Interview with Calvin Sun

21 May, 2019 | Blog, Interviews

Calvin, the man behind The Monsoon Diaries, is an MD with a travel passion: a true community leader, a prolific travel blogger and a true adventurer. He gives us his recipe for travel happiness, and explains how he has managed to be such an incredible all-rounder.

Sossuvlei, Namibia

Sossuvlei, Namibia


Calvin, tell us something about your early years and how your love of travel developed.

Winter 2010. It’s 3am. My eyes open to an unfamiliar ceiling, and in the darkness I salvage the little of what’s left of my short term memory. I glance around: I think I’m in Cairo? Familiar memories slowly return proving that I’m not dreaming. The echoes of last evening’s call to prayer still remain fresh in my mind — What am I doing here?

For the first 23 years of my life I never traveled. Except for an occasional trip with my father, I otherwise never desired or thought I would ever make efforts to leave home. Even worse, being a born and bred New York City native I had figured that the world would come to me anyway — what’s the point of spending all that money if I’m not going to live anywhere else but NYC?

In 2006 my father died of a sudden heart attack and my mom was diagnosed with Parkinson’s Disease. I was 19. And mired in hundreds of thousands of dollars in student debt and with no job or any foreseeable sustainable source of income, I felt even less inclined to travel. It seemed I was destined to be confined to the shackles of my birthplace and again being that it was NYC, I reasoned I would be OK with that.

For the next few years I was getting by with a few odd jobs and a handful of bartending gigs. Then in the winter of 2010, I jokingly made a bet with 2 friends that I would join them on their last minute trip to Egypt on the condition that roundtrip tickets would be less than $800. I was not serious at all: Flight prices were nearly triple that amount!

But then I checked the prices on a whim a few hours later: $650. Roundtrip.

Within less than 48 hours I woke up at 3am in an uncomfortable bed to an unfamiliar ceiling in Cairo.

What soon ensued afterwards was a series of unforeseen circumstances and comedy of errors that compelled the very same friends who I made the bet with to leave Egypt earlier than expected. So I ended up traveling solo the next 20 days without having planned to be alone. Although rough in the beginning, by the end of the 3rd week I couldn’t imagine having traveled any other way. I soon quit all my jobs and left for another 3 months, beginning the The Philippines and snaking my way to end in southern India. I also started a blog called The Monsoon Diaries to document my daily progress and the rest is history.

In other words: I was the last person you would have expected to travel. I was dragged kicking and screaming into this world and there’s a laughable sense of irony that I would be traveling as much as I am today.

Samarkand, Uzbekistan

Samarkand, Uzbekistan


You have founded a website, never missed a blogpost, travelled the world and completed full-time education as an MD. How do you possibly find the time to be such a fabulous all-rounder?

One of the most powerful forces in our lives are the habits we form. My 3 are losing bets, constantly going on micro-trips no matter how busy I am, and striving to fail.

1) Losing Bets: Having “learned” from the bet that led me to Egypt, I would lose another bet that led me to apply to medical school. …Say what?

After the death of my father, I initially rejected medical school believing it was his dream for me to be a doctor, and not my own. However, during my travels something stirred within my subconscious: perhaps I was rejecting an idea — an entire career in medicine — because of him. What if I was actually meant to be a doctor all along, but instead I was about to live my entire life rejecting that possibility as an act of rebellion against my father without ever knowing? Or was this a sick version of reverse psychology emanating from his grave? Like the Iocane Powder “Battle of Wits” scene from the movie “The Princess Bride”, I didn’t know which of my thoughts was the poison, or which one was more real.

In the end if I truly wanted to be free from his influence, I needed to decide for myself. But how? This mental jiu-jitsu frustrated me, so out of that psychological morass I said to hell with it and took concrete action, wagering a bet to myself to apply to medical school to see if I was even meant to get in. The expectation was that I would get denied everywhere, check that box off, and be done with it.

Although I had a sub-par collegiate GPA and poor test-taking skills, everyone loved a good travel story. So I did just that with my personal statements and interviews; I definitely didn’t half ass anything and always have put my best foot forward. And just as I didn’t expect the aforementioned $650 roundtrip flights to Egypt, neither did I expect to get in anywhere. But one school found me “an interesting candidate” and wanted to take a chance on me: I got in.

You know the impostor syndrome where you feel everyone else in your class/work is smarter than you are, and you feel that you’ve been faking it all along and got in through the back door? I’m the actual impostor.

Shocked at the admission offer, I decided to see this as a sign and I didn’t want to take an opportunity for granted. After all like travel, the only way to know for sure is to actually experience it, right? Thus, I decided see through medical school as far as I could without sacrificing any of my travels until I either graduated to become a doctor or failed out entirely knowing that medicine was not meant for me. I reasoned that if travel is what got me here in the first place, then the demanding schedule of medical school was going to give me the fuel to constantly travel. One should not exist without the other.

