conference. When I had my kids, this is what I did, and I went to conferences without my kids." The younger women with smaller kids said, "How can you call yourself a feminist and not allow babies and kids at the conference?" It's a really tricky generational knot. I couldn't solve it. I couldn't figure out a compromise. There was a Facebook group that organized a protest to take us down the weekend of the conference by using our trending hashtag to shame us. And I just remember crying in my hotel room and feeling like, “I'm going to have to resign in shame.” That’s what it felt like. This one tweet, I'll never forget, where they compared our conference to Donald Trump because there was, like, a moment when Donald Trump didn't want to hold a baby. He kind of, like, made this gross face and, like, handed the baby back to someone and they compared us to Donald Trump. And I just thought, like, “How much more hyperbolic can you get? We're, like, an intersectional feminist, trans-inclusive writing conference, and you're comparing us to Donald Trump. I can't even.” 

Some of the criticisms of the binder group are valid — like, can a group be inclusive if you need an invite to even know about it? But it’s not about whether the criticisms are valid or not, it’s just that there are so many. And they’re so few people working on the backend to resolve them. Any online group always seems to reach a tipping point where you just can’t make that many people happy, and where every choice is applauded by some and HATED by others. Some people find ith helpful. Some people find it hurtful. And I think if it’s your only job, and you’re paid well for it, and you have some balance, maybe you can handle it.  But naturally, like any good woman of this era, Leigh looks at the situation and looks at herself and says, “What am I doing wrong? Why is this so hard for me?”

Leigh Stein: I struggled with depression a few times throughout my life, and so I recognized some of those symptoms. But it was different than depression. It was so connected to work for me, because I kept thinking, "If I just work harder, I'll feel better." And so I kept trying to like, optimize. Like, I kept reading self-help books and listening to, like, "Being Boss," the podcast. And I was trying to be like, very girlboss. Obviously, I was not very girlboss, because I was making no money, but I was trying to be girlboss in the terms of mindset. I was trying to push through. I became so fixated on the things that irritated me, and I completely lacked the ability to think big picture. So it was like whatever was in my email inbox just consumed my thoughts. And I had such a negative reaction to everything I read, like, “How dare that person email that to me?” And I just spent every day in this mood of righteous indignation, which of course was exacerbated by whatever was happening on Facebook that day. I went back on antidepressants, thinking it was depression, so I started taking antidepressants again. But things just looked very bleak and very dark. It was hard to see a way out. And as much as I kept working — I was a workaholic, I worked all the time — it seemed like nothing ever moved forward. Nothing ever got done. It was never ending. And it wasn't satisfying. Work didn't make me happy the way it did at the beginning. When we launched, it was just like, so fulfilling and rewarding, and by the end, it felt so miserable. So after the dramatic event around our attendance policy and children and infants, I started working on a fundraising plan for the following year, so that I could make $40,000 a year. This was my goal. At the time, I thought, "If I could just make $40,000 a year, like, my life would be so much easier, because I wouldn't have to work all these side gigs. It would just be smoother." And then I started thinking, "OK, maybe the fundraising plan is so that someone else can do my job for $40,000 a year." And then I thought, "Who would want to do my job?” Like, who would want this? The only person who would want this was me, the person who was the founder, because I had the most skin in the game. I'm the one that loved it. I'm the one that built it. I couldn't like, give this 24/7 thankless Facebook moderation slash running a conference with a team of volunteers who, you know, thankfully liked me and respected me, I couldn't give that to someone for $40,000 a year. The last thing I tried was I went to our board of directors, and I said, "Can we just do one conference a year?" Because I thought maybe I could keep doing this if we could do one. And they said no. They didn't think that would be good for optics … which really hurt me. And then I said, "I'm sorry, I can't. Then I can't do it." I was afraid to resign, because it would mean that I was a failure. I was afraid of my reputation being “Leigh failed at this” instead of “Leigh organized six conferences and ran this group for three years.” I thought people would say she failed, and so this is really interesting to me, because it gets that like it gets at the danger of having a personal brand. That I thought resigning would be bad for my brand, that people would say, oh, she couldn't build it. But I did build it. 

