With her debut book, Stefanie presents a deeply researched examination of the hidden structural forces that continue to shape women’s careers. Her focus is on a phenomenon she describes as the ‘ambition penalty’: “the sum of the professional, financial, social, and personal costs women face when asking for or pursuing more.”

The result is a highly readable study which dispels the myth that women are simply lacking in professional ambition or the skills needed to succeed at their jobs. What remains at issue, rather, is how the outside world tends to respond to women’s contributions, both in the workplace and beyond—and, as we discuss, a good deal of inequality outside of the home stems from inequality within it.

I learned so much from our exchange.

—

IN THIS EPISODE, we talk about... 👇

• How growing up with a breadwinning mother shaped her views on gender and work
• The way she’s built a career through cold emailing and developing a resilience against rejection
• Why it’s so rare to see heterosexual relationships in which men are openly supportive of their more successful female partners (like Doug Emhoff with Kamala Harris or Travis Kelce with Taylor Swift)
• How she landed her first public speaking gig
• The alignment-based framework she uses to make decisions
• Why she’s always been a long-term thinker who frames her perspective in terms of “seasons”
• Seeing peers as collaborators instead of competitors
• The strategy she used to grow her widely popular Instagram to over 94,000 followers and sell her first book
• How she developed the deadline-driven workflow that enables her productivity
• ... and so much more!

—

Stefanie O’Connell is an award-winning writer covering ambition, money and power with bylines in The Guardian, Slate, Bloomberg, CNBC, Fast Company, MarketWatch, Glamour UK, Newsweek, USA Today and Business Insider. She also wrote, hosted and co-produced the WEBBY award-winning podcast “Money Confidential” for REAL SIMPLEmagazine. Her book The Ambition Penalty: How Corporate Culture Tells Women to Step Up—and Then Pushes Them Down (May 2026, Basic Venture) is an essential guide to dismantling the hidden forces that hold women back, burn them out & make us all pay. With over 100,000 followers across her social media channels and Too Ambitious newsletter, Stefanie uses data to expose how power and gender collide to keep women “in their place.” And shows how liberating women’s ambitions can liberate us all.

You can follow Stefanie at @stefanieoconnell and order her book The Ambition Penalty here.

——

Song: “Walk Through the Park,” by TrackTribe

Each month, between interviews, I hop on the mic to share a new episode of The Postscript: a Women of Letters segment which features a life update from me + a behind-the-scenes look at my conversations with our recent guests—in this episode, Candice Wuehle, Alissa Wilkinson, and Sophie Grégoire Trudeau.

IN THIS EPISODE, I talk about... 👇

• The launch of the first Women of Letters merch collection
• Why being able to write under any conditions is a superpower
• What it’s been like finding a doctor in Croatia
• The importance of publicly thanking others for their help
• How to ask for what you want
• .. & so much more!

To claim your spot on the waitlist for the namesake WOMAN OF LETTERS hat, go to womenofletters.org/merch. You’ll be the first to know when it drops, and you’ll secure exclusive launch pricing: free shipping + 10% off your order.

—

Jana M. Perkins, PhD, M.Sc., M.A., is an award-winning scholar and the director of Women of Letters. Her research has garnered over a quarter of a million dollars in funding from leading institutions across North America and the UK, including the University of Cambridge and the Social Sciences and Humanities Research Council of Canada (SSHRC). As an academically trained data scientist with a background in classical literary scholarship, her expertise extends across disciplines to yield the unique analytical frameworks which characterize her approach. Her forthcoming first book, co-authored with Miranda Brun Hickman, will be published by Routledge.

Visit her online at janajm.com or @janajm on Instagram.

——

Song: “Walk Through the Park,” by TrackTribe

The trajectory of Sophie’s career reads like a sustained masterclass in moving from strength to strength.

Today, she is the bestselling author of the runaway success Closer Together, a pioneering mental health advocate of 25 years, and a widely in-demand public speaker. It’s a path she’s forged on the foundations of her professional background in media and journalism, together with a nearly decade-long tenure spent in public service to a G7 country on the copolitical path as the unofficial First Lady of Canada.

