A Turnaround from Finance to Matchmaking
Find out how Cassindy Chao, a 57-year-old mother of three, moved from the high-pressure world of finance to a fulfilling career as a reputable full-time matchmaker. This Bay Area-based professional reveals how her age became an asset in her new career journey.
Discovering the Art of Matchmaking
With a background in Chinese studies and economics from Wellesley, Chao found her calling in matchmaking during her college days. Though her parents had envisioned a medical career for her, she discovered her passion for matchmaking at an Asian Association’s blind-date semi-formal event.
Navigating the World of Finance
Chao started her professional journey in 1990 at an investment bank, seeking a stable and well-paying job to support her parents. Despite initial rejections, she secured a role with JPMorgan in New York as Asia experienced a boom in 1993. Fluent in Mandarin, Chao moved to the bank’s Hong Kong office. Following this, she accepted an offer from Goldman Sachs in Hong Kong.
Despite the adrenaline rush and high pay that came with banking, Chao found herself struggling with numerical reports and the stressful environment. She also felt her creativity being stifled due to the corporate demands.
In 1999, she returned to California and reassessed her career trajectory, realizing that investment banking was not where her passion lay.
From Side Hustle to Full-time Matchmaking
Starting from 2002, Chao spent over a decade working on various financial consulting projects. During this time, she also nurtured her interest in matchmaking. In 2015, she began matchmaking as a side hustle, inspired by a magazine article about a Chicago-based matchmaker.
By 2019, she was toying with the idea of becoming a full-time matchmaker, despite feeling embarrassed initially about the career shift.
The Advantages of Age and Wisdom in Matchmaking
In 2021, Chao attended her first matchmakers’ conference, gaining valuable insights from seasoned professionals. By 2022, she made the shift to become a full-time matchmaker. This career choice turned out to be well-suited to her circumstances as a middle-aged woman with caring responsibilities, providing her with independence and control over her work.
Chao shares that the best part of her job is facilitating unexpected matches and bringing love to people who otherwise may never have met. She also appreciates the knowledge she gains from interacting with younger people in her line of work.
She firmly believes that age does not hinder success in her field. In fact, the wisdom that comes with age proves to be an asset, especially in understanding and guiding clients in their quest for love. Today, she feels more fulfilled in her career as a matchmaker than she previously did in her finance career, asserting that this career is sustainable as she grows older.
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