In Ambition Monster Memoir, Media Exec Explores the Dark Side of 'Making It'

If you are a writer who has worked in print and digital media and toiled in the startup scene, interviewing Jennifer Romolini about her memoir Ambition Monster is not so much a traditional Q&A session as it is a welcome and affirming therapy session.

Romolini, raised in a working-class family in Philadelphia, came to New York in the early aughts. She rose through the ranks of print media, landing at Lucky, the magazine all about shopping, before leaving for a blogging-turned-editing job at a tech company’s lifestyle site. Then, she moved to Los Angeles, where her roles included a C-suite position at a celebrity-owned website for women. Later, she ran content at a weed site in Ireland.

From the outside, it appeared that Romolini, who was an in-demand keynote speaker on topics like sales and marketing, enjoyed a successful, fulfilling career. But work became all-consuming for this self-described ambition monster. In her book, she writes about her descent into workaholism and the toll it took on her mind, body and soul—as well as her marriage.

Here, the Ambition Monster author—also co-host of Everything Is Fine, a podcast for women over 40—talks about classism in the workplace, the “girlboss” era and more.

MUSE: What was more difficult for you to share in the book—the personal stuff about your family and upbringing and romantic relationships, or your experiences in the workplace?

Jennifer Romolini: It was 100 percent my family. Who gives a shit about a company? Who cares? That company doesn’t love me. That company didn’t care for me in any way. The most painful and challenging thing about this book was writing about my family, because I love my parents, I respect them, I’m grateful to them. I also have all kinds of really deep, Catholic Italian-American guilt. You don’t tell family secrets. And that was excruciating. It brought up all kinds of feelings of being a bad kid. Not to use an overused word, but I think I was basically triggered writing that first 100 pages.

Was your husband, who is also a writer, understanding about you confessing the professional jealousy you felt toward him early in your relationship? And was he OK with you opening up about the hardships you have faced as a couple?

My husband was so incredibly generous with this whole process—reading things, giving me feedback. But mostly he said, “Burn it all down.” He was like, “You could be worse about me. You could say worse things. I think you are going easy on me.” He was very much of the mind that the book didn’t work unless I really talked about his failings because they were part of my ambition.

You and Kim France—the founding editor of Lucky and your co-host on Everything Is Fine—talk about everything from your careers to personal issues on your podcast. Did speaking so frankly about your life help get you to a place where you could write this incredibly honest book?

I don’t know if that played a factor. I think it’s more the opposite. I think I’m just a compulsively honest person. There’s some people who are like that. I wish to be a stoic person with a lot of emotional boundaries, but I found that the way that I move through the world is very intimate and emotionally honest. And I feel so much more comfortable in that space. That’s not necessarily my greatest quality, but it does help when you’re writing.

You share an anecdote in Ambition Monster about working with a privileged writer at Lucky who did not do her job well—leaving you and others to fix her work. And she wasn’t held accountable, though you tried. That really struck me. I once worked with a woman who my editor had to create a job for because her old money father knew the publisher. She left the office for hours to go to the gym and regularly napped at her desk, with no repercussions. And I would learn that people like her weren’t uncommon in print back in the day. As the first person in my family who went to college and someone who assumed you had to be a great writer and hardworking to keep a job at a magazine, I had no idea about the world I was stepping into. I was so naive.

I’m still surprised! The book’s about class, and it’s a lot about the work ethic of the working class versus the work ethic of people who grow up with a lot more financial privilege and class privilege and how they move through the word in a totally different way. There’s an entitlement there, and they understand that they don’t have to do all of the work. They understand how to negotiate for better wages. You are at such a disadvantage entering a white-collar world if you come from a working-class background. And I see very few people talking about that. It’s a system that works against anyone who’s outside of the elite 1 percent. And it’s like that across most everything.

Can you talk about the differences between working in print when print magazines were flourishing, versus working in digital media started by tech companies and celebrities?

I think that for better or for worse, media, New York publishing, it knows what it is, and everybody sort of cares about it, or at least they did. I don’t think that’s the case now. But, at the time, in print, the product was important. It was invaluable. Content meant something. We didn’t even call it content. It was design, it was quality writing, all of these things. We were all working toward this goal of making something good together.

