Moving from Insider to Outsider: Derek Webb’s Peaceful Disruption

Isn’t it fun to be part of the in-crowd? Where you can connect with people who are of like minds and spirits, where everyone seems to be headed in the same direction? But what if you start having nagging questions as an insider that don’t seem to get resolved, and even worse, are met with disdain or fear from other members of your group? This can be a scary place for so many of us. For the purposes of our conversation today–we’re talking about when it happens in religious spaces. For years, singer/songwriter Derek Webb was very much on the “inside” of what was happening in Christendom as a top selling, award winning Christian artist, songwriter and worship leader. It took a few disruptions to his own life that sent him down the road to evaluating his faith, his beliefs and how he wanted to move forward with the new information he’d gained. Now, decidedly an “outsider” who tries to still take up space in the Christian zeitgeist to potentially model a different way of living, Derek has gone on to record solo albums and also work with artists that aren’t typical to Christian music–like drag queen Flamy Grant—with whom, incidentally, he attended the Gospel Music Dove Awards in 2023 (and who also had a number one Christian song pop up on the charts), with the intention of making people who are Christian and LGBTQ+IA feel less alone. In this episode, Jen and Derek compare their journeys as “peaceful disruptors,” what it cost them and what they gained in the process.