On May 1st, 2017, Leigh resigned from Out of the Binders and BinderCon. That same day, she deleted her Facebook account – for good.

Leigh Stein: I think I was running on adrenaline for so many years that I just crashed. I basically went to sleep for months. I know I continued my freelance work, but it's very blurry. I don't think I was even working 20 hours a week. I got off antidepressants finally, and I started my own business. So I asked myself, “What do people always ask me advice about?” And people always ask me for book publishing advice. And that used to bother me because I would say, “But I have a whole conference. You can buy a ticket to the conference!” But they would just be asking me privately, and that used to irritate me. And then I realized like, “Oh, I could charge them money, and then I could answer their question.” And so I started my own business, and a lot of people have given me advice to scale up my business, and I have resisted all that advice, and I'm just one person, doing a business for one. I said at one point to my husband, “I don't think I'm ever going to be able to write again.” And that felt really sad to me, because I just spent three years helping other writers, and I didn't think I'd ever be able to write again. And he said, “You will.” And I set a low goal for myself. I told myself I was just writing a short story. And I still have my journal from that day, my process diary, for my novel Self-Care. And I started it that same day that I resigned: May 1st, 2017. 

Without the conferences and the Facebook groups, Leigh was able to actually … write. A very clever novel called Self Care, which I picked up on the recommendation of a friend I loved and — I do this with books I love – I read it in one sitting. It’s a clever parody of the self-care and wellness industry, the millennial-pink-washing of feminism, and girlboss culture. 

Leigh Stein: One thing I talk about when I'm talking about girlboss culture is that Sheryl Sandberg wrote this book, Lean In. And it was supposed to be a guidebook for navigating your career ladder in corporate America. That was the audience. As Sheryl had done herself, right? She's trying to teach the next generation. But the thing about the next generation, which is our generation, which is millennials: We don't want to advance in corporate America. We want to make money doing what we love. And so the girlboss founders said, “I'm not climbing the ladder. I'm making my own company. I'm disrupting an industry. I'm doing my own thing.” Like Emily Weiss with Glossier, selling direct to consumer cosmetics because millennials weren't going to the Macy's counters to try on Clinique lipstick. So there is a millennial ethos around figuring out how to monetize what you love doing and what you're passionate about. And I don't think it's necessarily wrong, though I do think it's true that you shouldn't have to monetize your hobbies. It's OK to have hobbies and things you love and things you enjoy. Like, if you love watching movies, that's great. You don't have to start a movie blog and get paid advertisers for your movie blog. There is this … that's the negative part, I think, is this pressure to somehow document, perform everything that we do online and to make it a part of our brand. So this is another part of it that I think about is, like: What's public and what's private? And if you take things that are private and make them public, what are the consequences of that? There can be good consequences. There can be bad consequences. So, thinking about what you keep for yourself. And this is the struggle all artists and creatives have, is: What do you have to do to pay the bills so that you can do the thing you really love? Because I've written five books. I do not make a living writing books. That's not how I make my living. I make my living through my business helping other people get their books published, just like many of my peers make a living teaching in MFA programs. And I’m able to schedule my time so that I can write, which is what I love to do. 

It’s no secret that women have been leaving the workforce en masse since the start of the COVID-19 pandemic. There are pressures of balancing work with child care issues and distance learning. According to a report from the National Women’s Law Center, women in the U.S. have lost more than 5.4 million net jobs since February 2020, and not by choice. Not by choice. So this burnout and stress is real.

And obviously, I think it goes without saying, but let’s say it: If it’s hard for white women with decent educations and safety nets, HOW HARD IS IT for people of different identities and socioeconomic classes? 

