Hope Comes to Visit

What Happens When You Trust the Next Step: A Conversation with Dr. Calvin Sun

• Danielle Elliott Smith • Season 2 • Episode 23

Share episode

Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.

0:00 | 57:06

Send us Fan Mail

What if one unexpected "yes" completely changed the course of your life?

This week on Hope Comes to Visit, I'm delighted to sit down with board-certified emergency physician, author, entrepreneur, and world traveler Dr. Calvin Sun, whose journey to every country in the world began with... a lost bet.

What started as a reluctant trip to Egypt eventually became a life dedicated to curiosity, adventure, and saying yes to experiences that most people only dream about. Along the way, Calvin earned his medical degree, practiced emergency medicine, founded Monsoon Diaries, and discovered that the greatest journeys aren't always measured in miles—they're measured by how much they change us.

Together, we explore:

• Why the biggest risk is often doing nothing at all
 • How travel teaches us to trust ourselves
 • The surprising relationship between fear and hope
 • Why uncertainty can be one of life's greatest gifts
 • How saying "yes" opened doors Calvin never imagined

Whether you love to travel or simply need a reminder that life often rewards courage over certainty, this conversation will leave you looking at possibility in a whole new way.

Connect with Calvin on his website the Monsoon Diaries.
And find his book by the same name, The Monsoon Diaries here.

Chapter Markers

00:00 – Welcome to Hope Comes to Visit
 01:55 – Meet Dr. Calvin Sun
 03:00 – The lost bet that changed everything
 05:45 – Egypt, fear, and discovering the joy of travel
 08:20 – Choosing medicine after losing his father
 13:20 – Why taking the next step mattered more than certainty
 17:30 – Traveling through medical school
 22:45 – Building Monsoon Diaries
 29:30 – Creating a global travel community
 35:10 – Lessons learned from visiting every country
 41:00 – Traveling with intention and ethics
 46:15 – Visiting countries most people avoid
 50:05 – How Dr. Calvin Sun defines hope
 53:00 – Final reflections

I’m so grateful you spent this time with us today.

If Hope Comes to Visit has become a bright spot in your week, I’d love for you to subscribe on Apple Podcasts, Spotify, iHeartRadio, YouTube, or wherever you listen so you never miss an episode.

And if this conversation resonated with you, sharing it with a friend, leaving a review, or simply telling someone about the show helps more than you know.

Until next time, take good care of yourself. And remember—your story matters.

New episodes drop every Monday, so you can begin your week with a little light and a lot of hope.

For more stories, reflections, and ways to connect, visit www.DanielleElliottSmith.com or follow along on Instagram @daniellesmithtv and @HopeComestoVisit



Sponsor And Redefining Sober Launch

Dr. Calvin Sun

I'd rather fail out of med school than to sacrifice my humanity.

Danielle Elliott Smith

Let's take a quick moment to thank the people that support and sponsor the podcast. When life takes an unexpected turn, you deserve someone who will stand beside you. St. Louis attorney Chris Duly offers experienced one-on-one legal defense. Call 314-384-4000 or 314-DUI Help. Or you can visit Dulilawfirm.com. That's D-U-L-L-E lawfirm.com for a free consultation. I'm thrilled to share that the Redefining Sober app is officially live. What began as questioning my own relationship with alcohol became a journey back to myself. And now I've created the support that I wished that I'd had. Redefining Sober is designed to help women explore, question, or change their relationship with alcohol while building self-awareness, self-trust, and a life that feels more aligned and fully their own. For a limited time, founding members can get a discount. Visit RedefiningSober.com today to learn more and begin your journey. I'm so excited to have you join

Welcome And Introducing Dr. Sun

Danielle Elliott Smith

us. When life changes in an instant, hope often becomes easier to recognize. But more often than not, hope arrives quietly in the people we meet, the stories we're willing to tell, and the moments that remind us we're never as alone as we think we are. I'm Danielle Elliott Smith, former television journalist, author, speaker, founder of Redefining Sober, and lucky to be your host here on Hope Comes to Visit. Each week on this podcast, I sit down with extraordinary people whose stories remind us that even in life's hardest seasons, healing is possible, resilience can be learned, and hope has an incredible way of finding us when we need it. Friends, I'm so grateful that you're here and you're listening and watching with us. Today's guest has built a life that, quite honestly, sounds almost impossible. Dr. Calvin Sun is a board-certified emergency physician, entrepreneur, author, and world traveler who has accomplished something that very few people can say they've done. He's visited every country in the world. Now that alone would be remarkable. But here's what makes his story even more extraordinary. He didn't put his life on hold to travel. He traveled while earning his medical degree in New York City, practicing emergency medicine, and eventually serving for more than a decade as the lead physician and chief medical officer as the finish at the finish line of the TCS New York City Marathon. He's also the founder of the Monsoon Diaries travel brand, leading group expeditions around the globe, and the author of The Monsoon Diaries, a memoir that chronicles not only his adventures around the world, but the lessons, challenges, and perspective that came from choosing a lifeless ordinary. Today we're talking about curiosity and purpose, resilience, adventure, and what happens when you're willing to say yes to experiences that stretch us far beyond our comfort zones. Dr. Sun, thank you so much for being here with me. While you're at the hospital waiting on something special, um, I'm delighted you are here with me. Thank you.

Dr. Calvin Sun

That's the way I do things. Never say no and always make a solution instead of an excuse.

Danielle Elliott Smith

Oh, I love this so much. Now I know right before we came on, you told us obviously you work in hospitals, but you're not there working today. What are we doing?

