The Modern Women's Playbook

When you first meet Cheryl Chan, she strikes you as both warm and composed. She is a seasoned OrangeTee real estate agent, a former air stewardess, a mother of two, and the newly crowned Mrs Singapore.

In a world that often asks women to choose just one role, Cheryl embodies multiplicity — showing that it’s possible to be a professional, a queen, and a mother, all while staying true to yourself.

This is her playbook for the modern woman.

Cheryl’s real estate journey began with encouragement to join the industry — but what kept her was purpose. She passed both licensing exams on her first attempt, and with her service background as an air stewardess, she quickly discovered the joy of helping people through life’s biggest decisions.

“It was the motivation of wanting to help people with their property needs that kept me in the industry,” she says.

Her anchor wasn’t commission — it was connection. “The smile, the happiness you see when clients get what they want — that’s what keeps me going.”

As a property advisor at OrangeTee, Cheryl has since built a reputation for her sincerity and her ability to guide clients through an often overwhelming market with clarity and heart. She also plays an active role in OrangeTee’s project marketing team — serving as Project IC for The Orie, Chuan Park, and Aurelle @ Tampines, as well as a dedicated project tagger.

With her children grown, Cheryl dusted off a long-held bucket-list dream: competing in Mrs Singapore. What followed was a three-month journey that pushed her in unexpected ways — talent showcases, interviews, even cooking cauliflower “fried rice” in a multi-cooker without a stove.

“The Mrs Singapore role is not easy. It takes a lot of courage, a lot of practice, and the willingness to push yourself beyond what feels comfortable,” she reflects.

But the transformation went deeper than stage presence. “These three months really changed me — the way I see things, and even how I carry myself. Pageantry isn’t only about beauty. It’s about heart, self, and how we walk and talk in the world.”

AAG Media proudly sponsored Cheryl Chan’s editorial feature on Mrs Singapore magazine, highlighting her journey as Mrs Singapore and an inspiration within AAG.

Her efforts were recognised when she was crowned Beauty with a Heart, for raising the highest amount for charity. That title, she says, mattered just as much as the crown itself. And the confidence she gained? It now flows naturally into how she meets clients, negotiates deals, and represents herself as an OrangeTee real estate professional.

As a mother, project-in-charge, and now queen, Cheryl knows the weight of expectations.

“Nobody is perfect, but we try as much as we can. People are looking up to us — if we aren’t right in our role, how can they be?”

The scrutiny of pageantry sharpened her awareness. Contestants were constantly reminded that when they wore the organisation’s T-shirt in public, they carried the title everywhere they went. Cheryl admits it was stressful — every move watched, every action judged.

Yet she embraced the lesson: image is about integrity, not appearance. In real estate too, she learnt that confidence comes not from pretending to be perfect but from preparation and sincerity.

“Clients can sense sincerity. You must serve with the heart. And you must have knowledge — if you don’t, you’ll fumble. That’s why training and constant learning are so important,” she explains, crediting OrangeTee’s in-house training for sharpening her expertise.

Cheryl wants her clients and colleagues to remember her not only as an agent, but as someone who instilled confidence and offered solutions.

“Confidence is what sets us apart. In real estate, once a client loses confidence in you, you lose the client,” she says.

She recalls one of her most meaningful relationships: a foreign client who first came to her struggling to rent out a single apartment. Cheryl stepped in, stabilised the situation, and eventually helped him build a portfolio across Singapore and even into Australia.

The trust ran so deep that when Cheryl mentioned she needed a male partner to walk her down the pageant red carpet, he offered to fly back in his tuxedo just to be there.

“From one rental to that kind of loyalty — that’s the trust we build,” she says.

Legacy, for Cheryl, isn’t about titles. It’s about leaving behind confidence, sincerity, and relationships that last beyond contracts. It’s also about mentoring younger OrangeTee agents and showing them that resilience and heart go further than any script.

For Cheryl, success is not a finish line — it’s a moving horizon.

Her next chapter is already in motion: preparing to represent Singapore at Mrs Earth in Manila. On the real estate front, it’s about mentoring younger agents and building larger teams within her organisation. Each goal is not about personal glory, but about resilience, balance, and the impact she can leave on others.

And to women who feel they must choose between career, family, and personal dreams, Cheryl offers reassurance:

“You don’t have to give one up for the other. It’s about portioning your time, being open with your family, and allowing yourself to pursue the things that light you up. When your loved ones understand your ‘why,’ they’ll be the first to cheer you on.”

Cheryl’s playbook isn’t about being flawless — it’s about being fearless.

• Anchor yourself in purpose.
• Say yes to courage.
• Redefine perfection.
• Build a legacy.
• Define success on your own terms.

Her reminder to every woman is simple, but powerful: “Confidence is the crown that never slips. And it’s the one crown every woman can wear.”