Despite more than a few close calls and almost getting kicked out a handful of times, I’m now a doctor and so so happy that I am. But it’s not the destination that really matters, it’s the journey. And what a journey it has been.

2) During medical school I decided to make a habit out of micro-trips: If I had 2 consecutive days off from school or work, I would try not to see those 2 days as another regular weekend to recharge, but rather an opportunity to make an international trip possible.

For example, if you can get on a flight out on a Friday night, you can reach almost anywhere in Europe, the Caribbean, Central America, or South America from the East Coast USA by Saturday morning. You can consider the same for west coast USA to Asia, southern USA to Central or South America, or the Midwest USA to Europe. Then the next 36 hours anywhere is enough to explore most medium-sized cities and towns before you have to return Sunday night.

My trip to Ireland in 24 hours with 7 people best exemplifies this. Even The New York Times has an entire column how to travel “36 Hours” for a weekend trip. We’re not the only ones.

3) Strive to fail: But I know there are those of you who get exhausted reading about this in the first place, thinking that these micro-trips “not be worth it” and “I’ll wait until I have more time.”

Is it fear that’s compelling the negative response? For fear never got us anywhere unless we reframe it as another challenge that we use to push our limits: The biggest risk you can take is to take none at all. Or rather, what I usually say, strive to fail — meaning, if I’m not pushing myself to one step away from figurative failure, then I’m not doing enough with my life.

We all feel fear — what matters is what each of us does with that fear. Perhaps fear shows us what the next step is to push our limits, existing also to motivate us to achieve things we never thought we could. That’s another habit I’ve formed.

West Iceland

West Iceland


Tell us something more about the Monsooners, what your community does, what you are trying to achieve and what you have learned on this voyage.

Do things for the right, genuine reasons, and the right people will come to you. My micro-trips soon attracted other like-minded wanderlusters and strangers who — rather than choose either the life of a nomad or the life of a working professional/student — would instead also choose both. I was not alone.

As more people who were reading my blog asked to join my trips, I couldn’t deny them the opportunity. On my trips they began calling themselves monsooners, even running into other self-ascribed monsooners around the globe on trips of their own. Serendipities and synchronicities were happening worldwide. A community emerged.

Even when it seemed obvious that taking time and money off to travel would jeopardize the stability of our lives back home (let alone our professional futures!), we continued to encourage one another to believe in the magic of travel. Whether it was just for a single day in Ireland, a 3 month epic from Turkey to North Korea, or just the magical eternity moment of complete strangers falling for each other, travel became an investment in our lives instead, not an interruption.

We were not alone.

“…Because the only people for me are the mad ones, the ones who are mad to live, mad to talk, mad to be saved, desirous of everything at the same time, the ones who never yawn or say a commonplace thing, but burn, burn, burn like fabulous yellow roman candles exploding like spiders across the stars.” – Jack Kerouac

Cairns, Australia

Cairns, Australia


Do you feel that so much focus on social media and communication with the outside world takes away a bit from the authenticity of travel or not?

Just like any tool, social media can be used responsibly or irresponsibly. My answer depends on the degree of self-awareness and self-control you have in using social media and what you’re using it for.

Social media has augmented my travels in various ways: Like-minded travelers formed this “monsooner” community through social media. I’ve run into people traveling on the same itinerary through social media updates. And through social media I would discover that old friends happened to also be in the very same city I was traveling in. Many of my best travel adventures and stories of synchronicity wouldn’t have otherwise been possible.

That said, I have also seen the toxic effects of social media when used irresponsibly. A dependency can warp someone to feel they can only enjoy a trip if their experiences are constantly validated externally by a group of strangers rather than from their own self. The enjoyment of a travel experience should come from within, and social media will distracts from that. People can go on entire itineraries feeling unfulfilled. They become tourists instead of travelers — going to a place just to “see things” and to “take photos of stuff” for other people rather than going in with an open mind and letting things naturally happen.

Everything must be in moderation and social media is no exception.




Tell us of a few travel experiences that have really stuck in your mind and made a difference to you.

My top travel moments:

The Philippines – Setting my eyes upon the rice terraces of Batad for the first time:

Iceland – Disembarking from my overnight red-eye flight to be greeted by the Northern Lights dancing above my head

Nicaragua – Scurrying up to the rooftop of our dingy hotel for unexpectedly beautiful views over the Tegucigalpa cityscape:

North Korea – Accidentally discovering and exploring the infamous hidden 5th floor in our hotel:

Antarctica – Our first sighting of land after 2 days sailing through the Drake Passage:

Ukraine – Gallivanting about and misbehaving in Kiev at night:

Jordan – Having shisha on a rooftop balcony overlooking Amman:

…and trekking to Petra at night:

India – Stumbling upon the evening puri ceremonies in Varanasi:

…and standing dumbfounded among a throng of worshipers at The Golden Temple in Amritsar:

Egypt – Riding by horseback in the desert as we watch the sun begin to rise over the Pyramids of Giza, before the call to prayer begins to echo through the streets of Cairo in the distance:

Namibia – Hiking among 45m tall sand dunes resembling blood orange skies in Deadvlei:

Myanmar – Sifting through the afternoon fog for our first glimpse of The Golden Rock in Kyaiktiyo:

Lithuania – Finding the only shisha bar open at 4am in the morning:

New Zealand – The perfect weather in the perfect atmosphere in Queenstown:

Slovenia – Caves, castles, evening outdoor shisha, charming European old towns, serendipities, run-ins, old friends, new friends, and a road trip into Italy, and this is just the first 24 hours!:

Japan – Pondering the profundity of the movie “Lost In Translation” at the very place where it was filmed — The Park Hyatt Tokyo — only to have a moment of serendipity literally a few minutes later, and then followed by a magical night strolling the streets of Tokyo (just like in the movie!) until 6am in the morning.:

And I’d like to give a few superlatives:

Most fascinating: Turkmenistan, North Korea & Myanmar
Most beautiful natural beauty: Antarctica & Namibia
Most magical: New Zealand & India
Most serendipitous: India
Most underrated: Slovenia & Armenia
Most fun: Cuba & Ukraine
Most consistently good food: Japan & Spain
Most convenient to travel around: Japan

Lahore, Pakistan

Lahore, Pakistan


Are there any countries that have been a disappointment to you? Why or why not?

If any country ends up being a disappointment to me, I believe it’s more of a problem with me than with the county itself. Perhaps I was not in the right mindset to explore the place, or that I needed a repeat visit. It’s like people, friends, and loved ones: Some places just “click” and others may need more time to unravel.

Countries like Kuwait or Morocco may need me to live there, or Pacific Island nations may need repeated visits to their smaller islands for me to truly appreciate and understand them.

Queenstown, New Zealand

Queenstown, New Zealand


Do you find you miss a ‘normal’ life or that you have had to sacrifice something in order to travel?

Never. My travel life is part of my “normal life”: My “normal life” at home gives me the impetus to travel, and my travels in turn ensures I can have a “normal life” at home. They co-exist. They need each other. This is my normal.

Perhaps the closest I can say to “missing” anything is that while I’m on a trip long enough, I begin to miss home, but that’s OK because I’d be back soon. And when I’m home, I begin to miss traveling, but that’s OK because I already would have scheduled a trip within the month. That’s balance.

Give us an example of a recent ‘average travel day’ that you had, so we better understand your style of travelling.

The best way I can exemplify are our 24 hours in Minsk, Belarus:

It begins with an unconventional border crossing by train where our passports are stamped out in a Lithuanian train station and stamped in by immigration officers on a moving train, being able to see literally every part of a capital city by foot including the must-sees public squares and the obscure oddities (such as the former residence of Lee Harvey Oswald), a little bit of the surreal, a little bit of the magic, and even a few serendipitous stories too crazy to believe. But they happened. And this is all in 24 hours.

Ulan Ude, Russia

Ulan Ude, Russia


You’ve met many other travellers on your travels. What, if anything, do they have in common and how are they different?

I found what has united us all on our travels is this insatiable curiosity to peek over the other side of the fence, regardless of their demographics, age, gender, sexual orientation, or backgrounds. And we all somehow tend to smile at any point when things get lost in translation.

I never have felt one’s age or nationality has ever played a big role in how they perceive the world.

What are your travel plans in the next few months? And what is high on your bucket list for the future?

June 2019 – A roadtrip to see all the Arab Emirates and the Omani exclaves, and then a week in Afghanistan!

August 2019 – Syria

September 2019 – The Eastern Coast of Africa including Tanzania, Zanzibar, Comoros, Mayotte, Reunion Island, Seychelles, Mauritius, and Madagascar

Mid September 2019 – Greenland

October 2019 – Sudan or El Salvador

January 2020 – A Saharan Odyssey through Algeria, Western Sahara, Morocco, Mauritania, Mali, and Burkina Faso

October 2020 – Svalbard

Islamabad, Pakistan

Islamabad, Pakistan


Finally, our signature question – if you could invite any 4 people from any period in human history to dinner, who would you invite and why?

Plato – His allegory of the cave is one of my most referred during my travels; how we all grew up chained staring at what we thought was our true reality, only to be proven wrong every time we have the fortune or courage to free ourselves from our socialized bondage — or perhaps even more daring — step outside the cave. I was that kid chained to the wall, believing I would never leave NYC. Then, I stepped out of my cave.

The late Anthony Bourdain – I just want to hear him speak. Perhaps how travel played a role in mental health. And why.

Tyler Durden – What he would think of our “Brave New World” today and his unbiased opinion on our generation’s fixture on wellness and mental health?

Bob Harris (from “Lost In Translation”) – What did you whisper into Charlotte’s ear before you two kissed goodbye?


The photos in this interview are from Calvin’s personal collection and we thank him for sharing his images with us here at NomadMania!

Our next newsletter will be out on June 5, continuing our Interview Series of Incredible Woman Travellers!