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Hagerty Group

Traverse City, MI










CEO, Former YPO Chair, and Thought Leader, McKeel Hagerty Redefines the True Nature of Success in the Modern World

McKeel Hagerty noticed a funny thing about people: we’re all inclined to accept, agree, and believe certain platitudes or conclusions because doing so makes things easier, or better suits our personal narratives about ourselves, our work, and our lives. In short, he noticed that we’re quick to impose limitations on ourselves, despite our boundless capacity for hope, ambition, and optimism.

McKeel’s innate curiosity led him to one question: why are we so quick to give up on our dreams and the people we always wanted to be? He had to discover what keeps people “bound.”

In 1995, when McKeel returned to Hagerty, the small local insurance agency, started by his parents, Frank and Louise, he wasn’t handed a director role or some cozy spot at the top. He got started in marketing, paid his dues along the way, and earned his role as CEO.

As leader of the company, he imported the lessons he learned while earning a master’s in Eastern Orthodoxy from Saint Vladimir’s Orthodoxy Seminary studied Philosophy and the Classics at Boston College to expand the business and turn Hagerty into an automotive brand dedicated to the love and protection of driving and the world’s largest provider of specialty insurance to collector car enthusiasts.

The success of Hagerty and McKeel’s experience as YPO Chairman had him asking broader questions about how we approach life and success in our increasingly technological age, one in which likes and hashtags can replace accomplishment and friend requests can replace human connection.

Ultimately, he concluded, we let other people define success for us. It’s not until we begin to assume leadership over our own lives, and live our own definitions of success, that we can flourish. It’s not until we stop measuring growth by material externalities and seek to grow our inner-self that we can become boundless.

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