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

“One of the hardest things in deconstruction, hard life stuff, or failure is the isolation and feeling alone. Feeling like I’m the only one. No one’s ever been here before. No one’s ever felt this. It wreaks havoc on your life to feel so isolated.”

Episode 02

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.


Episode Transcript

Hi everybody. Jen Hatmaker here, your host of the For the Love podcast. Buckle up and welcome to the show. We’re in a series called For the Love of Facing Your Fears. Today’s conversation with our guest was just super special. We went 40 minutes longer than we had planned because the conversation was so rich and so full and we barely scratched the surface. We’re talking about a topic near, dear, and personal to me today, which is facing the fear of questioning or even departing from a faith that you’ve always known. 

Now, Those of you who have been with me in our little For The Love community here for a while have seen the windy, up-and-down relationship I’ve had with faith systems and organized religion. I’ve asked hard questions. I’ve challenged my own beliefs, reshaped, reevaluated, and reexamined. So trust me when I say; anyone who was in that space doing this hard and sometimes scary work of testing the boundaries of faith, you have me standing firmly behind you and cheering you all the way. You are going to love today’s episode. Get somewhere where you can listen and pay attention. 

My mid-nineties Christian pals listening will certainly remember the contemporary Christian band Caedmon’s Call. They had a sort of innovative folk alternative rock sound. There was just nobody like Caedmon’s at the time in the genre; a soundtrack for that generation, truly. Derek Webb was an absolute pillar of the band. He was the Songwriter and lead guitarist. Caedmon’s Call got ten GMA Dove Award nominations, three wins, and six number-one Christian radio hits, for about a decade. In 2003, Derek left Caedmon’s Call to pursue a solo career.

One thing I love about Caedmon’s Call is that they were dubbed a thinking Christian band, and Derek’s lyrics, in particular, contributed to that. Highly introspective, led to lots of deeper conversations. Certainly, all of his music post-Caedmon’s Call is in that space. I know it’s kind of a buzzword now, but before the term “deconstruction” was kind of a part of the zeitgeist, this was Derek’s experience. He was trailblazing this for us in a lot of ways, and he reexamined his faith in a pretty impactful way. He doesn’t identify with some of those evangelical labels any more.

I love to hear him talk about this. Derek’s shaking things up which I understand. I’m not going to steal the thunder from the conversation but just this year at the Dove Awards, he made quite a splash. He attended wearing a dress along with queer singer Grace Baldridge and drag queen Flamy Grant. If you were anywhere near Christian social media, you saw this. It’s a lovely conversation and kind of a beautiful, inclusive intention around that peaceful disruption. We talk about everything. Evolution of beliefs. We talk about the Christian music industry. We talk about the label “Christian” as a marketing term. We talk about what it means to fail, what it means to reexamine, what we keep, what we hold. This episode is packed. This could have been three episodes, which is why it’s longer than normal. I promise you, it’s worth every single second. Without any further ado. I hope you love this conversation with the delightful Derek Webb as much as I did.




Caedmon’s Call 

Aaron Tate’s Website 

Second Baptist Church 

She Must and Shall Go Free – Album by Derek Webb

Essential Records

Third Day 

Jars Of Clay 


The Prayer of Jabez 

Wedding Dress by Derek Webb 

Grace Point Church 

The Jesus Hypothesis 

Boys Will Be Girls Music Video

Grace Semler Baldridge

Flamy Grant Instagram

Drag Queen at Christian Music Awards Sparks Backlash (Newsweek Article)



The For the Love Podcast is a production of Four Eyes Media,
presented by Audacy.

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