Over the past few weeks, I found myself doing the same thing twice.
After weeks together over winter break, I drove to the airport with Stella as she headed to Copenhagen for the spring. A few days later, I did it again with Gigi to drop her off for her spring semester at NYU. Same airport. Same routine. Same mix of excitement and weight that comes with watching your kids walk through security and disappear into the crowd.
Watching them walk away, I couldn’t help but think about the stories they’re starting to write right now. The kind you only get at that age. Stories built around independence, unfamiliar cities, new experiences, and the belief that everything is possible because nothing is settled yet.
Those stories are powerful. They should be. They’re meant to be loud. Idealistic. Forward-looking.
I know that because I had my own version once. A one-way ticket to New York. A head full of belief about who I was going to become and what that move would unlock. Those stories weren’t naïve. They were necessary. They gave me courage when I didn’t have much else. They focused me. They pushed me to take risks I wouldn’t have taken without them.
And for a long time, those stories did exactly what they were meant to do.
What I’ve come to realize, though, is that the challenge isn’t having those stories. The challenge is recognizing when a story has done its job AND when a new chapter is quietly asking for a different one.
In our careers, those stories often sound practical. Responsible. Even wise. “This is just how the industry works.” “This version of me is reliable.” “I should be grateful for this role.” “If I stop doing this, everything falls apart.”
These stories aren’t wrong. They were formed in a different context, when the risks were different and the version of you telling them needed a specific kind of certainty. Back then, they provided structure. They created momentum. They helped you move forward.
But stories don’t automatically update when you do.
What I’ve noticed is that feeling stuck usually isn’t about a lack of opportunity. It’s about continuing to explain yourself using language that no longer fits. We stay loyal to narratives that once kept us steady, even when they no longer reflect what we actually want.
Outgrowing a story doesn’t mean rejecting your past or dismissing what it gave you. It means recognizing that gratitude and growth can coexist. You can honor the role a story played without letting it dictate what comes next.
This is the subtle turning point. The moment you realize the future doesn’t require a new identity… just a new explanation. One that makes room for who you are now, not just who you needed to be then.
This Week’s Question: What story about yourself or your work once helped you move forward and may now be ready to evolve?
“Your 50” is a 50-week reflection series about realigning, activating, and expressing what comes next.