From Firewalls to Fairways: How a Career in IT Led Me to Golf

Ryan Drumheller grew up in Ovid, Michigan, a town of roughly fifteen hundred people, with no mentor, professional network, or clear path into technology. He could not have known that starting without a roadmap would become one of the defining advantages of his career. At twenty-nine, Ryan returned to college carrying more determination than certainty. What followed was not a straight climb. His career was shaped by relentless self-education, difficult leaders, painful setbacks, unexpected opportunities, and a refusal to let one bad decision determine the rest of the round. Over more than two decades, he earned more than 170 professional certifications, led technology organizations across multiple industries, built teams, launched a podcast, and helped create Dogleg Digital. Yet some of his most important lessons arrived far from the server room. Golf gave Ryan a language for everything his career had been trying to teach him: choose the right club for the situation, manage the course in front of you, accept the bad shot, make the recovery, and play the next hole with a clear head. Structured as a round of golf, From Firewalls to Fairways is the story of starting later, learning the hard way, leading through uncertainty, and building something worth leaving behind. Whether you are questioning your direction, rebuilding after a setback, or wondering if you started too late, this book offers an honest reminder: your score is not settled on the front nine. The back nine is where the real scoring happens.