My Industry is Failing: Writing Edition with Jennifer Romolini | Crooked Media
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April 12, 2023
Work Appropriate
My Industry is Failing: Writing Edition with Jennifer Romolini

In This Episode

Every decade or so, the entire writing-for-money paradigm shifts yet again. To write for money is to get very comfortable with constantly changing your expectations, your strategy, your skillset. It’s a lot, particularly when all you really probably want to do is… write. So to talk about how to navigate this ever-changing and increasingly unsustainable business, host Anne Helen Petersen is joined by Jennifer Romolini. Jennifer’s been in the writing biz for a long time, and she’s now the host of Crooked Media’s new podcast, Stiffed, about the rise and fall of Viva Magazine in the 1970s.

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Anne Helen Petersen: Hi, everyone. This is Work Appropriate. And I’m your host, Anne Helen Petersen. [music plays] Let’s go back to 2011. I am finishing up my Ph.D., which entailed doing a whole lot of writing for free. At that point, I’d been blogging on a WordPress blog for several years, also, of course, for free. And I start reading this website called The Hairpin, which at least in the beginning was held together by the work of one brilliant woman named Edith Zimmerman. I loved everything I read on the site and decided one night totally on a whim to submit something. Edith says, yes, I lose my shit. It’s the best day of my professional life. And even though the site had ads from like car companies and stuff, I did not even think to ask about money. All that mattered to me at that point was that I would be published on a website that I adored. Every few weeks I’d write a new edition to the series, which was now called Scandals of Classic Hollywood. And a lot of the stuff that I was writing about, I knew already I could just write it from top of my head. But some of it required detailed research, and I was churning out five, six, 7000 word features and my payment, at least the way that I think I conceived of it then was personal glory. At some point my brother convinces me to just even ask for $100 a piece. Edith says, yes. I once again lose my mind because I was getting paid to write. Now, remember, I was coming from a place that was very much outside of the system. I had no idea that I was in some ways kind of scabbing, or at least enabling a system in which writers labor is deeply depreciated. Now, I don’t blame Edith or anyone that was part of this, this website network for that model. In the wake of the financial crisis, the entire industry of getting paid to write particularly, but not exclusively online, it was in shambles. The old rules and norms did not apply anymore. People had been laid off or left the industry entirely, and in their wake a whole lot of people with other jobs, like in my case, academia, started writing for those basement rates every decade or so the entire writing for money paradigm shifts yet again. Sometimes it’s the result of larger economic shifts, like the bursting of the dot com bubble or the Great Recession. And sometimes it’s much more specific to the industry, like the infusion of venture capital money in the mid 2010s or the quote unquote “pivot to video” in the late 2010s. To write for money is to get very comfortable with constantly changing your expectations, your strategy, even your skill set. It’s a lot, particularly when all you really probably want to do is write. So to talk about how to navigate this ever changing and increasingly unsustainable business and to answer your quandaries about it, I wanted a co-host who’s been through it, like really been through it, and she doesn’t have a roadmap to share or even necessarily heartening, advice, but she does have a really, really good compass. 


Jennifer Romolini: I’m Jennifer Romolini and I’m a writer. I’m an editor and I’m the host of the new Crooked podcast Stiffed. 


Anne Helen Petersen: So you’ve been a writer and editor and in a bunch of different ways for a long time, so. 


Jennifer Romolini: Yeah. 


Anne Helen Petersen: Like when someone’s like, okay, what’s the, what’s the story? How did you get here? What do you say? 


Jennifer Romolini: I mean, my career makes no sense. [laughter] And this is why I— 


Anne Helen Petersen: Same, same.


Jennifer Romolini: My career makes no sense. You know, I’m a kid of teenage working class parents out of Philly, got married really young in a terrible first marriage, dropped out of college, failed out of college, stoned out of college like just a mess. My twenties were just like, who even knows what the hell they were? [laughter] And I had wanted to be a writer. Like, if I. If I had anything that I really wanted to be. I had wanted to be a writer. I had read Sassy Magazine when I was in my in my teens. And I wanted to be a Sassy writer like that seemed like, oh, my God, live in New York, be a magazine editor or a writer. Whoa. And so in my late twenties, that became my goal. And I put myself through school and I got to New York and I was like a 28, 29 year old assistant in New York making $30,000 a year, making less than I had made as a waitress. And I got laid off my first three jobs because, you know, that’s what happens, right? I finally got a job after like 30 interviews and I got laid off six months later, and then I got another job. I got laid off, and then I was at Tina Brown’s Talk magazine. Wow. I made it, got laid off again. 


Anne Helen Petersen: You where there? 


Jennifer Romolini: Yes, I was. [laughs]


Anne Helen Petersen: Oh, my gosh. That was like the pinnacle of what I felt like a cool magazine was because they advertised before the Miramax movies. 


Jennifer Romolini: Oh, yes. Right. 


Anne Helen Petersen: You know? 


Jennifer Romolini: But yeah, I worked at Talk magazine, which was a wild place to work and total chaos and total dysfunction and total toxic. Like you start to smell, oh, wait, this dream is not going to be what I thought it was going to be. 


Anne Helen Petersen: Mm hmm. Yeah. 


Jennifer Romolini: And then, you know, bounced around a lot, couldn’t make ends meet, you know, living off credit cards. The whole thing had slept on a futon on the floor in a shared roommate apartment into my thirties. Got my favorite job of my whole life at Time Out New York. Couldn’t get them beyond $35,000 a year. And I had to leave after two years because I just couldn’t survive. But I mean, if I think about what I love to do, I love coming up with ideas, I love chasing them down, I love describing things imaginatively, I love uncovering information, and I like putting sentences together in a way that is interesting and flows. And I have taken those core skills and used them in a number of different ways, in a number of different places. So, you know, that was my dream job, but it didn’t pay. 


