Leaning Into Vulnerability

While I love all the convos I have with people, I REALLY love the ones where I am talking to a fellow eldest child/sibling because there is an unspoken solidarity between us eldest kids. Today, I have a convo with my friend, Tom Farley, about all the things. We explore the complexities of grief, loss, and the unique bond shared by siblings who have experienced the death of a brother. We discuss the challenges of navigating family dynamics, the journey towards true vulnerability and authenticity, and the role of humor throughout it all. I hope you enjoy it!

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Tom Farley grew up in Madison, WI, and graduated from Georgetown University with a degree in Marketing. He began his career in banking and finance before running The Chris Farley Foundation (1999–2012), a nationally recognized nonprofit focused on substance abuse prevention. Through humor-based programs, he helped young people build communication skills and create supportive environments. In 2008, Tom co-authored The Chris Farley Show, a New York Times bestseller about his late brother, comedian Chris Farley. He has appeared on The Today Show, Good Morning America, and Larry King Live to discuss addiction and recovery. Now in recovery himself, Tom is a passionate advocate for mental health and addiction treatment. He works at Recovery.com as Community Outreach Director, connecting people with the resources they need to heal. As a speaker, he shares his journey to break stigma, inspire hope, and foster connection. Tom lives in Madison, WI.