The Memoir Land Author Questionnaire #19: Jennifer Romolini
"From a young age, I understood good storytelling to be social currency; I wanted to be good at it, was always trying to earn the floor — that kind of thing grows into your bones."
Since 2010, in various publications, I’ve interviewed authors—mostly memoirists—about aspects of writing and publishing. Initially I did this for my own edification, as someone who was struggling to find the courage and support to write and publish my memoir. I’m still curious about other authors’ experiences, and I know many of you are, too. So, inspired by the popularity of The Oldster Magazine Questionnaire, I’ve launched The Memoir Land Author Questionnaire.
Here’s the nineteenth installment, featuring , author most recently of Ambition Monster: A Memoir. -Sari Botton
Jennifer Romolini is the author of the new memoir Ambition Monster and the old career guide Weird in a World That’s Not and the co-host (with Kim France) of Everything Is Fine, a podcast for women over 40. She publishes the weekly Substack Extended Scenes, about ambition and aging.
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How old are you, and for how long have you been writing?
51 and I guess around 20 years, though it somehow feels like I’ve just started.
What’s the title of your latest book, and when was it published?
Ambition Monster, which came out on June 4th.
What number book is this for you?
This is my second “real” book — I’ve ghostwritten books and I wrote an audiobook for managers and I’ve had several failed book proposals which I guess don’t count, but I always feel like it’s important to explain to aspiring writers that the road to the success of something like Ambition Monster took literal decades and a lot of shitty-rejection/self-doubting weeks, years, days.
How do you categorize your book—as a memoir, memoir-in-essays, essay collection, creative nonfiction, graphic memoir, autofiction—and why?
Ambition Monster is categorized as a memoir, though I suppose it’s technically an autobiography because it covers my life as a whole, chronologically, from cradle to wherever I am now.
What is the “elevator pitch” for your book?
We pitched it as a Glass Castle meets Drinking a Love Story. To me, the book is an addiction memoir about work that connects childhood trauma to compulsive achievement-seeking and interrogates the root cause of ferocious/blind ambition within the scam of late-stage capitalism. I also wanted to dismantle the lie of one-size-fits-all conventional success. Along the way I tried to show what really happens behind the curtain at so-called “dream” jobs.
To me, the book is an addiction memoir about work that connects childhood trauma to compulsive achievement-seeking and interrogates the root cause of ferocious/blind ambition within the scam of late-stage capitalism. I also wanted to dismantle the lie of one-size-fits-all conventional success. Along the way I tried to show what really happens behind the curtain at so-called “dream” jobs.
What’s the back story of this book including your origin story as a writer? How did you become a writer, and how did this book come to be?
I grew up working class in Philly attending big family dinners surrounded by (mostly male) Italian-American raconteurs. My father in particular is a skilled storyteller with impeccable timing. I was a hyper-observant kid with an eye for detail. I watched these men closely, listened and learned. From a young age, I understood good storytelling to be social currency; I wanted to be good at it, was always trying to earn the floor — that kind of thing grows into your bones.
When I was in my late 20s, flailing around as a magazine assistant, just off a decade waiting tables, feeling like I’d missed my shot, I met the writer David Carr. David famously loved mentoring young writers he saw something in, especially when they were fuckups without pedigrees like me. One day he took me for coffee and said: “I know you want to be a writer and I know you’re afraid but, listen: You tell a good story. That’ll translate, pal.”
I started writing after that but I never felt good enough, always felt like a fraud. With this book, I very intentionally decided I was getting too old for all my bullshit. For the first time in my creative life, I didn’t get in my own way. I wrote as if my work was important and I had value as an artist. This book is the best thing I’ve ever written because of it. Also, I don’t think I’ll ever not miss David Carr. He was a force.
What were the hardest aspects of writing this book and getting it published?
I mean, where do I even begin? For starters, my former agent dumped me after the publication of Weird In a World That’s Not and told me he “didn’t see” me writing another book. I managed to get a new agent I love but, still, our initial proposal was rejected dozens (and dozens) of times. After multiple revisions on a new, tweaked proposal, only two editors bid on Ambition Monster, but the editor who finally bought it was the perfect editor for me. If you keep going, things tend to work out just as they’re meant to, though it certainly doesn’t feel that way at the time.
How did you handle writing about real people in your life? Did you use real or changed names and identifying details? Did you run passages or the whole book by people who appear in the narrative? Did you make changes they requested?
