Own Your Own Plan: The Cure for Imposter Syndrome | Between the Builds

In this reflective episode of Between the Builds, Chris Fay flies solo from his brand new studio to revisit last week's conversation with Admiral Sandy Winnefeld and unpack something nearly every competitive leader wrestles with at some point: imposter syndrome. Chris opens with honesty. Sitting across from a four star admiral, former Vice Chairman of the Joint Chiefs of Staff, and Top Gun instructor, then spending time in the fast pace of New York surrounded by towering accomplishments, he caught himself asking the same questions so many leaders ask quietly. Do I belong here? Am I worthy of this conversation? Am I doing enough? He shares how that feeling has followed him through the years, including time spent alongside highly accomplished CEOs in YPO who are buying, selling, and scaling businesses at a remarkable pace. That reflection lands right as Chris's own organization heads into strategic planning season, with the executive leadership team gathering to define where the company is going next. It's his favorite time of year, and it sparked the core idea of this episode: imposter syndrome usually isn't about the other person. It shows up when we lack our own plan, our own vision, and our own identity. Chris walks through the inputs that shape his personal vision, from keeping the business privately funded, to being home with his family while his kids finish high school, to protecting his health. Those choices define what success looks like for him, and they're different from what success looked like for Sandy. Once you own the inputs and the outcome, Chris explains, the comparison loses its grip. Highly successful people stop being a measuring stick and start being peers who pursued their own path well. The better question becomes how they set their vision and built toward it. Chris closes with two actions for the planning season ahead, a candid look at why he'll never monetize this podcast, and a preview of how the show will continue to evolve with new conversations and guests. Chris discusses: - What it felt like to sit across from a four star admiral and Top Gun instructor - How fast paced, high achieving environments can trigger imposter syndrome - Why competitive leaders are especially prone to comparing themselves to others - The real root of imposter syndrome: a missing plan, vision, and identity - How keeping the business privately funded shapes the company he chooses to build - Why being home for his family and protecting his health are part of his definition of success - Seeing highly successful people as peers instead of measuring sticks - Iron sharpens iron, and why you become who you spend your time with - The January 1, 2028 exercise for defining what success means to you - Why he'll never monetize Built With Purpose The Most Powerful Moment Chris describes a choice he gets to make every time he sits down with someone like Sandy. He can ask whether he's worthy to be in the room, or he can recognize that Sandy fought his own fight and pursued what he wanted from his life, and that it's okay if Chris wants something different. That shift turns intimidation into curiosity. Instead of measuring yourself against someone's success, you get to learn how they built a vision and achieved it. Key Takeaways - Imposter syndrome usually signals a missing plan, not a missing ability - It's okay to measure success differently than the people around you - Highly successful people are peers who pursued their own path, not a scoreboard - Iron sharpens iron; look closely at whether the people around you build you up or break you down - Planning season is for your life, not just your business Connect with Chris Chris Fay: LinkedIn /cjfay Built With Purpose: builtwithpurposepodcast.com