Growth Requires the Courage to Be an Amateur Again Why learning cultures outperform comfort cultures

Growth Requires the Courage to Be an Amateur Again
Why learning cultures outperform comfort cultures

Many organizations talk about growth, innovation, and engagement—but quietly struggle to create environments where people feel safe enough to learn again. Somewhere along the way, being “experienced” replaced being curious. And yet, the strongest organizations I’ve encountered share one uncommon trait: they are led by people willing to be amateurs again in pursuit of progress.

I was reminded of this recently in my own work.

The other day in my studio, I sat between two paintings that couldn’t have been more different. One demanded precision—architecture, proportion, patience. The other invited freedom—color, movement, interpretation. Despite years of experience, both made me feel like a beginner again. And it struck me that growth—whether in art, leadership, or organizations—often begins the same way: by stepping into unfamiliar territory.

Growth Begins Where Comfort Ends
If everything feels easy, nothing new is happening. A leader stepping into a new role. A team adapting to new expectations. An organization navigating change it hasn’t faced before.
In each case, growth requires letting go of certainty and embracing learning. Discomfort isn’t a sign that something is wrong—it’s often evidence that progress is underway.

Discipline Beats Inspiration
Showing up consistently matters more than waiting to feel ready. Organizations don’t improve because of a single initiative or moment of insight. They improve because people show up day after day—trying, adjusting, and learning. Whether it’s developing leaders, strengthening culture, or rebuilding engagement, discipline creates momentum long before confidence catches up. 
Consistency turns amateurs into capable contributors—and capable teams into exceptional ones.

Learning Requires Permission
Cultures grow when leaders model curiosity, not perfection.
The healthiest organizations are led by people willing to say, “I don’t have all the answers.” When leaders ask questions, listen, and invite others into the learning process, it gives teams permission to grow. That permission fuels trust, engagement, and ownership—far more effectively than directives ever could.

Looking back, the moments that stretched me most—both personally and professionally—were rarely comfortable. But they were always meaningful.

So here’s the question I’ll leave you with:  What are you willing to be an amateur at?