Generational Divides with Nick Gillespie: Are the Parents Alright?

Debate streaming on YouTube, Apple Podcasts, and Spotify.

Topics: Culture

Release Date: May 29, 2026

If you’ve ever scrolled through r/Parenting on Reddit or a mom support group on Facebook, you know raising kids has become a minefield. Every tip has a counter tip, every method a manifesto, and a quick Google can surface a myriad of new worries. Parents have splintered into camps — sleep train or co-sleep? Hand over the iPad or redirect to the Pinterest-perfect Montessori shelves? Somewhere along the way, older generations started looking at younger generations and asking: Are the parents alright?

In this episode of “Generational Divides”, three generations tackle some of the thorniest questions in modern parenting:

1. Has social media made parenting harder?

2. Does gentle parenting work?

3. Should kids be free to roam?

Our Debaters:

• For Baby Boomers: Lenore Skenazy, Co-founder of the Free-Range Kids movement

• For Gen X: Reshma Saujani, Founder of Girls Who Code; CEO of Moms First

• For Millennials: Kristin Gallant, Co-founder of Big Little Feelings

Guest Moderator:

Nick Gillespie, Editor-at-Large at Reason

About Generational Divides:

Smart, contrarian, and funny, Generational Divides with Nick Gillespie embodies Open to Debate’s commitment to lively, nuanced discourse in an age of echo chambers. With provocative prompts, generationally diverse guests, and Gillespie’s trademark wit guiding the way, the series invites listeners to question their assumptions and join a conversation that’s as entertaining as it is enlightening.

Special thanks to Liberty Ears Foundation who made this series possible.

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