I’m Sean Caldwell, a Career Ownership Coach with The Entrepreneur’s Source, where I work with experienced professionals who are evaluating whether the careers they’ve built still align with the lives they want moving forward.
Over nearly 30 years in Information Technology leadership, I managed database, application development, and operations teams across consulting, aerospace and defense, government, and financial services. Along the way, I saw how quickly industries evolve, how fragile “career security” can become, and how often talented professionals postpone important career decisions until burnout, restructuring, or frustration forces the conversation.
I’ve spent decades hiring, mentoring, and leading professionals through growth, uncertainty, and organizational change. Those experiences shaped how I approach coaching today. My role is not to push people toward a specific outcome. It’s to help them evaluate their situation honestly, understand the tradeoffs in front of them, and think more intentionally about the future they want to build.
Much of my leadership philosophy was also shaped outside the workplace through more than 20 years in Scouting. During that time, I served in leadership roles ranging from Assistant Scoutmaster to District Committee Chair and also instructed within Wood Badge and Powder Horn leadership programs. Scouting reinforced something I still believe strongly today: meaningful leadership is rooted in service, preparation, and helping people grow into what they’re capable of becoming.
Today, I work with professionals across the U.S. and Canada who are navigating career transition, evaluating business ownership, or reassessing what they want their work and lives to look like long term. I believe so much in this path, my wife and I are also in the process of opening a second business in the coming months with Vertica Fitness.
I live in the Dallas–Fort Worth area with my wife, Beth. Outside of coaching, I enjoy camping, astronomy, cycling, history, and Formula One racing. I also write a blog called Here Be Dragons, where I explore entrepreneurship, uncertainty, and the realities of building a different kind of future.
We have three children, a son-in-law, a grandson, along with a dog and three cats that keep life interesting and entertaining.