One of the ironies of living in a more technological age is that we also are experience greater loneliness and disconnection. Additionally, there can be a paralyzing sense of performance and judgement as people continuously put their lives out into the world through the posts that they share. As a result, the more we get pulled into the online world, the most we could use getting back to being offline. Howard Lewis is spearheading this movement through his Offline Dinner Parties and his book The Joy of Offline. We talk about what prompted this book, and how his offline parties helped to create great connection, curiosity, and risk taking. He describes how his hands-off approach helps to create an inner momentum that carry these event forward. He also discusses why it is important to have people from diverse backgrounds and interest to help break barriers and boundaries. Finally, we talk about his life in finance and the art world, and what lessons he carries from those into trying to break the grip of online.