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For years, I was the CEO of the company I founded. Just saying those letters — CEO — has a gravity to it, a sense of significance. I liked being needed in that role and the attention it garnered.

When the company grew to about twenty people, I realized that I no longer had the skills to take it further. Managing people and building processes wasn't where I thrived. It was someone else's zone of genius rather than mine. I resisted the transition but I knew it had to happen, and it was uncomfortable. Letting go of that identity felt like the death of my career and its meaning in my life. And in a way, it was.

Buddhism and the Sense of Self

Buddhism invites us to examine our relationship to the categories with which we confine ourselves. You may be a father, a mother, a friend, a happy person, an anxious person, an attorney, financial advisor, a meditation teacher, a business person, coach, a brother, sister, a son — these are identities, and they're not a problem in themselves. The problem comes from clinging to them so tightly that we inadvertently crowd out or limit who we might become.

The mind likes these "I am" boxes. They give it a sense of belonging, a kind of solidity. But that solidity comes with a cost. When we over-identify with a role, we start to see the world only through that lens. The best attorneys I've worked with see things from a legal and a business perspective. That wider view makes them more valuable and less replaceable. One's identity, held loosely, becomes an asset because the box has no sides. Held tightly, it becomes a box with thick walls.

And there's a practical dimension to this worth considering: if you've built your whole sense of self around a role, what happens when that role changes? When circumstances shift, when AI takes over a task you've always done, when you see a new opportunity — the person with a wider aperture for who they are recovers faster, adapts more readily, and recognizes that it's time to graduate from the old and commence something new.

Graduation isn't something that only happens after high school or college. It's happening as you're reading this. Whether you're 32 or 72, there is probably something you're ready to leave behind — a way of working, a limiting money story, an identity that once served you but is now ready for an upgrade.

Here's one practice worth trying. Write a letter today to yourself five years from now. Congratulate your future self on what you were able to achieve in that time frame, and then trust your wisdom to describe how you did it. How did you soften your grip on the identity that had been holding you back? What did you graduate from and what did you commence?

You'll often find that when you ask yourself these kinds of questions, answers come from a brand new part of the brain.

Conan O'Brien gave the Harvard commencement address this year. He told the graduates: "If you carry your victories lightly, other qualities — kindness, originality, courage, humor, and humanity — have room to emerge." 

That's the kind of graduation I'm talking about—not graduating away from what you've built, but opening to a larger version of who you are.