Paul Sullivan: From the New York Times to the Carpool Line - Redefining Success, Fatherhood, and Work

What happens when a dream career collides with real life and real priorities?

In this episode, I sit down with Paul Sullivan (see bio below), a longtime New York Times columnist, author, and founder of The Company of Dads, to explore a career journey that spans elite journalism, bestselling books, keynote stages, and ultimately, a bold reinvention.

Paul shares how growing up in a working-class Massachusetts town shaped his ambition, how mentorship and failure sharpened his voice as a writer, and what it was really like covering wealth, pressure, and power during the Great Recession. We talk Tiger Woods, golf under pressure, and the behind-the-scenes reality of writing 600+ columns for the New York Times.

But the heart of this conversation centers on Paul’s evolution into what he calls a “Lead Dad” and why millions of fathers are quietly redefining work, parenting, and leadership. From being an “undercover” caregiver while building a high-profile career to launching The Company of Dads, Paul unpacks how outdated workplace norms are colliding with modern family realities and what leaders are still getting wrong.

This is a candid, thoughtful conversation about ambition, identity, masculinity, work culture, and the courage it takes to rewrite the script when the old version no longer fits.

 

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About ​Paul: Paul Sullivan is the founder of The Company of Dads, the first platform dedicated to creating community for Lead Dads—men who are the go-to parents at home and allies to working caregivers. A former New York Times columnist for 13 years, Paul became a Lead Dad in 2013 when his wife launched her own asset management firm. After years of navigating this role while balancing a demanding career, he founded The Company of Dads in 2022 to support the roughly one-third of fathers in similar positions. Paul is also the author of Clutch and The Thin Green Line, co-hosts Bright Horizons' Work-Life Equation podcast, and lives in Connecticut with his wife, three daughters, and three dogs.