Anne Helen Petersen: Yeah. 


Jennifer Romolini: What do you do? Like, at every point in your life, you’re kind of deciding between the creative mode and money mode. Like you cause you usually don’t get both. 


Anne Helen Petersen: Well, and I’m glad that we have you here today, because I think there’s some glamorization of like, oh, before the Internet and before Internet publishing, it was possible to make a good living as a writer. And yes, it was for a rarefied few. Right but a lot of people—


Jennifer Romolini: And mostly men, and mostly white men. 


Anne Helen Petersen: Yes. And most people had jobs like yours at Time Out New York that had a ceiling that was barely cost of living still. Right. 


Jennifer Romolini: These were the options back then, right. My husband, who was my boyfriend at the time, was working at GQ, making a shit ton of money, just like as a staff writer. Just could write whatever the hell he wanted, right? 


Anne Helen Petersen: Yep. 


Jennifer Romolini: Those jobs were not really available to women. There were like there were five of them. And if you weren’t one of the five women, if you didn’t have the—


Anne Helen Petersen: Yep. 


Jennifer Romolini: —right pedigree, which I didn’t, for women, you had a choice. You could be writing for magazines and you could be talking about baby bumps and hair and J-Lo’s new perfume. Or you could be writing about like because I fact checked these stories, you could be writing about queefing, sorry, that’s disgusting. [laughter] But that was the thing I had to fact check. It was very horrible. 


Anne Helen Petersen: Yes, yes. [laughter]


Jennifer Romolini: Like and like and how to please a man. And I didn’t want any of that. And I eventually went into it. I went to a Condé Nast women’s magazine, Lucky, with a boss, that I love and still work with to today, but like, didn’t want to do any of this shit that I was writing. It made me a better writer, but I didn’t want to do it.


Anne Helen Petersen: Yeah. My friend Virginia Sole-Smith, who writes a newsletter now that’s like an anti diet  newsletter, her dream was like, I’m going to work for teen magazines. And then she got these jobs, and then she was writing all of this fat phobic shit—


Jennifer Romolini: Oh. God, oh, everything was fat phobic. Everything was that. It was horrible. It was horrible. 


Anne Helen Petersen: Right? 


Jennifer Romolini: It was horrible. Like I was I was I remember I was called portly, like I’m a size eight. I was called portly in a women’s magazine because like—


Anne Helen Petersen: Oh my God. 


Jennifer Romolini: Everybody was trying to be a size two. Now, I do think it’s worse now. Like. [laughs]


Anne Helen Petersen: Yes, to be clear. 


Jennifer Romolini: To be clear, it’s worse now, but it wasn’t that great before. 


Anne Helen Petersen: Yeah. And you know, you kind of went through the gantlet of digital media as well and found yourself on the other side with podcasting. And also you write books and like you do a lot of other stuff too—


Jennifer Romolini: Yeah. 


Anne Helen Petersen: —and we should, I hope we talk about that. But I’m really interested in how a lot of the writers whose work I have admired for so long, who have found themselves frustrated, fatigued, burned out by the writing economy, have found themselves in podcasting. Can we talk a little bit about your road there? 


Jennifer Romolini: Well, I mean [laughs] like it’s funny because it’s like, oh, well, here’s where the pot of gold is. There’s no pot of gold there either. [laughter]. 


Anne Helen Petersen: No, no, no, no.


Jennifer Romolini: Like, let’s, like, let’s just be really frank. This like, this is—


Anne Helen Petersen: Yeah. 


Jennifer Romolini: —just like, I’m just a cobbler, right? I have these core skills I just talked about, and I just, like, put them into different buckets as much as I can. I had been running a weed site out of Ireland, okay? [laughter] Like there was Irish cannabis site and it was based in Ireland, and I had this sweet job that paid me enough and that I could like live. And I went to Ireland every two months. And I, like, you know, taught people how to write SEO stories like can marijuana cure herpes? Answer, no. You know, like all these things. [laughter] Okay? 


Anne Helen Petersen: Yeah. 


Jennifer Romolini: And like, everybody told me not to take that job, like your career will be over. Like, that’s why there are no rules. Like, I was like, that job sounds fun and, like, low key, and I’ve been through some shit, and I deserve, like, a nice weed job in Ireland. But I got laid off from that because it went under [laughter] and as everybody, as everything good does. And my friend Jane Marie, who owns the Little Everywhere studio was like, I need somebody to come in and just help me around the office. Like literally, like water the plants, clean the bathroom, but also vet pitches and help me make pitches just like help, you know, a lot of admin. 


Anne Helen Petersen: Yep. 


Jennifer Romolini: And I was 46 years old and it was basically an internship. I mean, she paid me, she paid me for two days a week. And while I was there, I was like, wow, maybe I could do this. I wonder if I could do this. This seems like an interesting way to write, and I’m curious to see if I could take my skills and put them in this bucket now. Right? So I got laid off from there too, because again, my whole life is getting laid off, right? And because it was the pandemic and I got laid off. 


Anne Helen Petersen: Yep. 


Jennifer Romolini: And after I got laid off, I was like, I think I have this story idea that I’ve been thinking about for a really long time, and I think maybe this is the best way to tell this story is in audio. So I got a Canva Pro account and I came up with a deck and I, I tapped producer Megan Donis, who I’d been working with at Little Everywhere. And I was like, hey, do you want to, like, make the trailer for this? Do you want to go in this project with me? So yeah, so that was how I did it. And I really think a lot when I’m stuck because I was really feeling lost after the weed, I mean, the weed job was like a weird detour and I was really feeling quite lost, like, what’s going to happen next? And whenever that happens to me, I think, what do I still want to do? Like, what will I feel sad if I am, like, almost dead and I haven’t done? I try a bunch of things to see what sticks and most of it doesn’t. [laughs]


Anne Helen Petersen: Yeah. Tell us about Stiffed then. And like, how why did you want to do this project for so long and how did it take form as a podcast? 