I handled writing about people in my life on a case by case basis, most all of the names in my book have been changed and many identifying details, but you know, anyone who knows me, knows, which, like most every part of writing a memoir, feels at least a little fucked. I grappled with the ethics of this a lot — I didn’t want to hurt anyone — and often worried I was building an emotional bomb. In the end, I leaned into generosity and compassion, was ruthless in cutting any damaging details I didn’t need, went out of my way to not villainize people who hurt me, and took accountability for my own fallibility often. But I also accepted that my responsibility as a writer was to tell this story as honestly as I could, asking myself constantly: Is it true? Is it fair? You’re never going to make everyone happy when you’re writing a book like this. That’s not the job.
With this book, I very intentionally decided I was getting too old for all my bullshit. For the first time in my creative life, I didn’t get in my own way. I wrote as if my work was important and I had value as an artist. This book is the best thing I’ve ever written because of it.
Who is another writer you took inspiration from in producing this book? Was it a specific book, or their whole body of work? (Can be more than one writer or book.)
So many! I wrote a whole thing about the writers who influenced this book (and why). Here are a few from that list: The Chronology of Water by Lidia Yuknavitch, Goodbye, Again by Jonny Sun, the essays about family in Sam Irby’s We Are Never Meeting in Real Life, Isaac Fitgerald’s Dirtbag, Massachusetts, Lynn Steger Strong’s Want, Megan Stielstra’s The Wrong Way to Save Your Life, Carlene Brauer’s Girls They Write Songs About.
What advice would you give to aspiring writers looking to publish a book like yours, who are maybe afraid, or intimidated by the process?
Be intentional upfront about what you want from a book like this and how far you are willing to go (no one’s going to tell you to pull back on juicy/scandalous/traumatic details, you’ll need to set those boundaries yourself). The best you can, try to separate yourself from the work so you don’t take every rejection or note personally. It’s hard to be objective about your own story, but it’s really the trick to this going well. Last, if you don’t have a therapist, get one, posthaste. You want the work to ultimately feel gratifying, not exploitative and you need a shit-ton of self awareness to know how to protect yourself from your own worst impulses.
What do you love about writing?
I love the spaciousness of book writing — in a hot take world, the time you get with this kind of work is a privilege and a gift. I love the puzzle of writing, how solving it devours my entire brain. I love making something that didn’t exist before — even if it’s one good sentence. I sometimes bitch and moan about the slog of writing, but I mostly feel overwhelming, childlike giddiness and joy. I truly can’t believe I get to do this for a living.
What frustrates you about writing?
Like every writer, I hate when the writing isn’t coming, when all the sentences are trash, though I’m starting to understand that this is just part of the process and let myself off the hook.
What about writing surprises you?
The magic trick of wrestling with a paragraph for days and waking up one morning and suddenly knowing just what to do. I’ll never get over how satisfying this feels.
Does your writing practice involve any kind of routine, or writing at specific times?
It really depends on what stage I’m at and what draft I’m on. I find, for me, a blank page requires my full attention and I need dedicated, uninterrupted time (days, full weeks if I can) to get that first draft out. After that, I’m tinkering at any stolen hour available — on trains and planes, on my notes app in the car at school pickup. I usually write in the early mornings when the house is quiet, before I start my day job. As I get older, I’m completely useless at night.
I grappled with the ethics of this a lot — I didn’t want to hurt anyone — and often worried I was building an emotional bomb. In the end, I leaned into generosity and compassion, was ruthless in cutting any damaging details I didn’t need, went out of my way to not villainize people who hurt me, and took accountability for my own fallibility often. But I also accepted that my responsibility as a writer was to tell this story as honestly as I could, asking myself constantly: Is it true? Is it fair?
Do you engage in any other creative pursuits, professionally or for fun? Are there non-writing activities you consider to be “writing” or supportive of your process?
I have two looms and a filing cabinet full of the most beautiful yarn and I weave the world’s ugliest tapestries in my spare time. I find the movement of weaving and the sensation of the wool meditative but still active in a way that focuses and opens my brain. When I’m truly stuck with writing or feeling like a lost loser, I do Morning Pages. The entire Artist’s Way routine works even if I find it somewhat hokey and embarrassing.
What’s next for you? Do you have another book planned, or in the works?
I have two books I plan on writing next, if the publishing gods let me: a reported non-fiction investigation/memoir hybrid, and a germ of an idea for a novel. I’m super excited about both though I’ll spare you the details. Talking about books at this stage is a sure way to bore your friends.
Thank you, Sari! You are so generous to writers & a champion of writing & i am deeply grateful to you. xo
Sari and Jennifer: I just can't thank you both enough for this interview. It met me at the perfect time in my own memoir process; I know this because of how my heart and eyes kept welling up on their own!! Thank you forever.