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    Home»Lifestyle»From the Dugout to the Boardroom: Chris Cullen’s Playbook for Resilient Leadership
    Lifestyle

    From the Dugout to the Boardroom: Chris Cullen’s Playbook for Resilient Leadership

    Sandra PowellBy Sandra Powell5 September 2025No Comments5 Mins Read
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    When Chris Cullen walks into a room, he brings more than just a polished keynote or a neatly designed workshop deck. He brings the grit of a Division 1 baseball captain, the resilience of a professional athlete who fought for every inning, and the strategic discipline of a Fortune 500 sales leader who once delivered more than $100 million in capital sales. His story isn’t just about the stages he speaks on today. It’s about the journey from the dugout to the boardroom, and now to the global speaking circuit, where he is redefining what high-performance leadership really looks like.

    From the US Diamond to Global Audiences

    Cullen’s path began on the baseball diamond at Michigan State University, where he served as captain before moving into the Pittsburgh Pirates minor league system. The lessons from those years were simple but powerful: pressure is constant, adversity is inevitable, and the strongest competitors are those who control their mindset as much as their swing.

    After leaving professional sport, Cullen carved out a career in medical technology. At Stryker, he rose quickly, holding five different roles in eleven years across the US and Canada. By the time he was one of the youngest managers in his division, he had already generated over $100 million in revenue and built teams that thrived under pressure. For Cullen, the crossover between sports and sales was natural. “In both worlds, the scoreboard doesn’t lie,” he often says. “You can’t fake preparation, and you can’t hide when the stakes are high.”

    Building Win Within

    In 2023, Cullen founded Win Within, a mindset training company designed to help organisations rewire how they think about performance. The idea was rooted in a belief he had carried since his playing days: better thoughts lead to better outcomes. His clients now include global names such as Genentech, Qualtrics, Jersey Mike’s, USA Volleyball, Michigan State, and the University of Georgia Athletics. Each session, whether for corporate executives or student athletes, is built on the same principle — high performance starts with what happens between your ears.

    A Philosophy That Travels Well

    This summer, Cullen released his third book, I Get To, a simple but transformative philosophy built on gratitude and perspective. By swapping “I have to” for “I get to,” he argues, people unlock an entirely different level of energy, ownership, and resilience. The book combines neuroscience, personal anecdotes, and practical application. It has already caught the attention of teams searching for fresh language around engagement and perseverance.

    For British businesses grappling with burnout and disengagement — challenges just as prevalent here as across the Atlantic — Cullen’s work feels strikingly relevant. “We have nearly 60,000 thoughts a day, and 90 percent are repeated from yesterday,” he explains. “If those thoughts are negative or filled with obligation, we stay stuck. But if we shift to opportunity, we create momentum.”

    Beyond the Pep Talk

    What separates Cullen from the crowded field of motivational speakers is the way he packages complex ideas into stories and systems people remember. His signature keynote, Perform At Your Best, teaches resilience, confidence, and habit-forming as repeatable skills. Inspiring Others focuses on influence and leadership — principles he learned on both the field and in corporate boardrooms. And his I Get To perspective training has become a favourite for organisations trying to refresh culture without gimmicks.

    Testimonials underline his impact. At Genentech, a senior director praised his ability to “deliver tools that help us focus on what we can control and taught us how our thoughts impact behaviour.” Georgia Softball coach Tony Baldwin said, “Our team gets better week over week because of the curriculum he implemented.”

    A Compelling Voice

    Cullen is not the kind of speaker who reads off bullet points. His sessions are interactive, fast-paced, and infused with stories that connect — from gruelling Ironman competitions to tense hospital boardroom negotiations. He’s completed two Ironman triathlons (one just 48 hours after being hospitalised with the flu), run ultra-marathons, and founded a men’s health community. These aren’t side notes; they are proof points for his message that resilience is built in the moments most people want to quit.

    As a media guest, he’s equally compelling. Interviews flow with energy and authenticity, mixing data and narrative in ways that feel less like lectures and more like conversations. That blend makes him attractive to outlets covering business, sport, health, or culture. He’s a guest who can pivot from explaining neuroscience to telling a story about standing in the batter’s box against a 95-mile-an-hour fastball — and make both feel equally relevant to workplace performance.

    Why the UK Should Pay Attention

    With his speaking calendar now open for 2025–2026, Cullen is preparing to bring his message to new audiences across Europe and beyond. For British firms navigating hybrid work, stress-driven absenteeism, and the push for productivity gains, his approach — blending American sporting grit with universal performance science — could resonate strongly.

    Employee disengagement is not just a US issue. In Britain, surveys show rising stress levels, sharp drops in engagement, and mounting concerns about wellbeing. For Cullen, the fix isn’t more pressure. “It’s not about adding more metrics,” he says. “It’s about teaching people how to think differently. When you shift the story in your head, you change the story in your results.”

    Looking Ahead

    Cullen’s immediate focus is expanding the reach of I Get To and booking global speaking engagements. But long term, he sees an even bigger vision: reshaping how entire industries approach resilience. “Whether you’re an athlete, a sales rep, a teacher, or a chief executive, the mindset principles are universal,” he says. “If we can shift the language of performance at scale, we can shift cultures, and that’s when real change happens.”

    • Sandra Powell
      Sandra Powell
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