What’s striking isn’t just how much she’s already accomplished, but also how thoughtfully she’s positioned herself for what comes next—and, as we discuss, she’s just getting started. It was a privilege to connect with her over this interview.

—

IN THIS EPISODE, we talk about... 👇

• The new chapter unfolding in her fifties
• Her daily practice of tracking micro-successes
• The difference between breaking and being broken open
• Why she always keeps books of poetry on her bedside table
• The accomplishment she’s most proud of achieving
• Finding wisdom in the middle ground between being attached to the past and afraid of the future
• How she decides which opportunities to pursue and which to pass on
• The day she first met her longtime friend and mentor Gabor Maté
• How she thinks about social media
• Why the biggest risk she’s taken recently felt like jumping through “this huge circle of fire”
• The thriving portfolio career she’s building now
• ... and so much more!

—

Sophie Grégoire Trudeau is a Canadian-born bestselling author, public speaker, mental health advocate, television host, and certified yoga teacher for both adults and children. Her work for gender equality and empowering women and youth has been recognized by multiple organizations including the United Nations. Her instant national bestseller and Best on Audible (2024) book Closer Together: Knowing Ourselves, Loving Each Other has inspired readers across North America and beyond. Throughout her career, Sophie has met and interviewed some of the world’s most inspiring public figures who are shaping a fairer and more compassionate world—including Nobel Peace Prize laureate Malala Yousafzai and trauma expert Dr. Gabor Maté—deepening her lifelong exploration of justice, healing, and human connection. In 2025, she was named a Fellow of the Royal Canadian Geographical Society, recognizing her enduring commitment to education, exploration, and the preservation of Canada’s natural and cultural heritage.

——

Song: “Walk Through the Park,” by TrackTribe

Candice’s latest novel achieves what her widely celebrated Substack has consistently delivered: a sharp, nuanced critique of a key cultural moment, rendered with her characteristic verve.

The book follows a pop star through her rise to fame in its examination of topics that have long been at the heart of Candice’s work, like how women in public are forced to become theorists of their own image or the intellectual labour that’s hidden inside pop culture. It’s a timely consideration that extends beyond the level of celebrity to also offer insight into the complexities of female friendship, what it means to wield power, models of mentorship, and the nature of success.

It was a joy to talk with her about all of that and more when we spoke.

—

IN THIS EPISODE, we talk about... 👇

• What it’s like to have an essay go viral
• Why she still prioritizes saying ‘yes’ to most opportunities
• How she found success on Substack
• What she describes as “the great millennial woman deprogramming”
• Her unexpected transition from writing poetry to becoming a novelist
• Our top 3 Taylor Swift albums
• The declining impact of prestige media outlets
• How we identify desire and where our desires come from
• Why she now almost exclusively reads contemporary women’s fiction
• The “external hard drive” of shared memory in a friendship
• ... and so much more!

—

Candice Wuehle is a novelist, poet, and instructor teaching in the Honors Program at the University of Iowa. Her first novel, MONARCH, was selected as a Best Book of 2022 by NPR and her poetry collection, Death Industrial Complex, was a finalist for the Believer Magazine Book Award. Her latest novel, Ultranatural, follows a pop star reminiscent of Britney Spears as her highly surveilled and tightly controlled life contracts dangerously. Candice also runs the Substack newsletter Bimbo Summit: A Pop Culture Study, where she regularly writes about our relationship to modern day celebrity. She is from Iowa City, Iowa, where she currently resides.

——

Song: “Walk Through the Park,” by TrackTribe

Each month, between interviews, I hop on the mic to share a new episode of The Postscript: a new section of Women of Letters I’ve been working on which features a life update from me + a behind-the-scenes look at my conversations with our recent guests.

IN THIS EPISODE, I talk about... 👇

• My first month in Croatia has been like (both the good and the bad)
• How some of my other big moves over the years have gone and what I’ve learned from them that I’m applying to this one
• Why I always make it a priority to get things in writing
• How I’ve recently gotten super into Instagram Reels, to the point that I now have 20 or 30 of them recorded on my phone
• The way that seemingly small moments or interactions can radically reshape our lives
• .. and so much more!