Dr. Calvin Sun

We're waiting on, well, I haven't gotten public on it, but uh people probably can guess what it is, but not jinxing anything. We're just hoping for the best, and I am here as a supporter instead of as a physician today.

Danielle Elliott Smith

Okay. So we'll we'll keep we'll keep our fingers crossed and send good love your direction. So we won't spoil anything, but I'd love to talk about your story.

Lost Bet That Started Travel

Danielle Elliott Smith

So if you wouldn't mind, what inspired um the very idea? I'm I'm a traveler. I love to travel. I'm nowhere near 50 countries, let alone all of them. What inspired your decision to take this journey?

Dr. Calvin Sun

The irony that I wasn't inspired in the first place, and just appreciating how far I've come is the motivation that keeps me going. When I first started off traveling, I was at the time not doing it for the travel, but to fulfill a lost wager. I grew up in New York City, born and raised in Manhattan, and my attitude towards traveling at the time was everyone else does it, but not me. Why spend all that money to visit places I'm not going to live in anyway? And especially like New York City, where the whole world comes to me, I can just, you know, if I want to go to a country, I just go to a neighborhood in New York City. And that perpetuated up until I was 23 years old. My father had recently passed from a sudden heart attack four years prior. I was aimless, lost, but also free. When my father was no longer around, I was free to choose my own path. He wanted me to become a doctor. So after he died, I decided not to become one. And in that freedom, I became a bartender. And one of the customers I was serving won random gig. It wasn't like a regular shift. It was like a gig I picked up for just one night. It was a customer that never left the bar and made a bet with me as we chatted. And one thing led to another where after I had lost the bet, 72 hours later, I was in Cairo with her on our essentially first official real date. And I was there because I didn't want to let her down or let the future me down. And the whole notion that I would go back on a bet or not fulfill all my promises would eat at me for the rest of my life. So I picked up and then acted on it. And there I was and found out that uh I was there during a very precarious time in Egypt's history, where I spent the next three weeks by myself. She had to leave early. All the friends that were supposed to take care of me in Egypt left early. And during those three weeks, I had to learn how to be on my own. The first week I hated it. I had regretted to stay so long. So every waking minute, I thought I was going to die or needed to change my flights to get back home as soon as possible, like everyone else around me did. The second week, I was getting the hang of it. And by the third week, I started realizing this is why people travel. It took me three weeks being dry, kicking and screaming to appreciate something that everyone else automatically loves. Travel was the only space in my life up until that point where I could actually be on my own and learn how to become my own best friend again. I did not have a cell phone on me. I wasn't connected to the internet. I didn't get an eSIM. This is the time before everything was super highly connected. And I think even to this day, travel remains the only space where I don't speak the language, I don't know anyone, I can only commune with myself. And it's a space where I was finally disconnected. I would be finally disconnected to figure out everything in perspective. Not running away from something, but to come back from every trip knowing that something shifted and I could see things with a new light and do my routine every day with a different point of view.

Danielle Elliott Smith

Is there one particular place you visited where you feel like this shift in you was more fundamental, deeper, stronger than anywhere else?

Dr. Calvin Sun

I think right now I'm more able to carry this framework, this filter with me to anywhere I go. But in the beginning, starting off, like anything, any new thing, you'll gain a bigger impact the deeper the the deeper you sorry, you get a bigger impact if the jumping off you jump off when you jump off a bigger deep end, you'll get a bigger impact, is what I want to say. Okay. And that goes to uh if a country that you're heading towards doesn't speak the language, you don't understand the language, you can't even turn on the TV, understand what's going on, the signage doesn't make any sense to you, that's a bigger leap of faith. If you don't practice the language, you're really I can only commune with yourself. You can only talk to yourself. You you know, if I go backpacking upstate, some people would say, Oh, that's just getting away from things and it counts as traveling. To me, upstate New York, I can run into a friend, I can look at a sign that is in English, that in a language I understand, and I know where to go. I see an advertisement I understand. I'm not truly disconnected. Where the first couple of countries that I traveled to, something somewhere like Egypt or India, those are my first few countries. I didn't speak Hindi Urdu. I couldn't read Hindi Urdu or Arabic, and therefore I had to really just rely on my own senses that I had. And without internet, without a cell phone, without being connected, without an ESIM, I think is much more impactful. And that led to bigger shifts when I return home.

Danielle Elliott Smith

So you're really on your own, completely out of your element.

Dr. Calvin Sun

Out of my element, but that it's just a feeling, and it's like meditating. You realize you already have all the faculties within. You don't seek external things to gain external, external uh privileges or or uh skill sets, yeah, or validation. Like you do all these things on the external to realize what you already have inside. And now I can go even upstate New York, knowing what to avoid or to be disconnected from to truly get that same feeling that I got when I first traveled to places like Egypt and India for my very first few countries.

Travel As Disconnection And Self-Trust

Danielle Elliott Smith

So you feel that fundamental shift when you first go to Egypt. You're there by yourself. How does that manifest into the monsoon diaries? How does that manifest into I now would like to travel everywhere? And oh, by the way, I now am going to be a doctor instead of going back to being a bartender.

Dr. Calvin Sun

So the wager that I lost to this person was she beckoned me to join her on her trip to Egypt in like three to four days. And I said, No, I didn't want to go. And it's like, how do you know you don't want to go? Uh and I said, I'm not into traveling. And how do you not, how do you not know that you're into traveling? She kept pressuring me until I was had to find some kind of excuse. You should be stronger than your excuses. But at the time, I didn't know I didn't want to say no because I really didn't have a good excuse. Here's she, somebody was inviting me. What I was bartending. I've I had I was gig work. I can't.

