I quit finance at 54 to go full-time with my matchmaking side hustle. I love having a career where being older is an asset.
The finance sector is often perceived as a playground for the young, where long hours and unwavering stamina are seen as prerequisites for landing a coveted position. As I advanced in years, I couldn't help but ponder my place in this field as a middle-aged mother of three.
Aging was beyond my control, so in 2022, at the age of 54, I took the leap and became a full-time matchmaker.
For the first time in my professional journey, my age has become a valuable asset.
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My Introduction to Matchmaking: A College Discovery
As an American-born Chinese, my family had a clear roadmap for me: excel academically, attend a prestigious institution, and secure a well-respected job. My parents envisioned me pursuing a medical career, but chemistry wasn't my forte. Instead, I enrolled at Wellesley, majoring in Chinese studies and economics.
During my sophomore year, I got involved in the Asian Association's blind-date semi-formal event. Despite my less-than-stellar matchmaking skills at the time, I had a blast.
I became so captivated by the art of matchmaking that I began organizing the event during classes and even skipped some to focus on it. Little did I know that it would one day become my profession.
My Struggles in Finance: JPMorgan and Goldman Sachs
After graduating in 1990, I landed a job at an investment bank. Although I had a passion for art and creative endeavors, I needed a lucrative career to support my parents financially. Despite numerous rejections from JPMorgan in New York, my fluency in Mandarin became an asset when Asia's economy boomed in 1993, leading to a job offer in their Hong Kong office.
A year later, Goldman Sachs also extended an offer. The culture there was intense, competitive, yet tightly knit. Late-night deal-making sessions forged strong bonds among colleagues.
Working at Goldman was exhilarating—I earned well, traveled extensively, and generally had a great time. However, I struggled with the numerical aspects and report writing.
Cassindy Chao, who transitioned from finance to matchmaking. (Photo courtesy of Cassindy Chao)
I also felt like I was sacrificing my energy, creativity, and personal life to meet the demands of the organization. The fast-paced, high-pressure environment took a toll, and I recall my mother warning me that if I stayed at Goldman Sachs, I might never get married. I think she was onto something.
In May 1999, after five years at Goldman Sachs, I returned to California and got married shortly after. My mother's illness during that period, though painful, forced me to pause and reevaluate my career path. It became evident that investment banking wasn't my forte.
Matchmaking as a Side Hustle
From 2002 to 2016, I worked on various financial consulting projects, assisting venture capitalists in closing companies and helping businesses manage their overseas operations. The work was intense, but the pay was good, and I learned to set boundaries around my time.
In 2013, I stumbled upon an article about a matchmaker in Chicago and was intrigued. I had no idea matchmaking could be a career and devoured numerous books on the subject.
In 2015, I trained with a professional matchmaker and started offering my services as a side hustle. I built a website and emailed my network to promote my services, long before I understood the power of a well-crafted newsletter.
By 2019, I felt torn. Becoming a full-time matchmaker seemed embarrassing, yet I struggled to identify with my corporate restructuring role.
Age as an Asset in Matchmaking
In 2021, I attended my first matchmakers' conference, where I learned invaluable tips from seasoned professionals. This experience helped me grow my business through word-of-mouth referrals, and in 2022, I became a full-time matchmaker.
As a middle-aged woman with caregiving responsibilities, this career suits me perfectly. I have the autonomy to run my business on my terms and relish the independence it offers.
Cassindy Chao at an event, emphasizing that age is an asset in matchmaking. (Photo courtesy of Cassindy Chao)
The most rewarding aspect of my job is facilitating unexpected matches—bringing love to people who would have otherwise never crossed paths. Additionally, I enjoy engaging in conversations with younger individuals, from whom I learn a great deal and gain fresh perspectives.
One of the biggest fears associated with aging is becoming irrelevant or out of touch, but that hasn't been my experience. The younger people I work with teach me about SEO and PR, and in return, I share the wisdom and insights I've accumulated over the years.
I feel far more fulfilled in this career than I did in my previous one, and I believe it will remain sustainable as I continue to age.
Getting older doesn't hold me back; in fact, it enhances my abilities. After all, with age comes wisdom.