—

Jana M. Perkins, PhD, M.Sc., M.A., is an award-winning scholar and the director of Women of Letters. Her research has garnered over a quarter of a million dollars in funding from leading institutions across North America and the UK, including the University of Cambridge and the Social Sciences and Humanities Research Council of Canada (SSHRC). As an academically trained data scientist with a background in classical literary scholarship, her expertise extends across disciplines to yield the unique analytical frameworks which characterize her approach. Her forthcoming first book, co-authored with Miranda Brun Hickman, will be published by Routledge.

Visit her online at janajm.com or @janajm on Instagram.

——

Song: “Walk Through the Park,” by TrackTribe

If you’ve been a longtime reader, you’ll know that two of the subjects I most regularly gravitate towards in my personal reading are books about female friendship and books about the diaspora experience. So you can only imagine my delight at discovering Claire’s debut novel, Wanting, which contends with both.

In addition to having been called “Ferrante-like” by the New York Times Book Review, her novel has also been declared a best book of the summer by outlets ranging from LitHub to Harper’s Bazaar. I was grateful to have a chance to sit down with her and learn more about how her experiences living between two different countries as a Chinese-American have shaped the way she approaches her career.

—

IN THIS EPISODE, we talk about... 👇

• Spending a decade writing and revising her debut novel
• The trip to Paris that changed everything
• Why she decided to abandon her initial goal of becoming an ambassador
• What it was like going on a 16-city book tour
• How she would pursue a career in writing if she were starting today
• Why she’s not looking for her romantic partner to also be her best friend
• Where she’s turning to now as she looks ahead to the next 10 years
• What ‘home’ means for her
• .... and so much more!

—

Claire Jia is a writer from the suburbs of Chicago. Her work has appeared in The New York Times Modern Love column, The Rumpus, Reductress, and more. She writes for television and video games, including the 2023 Peabody Award-winning We Are OFK. Her family is from Beijing, and there’s nothing she loves more than haggling for stationary in a chaotic Beijing marketplace. Today, she lives in Los Angeles with her friends. Wanting is her debut novel.

——

Song: “Walk Through the Park,” by TrackTribe

Each month, between interviews, I hop on the mic to share a new episode of The Postscript: a new section of Women of Letters I’ve been working on which features a life update from me + a behind-the-scenes look at my conversations with our recent guests.

IN THIS EPISODE, I talk about... 👇

• Finally having my tickets to Croatia booked (!)
• The search for an apartment
• New York Magazine’s article on how much money people make
• The importance of introducing structure into your routine when you’re making a major life change
• Why the myth of the straight career path is damaging
• The wrong thing to say when someone shares some big news with you
• The way to get closer to a ‘yes’ from the gatekeepers standing in the way of a goal
• My best advice for how to improve your writing
• ... and so much more!

—

Jana M. Perkins, PhD, M.Sc., M.A., is an award-winning scholar and the director of Women of Letters. Her research has garnered over a quarter of a million dollars in funding from leading institutions across North America and the UK, including the University of Cambridge and the Social Sciences and Humanities Research Council of Canada (SSHRC). As an academically trained data scientist with a background in classical literary scholarship, her expertise extends across disciplines to yield the unique analytical frameworks which characterize her approach. Her forthcoming first book, co-authored with Miranda Brun Hickman, will be published by Routledge.

Visit her online at janajm.com or @janajm on Instagram.

——

Song: “Walk Through the Park,” by TrackTribe

With her latest book, Savala has accomplished the rare feat of building on a widely celebrated first book with a second book that—already, in its first month post-publication—is on track to be equally if not more so. (Ms. Magazine, for example, has proclaimed it a most anticipated feminist book of 2026.)

The 12 timely essays of Good Woman: A Reckoning offer a striking blend of cultural commentary, reporting, and memoir across topics like the surge in GLP-1 messaging that’s reshaping expectations around our bodies; the ways that racism amplifies misogyny; how women have been socialized to be agreeable and ‘good’; and why compliance didn’t bring her wholeness, happiness, or safety. It was a joy, when we spoke, to get to learn more about this collection alongside the experiences that have shaped her career.

