On this Monday Moment segment, John O’Leary shares how to be sure your ambition aligns with your values, relationships, and long-term significance.
Years ago, I spoke with 40 business owners. The goal of the event was to bring together some of the highest achievers, connect them with one another, and expand their businesses and their lives.
Wondering what success even meant to them, I kicked off the session by asking what they would do professionally if they could achieve anything and knew they could not fail.
After a moment of reflection, a brave gentleman stood and proudly announced, “I’d make it big. I mean, like really, really big!”
He wanted to increase sales, expand personal accomplishments and significantly achieve more success than any of his friends or former classmates.
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This conversation was eerily similar to one I was part of almost a decade earlier with another gentleman. He, too, had strived to “make it big. Really, really big.” The difference was that the conversation with him wasn’t taking place in a boardroom with a lifetime of possibility in front of him. No, this conversation took place in a hospital room with a lifetime of regrets staring back at him. Let me explain.

