A diploma doesn’t come with instructions for making friends, navigating workplace expectations, or walking into a room full of strangers. So where do we learn those things?

This week, Rachel and Jeana welcome Heather Redisch, creator of Adulting 101 Masterclass, for a conversation about building confidence and connection through the everyday experiences that stretch us. Heather shares what she’s learning from coaching Gen Z, why managers should say the unwritten rules out loud, and how parents can help their kids build independence without smoothing away every challenge.

We talk about giving yourself time to settle into a new city or job, why one meaningful connection makes a networking event worthwhile, and how small, uncomfortable moments become opportunities to grow. Plus, Rachel and Jeana reflect on advice they’d give their younger selves—and share why ordinary errands are better with friends and putting our phones away can help us be more present.

Whether you’re starting your adult life, raising someone who is, or navigating a transition of your own, this episode is a reminder that you don’t have to have everything figured out to take the next step.

Media mentioned in this episode:

• Adulting 101 Masterclass
• Heather's Instagram: @adulting101_masterclass
• Heather's Adulting 101 Masterclass podcast
• the book Anxious Generation
• Priya Parker's new book, The Art of Fighting
• Everything is better together - The American Time Use Survey
• The University of Chicago's Train Study
• Read Phoebe Bridgers' phone-free event policy here

What’s the difference between collecting contacts and building real relationships?

Award-winning communications executive—and lifelong super-connector—Jon Harris joins us to share what more than three decades of bringing people together has taught him about curiosity, generosity and the relationships that remain long after jobs and titles change.

Jon opens up about the difficult childhood that shaped his commitment to helping others, why he believes the best networkers give without keeping score and what he has learned about asking for help during a professional transition of his own. He also introduces us to the Truffle Club, the trusted community of communications leaders he created during the pandemic, and reminds us why we should never let someone’s title stop us from saying hello.

Plus, Jeana and Rachel debate the increasingly popular wedding-day Irish goodbye and reflect on Dolly Parton’s legacy of generosity, joy and making the world a little brighter.

This episode is sponsored by Eventually. Visit eventuallyticketing.com/the-connection-code and use code CONNECT10 for 10% off your first year.

Media:

• Jon Harris: LinkedIn and Instagram @jonjayharris

• Dolly Parton’s Imagination Library: Learn about the book-gifting program
• Coyote vs. Acme: Official movie site and trailer
• Dare to Serve by Cheryl Bachelder here
• SocialWorks: Chance the Rapper’s Chicago nonprofit

What does it mean to love a place deeply and know when it’s time to leave?

New York Times bestselling author and Pulitzer Prize finalist Xochitl Gonzalez joins Jeana and Rachel for an expansive conversation about the places that make us, the people who remember our earlier selves, and the courage it takes to enter a new chapter.

Xochitl reflects on Brooklyn as both a hometown and a living archive. She also talks about writing Last Night in Brooklyn as one final love letter to the place that shaped her. She shares what decades-long friendships have taught her about grace, why closeness doesn’t always require constant contact, and how pre-digital friendship allowed people to become part of a community without feeling watched.

She also opens up about beginning her writing career in her 40s after years as a luxury wedding planner, the way class can narrow our sense of what’s possible, and why we should periodically reconsider our own “aperture of opportunity.” Plus, Xochitl talks manifestation, intergenerational mentorship, the connections she still hopes to make, and learning to trust that the road we started on isn’t necessarily the one we have to stay on.

Before the interview, Jeana and Rachel share moments when an improbable future felt inevitable. And in Show & Tell, they consider children’s autonomy online and whether we should ask permission before sharing photos of the people we love.

Media in this episode:

• Xochitl Gonzalez’s website
• Last Night in Brooklyn
• Olga Dies Dreaming
• Anita de Monte Laughs Last
• Need Blind: A Memoir of Class and Climbing in America
• Xochitl’s Substack
• Xochitl on Instagram

• Billy Joel: And So It Goes — the documentary that led Xochitl to a remarkable new connection.
• “Robby Hoffman Will Always Feel Poor, No Matter How Rich She Gets” — the New York Times interview Rachel references.

• Eventually Ticketing — use code CONNECT10 for 10% off the first year.