Cup 9 | Lee Hup Kheng


After a rural adventure around the island of Borneo the next stop of the journey was Singapore: a squeaky clean commercial hub with great public transit and dazzling architecture. Unsure of how to navigate the new city, I asked friends on Facebook if they had any tips on Singapore.

My friend, and Michigan State University professor, Karl answered the call: 

I have friends at the newspaper there if you need some good people to ask what to do!

Before I knew it, I was messaging with Lee “Hup” Kheng, a Singaporean with great advice: Chinatown, the Mariamman Indian Temple, Marina Bay on the Sands Hotel for spectacular views of the skyline and more.

Hup was so gracious to offer his expertise, I asked him if he’d like to get coffee. Two days later I was in the art department of Singapore Press Holdings where Hup works as the Infographic and Design Chief for The New Paper.

Hup is an award-winning graphics artist. Born in the Rice Bowl region of Malaysia, he realized he had a talent for drawing and should try to make something out of his life. After high school he bought a one-way ticket to Memphis, Tennessee for art school. He then moved back to Malaysia and soon got a job in Singapore. He has been in the industry for 25 years and is now running the show at The New Paper—the best paper in Singapore.


We met at his office and sat on the rooftop deck overlooking the city. We talked about what makes Singapore unique, swapped travel stories and discussed lessons Hup had learned over the course of his career.

Our conversation was lively and it was clear Hup was an artistic guy. He’d use his hands or objects on the table to help me visualize the story he was telling.

My favorite part of the conversation was when he talked about art and trying to unlearn things.

He talked about drawing a face over and over again. Each time he starts with the nose, which means it’s now become a habit. He doesn’t know how to draw a face without starting with the nose because habits are hard to break.

It’s the same for life habits: we fall into a routine that is known and comfortable. Then we get stuck.

We pick the easy, expected, known route and suddenly a few years go by and we are in a rut that is safe yet boring. As Hup said:

We get stuck in patterns but sometimes the best things are when you can embrace the unknown… The best things come unexpectedly. It can be a bit dangerous but that’s okay, it’s more fun to follow the heart.

While his career has been vibrant, he said if he could do it again, he would have worked in Singapore for two years and then gone somewhere like Japan where a new challenge awaited. He would have switched things up more often.

To compensate, he’s now travels as often as possible, which is why he was so willing to share tips with me. He told me that when people are traveling he loves to help give them advice because, as a traveler himself, he knows what it’s like to be in the other person’s’ shoes.  

What I love about Cup 9 with Hup was how beautifully it illustrates one of my favorite ideas: the strength of weak ties.

Meg Jay talks about it in her book The Defining Decade:

[We] are in almost constant contact with the same few people. But while the urban tribe [our support network] helps us survive, it does not help us thrive. The urban tribe may bring us soup when we are sick, but it is the people we hardly know—those who never make it into our tribe—who will swiftly and dramatically change our lives for the better.

This is the power of having coffee with strangers.

We need a tight circle of friends and family to survive the ups and downs of life—but it is the wider circle of people in our lives that create the best opportunity.

Karl and I met a few years ago and have stayed in touch since. I greatly admire his work and cherish the opportunities when our paths cross. The same happened between Karl and Hup—they met and stayed in touch, it’s in Karl’s nature to connect.

As a result, when I was in Singapore, the strength of these weak ties led to an opportunity to for Hup and I to meet.

I am continually amazing that people are so willing to connect others. We love being able to share our experiences, our expertise and our connections with others when given the chance to help.

It’s magical.

And a great opportunity to get out of a rut. When you reach out to someone (whether a complete stranger or an old friend you don’t often see) you break out of the habit of talking to the same people about the same things.

If you’re looking for an exciting new opportunity you have to search in different places—old friends are a really great place to start.

Mine led me to a wonderful conversation inside a Singaporean newspaper art department. Where will yours lead?