Danielle Elliott Smith

There's no reason you couldn't go. You just couldn't. You just in your head, you didn't travel. Like I'm a person who doesn't travel, the world comes to me. So the answer is no.

Dr. Calvin Sun

Yeah, that's that's the irony. That's what motivates me to travel now because I've come such a far long way. And and the fact that I take thousands of people on my trips is why I keep going. But at the time, I didn't identify myself with that. I identified as somebody that didn't make excuses, but couldn't even say no. I couldn't even be definitive on what I wanted. I didn't even know what I wanted. I was in a lost space, like most of us right now, purposeless, aimless. And and the only thing I did know was to tell her, fine, I the only reason uh the only reason I wouldn't go is it's too expensive. And I will only go if tickets are like under $700 round trip. And I said that's very lazzie fair. And we took that and shook on it, and we kept checking the flights over the course of the night and the next morning, and it was a very long back and forth where tickets were like $2,000. And I just kept even pulling it up to tease her about that. I was this isn't not a reason to go because I just can't afford $2,000 on a round trip flight last minute. And then lo and behold, the universe will have it. And one time we checked a f 24 hours later while we were still together, and it dropped down to $650. So that excuse was taken out. I had no other excuse to rely on. I wanted to be a man of my word, and it was a great deal, so I didn't want to give up on that. So I went. And I didn't want to like back out on a deal and wonder what if for the rest of my life. Okay. That was the only reason. I was making a bet with the future me. And following through on that, that led me to decide after three weeks of hating travel to come back loving it. How do I know for sure I'm not meant to become a doctor? How do I know that me saying no to be a doctor so that I can live my own life isn't actually still an action influenced by my late father? If I'm going to say no to a career because of my dad, that actually makes me still doing something because of my dad. And I'm not really living for myself. I actually might be meant to become a doctor. How do I know for sure unless I do it? But then if I do it, do I then just give in to what my dad always w hadn't wanted? How do I know what's the right decision? How do you know what decision really comes from you versus an external social prowess?

Danielle Elliott Smith

What was pushed on you? What was what was how do you know what was meant for you but versus what everyone else thought your path should be?

Dr. Calvin Sun

Yeah, were these seeds planted? Was I being manipulated into it? Is this a long con that my dead dad did he pay this girl right before he died? Like three years ahead.

Danielle Elliott Smith

Like I thought make sure that you go to this bar, find my son, and make sure you plant the seeds of him being a doctor.

Dr. Calvin Sun

You are totally his type. Three years from now, he's gonna be at this bar. Like he didn't know I was a bartender. Uh I mean, I started bartending like crazy after he died, just to pay off college. And because he was the only breadwinner. My mom had Parkinson at the time. Like it would it would have been a very elaborate ruse. So I did think all those things. And that's the the issue that a lot of us right now feel hopeless about. Like, how do I know the thoughts that I have is an original thought versus something that's been planted by an external influence? I really people always want to live their life that was meant to be, but you don't know that until you look back. And that's a big risk to take when you may have made the wrong decision this whole time. And you don't want to wake up one day and go, what just happened? I didn't want that. But inaction is also a hopeless place. This analysis paralysis when you don't do anything and then your whole life passes by and you could have made an action that led to the right place. So the the trap, the the trap is that there's no right trying to find an answer when there's not supposed to be a right answer. And that travel, the whole losing the bet to Egypt with three weeks later, I came back loving something that I initially hated, influenced my decision to feel this and apply the same way to the decision board in

Choosing Med School Without Certainty

Dr. Calvin Sun

medical school. I'm just going to apply. That is an action.

Danielle Elliott Smith

Okay. Like agreeing that I dip my toe in. I see the water, I'm gonna dip my toe and see what happens.

Dr. Calvin Sun

Yes. And my hope, my secret deep down hope was to get rejected everywhere because I only had like a 3.0 GPA and a below average abcat score.

Danielle Elliott Smith

And then you could be like, see, Dad, I tried to work.

Dr. Calvin Sun

I checked that box off and I can move on with my life. Right. And that would give me such a relief. The emotion, I mean, it sucks to get rejected, but that would be my Oprah story. That I became a travel blogger uh because I applied to every medical school and didn't get in, and now I'm a full-time travel enthusiast.

Danielle Elliott Smith

Okay.

Dr. Calvin Sun

And that emotional label will be lifted. But then the universe will have its surprises. That's the irony. You do something, and you're the best plan is no plan. If you plan to get rejected everywhere, the universe will have other plans for you and prove you wrong. And I think that going forward with that lack of expectation in my personal statements, in my attitude during interviews, where I'm I wasn't like sounding like every other medical student. I want to be a doctor so badly. People on the other side interviewed me. It's like, how do you know for sure? I wasn't that. I went in with an attitude that's like, I really don't know. I'm gonna be very upfront that I don't know. You know better. You've graduated many great physicians from where you're sitting, and it's up to you to decide. I'm gonna just go in with open eyes and an open heart, willing to learn and willing to explore this if it's meant to be. Here's who I am. Take me as you are, take me as I am, and as you are, if you think there's any hope in me, then take it, accept me. And once school took me. And I remember opening the envelope that October 2010, 2009, and I was like, I'm gonna do it. I was literally, I I mean, I yelled out an excludive, a very long shit.

Danielle Elliott Smith

You can say whatever you want on here. We're we're open.