Jennifer Romolini: So I found Viva Magazine, which is what Stiffed is about. I found Viva Magazine while I was working at Lucky Magazine, while I was working in women’s magazines in Condé Nast, in the sort of belly of that aughts publishing beast. And I wrote a column about eBay shopping, and I found it while I was searching on eBay. And I saw this magazine. And it was so interesting because it looked like a magazine. It was already, at that point, 30 years old. It looked like a magazine that I wanted to work at, but it didn’t exist in the present day. 


Anne Helen Petersen: Yeah. 


Jennifer Romolini: I mean, the first issue I saw there were like articles about bisexuality. There were articles about, you know, your sexual fantasies. There were articles about, like all kinds of really independent, progressive minded things about desire and sex and work. And then also like an amazing, like six page spread of, like, sheer chiffon dresses with, like, nipples out. I was like, what the fuck is this? Right? And then when I found out it was owned and published by Bob Guccione, who we all think about is like this horrible, like sleazy and maybe not horrible, but definitely sleazy pornographer like, macho, like the picture of seventies masculinity, you know? Then I was like, okay, what’s the tension here? So I started collecting the magazines and eventually over, you know, 15, 20 years, I collected nearly a full set and I’ve just been hauling them around. And what I saw was Patricia Bosworth died. She was one of the editors of Viva, and she died at the beginning of the pandemic. 


Anne Helen Petersen: Really? 


Jennifer Romolini: Yeah, she was one of the editors of Viva. She was like a big editor at Viva, and she was like this amazing journalist. And she had also been an actress, and her career was really interesting. She eventually became like a celebrity biographer. Like—


Anne Helen Petersen: Yeah, she wrote a biography of Montgomery Clift—


Jennifer Romolini: Yeah. Like—


Anne Helen Petersen: —that I’ve read back and forth like three times. Yeah, Yeah. 


Jennifer Romolini: She was incredible, so far ahead of her time. And she died at the very beginning of the pandemic. And then I was like, oh shit, there’s a race for this. These these, these people’s voices are not going to be here for much longer. And another interest of mine is older women. And I really wanted to resurrect these women’s work. I really wanted to like excavated. I wanted to I wanted to highlight it. I wanted to showcase them because I loved it. I felt like such a pure love for what they had done and what they had created. 


Anne Helen Petersen: And at a really interesting moment, I think in the magazine industry, in feminism, like it’s kind of at this like pivot point almost, right? Like the fact that this—


Jennifer Romolini: Yep. 


Anne Helen Petersen: —magazine could get made was is meaningful. The fact that it died also meaningful. You know what I mean? 


Jennifer Romolini: Well, the story of Viva really follows the story of the seventies, right? There’s all this progression. There’s the sexual revolution, there’s the women’s liberation movement. And like 1973, all of that shit’s hitting, you know, Roe’s passed, you know, all of this stuff, they feel like they’ve won, right? And by the end of the seventies, Viva stops publication in early 79. We’re looking Reagan times are being ushered in AIDS is coming the moral majority’s like just fucking beaten at the door and feminists are at war with each other. 


Anne Helen Petersen: Mm hmm. 


Jennifer Romolini: And you know, there’s a big split in the movement which really weakens the movement. So what we were able to do with Stiffed, which I’m really excited about, was we were able to not only tell the story of this magazine and magazine like all that, like inside baseball of magazines, which was such a pleasure for me, but also track the story of the sexual revolution, how it wasn’t very revolutionary for women at all. Talk about porno chic and Deep Throat and what that meant, how that was actually a mockery of women’s sexuality. You know, how white men, like, stole all that progress back again. And we really were able to make a lot of parallels to today, which I think are really important, like our cycles of progression are really important.


Anne Helen Petersen: Mm hmm. So like what happened, the story of the magazine, do you see connections too to like? The hellscape of writing today, right? Like the quandary of how to make this magazine, how to make a living working for this magazine and the fate of the magazine with like. How hard it is now as well to make make anything that isn’t considered mainstream marketable in some way into a product that that is available and that pays a living wage. 


Jennifer Romolini: Yeah, I mean, it was funny because, you know, some of the writ— I talked to editors who were on staff who had more secure, you know, salaries. And then I talked to some of the the regular freelance writers. And, you know, one of them said to me, you know, we didn’t get paid anything. We made like $500 an article. And I was like what— [laughter]


Anne Helen Petersen: In 1970s dollars. 


Jennifer Romolini: 50 years ago, we made nothing. $500 an article. 


Anne Helen Petersen: [laughs] The first time I got paid to write for the Internet. It was $100 [laughs] and I was like, this is the best thing that’s ever happened to me in like 2012 dollars, you know. 


Jennifer Romolini: I’ve made $50 on an essay, you know, like I’ve made $50 on an essay that I spent a month writing. [laughter] But I was like, this has to get published in this place because if I self-publish it, it’s like it has less value, like it has to happen. It’s gross. But, you know, we always think we’re living in the aftermath of boom times. And there’s a very there are so many things we can’t control as creative people. And most of it is luck. And it’s always been luck. It’s just that’s just the way it is. And so I think if your desire and your deepest desire in your life is to be a creative person, then you need to get comfortable with precarity. And I know that’s like a sucky thing to say, but I really think it’s the truth. Or you take your skills, your core skills, and you bring them to a place that’s more secure and that might bring some satisfaction too. Like, you have to decide what kind of person you are and what period of your life you’re in. 


