Most of the articles I read about leadership competencies for future leaders say similar things — resilience, adaptability, problem-solving, creativity, collaboration. What strikes me is how similar these are to the very competencies we’ve tried to teach young people in schools. At one point, we called them “21st century competencies.” In my book, Where The Trails Lead , I write about how certain physical activities naturally foster leadership skills. Skateboarding, for examp

Writing my book, Where The Trails Lead , has led to so many new opportunities. Sharing stories from my book in keynotes and leadership workshops....and exploring how lessons from the mountains can guide us through uncertain times has been so much fun. I’ve been privileged to speak with leaders across corporate, education, and nonprofit sectors about what drives effective leadership, resilient teams, and purposeful cultures. My talks draw from decades of experience in mission-

Over the years, I’ve discovered one of the best ways to have meaningful conversations, whether with teenagers or team members, is while moving forward together. When my children were teenagers, the best conversations we had were in the car. No eye contact required, no pressure. Just the road ahead and space to talk. That same principle carried into my leadership. I learned that walking and talking with employees was far more effective than sitting across from them in an offic

In October I spent three incredible weeks of hiking and cycling through Andalucia, Spain. As I settled back into my routine, a colleague asked, “What do you think about as you cycle up those long hills, the ones where it’s probably faster to walk than to ride?” For me, those climbs feel meditative. There’s a rhythm that quiets the noise and opens space to reflect. I think about how I want to live more deliberately and continue working with leaders who are authentic, curious,

A recent LinkedIn connection asked me this simple but thoughtful question. I had to sit with it for a few days. In 2026, I want to continue working with clients who are genuinely committed to effective leadership and delivering real impact in their sector. The work I enjoy most through  Rudy Massimo & Associates  is with leaders who care about how they lead, not just what they achieve. For me, leadership has always been about authenticity and integrity....especially when deci

Some of the most important lessons in my life didn’t come from a classroom or working in a corporate environment...they came from travel. Travel teaches us through moments both big and small, by standing in unfamiliar landscapes that quietly shift our sense of scale, and by listening in communities that see the world differently than we do. It teaches us around shared tables as well, through meals, mangled languages, laughter, and the realization that when we slow down and pa

Looking back on Where The Trails Lead, I write about adventures, relationships, and leadership, but if I’m honest, the throughline has always been simpler, and deeper....creating opportunities for young people. In 2019, I spent a week in Wenchang, China with Denny Chan, Chairman of the Board of a rural school. What began as a visit quickly turned into full immersion. Denny put me to work, teaching in classrooms during the day and introducing rugby in physical education classe

Sometimes we reach what feels like the end of the trail. A role concludes, or a chapter closes. A goal we’ve worked toward for years is suddenly behind us and the future feels uncertain.   When that happens, it can feel unsettling, like the map has gone blank. In my book, Where The Trails Lead, I write about the importance of returning to basecamp from time to time. Not retreating in failure, but pausing with intention. Basecamp is where we take stock: What have we learned? W

Leadership lessons often come from unexpected places, and my recent knee replacement journey proved to be one of those unexpected...

Being an environmental educator in today’s world feels like you are asked to stop a rushing river armed only with a teaspoon. There are...

As I sat down to have my first cup of coffee this morning, I began to reflect on the many individuals who have influenced me as a leader....

ALIVE is an acronym that stands for Adventure, Leadership, Individuality, Values and Empowerment. They are an organizational affiliate...

"Literacy is a bridge from misery to hope. It is a tool for daily life in modern society. It is a bulwark against poverty, and a building...

The word courage comes from a Latin root cor- which means heart. How commonly do we hear people say, “listen to your heart and it will...

Ten leadership lessons from Shackleton’s Endurance Expedition are as relevant to today’s organization, as they were over 100 years ago.