Dr. Calvin Sun

Yeah, yeah. And it and I and I and I didn't know what to do next other than just take the next step.

Danielle Elliott Smith

You're like, okay, so I guess I'm going.

Dr. Calvin Sun

That's the important thing. I didn't know what to do except to take the next step, which meant I didn't know it was the right step. Right. I just knew it was the next one. In and people would say, and it would be very they they they it would behoove me to lie to you and say, oh, and I knew that was the next step. I didn't have that conviction. Right. I I generally remember and I wrote about it that day. Like, I don't know if this is right for me. I think they made a humongous mistake. This imposter syndrome just took over. But it just was the obvious door that I had to go through with deep down this insecurity, whether I was setting myself on a path that I would regret for the rest of my life.

Danielle Elliott Smith

Now, Calvin, at this point, were you traveling?

Dr. Calvin Sun

I was making plans to travel for the rest of my life.

Danielle Elliott Smith

Where where was this? Where did this fit in with the trip to Egypt? So, what is the timeline? Egypt and this acceptance.

Dr. Calvin Sun

It was one right after another.

Danielle Elliott Smith

So Egypt So had you gone anywhere else yet, or were you just in the throes of I've done Egypt. I think I'm a traveler now, so I'm going to do something else.

Dr. Calvin Sun

I think I'm a travel right now. I'm gonna plan this humongously long Philippines to India backpacking trip over at least two to four months.

Danielle Elliott Smith

Okay.

Dr. Calvin Sun

And that will be the next one. I picked that area because it was in my research the cheapest, the most affordable. Like I can survive under $700 a month. Okay. Uh, and sublep my apartment for way more rent. So the irony is like, I don't have time or money. Well, there are ways. Right. And I was like, wow, this actually works. If I sublep my apartment on Craigslist, somebody pays me X amount, and I can travel to a region for the next three to four months as I'm getting X times three X per month. Okay. Make sure that Y every month in Southeast Asia is cheaper than X, I'm actually making money by making money to travel. I oh my God. So like I wanted to take advantage of that. That hopelessness of I can't travel because of time and money became hopeful of I can I can do this. And then this medical school thing happened, and I'm like, well, this puts a wrench in my plans.

Danielle Elliott Smith

Okay.

Dr. Calvin Sun

So I I accepted the offer, which med school starts in August, and I decided that I will leave uh May to August before med school.

Danielle Elliott Smith

Okay.

Dr. Calvin Sun

On this huge long trip. I am a man of my word. I will commit to this plan that I had after Egypt that I will continue traveling. Okay, med school, the specter of med school is not going to get in the way. And you know, of all the times to do it would be before med schools with. So I did that from May to August. And the plan was to fly back and start med school the next day.

Danielle Elliott Smith

If I advise me, if I have the extra breathing time, no time to settle in, no time change time, start med school the next day.

Dr. Calvin Sun

Yes. 100%. And I did it. And that was the beginning of the monsoon diars where I created the blog to chronicle every day I was on the road, blogging from my first day in the Philippines to my last day through three and a half, four months later, in India to Singapore, back to New York. I blogged daily. People followed along, initially my family and friends, but then, you know, sharing it word of mouth. And then people follow into them the med school days where I blogged from meds the first day of med school. It's like here I am, I made it. And we didn't know if I was gonna keep traveling because at the time, we all know med school has this reputation where you don't have time for yourself. You want to take around? Spend the next 10 years just living for a medical training. Right. You're gonna sleep no to all his birthdays, you're not gonna take care of yourself, you're not gonna get any sleep. You're gonna cut yourself on all your friends, let alone traveling for yourself. So I thought that was the end of the blog. And I blogged about that.

Building Monsoon Diaries While Training

Danielle Elliott Smith

Okay. But did you keep going with the blog?

Dr. Calvin Sun

I spoke about this in my white coat ceremony speech I gave two years ago at my alma mater at that med school. Uh, now is a full-on attending clinical system professor in emergency medicine. They invited me back 10 years later after I graduated to give the white coat ceremony speech where I said I thought I was never going to travel. And then one weekend in October on my first semester, so two months into med school, October, there is an exam on Monday that I had to take. And by the Thursday prior, I had burnt out already. I got this invite to go to a wedding in San Diego. I said, fuck it, I'm gonna do it. I'm burnt out. I don't, I rather be a good person and then learn how to become a good doctor than sacrifice keep being a good person, backing out of this very important family wedding, uh, to learn how to be, you know, a good doctor and then to try to be a good person again after the fact. Like, no, I if I'm gonna fail out of med school, then I might as well at least not miss out on this wedding. That was the actual thought. Like, I'd rather fail out of med school than to sacrifice my humanity. Okay. That was a second wish, too, by the way. Like, I didn't think about getting to med school though, and I did if I didn't, I'll just check that box off. Now that I'm in med school, if I fail out of med school, I can check that box off, have my Oprah story, and then become a trap full time travel blocker. I that was still out there. This monsoon diers thing was turning out to be a good backup plan in case I got kicked out. And I knew this was like an opportunity that most people would kill for, so I did try my best at med school. I'm just not a good test taker, I'm not a good student. What I am good was trying to learn how to. Be good at is following through on my word. And I went to that wedding and flew out Friday, came back Sunday, and took the exam and barely passed by a few points because I studied on the plane. And when I realized when you study on a plane, when you're in a completely different environment, you recall information better. There's a whole study on that. Like if you change up your studying environments to be as unique as possible, the memory recall is much more formidable. It just comes back with a force when you do those tests afterwards. So I was like, wow, I'm actually, I didn't ace the test, but I'm actually remembering things to get by on this test by this, on the to get by by the skin of my teeth on this test to pass. And then a few weeks later, uh, we had another exam scheduled for December, the end of the semester exam. And it was the same thing. We got an offer to go to Hong Kong on a $200, $300 hack fare flight that I found at the last minute. And all the signs pointed just to go. And San Diego was a little, you know, dip in the pond with the uh the San Diego trip was a dipping my toe in the pond. The Hong Kong was, I would fly out Friday and a 20-hour itinerary flight to get to Hong Kong, spend 20 hours in Hong Kong, and then 20 hours back. I'll be spending more time on a plane than the actual destination. But the flight was the flight prices was unbelievably cheap that I was like, this is a one and and of a couple of years opportunity just to take up on this trip to Hong Kong right before my exam on Monday. Studied on the flight, did it for 20 hours, met a lot of people on that weekend trip that I'm still friends with to this day. And it was kind of like feels like an investment now looking back. But I made it back in time, also passed the exam by the skin of my teeth, and kept doing that as a lifestyle for the blog. And I would blog about how I was gonna keep doing this once a month, every month, throughout med school and residency until to this day.

