• Chia-Yi Hou

Episode 33: Calvin Sun | Monsoon Diaries

Do you really want to live the rest of your life angry at a stereotype and rejecting the possibility of becoming a doctor because of that stereotype?


Below is an abridged audio transcript of Episode 33, the ninth episode for Season 3 of Rock The Boat: Against All Odds, edited for clarity.


In this episode, we speak to Calvin Sun, and old friend of Lucia's. Calvin is a doctor by day and travel entrepreneur by night. Calvin and Lucia had met back in college prior to him becoming a doctor. His travel company, Monsoon Diaries, brings the solo travel experience to groups.


In this episode, we'll find out about:

  • taking bets and taking risks

  • losing a parent

  • not fighting stereotypes

  • a passion project that turned into a business

The following is an abridged transcript of the episode. To listen to the full episode, find us on Anchor, iTunes, Spotify, or wherever you listen to podcasts!


I. Calvin Goes on Adventures


Calvin: My name is Calvin Sun. I'm born and raised New York City New Yorker native without a driver's license. I'm an ER doctor by choice and as well run a travel company by accident for people to go backpacking around the world who have no time or money.


Lucia: So Calvin's been to over a hundred and fifty countries, but what's more impressive and unusual is that he traveled to many of these countries while he was in medical school. His trips weren't relaxing trips to the Caribbean.


Lynne: He's traveled to countries tourist normally won't consider such as North Korea and the Arctic and Iran.


Calvin's traveling actually came from an unexpected solo trip. A year and a half after college he decided to join a few friends for a trip to Egypt.





Calvin: I met somebody and I got a little drunk and I made a bet, and that person was supposed to go to Egypt. I never left the city. I never traveled, and I felt like the whole world comes to me anyway in New York city. So we made a bet, and the bet was if tickets are under $700 I would go with them. That night tickets went from $2,000 to $650, and I was too drunk to realize it, but they took my phone and they auto-filled it.


I'm a man of my word and I said, yeah, I lost the bet, go for it. And I find myself in Egypt in the winter of 2010.


Lynne: So Calvin went on the trip.


Lucia: Yep, and what was supposed to be a three-week trip with friends turned into a solo trip when his friends itineraries unexpectedly changed. In late 2010 there was a revolution in Egypt.


Calvin's friends immediately booked flights back to the U S and they urged Calvin to do the same.


Lucia: The first week Calvin barely left his hotel room unless it was to eat the hotel staff encouraged him to explore the city since he traveled so far to get to Egypt. He realized it wasn't worth it to sit inside and continue to be afraid.


Calvin: By the second week, I was like, okay, I'm still here still alive. Maybe I'm not gonna die.


For the first time ever, I had to be my own best friend. And I had to rely on myself and no one could reach me and I couldn't reach anyone.


I was just traveling alone totally free and came back on my bike. I was so happy.


Lucia: So Calvin describes Monsoon trips as groups of everyday folks who travel around the world while keeping their full-time jobs or studying as full-time students. They spend as little money as possible. He believes you don't have to quit anything to travel the world. You can have Monsoon Adventures that are challenging raw and unapologetic.


II. Calvin's Origin Story


Lucia: So we know Calvin has a travel company, but he's also a doctor. So we backtracked a bit to hear how he was able to do both at the same time. As always, we started by asking him about his childhood.


Calvin: Now looking back. I feel like I've grown up much more quickly than the average kid.





Lucia: As a native New Yorker Calvin was confused when people asked him where he was born. He didn't understand why his other friends and classmates didn't really get these. It's "Where you from? Where you're really from?"


Calvin: I went when I went to public school for the first half. My childhood I was one of like maybe 10, 20 Asian Americans out of my class of 60 people. I wasn't alone but definitely was picked on bullied for being a looking different.


I woke up every day knowing I was Asian-American because they've reminded me every day the fact that.

Lucia: Calvin's parents expected him to rise above these questions. His dad moved from Taiwan to California in the 1970s for a PhD. His mother moved to New York in the 1980s where they met and got married. Calvin describes them as quote unquote tiger parents who were very invested in their children's education.


This can feel stifling especially when the attention means two hours of piano practice a day, but he describes discipline as the biggest lesson he learned from them.


Calvin: So the whole time I was saying yes to them but deep down, I was feeling the same internal cognitive dissonance where I was like, 'I should be doing other things.' So I was definitely going and doing a lot of things that they didn't.


I wanted a job and my dad made me work in the lab when I was 16 years old. So I did actually work there but I also bartended and they didn't know about that. So I was working like nightclubs and bars all over New York City as a first-year, 18 year old kid.





We had this like very contentious childhood and a lot of people who knew me back then knew that, you know, it was not a happy home. I was fed. They care about my education. But then again the emotional language was one of antagonism and not one of nurturing and support.


My dad died during college when I was 19 years old. He and I got to know the argument screaming at each other and I went to work and he wanted to try and fail to blow off steam, and then the argument and he had a heart attack.


He and I got to know the argument screaming at each other and I went to work and he wanted to try and fail to blow off steam and then argument and it had a heart attack.


Lucia: As a 19 year old student at Columbia University Calvin wasn't equipped to take care of his mother who needed day-to-day medical support his mom moved in with his grandparents. Meanwhile, he had two funerals to prepare for his dad's first service was in Manhattan at the second funeral in Connecticut.


III. Coming to terms with his future


Lucia: Calvin threw himself headfirst into traveling he quit his job as a bartender DJ AM nightclub promoter. He decided to travel for four months and see if it was worth it to go to medical school. He made another bet with himself. But this time it wasn't about airline prices. What if he should be a doctor after all.


Calvin: I should decide for myself. I should learn to decipher myself and I should not just rejected being a doctor because of like that and what those of you out there with Asian American who are struggling with I don't want to be a doctor because of some of the stereotype. Do you really want to live the rest of your life angry at a stereotype and rejecting the possibility of becoming a doctor because of that stereotype?



I started med school at zero countries and I ended up traveling to 170 countries the past seven years.

Lucia: So while he was traveling Calvin gained a small following.


People reached out to him to ask how he was able to travel with so much debt to show them Calvin invited them onto his trips and they in turn invited their friends and their friends invited more friends and soon it became a tribe.


Monsoon Diaries was a passion project that became a full-fledged business.


Today, Calvin is an ER attending physician and a clinical systems professor at Mount Sinai. Calvin has also negotiated a flexible work schedule so he can maximize time running Monsoon Diaries.


Calvin: I'm not full time anywhere. It's kind of like dating. How do you know you're gonna sign full-time gig to any place after a one-hour interview?


Lucia: So what does it mean for Calvin to rock the boat as a person who seemingly has rocked many boats to get to the life he has today?


Calvin: Rocking the boat is taking yourself out of the things that you were taught or conditioned to believe in. Break all that, question everything and to start back from square one to figure out what you need and what you want to do. It's not about what you become...it's what you do, how do you get there?


It's about the journey.




Show Notes


Calvin really shows us that it is possible to find a way to travel that suits our lives and our budgets. He's been able to do it and has taken many people along with him through Monsoon Diaries.


You can find Monsoon Diaries on their website and Instagram.


Listen to Calvin's full episode on Anchor, iTunes, Spotify, or wherever you listen to podcasts!

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Rock The Boat is a podcast elevating the stories of Asian leaders, founders, and pioneers in their fields. Through candid and thoughtful conversation, the host Lucia Liu uncover stories of their upbringing, Asian identity, and the movements they've built. 

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