In the early aughts, Jennifer Romolini ascended through the ranks of the New York media world, followed by a lucrative transition to the blingy startup scene that was taking root on the west coast. “I kept getting kicked upstairs,” she says of her career’s upward trajectory; she went from clocking in at a fact-checking department at Condé Nast to managing editorial teams at Yahoo’s lifestyle sections and HelloGiggles, flying around the country to deliver inspiring addresses all the while. In 2017, Romolini published a career guide for idiosyncratic strivers, Weird in a World That’s Not. But that book didn’t tell the full story. Truth was, she was sick of hustling, and ready to find her own way.
Her new memoir, the fast-moving and dishy Ambition Monster, tells a tale of an overachiever who wore out her wheels pursuing success – and who finally looked up from her Outlook calendar and called it a night. “I knew I wanted to write about ambition as a toxin, and I wanted my book to be like an addiction memoir,” the 51-year-old Los Angeles resident said. Romolini now co-hosts the popular podcast Everything Is Fine, geared toward women over 40. She’s also a senior beauty editor at Yahoo, where she writes posts about sunscreens and serums and doesn’t manage a staff. “I’m always trying to find the sweet spot between neurotic and neglect,” she said.
Not long ago, you were a high-flying “girlboss”. Your previous book was about the ins and outs of things like office politics and promotions. More recently, though, you took a job as a beauty editor at Yahoo. How did you decide that this position made sense for you?
At a certain point I realized, this is what we all need to find in our careers. What if we made some kind of Venn diagram of what we like to do, what we are good at doing and what pays us enough? I realized that I had climbed too high on the ladder, and what I needed to do was to climb back down. And that’s actually really tricky. Nobody says you should stop striving. You’re supposed to keep going. But it sucks to be good at something you hate.
In your new book, it’s only when you are fired from your job servicing celebrity content creators that you are able to awaken to the fact that there might be another way of living.
Getting fired was like a thunderclap. It sort of broke something in me. It shattered an illusion about work. Because I was fired for no real reason. I had been working so hard and it didn’t make sense. My identity is so tied up with success, that when I was fired, the failure was a tremendous blow. It was a wake-up call and I had to really face myself down because I wasn’t in any shape emotionally to get another job.
Some of your former co-workers must be surprised that you didn’t line up another managerial job.
The illusion was broken for me. I knew that the big jobs were bullshit. That they were like a stress prison. I understood the game, and once I saw it, I couldn’t unsee it.
Near the end of your run as a baller-breadwinner, you lost your voice. Literally.
I had polyps on my vocal cords. It absolutely [came from working too hard]. It came from talking too much; it came from the acid reflux I had because of stress. I was drinking coffee all day long and wine most nights and I had gastrointestinal issues for years.
In your book you talk about Workaholics Anonymous. Is that a real thing?
Yes, they have a conference twice a year. I was in therapy when I started writing this book, and I’ve worked out a lot of what I needed to work out [so I didn’t join the program]. I mean, the workaholism was a symptom of early trauma. What I needed to do was not necessarily join a 12-step program; I needed to process the trauma underneath.
How is work an addiction?
You become addicted to the external validation and the process of working – it just becomes a real space to hide. It’s tricky because unlike drugs or alcohol, we all need to work to survive. You can’t just go cold turkey. So the question has been: how can I learn to work in a different way, to not go above and beyond just to get that high? I’ve started refusing to labor after hours. It’s so hard.
There are many romances you detail in the book, but the main love story is your relationship with your former boss at Lucky magazine and current podcast co-host Kim France.
It is really the only true fairytale of my life. I was a lost, angry and hurt 15-year-old reading a magazine that she helped put out [Sassy] and I was aspiring to be someone like her. And then I got to work with her. I worked for her at a really complicated time in her life. She was not an easy boss, but I loved her, regardless. Right before the pandemic, we met for lunch and I was so nervous. And then she asked me to come on her podcast [Everything Is Fine, which France initially steered with another co-host], and it was such a delight. When she asked me if I would be her new co-host, of course I said yes. We love each other and we protect each other. I’m so loyal to her.
You discuss the subculture of #girlboss and #workhustle in hilarious detail. It’s all so lame, and losing its luster. Do you have any idea what the new iteration of bullshit positivity will look like?
Isn’t it now how we’re pretending we don’t have ambition? We’re looking at “quiet quitting” and the “lazy girl job” and whatever. That’s fine, but we all have a purpose to fulfill on this planet. And a lot of it comes through work, so it’s not that work is bad and ambition is bad. It just needs to be directed in the right way.
I’ve heard you talk on your podcast about the ladies on your block in Los Angeles who you’ve started having a weekly tea with. What else do you have in your life to keep you grounded?
I have a community of women that I meet with every Tuesday, and I try not to dominate conversation, and I try not to talk about my book. And I started weaving. I have two looms, and I weave on my looms.
It must be strange to have written a memoir about overcoming your tendency to strive and now have to be in book-promotion mode.
Well, you don’t have to be a dick! There’s an aspect of honoring the work when you are promoting the work that you do. You’ve worked so hard on something, and there is a level of responsibility. But there can be a zone of frenzy – and becoming a bookzilla where you are just out of your mind. The challenge for me is calibrating my ego and fighting against my own tendencies toward ambition and workaholism and achievement. I’ve had to work on regulating myself because I know what’s important now.
How do you recalibrate when you find yourself tilting toward old habits?
I ask myself questions like: what are you going to do with your one wild and precious book launch? Do you want to be grateful for this opportunity? Or do you want to be striving? When you’re in that mode, you can’t even enjoy the things that you would have dreamed of 10 years ago. The monster wants me, but I am resisting.
Still, your book points a sturdy middle finger at capitalism, and here you are, on a call with me, promoting your book.
But we’re having an exchange with each other, right? That’s real. We’re having an exchange. You’re also [publishing a book and] going through a very similar thing to what I’m going through right now. And we can have empathy for each other, right? This is a meaningful conversation.
Ambition Monster will be published by Atria Books on 4 June