Danielle Elliott Smith

Wow. That is extraordinary. So now I I'm gonna ask you said we there in terms of San Diego and Hong Kong, and you mentioned that initial bet. Is that person still significant in your life?

Dr. Calvin Sun

We dated for a few more months, and uh didn't work out. I mean, the Oregon stories are never as good as pragmaticism, but uh stayed good friends with the family. Uh her sister, younger sister ended up joining a board, this 51c3 board, uh, that I was board of directors of and maintained a really good working relationship. Uh it's on socioeconomic justice for Asian Americans. And I, you know, we're we're not all on good terms. I I I may be a little embarrassing that I uh that she's part of an origin store or something bigger, but I don't name names.

Danielle Elliott Smith

No, that's okay. I wasn't asking for a name. I just because you had said we, I wasn't sure whether or not that relationship had had continued on.

Dr. Calvin Sun

So this is not, no, this isn't a the group more. We yeah, I was I'm I'm still fond of what we had.

Danielle Elliott Smith

And it's part of your story. It's I understand there are people in my past who are part of my story who are no longer part of my story. Um, but they're part of how I got here.

Dr. Calvin Sun

So I'm very grateful to her that she was in the right place at the right time. And I hope fond memories for her as well.

Danielle Elliott Smith

Inspired a piece of you to to begin this journey to find that side of your brain in a way, uh, that that wasn't activated at the time. Is there a place you visited? Are there places that you love more than others? Is there anywhere that has a now that you visited everywhere, where would you say you definitely have to go that isn't typically on someone else's radar?

Dr. Calvin Sun

My honest answer is my next trip is based on serendipity, has been all the trips I've done in the past in that order. One trip will lead to the the clue to the next trip. And the the ones that I find that looking back have activated the most amount of returns and serendipities that gets me to come back over and over and over has been mostly in the South Asia and Middle East regions.

Danielle Elliott Smith

Okay.

Dr. Calvin Sun

And uh I find that every time I go back there, it creates way it plants way more seeds. It creates many more opportunities for return trips, whether it's an invite to a wedding or running to somebody there, then then invites you to go back, or it you post something that leads somebody in your community or somebody following your social media to say, I always wanted to go there or another region of that area. The returns are much greater. But there have been plenty of other regions that I've come back to. I was in Finland for the third time just three months ago because two of our travelers got married there and wanted just to invite me and anyone I wanted to bring, even if they didn't know them, to get to witness their wedding uh in the ice chapel up in Lapland of Finland. Uh so that's an example of what happens over and over in like places like India, Pakistan, which I've been to numerous times, both of which, uh, and you know, many places in the Middle East.

Naming The Brand And Serendipity

Danielle Elliott Smith

Will you please explain the origin of the name Monsoon Diaries? Because I was looking at it on your website and I and I loved the sort of the mission that you have behind the travel you guys do.

Dr. Calvin Sun

The honest truth is I had no idea what my blog was supposed to be called. And we put it out there to my community of friends to come up with a name, and everything just didn't land well. It's probably the hardest thing you can work on, the hardest decision to make when you're starting off anything. But yeah, it's it's the title's a tricky one. You want it to hit right, and you it's very hard to change gears or change ladders once you settle on a title, and later on you want to re-market or redirect the the mission of whatever it is that you're building. And sometimes you want to build something and let that inform the name, but most people need to start off with a name. And I remember at the time I had just watched Monsoon Wedding at the advice of a former partner, an ex-girlfriend at the time. And I had just watched motorcycle diaries by myself, right? This is when Netflix was shipping out DVDs to everyone. And it just made sense watching them both back-to-back monsoon diaries. That uh because the motorcycle diaries is about a pre-medical student who travels on a motorcycle everywhere around South America and becomes inspired or led to a lifetime that's beyond medicine. So that kind of sparked the origin story of what I had already lived with the Egypt story and getting to med school. And the monsoon wedding part of this rainstorm where you're just running around in a deluge, a monsoon, is like one of my favorite things to do in the New York City summer. There's something magical when you're walking down, it's clear one minute, and all of a sudden you get soaked and you're just dancing in the rain because you've just given up on trying to stay dry and just like screw it. There's like an enormous weight being lifted off your shoulders when you're just past a certain threshold, event horizon, and you're like, you know what? I'm just gonna enjoy because there's no point in running away. I'm in it. And that's like the way I always have lived life. So monsoon writing as a film captured the whole notion of that in through the lens of a family getting married and multiple meet cutes and threads raveling together, uh unraveling and coming together and unraveling, coming together. Is is this the beautiful way I live through life, dance through life, if you will? And it's a lot of dancing in there. So seeing them back to back, I just felt was a sign from the universe that they're meant to be combined. And I said it out loud and it just landed with a lot of people that I said that to, and that's where I committed. It didn't turn into the concept of monsooning as a verb or noun, uh, the way we use it as a trip, until three years later in 2011, when I took one of my first group trips to Iran, and people in that group started using the word monsooning or calling it a monsoon. And I would overhear this, and it just like activated this organic resonance that makes you jingle a little bit. This is this this is happening. They are doing it. You build it and they were they are coming and they're filling the vessel that you built for you, you've built the environment and the right people just filled it up on its own without you you forcing it, and it's taking a life of

