Release Your Attachment to Outcomes | Shaena Harrison & Orlaith Brogan

I Don't Believe in Coincidences | Maria Doughty (The Chicago Network)

Maria Doughty has spent nearly five decades' worth of institutional wisdom at her fingertips — and she uses every bit of it to do one thing: bring people together who never would have found each other otherwise. As President & CEO of The Chicago Network, a 50-year-old invitation-only community of the city's most powerful senior executive women, Maria has turned the art of connection into a leadership philosophy. In this warm and wonderfully candid episode, Maria shares how a leap of faith (signed in February 2020, with an April start date — yes, that April) led her to the role she was meant for, and what she's learned about building community that actually holds — across industries, decades, and more than 70 events a year. ✨ Highlights from this episode: * Why the most powerful communities are built on threads, not topics — and what that difference means for how you connect * The two founding rules of The Chicago Network that have held for nearly 50 years (no guilt + the 24-hour rule) * How Maria plays the role of connector-in-chief — and why stepping away is often the most important move she makes * What high-achieving women get wrong about giving — and the one question that stopped a member in her tracks * Why Maria believes there's no such thing as a coincidence when it comes to connection Whether you lead a community, build one, or simply want to show up better in the ones you belong to — this one will stay with you. 👉 What connection in your life is quietly waiting to become something more — if only someone nudged it forward? SHOW LINKS: * The Chicago Network: https://www.thechicagonetwork.org/ [https://www.thechicagonetwork.org/] * Maria on LinkedIn: https://www.linkedin.com/in/maria-doughty/ [https://www.linkedin.com/in/maria-doughty/]

The Best Intros Feel Like a Friend Made Them | Meg McWilliams

Meg McWilliams knows the sting of networking gone wrong—and she’s building a better way. As the co-founder of Gobby Goblin, an AI-powered event networking tool, Meg is on a mission to make large-scale events more human, one meaningful intro at a time. In this refreshingly honest episode, Meg shares her founder journey, lessons learned from gaming and immersive tech, and what it really takes to create connection at scale without losing the personal touch. ✨ Highlights from this episode: * Why most event apps fail at real connection—and what to do instead * How Gobby's text-based AI mimics the intuition of a great friend * What founders need to know about timing, ROI, and meaningful growth * Designing tech that meets people where they are—no downloads required * The magic of asking surprising questions (like someone’s favorite smell) Whether you’re building a product, attending your next conference, or just tired of small talk that goes nowhere—this one’s for you. 👉 What would change if your next event intro felt like it came from a friend? SHOW LINKS:  * https://gobbygoblin.com/ * Meg on LinkedIn: https://www.linkedin.com/in/meg-mcwilliams-b1669976/

Release Your Attachment to Outcomes | Shaena Harrison & Orlaith Brogan

> “Human connection isn’t instant—rapport might be, but trust takes time.” >  — Orlaith Brogan, Co-Founder of Wing People What if networking wasn’t awkward, aimless, or based on chance? What if connection at events was designed—with intention, warmth, and actual follow-through? Shaena Harrison and Orlaith Brogan are the co-founders of Wing People, a company that places trained "wing people" inside events to make meaningful, real-time introductions. In this episode, they share the origin of their mission, the power of serendipity, and what it means to connect without agenda. ✨ Highlights from this episode: * How to make people feel safe enough to open up * The problem with pitch-slapping—and what to do instead * Why event ROI needs more human design, not just better logistics * Real stories of connections that changed lives (years later) * The magic of noticing who’s standing alone—and doing something about it Whether you’re an event organizer, a reluctant networker, or a lifelong connector, this episode will remind you that the best outcomes often come when we stop chasing them. 👉 Who’s someone you could introduce—just because? SHOW LINKS:  * https://www.wingpeople.io/ * Shaena: https://www.linkedin.com/in/shaena-harrison-professional-wing-woman/ * Orlaith: https://www.linkedin.com/in/orlaith-brogan-professional-wing-woman/

Connection is Not a Credit Card Swipe.  It's an Investment | Alli Kushner

Connection is not a credit card swipe.  It's an investment. In this heartfelt and energizing conversation, we’re joined by Alli Kushner [https://www.linkedin.com/in/allisonkushner/], Global Operations Lead at LinkedIn and founder of BeeKyn, a startup helping working parents find meaningful playdate connections for their kids and themselves. We dive deep into how modern life complicates authentic connection and how Alli is tackling that challenge head-on. From the emotional toll of postpartum depression to the triumph of building something that brings people together offline, Alli shares her story with grace, wisdom, and warmth. We discuss: * Why connecting as a parent is a logistical and emotional challenge * The surprising Venn diagram of building genuine friendships as a caregiver * How postpartum depression inspired Alli to create a solution for real-life connection * The difference between networking and investing in relationships * What it takes to show up, reach out, and build community without an agenda This episode is a beautiful, honest reminder of why human connection matters and how it can shape us in life-changing ways. Enjoy!  __________ 👉 Find Alli on LinkedIn: https://www.linkedin.com/in/allisonkushner/ [https://www.linkedin.com/in/allisonkushner/] 👉 Learn more about BeeKyn: https://www.linkedin.com/company/beekynco/ [https://www.linkedin.com/company/beekynco/] 👉 Follow Joy of Connecting Show on LinkedIn: https://www.linkedin.com/company/the-joy-of-connecting-show/ [https://www.linkedin.com/company/the-joy-of-connecting-show/] 👉 And get bi-weekly, actionable tips for building your network and connecting with meaning: https://thejoyofconnectingshow.substack.com/ [https://thejoyofconnectingshow.substack.com/]

Community Starts With a Question and Grows With Heart | Scott Tran

We’re pumped to welcome Scott Tran [https://www.linkedin.com/in/scott-tran-188815a3/], Founder at Support Driven [https://www.linkedin.com/company/support-driven/], a community serving customer support and customer experience professionals, to our show. Scott has built a thriving online community of more than 13,000 members who care deeply about support. In this episode, he shares how the art of listening shaped every stage of growth, why people stay for friendship (not only answers), and what it really takes to scale a community without losing its soul.  We discuss the importance of serving your community and Scott’s journey of growing Support Driven from a small Slack group to a full-fledged organization hosting conferences.  Tune in to hear: * How Scott built a global community from scratch * Why emotional stickiness matters in community building * The surprising signals that show your community is thriving * The power of listening and adapting If you're growing a community of your own, you’ll love this episode. Plus, it will inspire you to ask yourself: What’s one small signal that tells you your people feel connected? Enjoy! __________ 👉 Find Scott on LinkedIn: https://www.linkedin.com/in/scott-tran-188815a3/ [https://www.linkedin.com/in/scott-tran-188815a3/] 👉 Learn more about Support Driven: https://www.supportdriven.com/ [https://www.supportdriven.com/] 👉 Follow Joy of Connecting Show on LinkedIn: https://www.linkedin.com/company/the-joy-of-connecting-show/ [https://www.linkedin.com/company/the-joy-of-connecting-show/] 👉 And get bi-weekly, actionable tips for building your network and connecting with meaning: https://thejoyofconnectingshow.substack.com/ [https://thejoyofconnectingshow.substack.com/]