This as-told-to essay is based on a conversation with Cassindy Chao, 57, a matchmaker based in the Bay Area. This piece has been edited for length and clarity.
Finance is a young person’s arena. Long hours and stamina are treated as essential markers of a coveted hire. As I got older, I found myself wondering where that left someone like me: a middle-aged mom of three.
I couldn’t control getting older, so in 2022, at the age of 54, I became a full-time matchmaker.
For the first time in my career, my age is an asset.
I discovered matchmaking at college
I’m American-born Chinese, and in families like mine, there’s often a plan: get good grades, attend a reputable school, and secure a respectable job. My parents wanted me to pursue a career in medicine, but because I struggled with chemistry. I went to Wellesley and majored in Chinese studies and economics.
In my sophomore year, I became involved with the Asian Association’s blind-date semi-formal. I had a lot of fun, even though I made some of the worst matches back then.
I was so engrossed by match-matching that I started organizing the semi-formal event during classes and even dropping classes to focus on it. I never imagined it could be a career.
I worked at JPMorgan and Goldman Sachs, but didn’t thrive
I graduated in 1990 and got a job at an investment bank. I loved art and creative work, but I needed a career that paid well because I wanted to send money to my parents. I got rejection after rejection from JPMorgan in New York, but as Asia boomed in 1993, being fluent in Mandarin became an advantage, and I got a job in the Hong Kong office
A year in, Goldman Sachs offered me a role in Hong Kong as well. The culture was one of working hard and playing hard, ultracompetitive, yet tight-knit. You made close friends because you were working late nights together on deals.
Working at Goldman was addictive: I was getting paid a lot, traveling, and generally having a lot of fun, but I struggled with the numbers, and writing reports never came easily to me.
Courtesy of Cassindy Chao
I also found myself sacrificing my energy, creativity, and life to fulfill the needs of an organization. Deals were time-sensitive, people are accustomed to quick turnaround times, and it was all-hands-on-deck for various projects.
It takes a lot out of you, and I remember my mom telling me that if I stayed at Goldman Sachs, I’d never get married. I think she was right.
In May 1999, after five years at Goldman Sachs, I returned to California and got married soon after. My mom was sick at the time, and as painful as that period was, it forced me to stop and assess where I was going and what came next.
It became clear that investment banking was not where I thrived.
Matchmaking became my side hustle
From 2002 to 2016, I worked on various projects in financial consulting: I was helping close companies for VCs and businesses manage their overseas operations.
I had to draw boundaries around my time because it was intense, but the pay was good.
In 2013, I read an article in a magazine about a matchmaker in Chicago. I had no idea that it could be a career, and I read loads of books on the topic.
In 2015, I trained with a matchmaker and initially did it as a side hustle, which I publicized by building a website and emailing my network — long before I understood the power of a proper newsletter.
By 2019, I felt torn. Becoming a full-time matchmaker felt embarrassing, but I was struggling to be this corporate restructuring person.
Being older and wiser is an asset in matchmaking
In 2021, I attended my first matchmakers’ conference, where I learned tips and tricks from seasoned professionals. It helped me build my business through word of mouth, and I became a full-time matchmaker in 2022.
As a middle-aged woman with caring responsibilities, it works great. I drive the business and get to do what I want, how I want, when I want. I love the independence.
Courtesy of Cassindy Chao
The best part of my job is facilitating an unexpected match — finding love for people who would otherwise never have met. Another great aspect of my work is that I constantly talk to younger people. I learn a lot from them, and they give me new perspectives.
One of the biggest fears around ageism is becoming irrelevant or out of touch, but that hasn’t been my experience. The younger people I work with teach me about things like SEO and PR, and in return, I share the perspective and wisdom I’ve gained over the years.
I feel 100% more fulfilled than I did in my previous career, and it will remain sustainable as I age.
Getting older doesn’t matter. In fact, the older I get, the better because, after all, it means I’m wiser.