Turning Solo Trips Into Community

Dr. Calvin Sun

its own.

Danielle Elliott Smith

At what point did you think this can be a community? We can travel together. When did it move from you saying, I'm going to travel and have these experiences, I'm writing about them, to you saying, you know what? I bet we could all do this together. I can show people how to make travel accessible because one of the things that I've noticed about your traveling, this is not, hey, I'm putting together these exclusive trips that no one can afford. It's really making travel to like unusual places accessible. So people can't say, I can't afford this, there's no way I could ever go. It's it's special.

Dr. Calvin Sun

Yeah, it just struck me that it became a community far too late than I should have uh picked up on. I remember starting off traveling solo for the first monsoon diaries diaries, and the people who were following along some of them asked to join, and I initially said no. I didn't see the potential in that. And that saying no actually invigorated those people to want it to come even more.

Danielle Elliott Smith

And you can't tell me no, I want to join.

Dr. Calvin Sun

Yeah, is so many of you wanted, and I think even right now, everybody wants to be an entrepreneur and everyone's hustling to get more people to buy their product or get their service. And in the context, I mean, it is true that we're a product that is reacting to an environment around us. We're products of our environment. And the environment at the time was ever we're surrounded by a hustle culture where everyone wants to be the next big entrepreneur and the next big thing, and trying to solicit people for their business. And here I was starting a new thing, a travel thing, and saying no. Like, please go away.

Danielle Elliott Smith

Right.

Dr. Calvin Sun

But it wasn't a no as like a hard no, it was more like it's I didn't say like, no, you absolutely cannot come. I do not accept travel. It's more of a, are you sure you want to come? Like, this is not going to be comfortable. The way I travel is rough, is balls of the wall, trying to make things right before the the lecture starts, the way before your job starts the next day. Like we are getting in Monday morning at 6 a.m. and we're going straight to work right after at 8 a.m. Like I'm coming in, I'm flying at 5 a.m. before the lecture starts at 8 a.m. I am making it. And I don't know if you want that. Are you sure you want that? Are you sure? I'm right putting this writing. And people are like, wow, you're being so negative. Like, this is the this is how I want to live here. Like, I want to live like this. I'm actually reaching out to you because you're making a blog proving that it's possible. And to us, you feel like like you're making this all up. Like it feels like I'm reading someone that's just making this all up. And I want to see if it's actually true that you're actually going to these places, taking those photos and making it back in, making it back in time for med school class. And you're still a full-time med student. You didn't drop out yet. Like you're not.

Danielle Elliott Smith

I swear to God, you and my ex-husband are very much the same person. He and I are very good friends. This is how he travels. He does what he calls capers. And he, like, if he's sliding in at the last minute, he's making it. He and both of my kids, my kids are 22 and 20. The three of them love Disney. I've always loved going too, but not the way they do it. They had a one-day window and they went to Disney last Friday. They went to all four parks, 17 hours, 23 rides, 32,000 steps, 15 miles. Done. It was like an Olympic sport. I I felt like I needed a vacation after hearing them talk about it.

Dr. Calvin Sun

You need a vacation on that vacation.

Danielle Elliott Smith

Right. But it sounds like very much like you travel the same way. Like you pack it in, you are going. And if you've only got 20 hours in Hong Kong, you're going to make the most of it.

Dr. Calvin Sun

Yes. It is a very New York lifestyle, but also the way I see it, we're only we're never going to be as young as we are today. Correct. This is the only chance we have to travel like that. I don't want to postpone my life or give into the psychology postponement where I'll travel like that one day when I'm X, Y, and Z, when I reach this milestone, when I retire early. By then you're too far along to even want to travel like that, let alone do you have the physical capabilities or health-wise, like if there's enough things on your plate already that prevents you from doing that. And if you make a habit of saying, I'll do it later, then that becomes a habit. And it's very hard to bring to break, to bring any change to a habit you've already invested in for decades of saying, I'll do it later. The only time to do it is now. And if it's messy and unplanned or less planned, all the better because the best thing that can happen is that you went. The worst thing that can happen is that you went and came back with a really good story. And I think that when people saw me do this for two to three years in and still write about being in med school and being a full-time med student and having gotten kicked out, they were like looking at their jobs. And it was like, if this full-time med student is doing this and going to these places and bringing all these people, why can't I? And it just ballooned to more people trying to come along because I would do all the logistics for them because the goal was to all get back by Sunday night or Monday morning before their 8 a.m. to nine job, eight to nine job.