Anne Helen Petersen: This is very good pre advice for everything that we’re going to talk about today. So here’s—


Jennifer Romolini: Oh yes. 


Anne Helen Petersen: —our first question, and it really lays the foundation for some of the similarly philosophical issues at play here. This is from Claudia and our colleague Julia is going to read it. 


Claudia: Coming from the book publishing industry. Could you help me navigate the entry level pay gap? More generally it seems to reflect a generational disconnect where older generations in senior positions are exploiting workers of younger generations and seem to be waging a financial war against the young. Shouldn’t generations support one another? How might young people regain trust in their parent generations? 


Anne Helen Petersen: So this to me gets an issue that was at the heart of the HarperCollins strike. 


Jennifer Romolini: Yeah. 


Anne Helen Petersen: Which is that you have all these entry level workers who are getting these salaries in the 30,000 range, which, you know, now [laughs] you were talking about it in like the twins and like we’re, you know, 20 years in the future and New York is even more expensive, etc., etc.. But a lot of the people who have been in the industry for a long time are like, this is how I navigated the system. This is how I did it. So you should do it again. And I think this is at the heart of a lot of tension within our organizations. So what’s your take here? 


Jennifer Romolini: My take is, no, you’re never going to trust the other people [laughter] like the reason they were able to make it, most of them, and they won’t say it is because they had parents supplementing their incomes. 


Anne Helen Petersen: Yep. 


Jennifer Romolini: Because they have generational wealth. And for people who don’t have that, you’re fucked. You’re just always fucked. These are white, privileged, just the whitest [laughter] most privileged industries with, you know, parents who it’s like not a big deal to send your kid to an Ivy League school. Like the way you afford to have these jobs is you’re not carrying around the weight of college debt. And the answer to the question is yes, of course we should be paying people a living wage. We should pay people enough to live in the city where they work. Like it’s obscene that we don’t. But this story has been going on for so long. I don’t know if it changes. I mean, I wish I don’t know how we disrupt the system. 


Anne Helen Petersen: So my editor for the first three of my books, her name is, Kate Napolitano—


Jennifer Romolini: Wait, wait. That’s my editor. 


Anne Helen Petersen: [laughs] This is how we got, part of the reason we got connected then, you know, Kate’s story. 


Jennifer Romolini: Oh, I fucking, oh, tell me yes. 


Anne Helen Petersen: Is that, is that she like when she scrambled to get her first, like, assistantship job at one of the publishing houses, she lived with her parents at home in Jersey and took the train in, you know, an hour, an hour plus, like a long slog into the city, because that was the only way that she could survive on the salary that she was paid was to live at home. And even that was a privilege. And she grew up working class. And one of her huge goals is to make it possible for people like her and especially people who aren’t, you know, white as well like her. 


Jennifer Romolini: Right. 


Anne Helen Petersen: To break into the system. And so, like her assistants are always people like like she has never had an assistant that looks like what you think stereotypical assistant in the publishing industry is right. Anyone that she hires like and I think if you can look for the people who are, you know, who their previous assistants are, who they surround themselves with. 


Jennifer Romolini: Yeah. 


Anne Helen Petersen: Those are the beacons. 


Jennifer Romolini: Yeah. 


Anne Helen Petersen: In some way. And if you can find those people, like that’s how you can trust an older generation. 


Jennifer Romolini: Yeah. 


Anne Helen Petersen: That is the only way I think. 


Jennifer Romolini: And people my age should be. I mean, they’re the people who can change it. I’m no longer in a position of power to change this, this kind of a situation because I got burnt out of fighting all those battles all the time and it takes so much out of you. But if you are in a position to hire people, give them more money. [laughter] But also you teach people to ask for money. More money, demand more money. I mean, the problem is, is that there’s always going to be people who can afford to have these jobs and who will take them, and they will take them and be underpaid because they have that kind of parental support, family support. And that’s where the system is is so broken. I mean, yeah, the trust in the, the other generation, I don’t think you should. I mean, I’m very Gen-X when I say this, but I don’t think you should. [laughter]


Anne Helen Petersen: I mean, form a union so that you don’t need trust. 


Jennifer Romolini: Yes. 


Anne Helen Petersen: So that you can actually, like formalize the terms of the agreement. Because I don’t think that trust is something that you can rely on here. 


Jennifer Romolini: No, no. 




Anne Helen Petersen: Our next question is from someone who has been good at her job in the past but is worried she can’t keep at it like she used to. This is from Matilda and our producer Melody is going to read it. 


Matilda: I’m a journalist and a new parent. I feel like the second I had a kid, I lost my ability to compete with younger coworkers who can take on any assignment or deadline at the drop of a hat. How do I deal with this shift? Do I just be worse at my job for a few years? 


Anne Helen Petersen: So we talked about this a little bit in one of our early episodes of the show about how hostile work is to parents that was with Jessica Grose, about how you can tell who has kids based on like how demanding they are that you drop everything and do something at the last minute. But, Jennifer, you have a kid. How do you think about this in terms of being good at journalism and that dependency on being so available and responsive? 


Jennifer Romolini: Well, I think we get locked into an idea like that. Oh, my God, this is always going to be this way. Or what am I just not going to be good at my job anymore or, you know, whatever. So the answer is the first answer to your question is yes, like that’s what you do. You be a little less good at your job. You try to find the sweet spot with work that you’re trying to find with parenting, which is you’re trying to find the spot between neurotic and neglect. And you just are like, where is the center? And that’s where it has to be. Because because the thing is, careers are long, childhoods are actually short. Right. And this is how it is for me. I’ve made a lot of sacrifices, but they don’t really feel like sacrifices. I made a lot of decisions so that I could be a more present parent. And my child has needed me in different ways. They’re 13 now. They’ve needed me at different stages, differently. Right. So there have been times where in early stages when you know, you’re breastfeeding or whatever, it’s like, oh, again, I’m going to say it again. You’re fucked, like, just like it’s okay to take a step back a little bit. As long as your job is as long as your job is paying you. Let’s say that right. 


