The Unsuccessful Student

This is a special interview piece written by my friend Michael Wong. He helped inspire the idea behind this website. Enjoy!


“The Unsuccessful Student”
Written by: Michael Wong

Fact: everybody wants to travel the world. It’s an escape from the familiar and an opportunity to “soul search”. Does traveling really have the life-changing impact that people speak of? To answer the question, I enlisted help from my friend, Chester, to learn about his travels in Costa Rica and Southeast Asia.

He calls himself “the unsuccessful student”. It is one month away from his big day, not his wedding or graduation, but his move to settle in Malaysia. Despite his busy schedule of saying goodbye to his friends, learning to code, and packing, Chester meets with me at Revolver, a coffee shop located near the heart of Gastown.

While studying environmental sciences at UBC, Chester went on a one-semester exchange to South Africa. That was when he caught his first dose of the “travel bug”. Prior to his time there, he held a traditional approach to life. Attend university. Find a job in his field of study. Get married. Settle down. It was expected from societal norms and to a lesser degree, his family. As life happened, he didn’t feel “passionate”.

“When I returned, my best friend noticed a difference in me.” He explains. “It was like I didn’t care about school anymore. I was just doing the work to get by.”

Not many of his friends traveled after graduation, except for one. He started his own business when he returned and appeared to be living a happier life ever since, doing something he loves. “He came back with more focus, more motivation, and was much more driven.” Chester tells me.

“I think everybody wants to travel,” he continues, “and see, experience, and do new things.” After hearing about The Happiness Project, he realized that ultimately, we all strive for happiness, but find it in different ways. Traveling is one way of satisfying the need. The only problem, Chester warns, is that it isn’t sustainable. The satiety is temporary unless you constantly do it to remain happy.

Chester’s trip was split into two segments. He first visited Costa Rica, which was an “emotional rollercoaster”. It was his first time traveling with a romantic relationship back home and he became homesick. The physical separation reminded him the importance of his relationships. Had he made the right choice to leave his life at home and embark on a self-discovering journey?

Luckily, he met a girl named Floor in Costa Rica, who consoled him and provided a calming perspective. She advised Chester to be comfortable with not knowing, but understand that things will work itself out eventually if you keep searching. While the priority of Chester’s trip was to seek answers to his “big life questions”, there was no guarantee he would find them. He had to be familiar with the concept of ambiguity.

A month later, Chester returned to Vancouver for Christmas. It wasn’t long before he departed again. This time, to spend six months in the Southeast Asia region. He started in Hong Kong, traversed through Malaysia, Indonesia, Thailand, Cambodia, Vietnam, Singapore, and Laos before returning to his starting point.

Throughout his trip, he documented his thoughts and inspirations in a journal. Although he did the same thing in Costa Rica, he was much more focused this time. In his words, it was “time to reflect on everything, from what was important to what wasn’t.” Solidarity when commuting between cities and countries gave him ample time to do that.

Of all the places he visited, Vietnam was his favourite. He appreciated how accessible it was to travel away from the tourist-centric spots to more rural areas. “You can go into the big cities and [Vietnam] can be wild and chaotic.” He describes. “On and off the path, there are beautiful beaches, mountains… and great local food.”

“Vietnam is a country with a lot of heart,” he adds. He admires the pride amongst the people there, despite their turbulent past. “Regardless of what’s happened,” Chester elaborates, “they are still so positive on the future, and it’s not just the younger population, who are less connected with the pain of Vietnam’s past.”

Each country he visited provoked different thoughts. “Laos was the poorest country [that he had visited], but the people were super friendly,” he tells me. Indonesia has the appeal of being an “adventure playground” that has “everything from volcanoes to mountains.” Singapore, on the other hand, felt too “sterile”.

To put his journey into context, I ask Chester to discuss the most significant life lesson he had learned. He remembers a card a friend sent him over a year ago. On it was a quote he recalls up to this day: “Don’t settle; take chances now while you can because this is the time to do it.”

He always had the quote at the back of his head, but never understood how to apply it until his trip to Southeast Asia. To him, he took a chance when he left his life behind in Vancouver for six months to explore the world. Moving to Malaysia next month is an even bigger leap of faith.

His long-term goal is to start his own business. While he does not disclose many details, he mentions that this is the reason why he is learning to code after he returned to Vancouver. He is acquiring the skills he needs to achieve his goals. He explains that the low cost of living in Malaysia enables him to settle down first, yet he is close enough to Singapore to grow his business there if he’d like, hence, keeping his options open.

“I think I definitely have that drive now,” Chester says. “It’s much stronger than it’s ever been.”


  1. Amazing to see someone stepping outside their traditional way of thought completely and just taking chances 🙂 Excited to see what the future has in store Chester! And great post Michael!

  2. Pingback: Reviewing the Singapore trip | the unsuccessful student

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