Danielle Elliott Smith

That is fantastic. What is the best thing you've learned about yourself in these last years as you've moved from Calvin, the bartender, to Dr. Sun, the emergency room physician and director and the the person, the founder of Monsoon Diaries, who's visited every country in the world.

Dr. Calvin Sun

I just know that I can look in the mirror and say that it's possible. I can look back, having learned about myself, knowing that I have what it takes to do the impossible, that the biggest risk can take is not to take any risks at all. And I have come a long way to prove to myself in the future, now looking back, that I can trust myself making future decisions based on an actual repertoire, a resume of taking risks and getting back in time, taking care of communities of thousands of people to every country and keeping them safe so that when it comes to taking care of a family, taking care of my loved ones, taking care of myself, I can look forward in the rest of my life. No way, I have nothing else to prove. I can take it easy if I want to, but also show my future family a world of possibilities in a way that other people can only assume or guess at. And I've learned that it's okay to not know, to not know what the next step is. I and it's still hard for me to this day to still be comfortable with insecurity, but I'm a lot more comfortable now than I ever was 15, 16 years ago, where I didn't know what I wanted to do. The bartender in me knew that every night could bring unexpected possibilities. Every bartending night, every bartender can tell you every night is an adventure. And that attitude has led me to all the bets, lost bets, lost wagers, and detours that led me to become a doctor and all the insecurities of what it's like to become a doctor and taking care of patients with all these unknowns. And on top of that, going to all these countries with all these variables and unknowns, then that all comes together to the person you are today. And it feels like kind of like what I've learned is I'm capable of time traveling. I can look through the blog, read about the past, and live as if I was there because I blogged every day while I was on the road, knowing that I can reach back into my past self and reassure them if that's a possibility that resonates vibrations I can give to my past self, knowing that no matter what insecurity they're feeling at the moment, here I am right now, knowing that they'll they'll make it, they'll get there, and the it'll always work out.

Danielle Elliott Smith

I noticed that one of the things you said was that you try to always say yes.

Dr. Calvin Sun

I always will try to be stronger than my excuses. So if that leads me to saying yes more often than not, it's always led me in the right direction. I do think it's important to know when to say no and have boundaries. Boundaries are very important. You should know what you're capable of and what you're not, and not try to put others in harm's way because of an assumption or presumption. But if you have all the information in the hand and you're not making a decision based on fear, but more on an informed experience and gut intuition that you trust or have developed a trusting instinct in your tuition, then you are more likely will say yes from a very informed point of view than a risky one.

Danielle Elliott Smith

What does someone who has visited every country in the world put on their bucket list next?

Dr. Calvin Sun

I would start what depends on where you are when you want to start this. The way I set off to do is was not to actually visit every country in the world. I just wanted to go to a new place that I'd never been, that I can't judge, and follow through on the signs that pointed to that place as the next place. So an invite, someone mentioning something, something that sparks intuition. We're like, uh-oh, I do want to go there because I haven't been and you mention it, must be a sign. Somebody wear a t-shirt of a country that I was already thinking about on a boat. That's how it got to Cabo Verde. You know, that if somebody's sending me a screenshot of a country that was on someone's shirt, I have I have followed through on that. I've made decisions based on these very seemingly random, whimsical happenstances. I love that.

Danielle Elliott Smith

Is there anything that's on your list now? Is there anything now that you've visited everything? Is there anything that you're like, I still need to No, I've that is I'm retired.

Dr. Calvin Sun

That's the beauty of it. That's the beauty of it. I mean, there's Sudan in Julie in January that somebody had just gone, made a referral, told me to go with this guy. We had a really good rapport, and he said everything has normalized and stabilized. And if I want to come by for a few days or one week trip, he'll take care of us. And he has taken many of my friends to Sudan. And if the if it feels right and the weather is good and the political climate is stable, and I'm not depriving any locals of their resources or time to show us around. And if it only has a net positive, have a travel ethicist for that, then there's no reason not to go because I've already practiced a lifetime of not giving into any excuses. So you have it. Yeah.

Travel Ethics And Hard Destinations

Danielle Elliott Smith

But explain travel ethicist to me. I mean, I I I have a have an idea, but I I love that that is a piece of the traveling you're doing, that you are being really intentional with where you go and how you are not taking away from the people or the environment when you visit.

Dr. Calvin Sun

So there are a lot of controversies inherent in some places that you visit and also the timing of when you visit. I try to make as minimal of an impact as possible to uh that's why we call the monsoon diaries. I didn't call the hurricane diaries or the typhoon diaries, where you know it hurts a lot of people and it's a natural disaster. Monsoon brings the harvest. It is seen as a very positive weather pattern where rain dumps and it the harvest season comes and it brings food and joy and people dance in the monsoon. I mean, it is can it can be lethal, but the way I lean towards that word is because we go to see a place really quickly and we leave as soon as we came in. So it has minimal negative impact. It's a monsoon comes in and comes out. And that's the and that's why it stuck with me as we're monsooning. We are looking, we're we're experiencing, we're a wallflower. We're not trying to impose anything on anyone. And the only thing we're trying to do is a net positive. But I understand with some countries, in some timings, it could be a little fraught with some controversies, but not even God pleases everyone. And anything you do, someone will find something wrong with it. But at least I went in having thought about it, having been informed and intentional in trying to minimize the carpet footprint or any kind of footprint that negatively impacts the locals of the people around us taking care of us. And here for hiring somebody to see my backside, see my blind spots, to look out for things, to do all the research, uh, it's a uh it's it's it's crucial to at least make the effort. We're never going to be perfect, but there is a certain timing when you can go to certain countries where people will not complain as much when they're outside looking in. And uh I think that is it's it's it's the least. That we can do. So it's a so she's a social epidemiologist. We are very intentional when we choose to go to places. And uh we are very intentional when not to go to places and saving it for later. And so far, knocking on wood, we really haven't been canceled. I've not gotten any any, not a single one comment of how could you go there? Uh I expect at least one. Give me at least one. Maybe not enough people are watching us, but if I take thousands and thousands of people to these countries from word of mouth with zero marketing PR, then we do have a wide audience. And to have zero, I mean, I come on, give me a give me a little pushback. But I think it's because of all the research we do.