Leigh Stein: I'm seeing so many people, especially women, burning out during this time. And I know how painful it is, because I've been there. And you just feel like, “I can't push through.” You pushed through for so long and then you reach a point where you're like, “I cannot keep pushing. I have nothing left to push with.” I think a big question after the end of girlboss culture is, like, where does women's ambition go? Could we, could we use our ambition to reimagine the work culture we want to live in? I think I'm much better today with boundaries than I was four years ago, around my work, and about what I say yes to, and about what I say no to. I don't have that scarcity mindset that I have to say yes to everything, because then maybe people will stop asking me if I don't keep saying yes. And like I said, I have a better sense now of: When do I need to be in private and when do I need to be in public? Because actually, I don't need to be in public all the time. But yeah, where does our ambition go? I also feel … there's a part of me that's sad when we talk about how negative competition, is because I am so competitive, and I get fired up by competition. You know, I get my self-esteem from working, and I'd like to work on the things that I would like to work on, and I've designed my life in a certain way so that I'm able to do that. But I don't know. Like, we can't have this boomerang effect where we suddenly tell women that, like, having ambition and working hard is bad for them. Like, that doesn't seem like the answer, either. 

It doesn’t seem like the answer! Like Leigh, I’ve reflected on this a lot over the past few years, and I think part of the problem is that women like us wanted what men had, without considering whether it would actually work for us, or if it was good for other people. Because I would also argue that our current work ecosystem doesn't really work for anyone! It doesn’t! Except for a very, very select few. 

And also by the way, I’m fine. I make a podcast. But am I fine? Was I fine when I brought a literal newborn, two or three days old, into the studio in 2016 to make the first season of this podcast because I didn’t want to lose the opportunity by showing a weakness? No. Was I fine when I brought a laptop to the hospital so I wouldn’t lose my billable hours while my husband was being treated for brain cancer? No! I was not. Was I fine in my 20s when I worked 14-hour days and I watched an intern have a literal mental breakdown on the bathroom floor because she had couriered shampoo samples to Allure in time to be considered for the Best of Beauty issue? No! We were not fine! 

But being burned out is a privilege, and the vast majority of the United States can’t just go burn out and quit their job, or burn out and leave the workforce, or burn out and go to a meditation retreat or something. They can’t. 

Girlbossing reflected a limited scope of imagination, where women like me were like, “Look! Here we are! We can do it all!” Instead of asking, “Wait, what are we doing? Why are we doing it? Is this really a thing? Is this really the thing? Is this really the best we can do, where a minimum wage doesn’t cover the cost of living for anyone in any major city? Where the majority of people in our country are living paycheck to paycheck? Where most of us are one bill away from absolute ruin?”

Is that the best we can do? 

And for all that talk about doing it all … what did we actually do? 

Our best. 

We really did. 

Whenever something goes out of vogue, when the empress is proven to be wearing absolutely no clothes, it’s hard to look back at your participation in a movement through anything but the critical lens of the present moment.

But our anger is not best directed just at ourselves or at each other. We gotta aim it a little bit higher – at the systems that yes, we work within, yes, we sometimes uphold, but that predate all of us. 

And that era wasn’t for naught. It was filled auditoriums and that intoxicating energy of a group of women who are focused and excited and there for each other. It was sharing our salary information with our colleagues and reaching out to be the mentors we didn’t have. It was having our ambitions validated and encouraged by a group of people who really wanted to see each other succeed. 

And it was millennial pink … which is still one of my favorite colors. It wasn’t perfect, and I’ll be damned if I ever do it again, but for a minute there? It was pretty magical being a girl boss. 

Nora McInerny: You mentioned this fear of people perceiving you or your brand as a failure. Has that happened?

Leigh Stein: [laughs] No, no, I wasn't. No one sees me as a failure. That was all psychological. That was totally … that was totally detached from reality. And one of the sweet things that happened when I wrote this piece for LitHub about this topic about burning out is that I heard from so many people that attended the conferences, and they said, like, “That was so amazing.” I heard from someone on Instagram who was like, “I was on welfare at the time, and if you hadn't given me a volunteer spot, I never would've been able to come to the conference, and it was such an amazing experience.” And so I know, like, this thing that I built touched so many women's lives. And I still hear from them, and I'm still in touch with them. And so I'm just proud of what I did. I don't have any regrets about starting it, and I don't have any regrets about leaving, because it was just this moment of time where I did as much as I could, until I couldn't anymore.