The Tyranny of 'I'm Not That Person': A Case for Engineering Serendipity

We build our identities as much by what we reject as by what we embrace. "I'm not a 9-to-5 person." "I'm not the settling-down type." "I'm not a traditional wedding girl." These declarations are efficient, a shorthand for who we are. They carve out our space in the world and protect our time.

But what if this curated identity, designed for efficiency, slowly becomes a cage? What if the most expansive, profitable, and soul-stirring version of our lives lies just on the other side of a firm "I would never"?

I was recently confronted with this question when I attended a friend's wedding. I went with love for her but skepticism for the institution. I left with a new business connection, a deepened sense of community, and a profound understanding that our most rigid beliefs about ourselves are often the very things holding us back from our next evolution.

Deconstructing the 'No': A Paradox of a Past Self

My aversion to weddings was, I thought, well-established. But looking back, it was also a paradox. As a child, I was obsessed with bridal magazines, not for the romance, but for the design. I would meticulously cut apart wedding dresses to study their construction, an early fascination that eventually led me to study fashion at Parsons.

As a child, I deconstructed the dresses to understand their form. As an adult, I deconstructed the idea of weddings to reject their form.

This is a trap many of us fall into. We build adult identities in opposition to something, forgetting the kernel of genuine interest that started it all. My "no" to weddings wasn't just a preference; it was a wall I'd built, and I hadn't bothered to check if it was still serving me.

The Unexpected ROI of a Reluctant 'Yes'

My friend Courtney's wedding at the Inn at Perry Cabin (yes, the iconic location from Wedding Crashers) was the perfect storm to dismantle that wall. I said "yes" for my friend, but what I received was a multi-layered return on investment that no scheduled networking event could ever replicate.

The Return on Community:

Beyond the chic photos and fab location, the weekend was a masterclass in communal love. To witness the profound adoration Courtney's family has for her and her now-husband was to see a support system in its purest form. It was a powerful reminder that our individual successes are so often nurtured by the collective love of our chosen and given families.

The Return on Serendipity:

The real magic happened in the unplanned moments. I spent the weekend with my best friend Ariana, her brother Vincent, and their mom, Kim. For a few days, I felt like an adopted member of their family. In one of those relaxed, authentic conversations, I learned about Kim's dream of becoming a public speaker. A spark ignited. An idea formed. And now, I can't wait to help build her website. This wasn't networking; it was connection. And from that connection, a beautiful opportunity for mentorship and business was born organically.

The Return on Inspiration:

As a founder and creative, aesthetic nourishment is not a luxury; it's a necessity. The sheer beauty of the event, the celebration, and the location refueled my creative well. It reinforced a core belief: surrounding yourself with beauty and joy is a strategic investment in your own output.

A Founder's Guide to Engineering Serendipity

My experience crystallized a new thesis: we can't plan for serendipity, but we can create the conditions for it to strike.

1. Audit Your 'Nevers.' Once a quarter, interrogate the things you tell yourself you "are not." I'm not a "conference person." I'm not a "golfer." I'm not a "book club person." Ask why. Is that belief a conscious choice that still serves your current goals, or is it a lazy relic of a past self?

2. Say 'Yes' to the Container, Not Just the Content. You might believe you hate the "content" (e.g., weddings, corporate retreats). But what is the "container"? Is it an opportunity to support someone you love? To visit an inspiring location? To spend unstructured time with brilliant people? Say "yes" to the container, and you might be surprised by the content.

3. Show Up as an Anthropologist, Not a Critic. When you do the thing you think you hate, suspend judgment. Go in with a mindset of radical curiosity. Your mission isn't to have fun; it's to gather data. What can you learn here? Who is the most interesting person in the room and why? What systems or rituals are at play? This intellectual approach removes the pressure and opens you up to profound insights.

Our curated identities keep us safe and focused. But it's the unplanned detours, the reluctant "yeses," that make us wise, wealthy, and whole. The most expansive version of your life is waiting for you—often in the last place you'd ever think to look.