Anne Helen Petersen: Yeah. 


Jennifer Romolini: As long as you’re not in danger of losing a job that you need to put food on the table, a roof over your head. Taking a step back is okay because the parenting is going to ebb and flow in a couple of years. That kid’s going to be in elementary school and they’re going to need you a lot less. And a couple of years after that, they’re going to need you more when they’re in middle school and you might need to readjust. We need to think about our careers as something that is that is fluid, that’s not fixed, that this should be about what you need as much as what your employer needs, as much as you can wrangle that. You know, I’m always wary to give that kind of advice because it’s not always realistic. But as much as you can wrangle some boundaries, because a lot of times it’s about the good enough performance is good enough, but it’s about your own ego. So making sure that you’re checking like, well, I don’t need to be the star for the next six months. 


Anne Helen Petersen: Yep. 


Jennifer Romolini: As long as I’m doing the work. My boss is satisfied with the work. Don’t go into overdrive with work if you don’t have to. It’s totally fine to just be like, this is chill right now. 


Anne Helen Petersen: I can just imagine how that feels of like that contrast with here’s the sort of journalist I used to be and here’s what I am now. And like, is this ever going to end? Kind of like, is my child ever going to grow past 11 months? Like, I’m here forever? And it’s not the case. 


Jennifer Romolini: It’s not the case. And the worst thing you can do is catastrophize, right? Like, the worst thing to do is to catastrophize. You don’t know how you’re going to feel in six months. You might, you or, in a year like but equally around around the time when my my kid was eight or nine, I was really just full steam in my career, like just crazy. I was just like, okay, this is this is the moment I was in, like the hot center of, like my biggest success. And my kid was struggling and I really had to make a decision because I could not do both. And I really had to make a decision about my child’s mental health versus my own success. And I chose my child’s mental health because also it was like, I’m missing this whole childhood. I’m missing things that I’m never going to get back again. And I don’t think you regret that as long as you keep your toe kind of dipped into your career. I mean, there’s one thing to back all the way out, and then that’s its own set of issues. 


Anne Helen Petersen: Yep. 


Jennifer Romolini: But as long as you’re keeping your toe dipped in, I don’t think you regret the time you devote to your child. 


Anne Helen Petersen: One progression I see a lot in journalism is actually like writing a ton, on the trail a ton, like doing all sorts of intense journalistic work, have a kid and maybe move a little bit more into editing, you know, stuff that—


Jennifer Romolini: Yeah. 


Anne Helen Petersen: —allows you to stay in one place. 


Jennifer Romolini: Yeah. 


Anne Helen Petersen: And then kids out of the house or older needs you a little bit less. And then—


Jennifer Romolini: Yeah. 


Anne Helen Petersen: —you get to go back and it’s almost like like going to college again, you know? 


Jennifer Romolini: Yeah, it’s that’s the thing. It’s never there’s no rules and it is never over. 


Anne Helen Petersen: Yeah. 


Jennifer Romolini: It’s never, never over. Like, that’s a thing that we really think like, oh, if I get off this ride, they’re not going to let me back on. They will. 


Anne Helen Petersen: Do you have any, like practical tips that you can remember from when your kid was a little younger about adjusting to this new normal? I really loved what you said about a lot of this is about your personal ego. 


Jennifer Romolini: You know, I think that one thing that’s really important that we’re especially in journalism, when we have deadlines, everything else, like we really treat things like they’re an emergency. Everything’s an emergency. 


Anne Helen Petersen: Yes. [laughs] Yes. 


Jennifer Romolini: It’s all things are not an emergency. Like, barely anything unless somebody is like, having like, unless you’re a doctor and you’re doing open heart surgery, like, things are not an emergency. And I think that we really want to show our work a lot. But we and it’s unnecessary. Like, oh, I answered the email first. I was the fastest to Slack, you know, and I think I started moving back from that and really not answering emails after a certain time, really creating the boundaries that we need. And if you’re do if you’re good at your job, those small adjustments don’t mean much to your employer. It doesn’t matter, but they mean a lot to your mental health. 


Anne Helen Petersen: Your employer is not actually noticing that you are the first to Slack. You personally are noticing and you are like, This is evidence that I’m still on it. 


Jennifer Romolini: That’s right. Or like or like, you know, and I don’t know how this is now, but like being the last one in the office, like, I was I was a big last one in the office person, like. 


Anne Helen Petersen: Mm hmm. 


Jennifer Romolini: You know, and that’s just like some martyr shit. You don’t need to do it. [laughs] Like, you don’t need to do it and nobody cares. 


Anne Helen Petersen: Yes. 


Jennifer Romolini: And really sort out what does matter what matters about this job? What does my boss care about? And once you know that, you can make a lot of adjustments. Actually. 


Anne Helen Petersen: Yeah. Having that sort of clear communication with your manager. 


Jennifer Romolini: Yep. 


Anne Helen Petersen: Especially if your manager has ever had kids. Like, I think that there is a real clarity that can be gained there, like, all right, we’re on the same page about what matters, and I can prioritize that. 


Jennifer Romolini: Yeah. 


Anne Helen Petersen: And, and prioritize all of this performative I’m still on the job bullshit that. 


Jennifer Romolini: That is, the performative thing. But also really knowing your value I think is too we—


Anne Helen Petersen: Mm yes. 


