From Heartbreak to Healing
At 24, Cindy Leong faced what many would call a personal collapse—a failed marriage and a string of broken relationships. Instead of giving up, she searched for answers. That search led her to the Enneagram, a personality framework that not only explained her blind spots but also gave her a path forward.
Today, Cindy is known as Singapore’s relationship coach and Enneagram master trainer. Through her academy, she has helped thousands understand themselves, repair relationships, and build stronger teams at work.
Discovering the Enneagram
Cindy had already studied psychology and tried common profiling tools like DISC and MBTI. None of them gave her the raw truth she needed. The Enneagram did.
It didn’t just describe her strengths. It showed her weaknesses. It revealed how she treated relationships like “projects,” complete with milestones and deadlines. That realization was painful—but also freeing. It explained why connections felt forced and why disappointment followed when others didn’t meet her expectations.
Armed with this clarity, Cindy invested in her growth. She flew to California to study under experts, including Dr. Claudio Naranjo, who integrated Enneagram wisdom with modern psychology.
Becoming the Coach She Needed
When Cindy was struggling, she didn’t have a guide. That’s why she chose to become the coach she never had.
She started as a one-to-one coach, later building group programs, certifications, and a thriving academy. Along the way, she realized the Enneagram wasn’t just for couples or personal struggles—it applied to workplaces, parenting, and leadership.
Today, her clients range from singles looking for love, to corporate teams seeking cohesion, to parents learning how to connect better with their children.
Building Credibility and Voice
Cindy’s expertise has been widely recognized. She became a resident love expert on Class 95FM, answering live questions on relationships. She has also written books such as Knowing Me, Knowing You, which maps out 45 different relationship combinations at work and in love.
Her voice has also extended to schools, workplaces, and even international conferences. She doesn’t just teach theory—she offers frameworks people can use daily to improve communication and empathy.
Why the Enneagram Works
According to Cindy, the Enneagram is powerful because:
- It uncovers blind spots, not just strengths.
- It helps people understand motivation and fears.
- It explains why conflicts arise and how to resolve them.
- It creates empathy by showing nine distinct worldviews.
Unlike quick online tests, Cindy emphasizes discovery through coaching conversations, group learning, and reflection. It’s not about being told your type—it’s about recognizing yourself in the process.
Parenting and the Next Chapter
As a mother of two, Cindy saw firsthand how personality awareness changes family life. Children bring what she calls a “random variable” into marriage—each with unique motivations and quirks.
Instead of trying to mold children into mini versions of their parents, Cindy advocates for guiding them to be the best version of themselves. This insight inspired her newest book on parenting, written with Singapore families in mind.
Extracting Golden Nuggets
Cindy Leong’s story shows how self-awareness can turn crisis into clarity. The Enneagram saved her future by:
- Helping her confront hard truths about herself.
- Guiding her from failed relationships to healthy growth.
- Giving her tools to coach others with empathy and structure.
- Showing how personality shapes love, work, and family.
👉 If you’re curious about your own blind spots or want to improve your relationships, explore Cindy’s courses at The Enneagram Academy.
And for more founder journeys like Cindy’s, filled with lessons you can apply today, subscribe to The Golden Nuggets Newsletter—where every story brings you insights worth keeping.
