School of Self-Worth

96: Dating with Purpose with Modern Matchmaker Cassindy Chao


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Feb 05 2025 47 mins  
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Have you ever wondered if you really should be doing something other than the job you currently have?

Cassindy Chao had an answer to that one — matchmaking.

In today’s episode, Cassindy shares her journey from crunching numbers to connecting people through matchmaking. Plus, she throws in some great dating tips for those of you looking for your person.

Cassindy shares about her own struggles leaving a prestigious career, the challenges of dating as an Asian American, and the importance of setting boundaries AND asking for help!

Whether you're in the thick of dating or contemplating a major career change, you don’t want to miss this episode!

The TOP Learnings in this episode:

  • Transition from finance to matchmaking [00:03:05 - 00:05:45]
  • Importance of boundary setting [00:25:57 - 00:27:06]
  • Self-worth and conditional love [00:22:41 - 00:24:23]
  • The "Dating Buffet" approach [00:16:37 - 00:17:35]
  • Energy and openness in dating [00:39:07 - 00:40:03]
  • Different approaches to matchmaking [00:33:44 - 00:34:39]


Cassindy Chao is an expert matchmaker and the founder of Ancient Wisdom, Modern Love. Her fascinating career journey includes transitioning from being an investment banker at top firms like J.P. Morgan and Goldman Sachs to fully dedicating herself to matchmaking. Cassindy combines her analytical background with her passion for connecting people, creating meaningful relationships through her unique methods. She specializes in working primarily in major cities like New York, Los Angeles, and San Francisco, and also has clients in Seattle and Vancouver. Cassindy is known for her thoughtful approach to dating, helping individuals understand themselves better and find fulfilling relationships.

If this episode inspired you in some way, take a screenshot of you listening on your device, post it to your Instagram stories, and tag @nicoletsong and @matchmakercassindy so we can give you a shout-out and thank you for your support!

Do you struggle with boundaries? Discover the blind spots holding you back and take the Boundary Tendencies Quiz >> nicoletsong.com/quiz

Want to build morning habits that last so you jump out of bed with energy and clarity every morning? Join Nicole’s 5-Day Morning Challenge >> go.nicoletsong.com/morning-habits

For full show notes, transcript, and links, visit nicoletsong.com/podcast.

Have a question or topic you’d like Nicole to touch on in a future episode? Email [email protected] to share any thoughts or feedback.

Learn More About Cassindy Chao:

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