Meet Cindy, a visionary entrepreneur and the driving force behind The Enneagram Academy. With a passion for personal growth and self-awareness, she has dedicated her career to helping individuals and organisations unlock their full potential through the transformative power of the Enneagram.
Her academy offers tailored programs that delve into the intricacies of personality types, fostering better communication, stronger relationships, and enhanced emotional intelligence. Known for her dynamic teaching style and deep expertise, Cindy has empowered thousands of people to better understand themselves and others, creating a ripple effect of positive change in their lives.
What inspired you to establish The Enneagram Academy, and how did your journey with the Enneagram begin?
When I first got to know about the Enneagram, it wasn’t about work—it was about my personal relationship. At the young age of 24, I went through a divorce. During that time, I felt very lost and wanted to find answers about my life and relationships, like why they had failed. One of my friends, who is also a coach, introduced me to the Enneagram. When I read about it, took the test, and had it explained to me, I thought, “Wow, this really makes sense.” As a psychology student, I had done many profiling tools like MBTI and DISC.
However, none of them were like the Enneagram. Most profiling tools tell me what I am like—which I already know—but they don’t tell me what I can do about it or how I can improve. When I learned about the Enneagram, I had that “aha” moment: understanding why I am the way I am, recognising my relationship blind spots, and why relationships fail.
At that time, I wasn’t thinking about starting a business. It was more about helping and sharing with people to improve their relationships. Over time, as more people shared how much the Enneagram helped them, it grew organically and eventually became an academy.
How do you think the Enneagram helps individuals and businesses achieve personal growth and success?
The Enneagram provides insights into our motivations—why we are the way we are. It explains our thought processes, emotional patterns, and how they manifest into behaviours. It gives us answers to the “whys” we don’t often think about because we act intuitively without reflecting on how we process things internally.
This self-awareness helps individuals manage blind spots and understand how they might come across to others. For example, I might be enthusiastic, but some personality types may perceive it as aggressive. Or I may have strong opinions, which could come across as overly opinionated to others. With self-awareness, I can adjust my behaviour to build better relationships and make others feel more comfortable around me. In business, this self-awareness is crucial.
Professionals need to communicate, persuade, and collaborate with different people. Understanding personality types makes communication and relationship-building easier. Leaders benefit greatly, as they can build stronger teams, motivate effectively, and work on their blind spots. I’ve seen the Enneagram improve team dynamics, uncover issues in business strategy, and resolve personality conflicts within teams.
It’s versatile and applicable in HR, talent management, sales, client relationships, team building, and even co-founder relationships. It’s like a marriage—without strong relationship-building, conflicts arise. Beyond business, it’s invaluable in marriage and parenting, making its applications incredibly broad.
Can you share a memorable success story where the Enneagram made a significant impact on someone’s life or career?
One of the most memorable stories for me is a marriage counselling case. I was coaching a couple on the verge of divorce. Someone recommended they give the Enneagram a final try. During the sessions, we uncovered the challenges between them—unrealistic expectations and poor communication. They didn’t speak up until it was too late, which led to breaking points.
Through four sessions—one together, one with the wife, one with the husband, and one final joint session—they started to see the light. They realised their marriage wasn’t as broken as they thought. They learned to communicate and manage expectations. Saving this marriage was a deeply fulfilling experience for me.
With self-awareness, I can adjust my behaviour to build better relationships and make others feel more comfortable around me. In business, this self-awareness is crucial.
How do you tailor your Enneagram programs to meet the diverse needs of your clients, from personal development to corporate training?
It varies greatly. For personal development, we work with inmates as part of their reintegration into society. These classes focus on managing personal stress, emotional well-being, mental health, choosing the right friends, setting boundaries, and learning to say ‘no’ or ‘yes’ appropriately.
For corporate training, it ranges from team bonding for IT or HR teams to sessions for C-suite executives like CEOs and CTOs. These sessions are more fast-paced and goal-oriented, as high achievers tend to be more self-aware. Corporate training often involves government funding, so there are timelines to follow, such as completing sessions within two days.
Personal development programs are more exploratory and discovery-based, while corporate sessions focus on immediate application.
What challenges did you face when starting the Academy, and how did your understanding of the Enneagram help you overcome them?
Starting the Academy at 27 came with challenges. At that age, people questioned my competence, asking, “How old are you?” Age was an issue because I looked young, and clients doubted my credibility. But after experiencing the coaching, they realised the value I brought. I focused on becoming very good at what I do.
Since I was passionate about helping people build relationships and achieve “aha” moments, I invested in upskilling and personal development to walk the talk. When I started, I had only $1,000. I overcame this by starting small, even working pro bono initially to build case studies and coaching hours. Over time, as my expertise grew, I was able to charge higher rates and establish credibility.
What do you believe sets your Academy apart from other personality and development programs?
If compared to other development and personality courses, I would say my Enneagram classes are very experiential, real-life, and hands-on. It’s not just theory. We also invite overseas trainers to conduct masterclasses at affordable rates.
Additionally, we are WSQ and SkillsFuture funded. Singaporeans can use SkillsFuture credits, making training accessible. This funding encourages more people to explore the Enneagram and its benefits.
What are your future plans for The Enneagram Academy, and how do you see the Enneagram evolving over the next few years?
This year, we are hosting our second Enneagram conference in Singapore. Two years ago, we had 170 delegates and 20 speakers. This time, we aim for 200 attendees at the Peninsula Excelsior Hotel, with over 10 overseas speakers from countries like France, Denmark, and Ireland.
We also aim to make the Enneagram a common language. People should know their Enneagram types and use this understanding to reduce conflicts and improve relationships. We envision the Enneagram impacting various societal pillars, from media and arts to business and families.
Regionally, we’ve introduced Chinese-language programs in Taiwan and Hong Kong. We hope to expand to more Southeast Asian countries. The Enneagram has applications in healthcare, such as understanding how personality types relate to illnesses and self-care. It’s also gaining traction in sports, helping athletes find motivation and improve performance. The potential for growth and impact across industries is immense.
Where do you see yourself and what’s your vision for Singapore in the next five years?
I see myself continuing to lead The Enneagram Academy, bringing the Enneagram to various societal pillars and regions in Asia. My vision is to train like-minded, passionate Enneagram trainers worldwide to make a positive impact on lives.
For Singapore, I hope more people will adopt the Enneagram not just for workplace skills but as a framework for personal growth and relationship building. After COVID, there’s been greater focus on mental wellness and meaningful relationships, and I hope the Enneagram can be a tool to support this journey.
Connect with Cindy: TheEnneagramAcademy, LinkedIn and Instagram.
Singapore Enneagram Conference 2025
Unlock the power of self-awareness and personal growth with The Enneagram Academy! As part of an exclusive collaboration, we’re thrilled to offer you a special discount for the Singapore Enneagram Conference. Simply enter the promo code SGVISION at checkout to enjoy S$300 off your registration! Don’t miss this opportunity to deepen your understanding of the Enneagram and transform your life.
6-7th March 2025, 9am to 6pm
Peninsula Excelsior Singapore, A Wyndham Hotel
Address: 5 Coleman St, Singapore 179805
Visit for more details: https://theenneagramconference.com/
