Women of Letters
“I’m someone who thinks in seasons”: Stefanie O’Connell on her career as a writer
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 SIMPLE magazine. 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
