Jenn Romolini and I have a lot in common. We’re roughly the same age; we’ve both spent most of the past 20-plus years working as ambitious (female) editors and executives in digital media. We even worked at the same tech company at the same time. But we’ve never really known each other. When I joined the tech company, Romolini had already decamped to the sunny if sterile Los Angeles mother ship while I was in a crummy cubicle in midtown Manhattan. I have followed her career from afar with occasional envy. She shot up through women’s magazines and lifestyle websites and celebrity-helmed “digital media companies,” and then landed, improbably, at an Irish website devoted to weed. Meanwhile, I questioned my continued commitment to newsrooms and all the grind they entail.
Turns out my envy was misplaced. Romolini’s addictive memoir Ambition Monster snuffed out any twinkling of lingering nostalgia for mid-aughts media, or for the endless hours of networking, schmoozing, and work I put into those years. For Romolini, workaholism was a trauma response. She was born to teenage parents who had less than no idea what they were doing. It took most of her 20s to sort out how to direct her innate ambition—to get out of a marriage she never should have been in, to hustle her way to New York and into the raucous and male-dominated media world of the new century, to remarry (to a popular and talented writer) and have a baby. And then a whole other set of problems arrived.
There’s sex, cigarettes, perfectly assembled outfits, and tons of misery—hers and others’. And there’s work: A way to succeed, a way to hide, a way to squash the past, a way to formulate a new self—perhaps one you don’t even like that much—and make it seem like everything is great even when you are falling apart. It’s to readers’ benefit that in Ambition Monster she starts to explore other ways to live.
I spoke to Romolini over Zoom about ambition, power, control, regret, and forgiveness. Our conversation has been edited and condensed for clarity.
Hillary Frey: Is ambition good or bad?
Jennifer Romolini: Ambition is fundamentally a good thing. I think it’s a charge, it propels you forward. There are a lot of good things about ambition, just like there are a lot of good things about competency and mastery. But the problem is that our ambition is often directed at the wrong things—at external validation, at the way things look to other people, at unachievable dreams, like “having it all.” So that’s the problem. I am a very ambitious person and I hope to be forever an ambitious person.
What’s the difference between ambition and workaholism?
Workaholism is just always toxic. Workaholism is an addiction like anything else; it’s filling a hole, it’s compulsive, it’s itchy. Ambition actually can be an energetic force that provides a value in your life that propels you forward. Workaholism is: You’re hiding.
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It’s easy to know that you want power and control, but then you have to figure out what to do with it if you get it. You write about your early career and taking an editing path over exclusively pursuing writing, even though you wanted to be a writer. I did too, but early on I perceived that editors had more power, and I liked that. (Still do!) Did you think about that too?
Absolutely. First off, I hate to be told no. I was a very bad freelancer because I don’t like to kiss ass. I don’t like to curry favor. I also was not positioned financially to do it. Editing provided a consistent paycheck, and when I did get to write and edit, I would do two jobs at once. I often had a day job where I was editing and then freelancing on the side. I needed money.
For me, the tech company we both worked for was a nightmare. But you ended up mastering the system and lasting much longer than I could.
Well, when I was at the tech company, I had painted myself into a corner. I had a partner at that point who was not earning. He had made some bad decisions. He was the creative one and I really wanted to have a baby. And there was no foundation. People build their lives on top of something. There’s either generational wealth or there’s a nest egg or there’s something. They don’t build it on spit and a paperclip like we did.
It was like, all of a sudden I’m 35, and I’m 36. And I’m like, “Holy shit, the clock is running. I know I want to have a kid. Let’s just sit down in this musical-chairs romance, whatever the hell we’re doing, let’s sit down. It’s time.”
And that was not a pragmatic decision. Our financial picture was a mess. So I’m in this tech company and I’m finding that I’m really good at this. I’m mastering the system and they’re giving me another job and I’m mastering it again. And it’s a game, it’s probably the thing I’m best at in my life. It sucks to be good at something you hate, but I was really good.
Every way that I was good at corporate life had to do with childhood trauma.
Please say more.
I was incredibly good at tracking adults from an early age. And that’s very similar to when you’re in a corporation. I was hypervigilant, I could read a room like nobody else. So I could tell if I was losing somebody, I could tell who was trying to get one over on me. I understood the politics of that kind of workplace.
And then you start to say things to yourself like, “Well, I have this team of 30 people, 40 people, I take care of them.” I became a mother almost at the same time I became a manager.
“I’m taking care of all these people, I’m growing their careers, I’m helping all of them reach goals they didn’t think they could reach.” And then that’s a different kind of game, right? Now you’re not thinking about yourself or your career. You’re thinking about a roof over your kid’s head and the 30 women working for me that I cared about. So then it was very much, “Don’t give up the ship.”
