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.

People-pleasing can look like kindness—but is it actually bringing us closer to one another?

In this episode, Rachel and Jeana examine how people-pleasing shows up at work, in friendships, in romantic relationships and even in hospitality. Inspired by Adam Grant’s writing on the subject, they explore the fear of disappointing others, why saying no can feel so loaded and how trying to earn someone’s approval can create an “authenticity gap” in the very relationships we’re hoping to strengthen.

They also discuss rejection as data, the difference between caring for someone and managing their feelings, and why clear communication may be one of the kindest relationship tools we have. Plus: a simple daily journaling practice, an invitation dilemma involving a Mother’s Day brunch and the question we can ask whenever we feel ourselves slipping into people-pleasing mode: Is this actually bringing me closer to this person—or am I simply trying to avoid discomfort?

Media mentioned in this episode:

• “The Truth About People Pleasing” by Adam Grant — the newsletter that inspired the conversation and includes the Kristen Bell example.
• "I Got Rejected 101 Times” by Emily Winter — the essay Jeana references about intentionally becoming more comfortable with rejection.
• “I Got Uninvited From Mother’s Day Brunch Because I’m Not a Mom” from Kramer & Jess — the call-in segment discussed during Show & Tell.
• Eventually — listeners can use code CONNECT10 for 10% off their first year.

• The Likability Trap by Alicia Menendez
• Suzy Welch’s Becoming You