Jennifer Romolini: We really, we really like in this moment we’re like, well if I’m not answering the email first, if I’m not that fast at stories. If I’m not filing six times a week, that might not be what your value is. And I bet you have a lot more value than that. Right? And I’m always wary to give this kind of advice because you’re not inside of it. And that’s the problem with all career advice, because careers are so personal and all of this is so case by case, right? There’s no one size fits all. So like, if it’s a scary situation and you’re feeling like, oh, I might lose my job and you need that job. 


Anne Helen Petersen: Right. 


Jennifer Romolini: That’s a different situation. But there are times where you can kind of take a small step back. And I’m not talking about like quiet quitting. I’m not talking about [laughter] some passive aggressive shit. I’m talking about like, I could dial this down a notch or two, free up some more space so I’m more calm at home. I’m more present for my child care that I have to do. And I’m not having such an overlap between work and home. And that’s really what you’re looking for, is to separate the two as much as you can. 


Anne Helen Petersen: Yeah, I mean, most people I know are already operating at like 130%. 


Jennifer Romolini: Yes. 


Anne Helen Petersen: And so dialing back doesn’t mean this has always been my problem with like the quiet quitting discourse is that it just means that you’re doing like 100% [laughs] instead of 130%, right? 


Jennifer Romolini: Yeah, exactly. And you’re not fighting battles that are not yours to fight. 


Anne Helen Petersen: Mm hmm. 


Jennifer Romolini: I feel like that was a big thing that I got into when I was [laughs] I was freely just like a—


Anne Helen Petersen: Yeah. 


Jennifer Romolini: —ambition monster, which is, by the way, my next book. But, you know, looking at your own workaholic tendencies too, you know, what is what is this about you and what hole—


Anne Helen Petersen: Yep. 


Jennifer Romolini: —is this work filling for you, too? Like there’s all of that stuff. 


Anne Helen Petersen: Yes, 100%. Like what is going on with myself? Like, why am I? I mean, motherhood, parenthood, caregiving. Like, it just brings up so many other questions about identity. 


Jennifer Romolini: Yes. 


Anne Helen Petersen: So it’s part of this larger question of like, how can I hustle again? Is also like, am I going to be the same person that I was before and no, like you said, it is it is a continuum, it is an evolution, it is all of these things. And it can’t be it’s not going to only be one thing for the rest of your life. 


Jennifer Romolini: And also making sure you’re not caring about what it looks like to the outside world. 


Anne Helen Petersen: Mm. Yeah, yeah, yeah.


Jennifer Romolini: Right. Because the outside world doesn’t matter at all. This invisible audience that we’ve all created for ourselves and that social, that we had forever but social media has made so much worse. Oh, my God, I don’t have it, people aren’t seeing my bylines go up on Twitter. Oh, my God. Oh, my God. That’s just nonsense. 


Anne Helen Petersen: Yep. 


Jennifer Romolini: You just have to quiet that shit down. 




Anne Helen Petersen: Our last question is from Dave, who has seen the industry fail throughout his career. Our colleague Austin is going to read it for us. 


Dave: So I started working as a journalist right out of college at the beginning of the Great Recession. And since then I’ve just seen the industry completely fall apart. Now, a lot of this has been because of certain financial and technological challenges, but some of it is due to the way that the industry has tried to address those challenges. Chasing clicks, eliminating beats, shortening everything, pivoting to video, obsessing over breaking news. Right now, I’m just really unsatisfied in my current job, and I really don’t see myself being happy with any other positions in the industry. They no longer value the kind of things that I think I’m best at. So should I stick with work that I know I can do but really don’t enjoy doing? Do I give up and try another field? I don’t even know how to go about choosing one. This is really all I’ve ever wanted to do, or is there some way to cope and not be brought down by all the bleakness?


Anne Helen Petersen: All right. So as someone who has been through a lot of what Dave describes in terms of how the industry has changed personally, like I did have to get out and I also knew that freelancing was not viable unless I had a very certain structure freelancing, which is my newsletter. But like I think like so much in any career, a specific path is not replicable. You know, like, not everyone can go and write a newsletter, right? So what sort of advice do you give to people in this situation? 


Jennifer Romolini: I think it’s a lot about flexibility, endurance, perseverance, blah, blah, blah, blah, blah. But actually, I think it’s about flexibility because I read this and I thought, well, what is it actually that you like to do? 


Anne Helen Petersen: 100%. 


Jennifer Romolini: What is it that you actually he’s saying he likes to do something. And I will go back to what I said at the beginning of this. My core skills, I can describe things imaginatively. I can I like uncovering information. I like putting sentences together so it’s interesting and flows. I love those three things, and I’m good at all three. I’ve taken those three skills and I have done all kinds of things. I have ghostwritten billionaires newsletters. I have you know [laughs] I have, I’ve done lots in writing, right? And I do not think you stay in a job that is miserable. And I think that you don’t stay in a job that is miserable, not because of your career, but because of your life. I think that you leave a job that is miserable and you find something else that is less miserable. And that might not be the thing that gets your professional rocks off. Your professional rocks off might be writing, you know, having a just a daily writing practice that’s just for you, writing a crime novel. You know, there’s a million things that you can do as a as an artist, as a creator, that have nothing to do with what the world sees and what pays you money. 


Anne Helen Petersen: Yep. 


Jennifer Romolini: And I think disentangling those two when you see an industry collapsing is the only way to survive. And also just being like, I don’t care. I’ll do content for AT&T to pay my health insurance and to bring in the bills, and I’ll do something cool for myself. And that gets into side hustles, which I fucking hate. But sometimes as a creative person, you have to separate the money from the professional, from the satisfaction. Let’s say that. 


