This week, Matt is joined by creator Benjamin Chipman for a conversation about navigating your twenties when everyone else seems to have it all figured out.


From growing up in New England and navigating Boston’s unique gay scene to graduating during COVID and entering adulthood in a world full of uncertainty, they reflect on the experiences that shaped them. They share the biggest lessons they’ve learned in their twenties, discuss building a career outside of your 9-to-5, and debate whether Boston or New York really comes out on top.


Plus, they answer listener submissions about quarter-life crises, career anxiety, relationships, and the pressure to have your life together before you actually do.

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