—

IN THIS EPISODE, we talk about... 👇

• The one book she thinks everyone should read
• Opting for ‘good enough’ instead of over-optimizing every aspect of our lives
• How volunteering for Obama’s 2007 campaign unexpectedly changed her career
• The spokes-on-a-wheel concept she’s used in crafting both of her widely celebrated books
• Why expectations around gender roles harmed both her and her ex-husband during their marriage
• The under-appreciated power of peer-to-peer mentoring
• How she makes time for writing
• ... and so much more!

—

Savala Nolan is an essayist and professor who writes about race, bodies, and gender. She helped create the Peabody Award–winning podcast The Promise, and directs the social justice program at UC Berkeley, School of Law, where she teaches about the role of identity in lawyering. Her work has been featured in Vogue, Harper’s magazine, The New York Times Book Review, NPR, Time, Forbes, LitHub, and more.

——

Song: “Walk Through the Park,” by TrackTribe

Victoria’s latest novel is the rare book that is so wide-ranging and lushly articulated that it eludes description.

To simply say, for example, that it’s a work of historical fiction about two women painters in 17th-century Amsterdam would be to fail to capture so much of what it also is: an ode to women excelling, against all odds, in their chosen professions; a meditation on who has power and how it’s wielded; a decades-long love story; and a nuanced study on the complexities of mentorship.

And yet, for Victoria, it’s only the latest in the string of successful works that have marked her prolific writing career. I was delighted to have a chance to sit down with her and talk all about it.

—

IN THIS EPISODE, we talk about... 👇

• The routines that have made it possible for her to have a prolific writing career
• What it was like working as an assistant to Adrienne Rich
• Her initial mistake of going to college to become a painter
• How the sense of discipline she developed from ballet has been useful throughout her life
• The night she served spanakopita for dinner with Denise Levertov and Alice Walker
• Why failing and making messes is more important than getting something right the first time
• The reason she doesn’t focus on scarcity and feelings of hopelessness
• How to know if it’s time to return to a long-abandoned idea
• What she’d do differently if she were starting now
• ... and so much more!

—

Victoria Redel is a first-generation American author of four books of poetry and six books of fiction, most recently the poetry collection Paradise and the novel I Am You, published in October 2025 by Zando Project/SJP Lit. Victoria’s work has been widely anthologized, awarded, and translated into many languages. Her novel Loverboy (2001) was adapted for feature film directed by Kevin Bacon. She’s received fellowships from the Guggenheim Foundation, The National Endowment for the Arts, and The Fine Arts Work Center. Victoria has taught at Columbia University, the New School, Vermont College of Fine Arts, and was the McGee Distinguished Professor at Davidson College. She is a tenured faculty in the graduate and undergraduate creative writing programs at Sarah Lawrence College and lives in New York City and Utah.

——

Song: “Walk Through the Park,” by TrackTribe

If you’ve been a longtime reader or listener, you’ll know that this kind of one-on-one is something I haven’t done before. So I’m definitely feeling a little bit nervous in this moment.

But I also have a lot of excitement around it, because with this episode we’re launching a new section of Women of Letters called The Postscript. Listen in for a personal note from me, with a behind-the-scenes on our interviews with Alia and Melissa, a life update on why I’m moving to Croatia, and a peek behind the curtain on Season 3.

IN THIS EPISODE, I talk about... 👇

• The inspiration behind The Postscript
• My conversation with Alia Hanna Habib (full interview here)
• My conversation with Melissa Febos (full interview here)
• A life update on what’s been happening in my world these days
• Behind the scenes on the production of Season 3: why the planning for a new season begins about 6 months out from the publication of the first interview, how I decide on each season’s new set of questions, and one of the projects I’ve been wanting to take on for a long time that we’re finally getting to do now
• .. & so much more!

—

Jana M. Perkins, PhD, M.Sc., M.A., is an award-winning scholar and the director of Women of Letters. Her research has garnered over a quarter of a million dollars in funding from leading institutions across North America and the UK, including the University of Cambridge and the Social Sciences and Humanities Research Council of Canada (SSHRC). As an academically trained data scientist with a background in classical literary scholarship, her expertise extends across disciplines to yield the unique analytical frameworks which characterize her approach. Her forthcoming first book, co-authored with Miranda Brun Hickman, will be published by Routledge.

Visit her online at janajm.com or @janajm on Instagram.

——

Song: “Walk Through the Park,” by TrackTribe