Subject: Derek Webb
Location: Nashville, TN
Domain: Independent Music, Songwriting, Entrepreneurship
Project at Time of Interview: Ongoing touring
Format: Transcribed telephone conversation
Date: 2018-07-16
Introduction: This was my third recorded conversation with Derek Webb in a five-year span. By this point, a working familiarity had settled into the exchange, allowing the questions to move more directly into complexity without extended setup.
At this stage of my work, I was beginning to test larger conceptual frames against the particularities of individual practice. Derek met those questions with his usual openness, articulating dimensions of craft, sustainability, and departure that had not surfaced in our earlier interactions.
Ryan Brymer:
I was listening to Seth Godin’s Linchpin on audiobook, and he quoted Steve Jobs: “Real artists ship.” Meaning, they put product into the world—anyone else is just a dreamer or ideator. That sent me down a line of questioning about how this applies in business as much as art. I don’t make art, but I know a lot of people who do, so I started making phone calls.
For each conversation, I picked a quote I thought would resonate with the person. For you, I chose one from Angela Duckworth’s Grit. She says that for beginners, novelty comes from anything new, but for experts, novelty comes from nuance. It reminded me of you talking about your daily tea ritual. How does that idea—novelty through nuance—play out in your career and in the careers around you?
Derek Webb:
Wow. What a great quote. My brain is already running circles around it.
I used to meet with a small group of friends here in Nashville—a writer, a speaker, a photographer, a marketer. We were all trying to stay focused on the work that mattered, and we constantly had to pull each other back from the temptation to chase novelty. These were all guys with more than ten years each in their fields, firmly in the “expert” category. And yet the main work we did for each other was exactly what that quote describes: resisting the pull toward something shiny and staying with the familiar work that actually mattered.
The hardest work—writing a hundred more pages, spending six hours in the studio chasing something you might or might not find—was always the work we avoided. It’s easier to chase a new idea because the new idea doesn’t carry the emotional baggage of familiar stuck points. But you can waste a whole life—and a whole talent—chasing new ideas.
I have friends in Hollywood whose entire careers are in pilot development. They write outlines, treatments, pilots, and maybe one in a thousand becomes a show. They’re constantly creating things that never get born. Same in Nashville: I know artists who have spent their whole careers “in development”—writing songs, working with producers—and never releasing anything. And you can make a decent living doing that because labels only need one hit to subsidize the nine that fail.
Ryan:
And with those new things, it’s easy to get a quick high and feel like that’s success—just dipping your toe in and calling it a win.
Derek:
Exactly. A “win” at that stage is often just learning four new things in two hours by Googling. And you feel great—but it’s not the work.
Ryan:
So at your stage now, how do you define success when you know that 90% of what you make may never “hit”?
Derek:
I’m wired as much businessman as artist—maybe more. And honestly, the only reason I’ve made a living in music for almost twenty-five years is not because I’m freakishly talented. I’m not even middle of the pack among my friends here. It’s because I’m tenacious, adaptable, and a decent businessman.
I run lemonade stands. I take whatever mess I have in front of me, toss a grenade, walk into the rubble, and figure out what I can make from it.
My definition of success has changed. It used to be record sales or chart positions. In my old band, a “bad” first week was selling ten thousand copies. I don’t sell ten thousand copies in a whole album cycle now. But my metric has shifted. I have two kids—nine and eleven. Part of success now is: can I close my laptop and actually be with them? Am I maintaining friendships? Am I healthy and not grinding myself into dust? Hustle is fine—but hustle unto what?
Ryan:
In the office world, you often work on things you didn’t choose. When songwriting duties began shifting around album four or five in your old band, how did you stay creatively engaged while playing someone else’s material?
Derek:
It’s tricky. But some of the greatest artists who ever lived never wrote a song—Sinatra, for example. His genius was interpretation. You can make an artistic statement using other people’s work. But the real question is how you’re wired.
Some people are fulfilled supporting someone else’s vision. Others—like me—are not. That’s why when songwriting responsibilities began shifting in my old band, I eventually left and started making solo records. I wanted to say more, not less. Knowing how you’re wired is everything.
Ryan:
That kind of self-knowledge seems to require a lot of soul-searching.
Derek:
It really does. Jeff Goins once said, “The most miserable I ever was in my life was when I was most successful at the wrong thing.” Failure isn’t the worst thing. Success at the wrong thing is.
A lot of people are pushed toward being “the leader” or “the star,” but they’re not wired for it. Culture rewards the wrong things.
Ryan:
I could derail us on that for an hour. One more question: when an idea falls flat with your audience—when someone you expected to resonate doesn’t—how do you deal with that disappointment?
Derek:
I’ve always said I’m comfortable churning a quarter to a third of my audience every year. The world changes, I change, and the people listening change. That’s natural.
The danger is getting anxious about losing people and trying to win them back by course-correcting your work. That never works. You can’t go backward. You can only move forward and hope for a future point of resonance.
The ones who stay—I know their names, their spouses, their kids. That’s rare, and I value it deeply.
Ryan:
It sounds like the only real guarantee is to keep working, not to expect the same people to follow forever.
Derek:
Exactly. And losing people never feels good. It always matters to me. But I’m grateful they were with me at all.
Ryan:
Let me ask one final question. You’re the only one I know from Caedmon’s who’s still doing this full-time. How do you walk away from a fifteen-year career?
Derek:
It was slow—like the boiling-frog thing. Leadership, vision, conscience became decentralized. No one knew who was steering. Everyone assumed someone else was.
And honestly, I lacked perspective. I wasted opportunities. I wish I had worked harder. I wish I had realized how significant the moment was instead of taking it for granted. But looking back, I think we did the best we could with the maturity and resources we had.
Now my vision outruns my opportunity—the opposite of back then. And maybe that’s permanent. I’ll always have something to say, and I’ll always be grateful for whatever platform I have.
Ryan:
That’s fantastic.
Derek:
Yeah—and that doesn’t have to be off the record.
Reflection: This conversation unfolded with a level of mutual familiarity that allowed the questions to move quickly into complexity without preamble. At this point in my work, I was beginning to press more intentionally into the tension between execution and identity, between longevity and visibility, between success and sustainability. Derek met those questions without abstraction. His answers returned repeatedly to wiring, cost, and the quiet negotiations that shape a career over decades rather than seasons.
What stayed with me was not any single insight, but the steady refusal to romanticize either success or departure. The language of “vision outpacing opportunity” gave a name to a condition I would later recognize elsewhere: the persistence of vocation without the guarantees of scale. This exchange marked a maturation in how I listened – not for aspiration, but for the practical theology of staying.