From JP Morgan to Matchmaker: A Career Reinvention at 54

Cassindy Chao spent over two decades navigating the high-stakes world of finance, working at prestigious institutions like JP Morgan and Goldman Sachs. Despite the lucrative career and international experience, she never felt she truly thrived in the corporate environment.

In 2022, at the age of 54, she made a bold decision that would redefine her professional life. She left finance behind to pursue her long-held passion as a full-time matchmaker. What she discovered was that her age and accumulated life experience—often seen as liabilities in other fields—became her most valuable assets in building meaningful connections for others.

Chao's journey began with a classic immigrant family expectation: excel academically, attend a reputable school, and secure a respectable job. Her parents envisioned a medical career for her, but chemistry proved challenging. Instead, she attended Wellesley College, where she majored in Chinese studies and economics.

Her fascination with matchmaking emerged unexpectedly during her sophomore year. While involved with the Asian Association's blind-date semi-formal, she discovered a natural talent for bringing people together.

I had a lot of fun, even though I made some of the worst matches back then.

She became so engrossed in the art of match-making that she began organizing the event during classes, even dropping courses to focus on it. While she never imagined it could become a career at that time, the seed was planted.

After graduating in 1990, financial reality pushed her toward investment banking. She needed a career that paid well to support her parents, and despite initial rejections from JP Morgan in New York, her fluency in Mandarin became a crucial advantage when Asia's economy boomed in 1993. She secured a position in the Hong Kong office, where a year later, Goldman Sachs offered her a role.

The culture at Goldman Sachs was ultracompetitive yet tight-knit, characterized by a "work hard, play hard" mentality. The long hours and late nights working on deals created close bonds among colleagues, but the demands were relentless.

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.

The intensity of the work took a significant toll. Chao found herself sacrificing her energy, creativity, and personal life to fulfill organizational needs. Time-sensitive deals required all-hands-on-deck approaches, leaving little room for anything else.

Her mother's intuition proved prescient. She recalled her mother warning that if she stayed at Goldman Sachs, she would never get married. After five years at the firm, Chao returned to California in May 1999 and married soon after. Her mother's illness during that period forced her to pause and reassess her trajectory, making it clear that investment banking was not where she would thrive.

From 2002 to 2016, Chao worked in financial consulting, helping close companies for venture capitalists and managing overseas operations for businesses. While the pay was good, the work remained intense, requiring strict boundaries around her time.

In 2013, a magazine article about a matchmaker in Chicago sparked a revelation: matchmaking could be a legitimate career. She began reading extensively on the topic and eventually trained with an established matchmaker in 2015.

She launched her side hustle by building a website and emailing her network—long before she understood the power of a proper newsletter. By 2019, she felt torn between her corporate identity and her growing passion.

Becoming a full-time matchmaker felt embarrassing, but I was struggling to be this corporate restructuring person.

The turning point came in 2021 when she attended her first matchmakers' conference. Learning from seasoned professionals helped her build her business through word-of-mouth referrals, giving her the confidence to make the leap.

In 2022, at age 54, Chao became a full-time matchmaker. For the first time in her career, her age transformed from a potential liability into a distinct advantage.

As a middle-aged woman with caring responsibilities, the independence of running her own business proved ideal. She controls her schedule and methods, working how and when she wants.

For the first time in my career, my age is an asset.

The best part of her job is facilitating unexpected matches—finding love for people who would otherwise never have met. She also values the intergenerational exchange: younger professionals teach her about modern tools like SEO and PR, while she shares the perspective and wisdom gained over decades.

Contrary to fears of ageism and becoming irrelevant, Chao finds that her experience keeps her connected and valuable. She feels 100% more fulfilled than in her previous career, and the work remains sustainable as she ages.

Getting older doesn't matter. In fact, the older I get, the better because, after all, it means I'm wiser.

Chao's story demonstrates that career reinvention is possible at any stage of life, even in fields traditionally dominated by younger professionals. Her journey from finance to matchmaking highlights several important lessons.

First, passion projects can evolve into fulfilling careers with patience and strategic planning. Second, life experience and accumulated wisdom are powerful assets that shouldn't be undervalued. Third, intergenerational collaboration creates mutual value—older professionals gain new perspectives while younger ones benefit from accumulated wisdom.

Most importantly, Chao's success proves that age is not a barrier to meaningful work. In fact, in fields like matchmaking where emotional intelligence and life experience matter, being older can be the ultimate competitive advantage.