What drives us?
This week I’m visiting family and friends in Connecticut and Nantucket, and I couldn’t help but think about the childhood memories that shaped me.
Back then, Nantucket was where so many New Canaan families spent their summers. To me, it represented a world I desperately wanted to belong to.
One memory still makes me think and reflect.
I was in fifth grade and wore my favorite Marona rugby shirt—the “it” brand at the time. By pure coincidence, one of my crushes, showed up wearing the exact same shirt.
I thought maybe, just maybe, we’d laugh about it.
Instead, he looked at me with complete disgust.
I didn’t fit the part. I didn't fit in.
I had dark circles under my eyes from too many sleepless nights. I was the only kid with divorced parents, living between two homes, trying desperately to belong.
The only place I felt I could compete with the preppy boys was math class. I loved solving problems.
Years later, in college, I dated a boy who lived around the corner from my dad’s house in New Canaan. In a strange way, I had finally been accepted by the very community I’d spent years trying to impress.
And that’s when I realized…
It wasn’t my community.
He wanted a traditional wife. Ironically, The Stepford Wives was filmed in New Canaan, and I knew that life wasn’t for me. I wanted a career. I wanted independence. I wanted to build something of my own.
Looking back, I can see what was really driving me.
It was the little girl who wanted the preppy boys to think she belonged.
Wall Street was never the destination.
It was simply the road that taught me I didn’t need anyone else’s club after all.
Looking back, I’m grateful for NC rejection.
And I’m equally grateful that I eventually rejected a life that wasn’t meant for me.
Sometimes what feels like rejection is actually redirection.
The people, jobs, schools, or communities we desperately want to be part of aren’t always where we’re supposed to end up.
Sometimes the thing that drives us isn’t the acceptance we receive.
It’s the rejection that forces us to discover who we really are.
If you are in a transition, sometimes it is good to reflect on our past so we can move forward.
Tiffany Kent
Your Friendly Wealth Engagement Guide
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