A former guitar teacher of mine once told me, “If you’re the best player in the band, it’s time to find a new band.” His point was simple: growth requires friction. If no one around you is pushing you, challenging you, or showing you what’s possible beyond your current limits, it’s easy to fall into the trap of thinking you’ve made it.
Once you reach that plateau, you stop trying. You stop learning. You stop pushing yourself. You stop taking risks. You stop experimenting. You stop failing. You stop growing.
It’s comfortable until you look outside and realize the world has moved on. You’re still playing the same notes, but the music has changed.
Over the course of my career, I’ve worked with a wide range of teams: small startups, market leading orgs, and the all to frequent dysfunctional ensemble. I’ve come to realize that the environments where I grew the most weren’t the ones where I was the smartest or most experienced. They were the ones where I was surrounded by people who challenged me, pushed me, and made me feel like I had to step up my game.
Ask most people in tech what drives them, and you’ll hear a range of answers: mastery, impact, recognition, autonomy, purpose. Some want to be the best, full stop. But more often, people want to feel they’re progressing and contributing in a meaningful way.
The problem is that subjective measurements like “the best”, “the smartest”, or “the most experienced” are often based on local context. They’re relative, not absolute. They’re about comparison, not growth. This is exceptionally true in tech, where the pace of change is relentless and the bar keeps moving.
And here’s where it gets tricky: we’re notoriously bad at judging our own ability. The Dunning-Kruger effect reminds us that the less we know, the more confident we tend to be. It’s not arrogance. It’s a calibration issue. Socrates captured it centuries earlier: “I know that I know nothing.”
For me, the more I learn the more I realize how much I don’t know.
We are currently hiring, and I see this pattern play out frequently. They may not claim to be “the best” but they often have a strong sense of their own abilities. They’ve been told they’re high performers, and they’ve internalized that narrative. They’ve been in environments where they were the smartest person in the room, or at least one of the smartest. Yet their definition of “the best” often translates into being the most consistent, the safest, or the most senior — not necessarily the most curious, adaptive, or driven.
Many of these candidates truly believe they’re high performers. And in their specific context, they often are. But when they step into an interview loop at a faster-paced organization, the gap becomes clear. What counted as “excellent” before was really just “comfortable.”
It’s not a failure of intelligence. It’s a failure of challenge.
What’s striking is how people react to that realization. Some take it in stride. Others double down and try to explain away the discrepancy — dismissing the new environment as unrealistic, or assuming the problem lies elsewhere.
That moment is a crossroads. It’s a moment of reckoning. It’s a moment of truth.
Realizing you’ve overestimated your skill level is incredibly humbling. But it’s also an opportunity.
Some people sit with the discomfort and use it as fuel. They ask questions, seek feedback, find mentors. They stretch. They learn. They want growth.
Others… retrench. They justify, deflect, and rebuild a narrative where they’re still the best — and everyone else just doesn’t get it.
Unfortunately, once you’re sure you’re right, there’s nothing left to learn.
It’s like insisting your solo is perfect because everyone in your last band cheered, even though the new band is playing a different music style, in a different key, and in a different time. The result is a discordant mess.
The happiest I’ve been in my career wasn’t when I was holding everything together, serving as the source of all wisdom, or operating at the edge of burnout. It was when I was surrounded by people I could learn from. People whose work made me want to raise my game.
Those teams were collaborative, challenging, and generous. And that kind of environment doesn’t just produce better work. It produces joy.
When I thought about why I felt that way, I realized something important. I didn’t have to be the expert in the room — just someone worth playing alongside.
Now, since I have studied organizational leadership and leading innovation, I want to go a step further. As a leader - either formal or informal - how do I create that environment for others? How do I help them find their own band?
If you’re in a leadership role, your job isn’t to be the star of the show. In fact, if you are, you’re doing it wrong. Your job is to create an environment where everyone can shine. Where everyone can learn. Where everyone can grow.
How do you do that? You need to create a culture where growth is the norm, not the exception. A culture where people are encouraged to take risks, to experiment, to fail, and to learn. A culture where feedback is a gift, not a punishment. A culture where people are celebrated for their growth, not just their results.
That’s a tall order, but it’s not impossible. It requires intentionality, vulnerability, and a willingness to embrace discomfort. It requires you to be the kind of leader who is willing to step back and let others shine.
Finally, it requires being able to help someone find their new band when they’ve outgrown you. That’s not a failure. It’s a sign of success.
One of the best leaders I worked for told me when I was hired that he was hiring for people who would outgrow him and the team. I think of that often; it’s simple but powerful.
The goal isn’t to be the best. It’s to be around the best. To keep learning. To keep stretching.
So if you look around and realize you’re the strongest player in the band?
You know what to do.