Once I got into digital media, that was no longer the case. In print, the business side and the editorial side were separate. Your job in editorial was to make a good product, and the business side was there to sell that product. Then, sales became dependent on clicks, and everything sort of mashed together. Now, nobody cares about the product anymore. Everybody just cares about the clicks, and it became so undervalued—the work that I did, that the editors did. It was just cranking out, cranking out, cranking out in an assembly line, and it had so little to do with craft.

And the thing was, I was well-suited to a business structure because I’d grown up watching small-business owners [her dad was in the produce business] negotiate all types of things. So, I was ultimately very good at working in a corporate structure and being a digital media executive. But I hated it. One of the worst things in life is to be excellent at something you despise and to be rewarded for something you despise—financially rewarded. You become dependent on something you despise, and then you feel entirely jailed by that.

Working at the celebrity startup kicked your workaholism into even higher gear. You were working around the clock. You had two phones. Why do you think that job had that kind of impact on you?

When I was at the tech company, I had HR protections and a salary structure. If you’re at a certain level, you’re making a certain amount, you’re guaranteed benefits, a bonus, all of that. So, I went from rising through the ranks in that environment to the wilds of a startup—the worst working situation you can be in. There’s no HR protections, there’s no org chart, there’s no idea of who does what. It’s a spaghetti strategy. It has to move fast. The end goal is so cynical. You’re looking for an exit. You’re staging this house for somebody else to buy. So, it’s not even authentic at its core. Everything about it is very fast-paced and toxic.

I found those environments the worst because there’s no boundaries. It’s all hands on deck. You’re taking this big bet that you’re going to be sold, and you’re going to make this equity—that you have this magical money that might sometimes turn into real money. You’re making this bet.

And, for me, a person who had for a long time sought external validation, the pat on the back of success meant everything. It almost became an addiction. Having that unbelievably high and unrealistic goal and trying to meet it—it was a carrot and a stick for me. I was perfectly placed in that job in a way that was just also perfectly damaging.

We kind of lost our way right at this girlboss time. It was like these inflated fantasies of what work was supposed to be, how much time we’re supposed to dedicate to work, how much work was tied to our identities, and how much our value was tied up in working hard. It’s so embarrassing how much we blurred the line between our lives and our careers. There was just this expectation that you would be giving it your all every single day. Anything was an emergency.

Is the girlboss era over?

I hope we’re done with it. I think we’re done with it. But we don’t know what conversation to have about work right now. This is a very confusing time. We’re having these annoying and wrongheaded debates where it’s like this false dichotomy between, “Oh, I’m going to be happy being a trad wife and churning butter,” and “No, I still need to be a gung-ho boss bitch and go after my career.”

The truth is, our ambition is personal, and it changes all the time. And it’s not one or the other necessarily. We’re getting these broad, one-size-fits-all definitions of success, when success is personal, it’s in the moment. It’s a lot more balanced than anything we’re talking about.

Now, for a silly question: Who is going to play you when Ambition Monster is made into either a movie or an 8-episode Netflix series? Have you even dared to think maybe someone will option this book?

Oh my God. I haven’t really thought of it because I’m so cynical, and I’ve just been around too much to allow myself to have those kinds of dreams. And to be honest, with this book—and I don’t know if I’ve ever been like this before in my life—the accomplishment was the most internal accomplishment I’ve ever had. I felt when I turned this in, “Oh, I really did something, and everything that comes after that is just kind of extra.” And that’s really weird—that’s not who I’ve ever been. But something shifted in me with this work, because it was so important to me personally.

I like hearing that you wrote the book for yourself.

There was nothing responsible about this decision. We were not in a good financial place. I probably should have looked for another big job instead of letting all our bank accounts drain. But I didn’t want that. I wanted to create something. I wanted to become the writer I always wanted to be. I wanted to prove to myself I could do it. It was the purest ambition I think I’ve ever had. It’s not like the force of authentic ambition is always with you, but when you feel it, I knew not to shut it down. I would have regretted it for the rest of my life. So, I went for it, and it worked out. I’m not rich, but it worked out.

 

 

 

 

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