This article is part of a larger series exploring leadership with a journey mindset. Journeys invite us to see leadership not as a fixed destination, but as an unfolding process—one that begins with possibility, moves through challenges, and opens up new perspectives along the way.

Following my first year of being a camp counselor, I determined that adding a guitar to my toolkit was necessary. I had grown up with my mom leading singing with her guitar in church, around campfires, at retreats. Guitars belonged with singing around campfires. Plus, I knew it would make me look cool.

With a songbook, a chord chart, my mom’s acoustic nylon-string guitar, and determination, I began my quest in the evenings. Sitting cross-legged on my bedroom floor, biting my bottom lip, I would place finger by finger into place on the strings. Then, strum.

If I was lucky, a whole song line would stay on that chord before I needed to change. But when the page signaled a new chord, it was like a game of musical chairs. The music stopped, I checked the chart, carefully placed each finger, checked again, then strummed. Again.

Musical-chair-style guitar learning took far longer than I thought it should. I had been singing and playing flute for over ten years. I knew music. But chords and strings were so different. And where I had easily picked up flute, guitar was messy. I wondered: Was this the best use of my time? Would my brain, fingers, and voice ever align into something that sounded like a song?

Eventually, I could place my fingers without looking. The pauses grew shorter. Later came a new challenge: shifting from nylon strings to metal strings—no small feat. But by the time I returned to camp, I could lead songs around the fire and even play alongside other guitarists.

Six years later, Marc enthusiastically told someone I played guitar. Suddenly, I was signed up to lead in a weekly adult group. These weren’t campers—they were peers, maybe even more skilled than I was. All my insecurities rose up: I still couldn’t play bar chords, I transposed songs to avoid the dreaded F, and I strummed mostly by instinct. Yet despite a hundred reasons to say no, I didn’t want to miss the chance to grow. So I stepped in before my doubts grew louder.

Another six years later, I found myself leading music on Sunday mornings at church. My fingers and voice knew what to do so well that I could focus on the people, dynamics, and energy of the room. I could improvise, adapt, and even lead with my eyes closed.

Leadership Connection

That journey with the guitar followed a pattern: excitement at the start, frustration in the middle, and satisfaction at new levels of growth. It’s the same pattern leaders experience. We begin with energy, hit obstacles, doubt our abilities, and—if we keep going—reach new levels of confidence.

“Growth comes when you stay long enough for frustration to turn into fluency.”

Without recognizing the pattern, it’s easy to abandon the work too soon. Leaders who normalize the “messy middle” create space for perseverance—for themselves and for their teams.

Coaching Connection

Coaching helps surface these patterns. When a client says, “I feel stuck,” a coach can help them see: this isn’t failure, this is a stage. Recognizing patterns turns frustration into perspective.

Reflection and Practice

• Reflection: Think back on a time you stayed with the process long enough to break through. What helped you endure the messy middle then?
• Practice: Choose one of those same supports—patience, humor, encouragement, structure—and apply it now.

Journeys begin with a possibility – but they grow stronger when we stay with the pattern long enough to discover what’s on the other side.