How We Connected

Friendship Isn't Magic: Jessica Gifford, Founder, ProjectConnect

September 15, 2026·51 min
Episode Description from the Publisher

Jessica Gifford grew up in a tiny community of hippies, peace activists, and draft dodgers who built their own one-room schoolhouse. From kindergarten through eighth grade she was with the same 15 kids, so she never learned how to meet people. Her fix came at college: become the RA. It's easier to create the community you want than to break into one that already exists.Years later, as a social worker on college campuses, a survey crossed her desk showing loneliness rates off the charts. What they were doing wasn't working. So she built ProjectConnect, a program now used by more than 100 organizations, on the idea that friendship isn't magic. Jessica boils it down to three practices: sharing, caring and repairing. And the conditions matter: an hour of icebreakers between strangers who never see each other again is, in her word, pointless.Jessica's newest program is a 30-day challenge of acts of social courage. Do the awkward thing on purpose, because awkwardness is often the first step to connection.Over at the Chamber, Aaron and Charlotte workshop the Chamber's new message out loud, and Aaron previews Pickle at the Palms, where his Oura ring ruled that a pickleball session had earned him a couple of extra desserts.00:00 Welcome to How We Connected06:17 Sharpening the Chamber's Message14:18 Meet Jessica Gifford16:35 From Social Work to Project Connect22:15 The Arthur Aron Aha Moment25:50 Six Conditions for Connection31:16 What Makes an Organization Invest36:29 Advice for Leaders46:04 Reflection---The most creative artists in America right now aren’t in galleries. They’re in your neighborhood. How We Connected is a front-row seat to the social artists rebuilding human connection. Hear inspiring stories about roller skating crews, bad art clubs, jousting societies, city saunters, Georgian dinner parties, catch-playing challenges, midnight runners, and picnic societies. Hosted by Charlotte Massey and Aaron Hurst, co-founders of the US Chamber of Connection.Aaron Hurst is the co-founder of the US Chamber of Connection. He’s a longtime entrepreneur focused on purpose and community. He founded Imperative and the Taproot Foundation and wrote The Purpose Economy. Charlotte Massey is the co-founder of the US Chamber of Connection and leads community programs nationally. A Forbes 30 Under 30 honoree and former organizer and founder, she works at the intersection of civic life and entrepreneurship.Connect with Uswww.chamberofconnection.orgJessica Gifford, Founder and Chief Connection Officer, ProjectConnectJessica grew up in a small community of hippies and peace activists, sharing a one-room schoolhouse with the same 15 kids from kindergarten through eighth grade. She learned to make community by creating it, first as an RA at Antioch College. She became a social worker, earned her master's at Smith College, and spent years leading mental health promotion at Amherst College. When campus surveys showed loneliness off the charts, she built ProjectConnect, a six-week program that turns Arthur Aron's research into a repeatable recipe. More than 100 organizations have used it, from colleges to corporations. Her latest challenge invites people to commit 30 days of acts of social courage, because awkwardness is often the first step to connection.Learn more: https://projectconnect-us.comHeylohttps://www.heylo.comHeylo is a community-management platform built for real-world groups of every kind, giving leaders a clean, branded home base to run events, manage members, communicate clearly, and handle payments without friction. It brings scheduling, RSVPs, waivers, announcements, topic-based chats, and membership tools into one place so clubs, teams, and interest groups can stay organized and connected without the noise of traditional social platforms. Hosted on Acast. See acast.com/privacy for more information.

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