Girl Bosses Walked So Ambition Monsters Could Realize ‘Everything Is Bullshit’

I inhaled Ambition Monster in roughly five hours, like a cartoon character at a pie-eating contest. Mostly because I found it impossible to put down, but also because I wanted to sit with its story for as long as possible before writing this review. Jennifer Romolini , author of the memoir Ambition Monster and former media exec at some of the biggest fashion and lifestyle publications you definitely have heard of (and your parents definitely still use as their homepage) was my first boss. I was 23 and emailed her, unprompted, telling her I was in Los Angeles on vacation (a lie) and would she like to get coffee with me, since my hotel was near the office (another lie) of the website she ran. She said yes.

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The thing is: Nobody says yes. Nobody responds to the wannabe-writer with not enough work experience or impressive pedigree who is cold-emailing you. But Romolini did — and I’d like to think it’s because she saw the ambition monster in me .

What drew me to Ambition Monster over a decade later (I’ve been working in media ever since) and why I think it will speak to so many women who have dedicated so much of themselves to their careers, is that it critically examines the consequences of success in a way that our pre-2020 girlboss hustle culture purposely didn’t — and could never. Ambition Monster is a memoir about the addictive nature of ambition and how it was born out of childhood trauma and resilience. Your (and my) upbringing may look completely different from Romolini’s — but it’s also likely that we all share some common ground.

This is a no-bullshit origin story of a powerful woman who had a messy, late start to her career. This is not Devil Wears Prada . It’s not Sex and the City . In Ambition Monster , Romolini flunks out of state college, waits tables throughout her 20s, marries young to a toxic man and stays with him for four toxic years, and goes on to date a slew of abusive artists and media guys. Romolini drinks and parties, and she’s self-destructive, even when she lands fact-checking gigs at impressive magazines in New York City. She wonders why she even wanted to become a writer when waiting tables makes a billion times more money, and this realization further delineates herself from the many media colleagues who are able to fund their way to the top of the food chain through generational wealth and social status.

Eventually, and this isn’t a spoiler, the hockey stick trajectory pans out. Romolini crawls and scrapes her way to the top, and she has everything she ever wanted (the Fancy Magazine Job, the nice, marriable guy, the cute baby, the roomy New York City apartment, the expensive haircut). But the price of this ambition is higher than she ever expected. One day, sitting in her c-suite Hollywood office, working for one of the biggest producers in the industry, it all comes crashing down — and while it’s humiliating and ugly, it’s also the wake-up call Romolini needed.

So, what happens when you finally divorce your identify from your work? The aim of Ambition Monster is to answer just that.

Ten years after sending Romolini that first email, I emailed her that I’d love a copy of her book — and could I ask her some questions? Of course, she said yes.

Gina Vaynshteyn: What did you learn about yourself in the time you spent writing Ambition Monster?

Jennifer Romolini: I gained a lot of clarity about my past and a more nuanced understanding of my life and relationships — we all want to be the heroes of our own stories but it’s truly not always the case. I was a hurt, messed up kid and, as a result, a chaotic adult. Reckoning with this was not the most fun I’ve ever had, but it was better to face it, deal with the lingering shame, make amends where appropriate, forgive myself the best I could and move on.

Kim France [the founding editor of Lucky Magazine and Romolini’s former boss] gives you the advice, “Don’t try to be in charge, it’s not worth it,” back when you were deputy editor at Lucky . You went on to run the biggest women’s lifestyle website, transformed a celebrity blog into a legitimate brand that was eventually acquired by a major publishing corporation for many millions of dollars, and then turned a well-known Hollywood producer’s vision into a high-profile digital destination. Was Kim right?

The short answer is “yes” but whether she was right or not matters little because this was a lesson that, as it is for most people, I had to learn for myself. I spent a lot of time with misdirected ambition, in this sort of hopeful/naive but ultimately damaging and distorted fantasy about conventional success, projecting all these ideas of how great much better I’d feel if only I could reach X goal and then X next goal, if I could just make it to the top. The accomplishments you list look impressive (even to me), but the emotional, physical and social sacrifice it took to acquire them was certainly not worth the shiny-hollow reward.

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In 2024, do we as a collective workforce have a healthier relationship with work? Are we getting any better?

I really don’t know the answer to this in any global way — and I am sure this is not the case in every industry — but from my experience, whether it’s lip service or not, people are generally more respectful in workplaces now than they were even 10 years ago, less overtly aggressive, more encouraging of work/life boundaries. Gen Z seems especially amazing at this. A young colleague asked me the other day if 9am was too early for a meeting because they wanted to be respectful of my time, an unthinkable consideration when I was coming up.

How do you think social media played a part in 2010s grind (fempowerment/girlboss/hustle, etc.) culture? What about now?

Social media is an ongoing performance of identity, and those early #bossbitch #riseandgrind days when we were fetishizing labor, bragging about “dream” jobs, documenting side hustles — all of it helped perpetuate an idea that our value is tied up in our productivity, an idea we’ve always had in this country, but Instagram painted pink and sent into overdrive. As for today? I mean social media still sucks, but now the effect is more chaotic and diffuse. Is the non-stop bombardment of self-helpy placards, atrocities, self promotion, ads for cat litter and jokey dystopian memes better or worse? You tell me.

What does your relationship with work/labor look like these days?

I’ll probably always have perfectionist, workaholic tendencies but I’ve learned to direct them in healthier ways, not to go above and beyond for external validation or a pat on the head but for projects that mean something to me, work that lights me up, that I absolutely love. I’ve also become more judicious with my time and what I say “yes” to.

Weird in a World That’s Not , your first book, is kind of Ambition Monster ’s polar opposite. It’s a career guide that doesn’t really reveal the true cost of having a drive that runs on fumes—because it’s just not that kind of book, and it’s also been seven years since it was published. If you could go back in time and rewrite Weird in a World That’s Not , would you? What would you change?

This is an amazing question! Even though Weird In a World That’ was meant to be somewhat subversive, a counter-narrative to the Girl Bossian movement I disdained, I don’t think I could write it today — or rewrite it. I’m just not jazzed enough about careers anymore. If I did attempt a revision, it would be pretty short: love yourself, be kind, don’t stress too much, sort out what you want for you , stop worrying about how it looks to the outside world. Remember that most of this is bullshit and it’s all going to work out. Try to have some fun along the way.

What advice would you give women/fellow ambition monsters early in their careers?

Once you’ve sorted out basic survival, slow down. It’s not going anywhere. Also, put at least a small, non-negotiable amount of money into a 401k or a Roth IRA every month. In 30, 40 years you’ll be so grateful you did.