Anne Helen Petersen: We had Rainesford Stauffer on a couple of episodes ago to talk about ambition, and—


Jennifer Romolini: I love her. 


Anne Helen Petersen: And one of the things she says is like, you don’t have to be ambitious about work. Like you can be ambitious about so many other things. 


Jennifer Romolini: Yeah. 


Anne Helen Petersen: So if you can decouple your ambition from the thing that pays the bills, that can be revelatory. Like there are so many things that this person, there’s so many skills that this—


Jennifer Romolini: Okay, okay. 


Anne Helen Petersen: —person clearly has. If they’ve been in the industry for a really—


Jennifer Romolini: That’s right. 


Anne Helen Petersen: —long time. They can take those skills that skill set and do so many things. And there are thousands of ex journalists who have gone on and done those things. 


Jennifer Romolini: Exactly. 


Anne Helen Petersen: And it’s very easy to look and see what they’ve done. But I think what we see at the heart of this question is kind of like a mourning. Right—


Jennifer Romolini: Yes, the grief. 


Anne Helen Petersen: Yes, there’s a real grief. And like as someone who left a profession behind in academia, like, I understand that grief. 


Jennifer Romolini: Yep, yep. 


Anne Helen Petersen: It is so real and it is authentic and there will be a mourning. But like those other things that you love about journalism, is it the creation? Right?


Jennifer Romolini: Yeah.


Anne Helen Petersen: Maybe this person’s really good at video editing. Like, I want to tell every person who loves video editing that they should get really into TikTok because it is—


Jennifer Romolini: Yeah. 


Anne Helen Petersen: —so fun. 


Jennifer Romolini: Yeah. 


Anne Helen Petersen: Like, actually joyful. 


Jennifer Romolini: Yeah. 


Anne Helen Petersen: Maybe they love reporting. Like, there’s so many different ways you can do oral histories. Like, there’s just a lot out there. And if you can separate the two things that like the thing that gets your rocks off and the thing that you’re good at like that, those have to somehow be adjoined and be the thing that also makes you money. That is a myth that we’ve been trying to dismantle. 


Jennifer Romolini: And focus on what you can control rather than what you can’t. This person is very stuck in all the ways this business is broken. I mean, the pivot to video, we’ve been bitching about this, all of us, for, you know, five, seven years [laughter] like we all watched what happened to this business. Like we all watched them. Somebody just come in and just with a wrecking ball and destroyed the things we liked. Right. And we can’t control that. We just can’t. So start thinking expansively. What do you want out of your life? Is there a book you always wanted to write? Pitch the fucking book. Pitch the book. And you’re probably going to only get paid enough to not really live to write that book. And you’re gonna have to—


Anne Helen Petersen: Right to take book leave, yes. [laughs]


Jennifer Romolini: Yes. You’re going to have to have some dumb job on the side that brings you in money, but that we’re always balancing those two things. And it has been very rare in the course of entire history of writing and journalism that people have been paid a livable wage to put down words. It’s just it’s it’s been rare. And if we look at it that way, then we realize, oh, this is just the way it is and I really want to keep doing this. So I’m going to find a way to take the skills I have and put them somewhere else. 


Anne Helen Petersen: So I think that we have covered the emotional component of this question. 


Jennifer Romolini: Yeah. 


Anne Helen Petersen: We have in previous episodes have talked about like if you want to get out of your industry, how do you figure out what people have done like and how LinkedIn is your absolute friend and also people who have left the industry? Like just getting on the phone with them or emailing them and seeing what their what their path is. What advice do you have about like developing new skills, especially since like you just taught yourself to podcast? 


Jennifer Romolini: I mean, I took a class. I mean, I worked I basically worked as a 46 year old intern, number one. 


Anne Helen Petersen: Yep. 


Jennifer Romolini: And I had other jobs. Like that was my other job. I had like many other jobs at the time, right? So I was just like, taking whatever. Like, I was like writing gift guides. I was taking whatever I could get, right? I was hustling for work that was very junior to me. But that added up to a salary, right? 


Anne Helen Petersen: Yep. 


Jennifer Romolini: While I was learning, while I was sort of in the bridge between where I was to where I wanted to be. But I also took some classes online. I took narrative podcast classes online so I could I could learn because it’s really scary when you don’t know what you don’t know when you’ve gained mastery in one career and you know all the rookie mistakes. There’s like, there’s a confidence there, right? 


Anne Helen Petersen: Yeah. 


Jennifer Romolini: And when you enter something new, you’re so vulnerable and it’s so scary and you feel so much shame, especially if you’re older. So set yourself up in a way, whether it’s reaching out to people on LinkedIn and doing a bunch of information interviews, whether it’s like Googling, what are rookie mistakes in this industry, just are just treat it like treat it like you’re in school, even if you’re not in school, I think is what I would say. And like I, I looked at a million scripts. I looked at a million podcast scripts before I wrote my first podcast script because I really was scared. I just didn’t have I know I’m a good writer, but I didn’t know how to do it in something new. So I just got really curious about it, and I think that’s the best advice I can give. But also do not do a thing ever, which is it’s over for me. I’m too old. This is what I know how to do. 


Anne Helen Petersen: Mm hmm. 


Jennifer Romolini: Or limit yourself and think I can’t find satisfaction because this is the only thing I’ve ever loved. There are so many other things that you just have not you haven’t uncovered yet. And think of it as a scavenger hunt. You’re uncovering what you’re going to want next, and each place you go is another going to give you another clue. 


Anne Helen Petersen: Two things. One is that I am firmly in the camp, that life has so many acts. There’s so many different fun developments. 


Jennifer Romolini: Yeah. 


Anne Helen Petersen: Some of them not so fun, but like there’s a lot more to come. And then the other thing is that as a journalist, we are very good at learning everything about something. [laughs]


Jennifer Romolini: That’s right. 