In the book, you talk about how deluded you were about what life would be like once you had a baby. When my ex-husband and I were pregnant—he was working at the same magazine as your husband, actually, and I was at the tech company—we really thought we could be different, that we could have different problems than other people.
“And we can stay cool, we’ll still be engaged with life, and how hard can it be?” And all of that. I mean, my husband and I love each other. We’ve been together for 20 years and we are as obsessed with each other as we were 20 years ago. We are not great at adult living. There is not a person in this partnership who’s like, “Oh yes, I’m the one with the great executive functioning.”
So I think instead of playing a game of hot potato, which is what we had kind of been doing before we had the baby, the potato just wound up with me. We didn’t have the skills or the tools to have the kinds of conversations we needed to have. We didn’t even know how to have healthy conflict, we didn’t know how to express ourselves. The whole system is set up to just drive you to the moment of love and marriage and then, “Whoop, you’re on your own.”
We had no idea how to do anything. And it’s shameful to me that we didn’t know, but who would’ve taught us? Nobody taught us. We were creative types, we were bad-at-math kids. Nobody taught us how to be good at anything. We had addictive tendencies; even if we weren’t full-blown alcoholics, we were certainly drinking too much.
I read somewhere: “80 percent of how we behave in a relationship is what’s been modeled for us.”
Mm-hmm.
So immediately, not only was I my father in this relationship, where I’m the breadwinner and I’m super ambitious, because I also married somebody who’s not very ambitious—I also became my mother, taking on every single role. I did everything. And I was so resentful. I remember my husband walking down the street and us seeing people and he had the baby in the Bjorn. And my friends are like, “Oh my God, he’s so cute with the baby.” And, “Oh, he changes diapers?” And I was like, “He’s not a fucking dog playing saxophone. This is ridiculous. I have to be so grateful, but I’m doing everything.”
I became such a woman I hated in those moments because I reflexively tried to protect him because I wanted to protect the relationship and I didn’t want to lose him, and I didn’t want to be a bitch. It got worse and worse. The imbalance got worse and worse and worse. And we were bitter and bitter and bitter and bitter.
And he didn’t understand because I didn’t know how to communicate. I did nothing to advocate for myself. And so, 10 years in, with the snowball of trauma, with everything on top of it, I was a mess. I collapsed.
Years of fighting to the top of a variety of digital media companies, dealing with celebrity owners and misguided and malformed strategies, providing for your family but at a cost to yourself and your family … it all crashed down when you were fired without notice from your last big corporate job. The last part of your book is about the rebuilding, the therapy, the searching. It’s a new kind of work.
Therapy was amazing. I did very intense therapy for five years, including EMDR. And let me just say, because I think this is fair to say, I was complicit in my own subjugation in my marriage. I was complicit in it because I was withholding, I was critical. I also started building a wall around myself because I had not really ever dealt with my own lack of self-esteem, my insecurity that I was stupid. So I was no prize: Let’s be honest here. I was not easy to live with, especially once we stopped drinking like we were. So there was not that buffer anymore.
I got off the train of working all the time and making all of the money. The playing field was evened. No one’s making all the money and we have to figure this out together. Our life is much more collaborative.
My life since that crash has been much more intentional. I say no to things, I don’t make money much beyond survival. I don’t try. I’m not pulling in a big paycheck anymore, and I haven’t for years. We just kind of changed our lives so that we could live more intentionally and live more as artists.
Toward the end of the book, you wrote, “No amount of personal success is achieved without at least a bit of cost to someone else.” Do you have some mistakes along the way that you regret—
Yeah.
—that aren’t in the book? It’s your memoir. But I was wondering about the ghosts of collateral damage out there—are any haunting you?
I mean, I certainly hurt myself more than I ever hurt anyone else. I tried to talk about the ways in which I think I was a villain at times, how I acted out, how I made people feel uncomfortable. How I was performing an identity—this intrepid kind of bitchy identity, just, “I’m just going to say whatever’s on my mind, tell it like it is.” I did not think it was necessary to rake myself over the coals in this book. Are there decisions I regret? I think it’s abundantly obvious that there are decisions I regret.
When I was really having a reckoning with the last decade of my life and my professional life, I really thought about the systems that I had upheld. I mean, I fired somebody when I was told to, and chose myself over doing the right thing. I fired somebody, I think, when they were on maternity leave, or the day they got back from maternity leave. Yes, I regret that.
I have a ton of shame about the ways I behaved, but eventually you have to let yourself off the hook. I was a broken person walking around the world. Part of healing is knowing you just didn’t know any better and you can’t go back and change it. So you can make amends where you can, and you have to give yourself grace because, what, I’m going to spend the next half of my life hating myself for what I did the first half? No, I refuse.