Some days do not arrive with the triumphant swell of “Gonna Fly Now” from Rocky. Some days move with less momentum and more contemplation.

Over the last several months, I have been seeking connection, meaning, and understanding as I wrestle with the mixed emotions of grief and empowerment. Walking away from a role that was breaking my heart and impacting my health required courage. There are days when I feel the strength of that decision. There are other days when I am reminded of failures, shortcomings, and mistakes.

Miles Davis once said, “Do not fear mistakes. There are none.” During a concert in the 1960s with his Second Great Quintet, that philosophy became visible in real time. Herbie Hancock struck what he believed to be a wrong note on the piano. He braced for Miles to glare at him or turn away. Instead, Miles responded by playing notes on his trumpet that reframed the so called mistake. He did not correct Hancock. He absorbed the moment and transformed it. In doing so, he gave Hancock belonging and permission to continue.

I have written before about this moment. I have also reflected on similar moves by Duane Allman and other musicians who leaned into mistakes rather than shrinking from them. These moments have long stood for me as emblems of human centered leadership. They demonstrate that belonging is created not by perfection, but by response. The best leaders know how to meet imperfection with presence.

I remember a similar moment during my first gig with The Skydogs. In the middle of an energetic rhythm section, my hand slammed awkwardly against my guitar. The band paused for a split second. What could have been embarrassment became improvisation. I began striking the body of the guitar like a conga drum. The band joined in, and what began as a mistake turned into a wild percussion breakdown that I still smile about more than thirty years later.

Leadership requires that same posture.

We operate in spaces driven by metrics, evaluations, and constant measurement. Perfection becomes a quiet trap that drains the marrow from leaders who care deeply. When mistakes happen, the instinct is often to retreat, self criticize, or withdraw.

Leadership is lonely on certain days. When failure visits, that loneliness can intensify in ways that feel overwhelming.

Yet failure is not proof that we are unqualified. It is proof that we are engaged. Mistakes are not verdicts. They are invitations to respond differently.

What might happen if we made that move the norm rather than the exception? What would it look like to build cultures where leaders instinctively play the wrong note back with grace? How might our schools, teams, and organizations change if belonging was reinforced in moments of error rather than withheld?

We need more leaders who know how to transform a misstep into momentum. We need more pauses in the mania. We need more small moments of belonging that remind us that growth does not require perfection.

Leading while human means accepting that we will strike the wrong key from time to time. What matters is how we respond, and how we respond to one another.

Today I am choosing to keep playing.