“And a cascade of lace here, here, and here.” I thwacked my pen against the notepad to emphasize each word while my cousin nodded vigorously. At 8 and 10, we carefully reviewed our wedding dress designs as if our big days were just moments away. While our parents prepped dinner, we rehearsed our grand bridal entry in painstaking detail.
I’m probably not the only person who had this fantasy when I was little, but what I didn’t realize was just how that role-play would translate into the career that I have right now. It all started with my own elopement in 2021, and the subsequent blow-out bash a year later. My husband and I juggled countless chaotic spreadsheets, email chains, invoices, journals, and Post-its.
I felt overwhelmed by the lack of tools to orchestrate this complex logistical feat, and I realized that I could make a living by fixing this chaos.
My unconventional career path
What I loved about weddings were the systems and the operational aspect. But in addition to planning a wedding, it took me a few jobs to understand that. The summer after I graduated from college, I worked as a tutor for middle and high school kids while I looked for a full-time job. Just days in, it became clear that the tutoring company was in full operational shambles. I started mapping out a plan to transition the company to electronic records, using homework assignments and practice flashcards.
My next job was at a boutique marketing firm. A few months on the job, I realized it was on the scrappier end of the spectrum than I initially expected. Soon, the quirky operational novelties I had loved at first were starting to make me itch. I started to scheme to make things more efficient again.
My next role allowed my skills to find a true home. I was leading a team of operations specialists at the unicorn startup, Carta. This experience would end up being crucial to my wedding planning business that I’d later start.
Doing my best work in chaos
The refrain that continued in my mind over the many months of wedding planning was, ‘Why is this so hard?’ When about 2.5 million people get married in the United States every year, it felt like I (and every engaged person I knew) had to reinvent the wheel while undergoing a deeply frustrating and time-consuming exercise.
And as my husband and I lived through the organizational chaos of our wedding planning journey, I began to think to myself, ‘someone should really fix this problem. Someone who is obsessed with the details, thinks like an operator and a consumer, and someone who loves bringing clarity to chaos.’
That was the moment I began to connect the dots together. Without any context, someone can look at my professional history and feel disconnected. But at that moment, I’d realized that all my personal and professional experiences up to this point had led me to this challenge, and that I was ready to meet it head-on.
Your interests can provide career clues
Before I knew what careers existed, the common threads of how I thought and how I solved problems were there right in front of me. I took the concept of loving systems and organization as a personal interest rather than a professional secret weapon. At times, I interpreted my drive to improve operational circumstances as a distraction to the job at hand. There were also instances where it felt like an inconvenience to my managers (who weren’t always receptive to it).
My previous roles didn’t grant me authority or purview over the messy systems or inefficient processes, but I couldn’t stop engaging with it. I didn’t realize how unique my perspective was. Identifying inefficiency came naturally and easily to me, so I naturally assumed that it was the same for other people.
Why it’s important to pay attention to what you think
When deciding how to approach the professional world, people ask us, ‘What are you passionate about?’ or ‘What do you want to be?’ We build resumes and write cover letters, highlighting the projects we led and the metrics we moved. But in the process, we overlook what feels natural.
We’ve placed ourselves in organizations and teams and roles, but never stopped to ask ourselves the critical question: How do I think? What challenges are my brain hard-wired to solve? What is the recurring thread in my life that I haven’t paused long enough to see?
The throughline is usually there. We just don’t think to look for it.
I close my crisp notebook with a satisfying snap. I’ve just finished explaining to my cousin that the processional music must begin exactly as Mr. Bear arrives at the steps, so that it will reach the perfect crescendo as he reaches the altar.
The chairs are straight. The timing is perfect. The experience unfolds exactly as planned.
In hindsight, I wasn’t pretending to be a bride. I was designing flow, sequencing emotion, and building structure around what is supposed to be a joyful and effortless moment. Long before I had the language for systems, operations, or user experience, I was already drawn to the architecture beneath the celebration.
Maybe you had your version of playing wedding as a child, and it looks completely different from mine. Look closely and think about what it is about that scenario that interests you. Because if you look closely, you might just have been rehearsing what you’re meant to do all along.
