Sister Kenneth and the Leaders Who See Us Before We See Ourselves

RIP Sister Kenneth Regan, a leader who made a difference in my life and so many others.

I learned a lot about leadership in conference rooms, board meetings, and classrooms as an adult.

But some of the most important leadership lessons I ever received happened much earlier — in the office of Sister Kenneth Regan, my principal and religion teacher at St. Mary’s Catholic School in Waco, Texas.

Sister M. Kenneth Regan CSC passed away on December 24, 2025, at 99. Even writing that feels surreal. She lived a long, faithful life, and she shaped more people than she likely ever knew — myself very much included.

When I was a kid, I spent a lot of time in her office. Talking too much. Being the class clown. Pulling pranks that I thought were hilarious at the time, to name just a few of my crimes.

If I’m being honest, I was scared of her. Not because she was harsh or mean, but because she was consistent. Clear. Grounded. She didn’t yell. She didn’t posture. She didn’t need to.

What I remember most is not the discipline — it’s what she said with it.

She would tell me she was disappointed in my behavior because she saw so much potential in me. At the time, that landed heavy. I didn’t fully understand it. I just knew I didn’t like letting her down.

As the years have gone on, I’ve realized how rare that kind of leadership really is. She didn’t see me only for who I was at that moment. She saw who I could be.

That’s something I write about often now — how leaders can get stuck in what I call the “Upside Down.” When fear, frustration, ego, or impatience take over. When we react instead of reflect. When we discipline without care or avoid hard conversations altogether.

Sister Kenneth never led that way.

She held standards. She enforced boundaries. But she did it with patience, humility, and a deep sense of purpose. She believed formation mattered. Character mattered. People mattered.

Looking back, I can see how many times she pulled me out of the Upside Down — even when I didn’t know that’s what was happening. She kept pointing me toward the Daylight. Toward responsibility. Toward self-awareness. Toward becoming someone who could use their energy and voice for good rather than disruption.

She didn’t give up on me. She didn’t label me. She didn’t lower the bar. She stayed present.

That is leadership.

Her life was a quiet masterclass in what it means to live virtuously and lead humbly. She didn’t seek recognition. She didn’t chase influence. She simply showed up, day after day, forming young people with care, conviction, and faith.

As I’ve grown into leadership roles myself — as a coach, a business owner, a father, and a husband — I find myself returning to her example more often than I ever expected. Especially when it comes to patience and to believing in someone before they believe in themselves.

Sister Kenneth also fought — quietly but relentlessly — to keep St. Mary’s Catholic School open. Long before I understood budgets, enrollment numbers, or institutional pressure, Sister Kenneth was doing the hard, unseen work of advocacy. She showed real guts. Perseverance. A deep passion for the mission she had been entrusted with. She didn’t walk away when things got difficult or uncertain. She stayed, she pushed, and she carried the weight because she believed the school mattered and the students mattered. Looking back now, I see that fight as another form of leadership — the kind that doesn’t make headlines but changes lives. The same steady conviction she used to pull me out of my own small Upside Down moments is what she used to protect a place that shaped generations, including mine.

My new book, The Upside Down Leader, is about helping people step out of the darkness and into clarity.

Sister Kenneth lived that work long before I had words for it. She didn’t lead loudly or for recognition. She led with steadiness, conviction, and faith. She was Daylight for so many of us — often when we didn’t realize we needed it. I am deeply grateful that she saw something in a talkative, mischievous kid and chose to invest anyway. Her leadership, her patience, and her belief continue to shape the leader and person I am today.

Rest in peace, Sister Kenneth.

Your leadership lives on in more ways than you’ll ever know.