I wasn’t expecting, through Jennifer Romolini’s memoir Ambition Monster, to feel as seen as I was. About workaholism. Ambition addiction. Achievement addiction. Why I am that way. Why I experienced debilitating burnout, which, if you’ve ever experienced true burnout, you know what I mean when I say it is truly debilitating. And then, from the book to this conversation—I don’t like to play favorites, but this conversation has to rank up there with my absolute favorite episodes of this show’s 215 or so episodes. It felt more like a therapy session than an interview. Whatever you want to call it—hustle culture, Girl Boss-ing it, I heard a new term this week actually called “grindset” instead of “mindset”—whatever you want to call it, I know I’m not the only one influenced and affected by it. Jennifer’s book is about what happens when ambition—which certainly is a good thing—turns bad. What happens when workaholism sneaks in, and how this actually relates to childhood trauma. What happens when you get everything you’ve ever dreamed of, and then realize that it’s not enough to fill that hole inside you. And, at last, filling that hole with what is really sustaining, and it’s not work. Achievement addiction and ambition addiction and constantly trying to prove yourself, that addiction—it may not be drugs or booze or gambling or shopping, but it’s an addiction, nonetheless, and nothing done to excess like that is good for you. Jennifer raced up the professional ladder and reached the apex of success: she had a high-profile, C-suite dream job, and even traveled around the country giving speeches on how to make it and what it feels like to have made it. Beyond that, she had a handsome husband, a beautiful child, but, as the book puts it, “beneath this polished surface was a powder keg of unresolved trauma and chronic overwork. It was all about to blow.” This book will make you rethink the way we work, and rethink ambition on the whole. Jennifer co-hosts the podcast “Everything Is Fine,” which examines life for women over 40, with Lucky magazine founding editor Kim France (the show is one of my all-time favorites, though I’m not quite 40); she’s also the author of Weird in a World That’s Not: A Career Guide for Misfits, Fuckups, and Failures, and her work has appeared in outlets like The New York Times, Elle, Fast Company, Vogue, and more. She was a magazine editor in the 2000s, won awards for websites she edited in the 2010s, was a former deputy editor at Lucky alongside Kim, and was also the former Chief Content Officer of ShondaLand.com (as in, yes, the one and only Shonda Rhimes), Vice President of Content for Zooey Deschanel’s HelloGiggles, a writer, speaker, and digital media consultant who likes talking and thinking about women and work. In 2019, Jennifer was asked to be one of 10 authors tasked with creating The New York Times’ “Working Women’s Handbook,” so, yeah, she knows a little bit about women and work. Ambition Monster examines the lies women were and are sold about work and one of my least favorite three-word combination ever, “having it all,” and before we get into it, I should warn you that there is some ample cursing in this episode, as there tends to be when a subject resonates so close to home.

Ambition Monster: A Memoir by Jennifer Romolini

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