Anne Helen Petersen: So like apply those journalistic skills to learning about a new skill. 


Jennifer Romolini: And, you know, when I when I’m looking at what I’m looking at, what do I want to do next? It’s always what I’m most jealous of. 


Anne Helen Petersen: Yes. 


Jennifer Romolini: I think that that is really the sniff test, right? Like, the thing that is just irrationally I’m jealous about is the thing that I probably really want to do. I mean, this happened with me with books that happened with podcasts, like it happened when I wanted to be an editor in chief. It’s always the thing that I’m like, I’m jealous, you know? [laughs] Like. 


Anne Helen Petersen: Yeah. 


Jennifer Romolini: So like uncovering that and getting right with yourself, what is it that you want to do? 


Anne Helen Petersen: Also allowing yourself to think outside of the box on that in terms of like, I think a lot of journalists feel like, oh, what are you jealous of? And saying, oh, I want to write longform journalism for The New Yorker? 


Jennifer Romolini: No, no, no, no, no, no, no, no, no, no. [laughter]


Anne Helen Petersen: No. Like, great, that’s great. Like, but also not available, probably. So what are the other professional things that you’re jealous of and I often like? There’s this. Bloomberg does a collection of, like, stories that made them jealous every year. 


Jennifer Romolini: Yeah.


Anne Helen Petersen: I just love how imaginative it is because it’s not just longform journalism from The New Yorker. It’s a whole expanse of understanding of what journalism can look like. 


Jennifer Romolini: And yeah, and it can’t be something that’s specific as like, I want to write long form for The New Yorker. It has to be more like, I want a job that will let me travel. I would like [laughs] it has to be like it has to be a little broader than that because the specific dreams, they limit you too much. This has to be an expansive exploration. 


Anne Helen Petersen: Yes. 


Jennifer Romolini: I think, again, like I’m out of the advice business, but like, this is this is what I think. [laughter] 


Anne Helen Petersen: It will, okay, out of the advice business but have given some of the best advice that we’ve had on this podcast. I love also that we managed to give advice that was at once practical and like philosophical, emotional and psychological. This is this is what we do here. Is there anything I think, lastly, that gives you a lot of hope when you look at the world of writing broadly defined. 


Jennifer Romolini: I mean, no [laughs] it feels like every single feels like every single aspect of it is broken. From book publishing to digital publishing, what’s print anymore? You know? 


Anne Helen Petersen: Mm hmm. 


Jennifer Romolini: The New York Times is just, you know, transphobic. Television writers are going on strike. You know, it’s like it almost feels like every safe haven of like yeah we exist because we want to do it. And that’s the thing that gives me hope. 


Anne Helen Petersen: Yep. 


Jennifer Romolini: Because I have amazing communities of writers, because we may all be beaten down, but we’re still making something happen somehow. And that’s why there’s there’s no like sort of practical solution to this. It’s more like, oh yeah, it’s fucked, but I, we keep going. 


Anne Helen Petersen: Well, this is why I’m not scared of AI. I mean, I’m scared of AI for like, so many reasons, but I am not scared of their ability to, like, really absolutely replace all writers. Like, we are too weird. We are too weird. There is just not a way to replace our sensibilities full scale.


Jennifer Romolini: No. Get in community with other writers. Go to your friend’s readings, enjoy writing again. Like that’s. That was the thing that happened to me with this podcast, and I did it simultaneously while writing a second book, and I just wrote seven days a week for about six months, and I was like, oh my God, I love writing. And I don’t think I’ll ever let writing go again, even if nobody’s going to read it. 


Anne Helen Petersen: That’s what makes it worth it, right? Is that like it’s actually something that nourishes you? 


Jennifer Romolini: Yes. 


Anne Helen Petersen: It’s not something that like is impressive to other people that is financially lucrative. We all need to live and we have to find ways to do that on this earth. But we also all need ways to like, figure out what we love and sustain us. 


Jennifer Romolini: Yeah that’s right. 


Anne Helen Petersen: And. You can do both. You can. 


Jennifer Romolini: You can do both. You just have to have a good imagination. [laughter]


Anne Helen Petersen: Jennifer, thank you so much for coming on the show today. Tell us where people can find you on the Internet and everyone also, please listen to Stiffed. It’s coming out when? 


Jennifer Romolini: It’s coming, oh it’s out, it’s out in the world. You can find me @jennromolini j e n r o m o l i n i.  Across every place. I barely try. I try to not be on Twitter, but mostly Instagram. I have a website,, that I built on top of a wedding website. And it’s real, it’s real janky. But it’s okay. [laughter] It’s okay. 


Anne Helen Petersen: Thank you so much.


Jennifer Romolini: Thank you. [music plays]


Anne Helen Petersen: Thanks for listening to Work Appropriate. If you’ve got a workplace quandary, you need help figuring out get in touch. You can find submission guidelines at or send a voice memo with your question to Work Appropriate at Don’t forget to follow us @CrookedMedia on Instagram and Twitter for more original content hosts takeovers and other community events. You can follow me on Twitter @AnneHelen or on Instagram @AnneHelenPetersen. You can sign up for my newsletter Culture Study Also, you know what we need more of? Reviews. If you have an extra few moments, go give us one. It really helps others find the show. Work Appropriate is a Crooked Media production. I’m Anne Helen Petersen, your host. Our executive producer is Kendra James. Melody Rowell is our producer and editor. Alison Falzetta is our development producer. Music is composed by Chanell Crichlow. Additional production support from Ari Schwartz and a special thanks to Katie Long and Sarah Geismer. Next week, we’re talking all about parental leave. Be sure to subscribe so you don’t miss it. [music plays]