Danielle Elliott Smith

It's because you're doing the right thing. It's because you're being intentional. Where is your next trip?

Dr. Calvin Sun

We ended up able, and then I think it's after the fact we visited every country in the world without trying to do it. I don't do it for the number. I don't do it because I have to become a person that travels to every country in the world. You'll just go to new places and we make it a habit and consistency. You'll eventually hit every country in the world. I didn't start realizing I had a number or counting until I was about 140, 150 in where these websites start tracking us uh based on our blog posts and there was some rankings and it became a little fun thing. And I started it to pay attention to them. They started interviewing me. He's like, You are at X number of countries. Like, am I? Really? Well, that's a course.

Danielle Elliott Smith

Okay.

Dr. Calvin Sun

And you know what? I was like, might as well just that actually help.

Danielle Elliott Smith

Try to go to places then.

Dr. Calvin Sun

Where then, yeah, the ones that have yet to go. And it does actually inform me of places I never thought of going because some places are counted as territories or exclaves or enclaves of a country I've already been to. So Greenland belongs to Denmark. But it's if you go to Denmark, Greenland would automatically shade it. I would totally miss out on Greenland, Greenland if I only focused on countries that I never been to before.

Danielle Elliott Smith

Okay. I love that. Is there anywhere you're going next?

Dr. Calvin Sun

Uh never been to Greenland. That was September 2019. Uh, another another good example is UAE. Everyone goes to Dubai and says I've been to the UAE. Well, if you just are country counting, and that's your purpose, you will miss out on all the awesome exclaves and enclaves that the UAE has outside of Dubai and Abu Dhabi. There are exclaves that Oman owns in Khasab, that's right to the north of the UAE, that is not in the physical area of Oman, that's really cool to visit, and you can count that as two separate places. There's an exclave within a Musanan Oman, that's an exclave within an enclave and then an exclave. There's it's just so fascinating of like what people demarcate as as as borders.

Danielle Elliott Smith

Okay.

Dr. Calvin Sun

Country counters will totally miss that. If you're someone that generally wants to travel to far-off beaten places and just to have your brain changed, yes, because there's so much we don't know, right? Why do you call this place belonging to Oman and this one belongs to UAE? Oh, yeah, that city in Belgium, Amsterdam on the border, where literally like every foot is like a different part of different cities. If you zoom in on that, it's like pockets that belong to um the Netherlands and Belgium that's in scattering different cities. So that parking lot belongs to Belgium, and then right across the street, that cafe belongs to the Netherlands. But then right next to the cafe belongs to Belgium again. And everywhere you walk, you're like going in and out of the country. Like Bartley, Bartley Herdlog, I think is the name of the city. I'm may maybe pronouncing it wrong. But yeah, it's just surreal that there's so many places like that in the world that changes the way you look and think that when you come back, you literally are tripping, but without having to take a substance.

Danielle Elliott Smith

How do you go to countries that are traditionally difficult for Americans to enter? North Korea, Russia?

Dr. Calvin Sun

Timing is a very important thing. So we went to North Korea in 2010, back then when it was assumed that Americans had a hard time getting it, but it was actually the hardest in uh sorry, it was actually hardest in terms of of the perception, but the easiest in terms of getting the visa. People assumed it was so hard in North Korea, no one bothered to try. But if you did try, just or email, just asking, okay, it's a five-minute visa. You fill out something that they made up on Microsoft Word, and within like a day, they were like, your visa's ready. You just have to pick it up in Beijing. And they're probably not at least uh to get to Beijing to pick it up. But that's it.

Danielle Elliott Smith

Were there moments where you thought, okay, now that I've crossed into North Korea, do I is there any danger that I will not be able to cross back?

Dr. Calvin Sun

No, at the time in 2010, not a single bad thing happened to an American tourist. And that's in 2010. Right. I mean, now I would be a lot more careful. I would do my due diligence like a hundred times over than I did back in 2010. But it was a just different climate. Like Russia, I went in 2017, 2016, 2015. It was a very different relationship with America at the time. You just get a visa in Russia. I mean, it is a hard visa to get, but as you don't show the consulate and have some patience, wait through to five weeks, you'll get your visa. And we did the Trans-Siberian from end to end. And it was it felt like I was visiting at just another semi-difficult country. Uh, I would say on the same level as India. Yeah, and it's it was just different in the way I had to, you know, go about safety precautions. I mean, Russia isn't unsafe, but you know, has its own things that are are are culture shocks for most people who are not as traveled. But overall, I'm like 100% safety rate since then when I I think I took a group of 17. Now I will probably get a lot more fixers, local Russian friends. I have a former partner that uh is Russian American. So I would like to call someone like her and say, get all your people, all your family in f in Russia to look out for us. Like, there's an example of the things I would do now based on the timing. But back then I didn't have to do that. I all I did was I called her and I was like, hey, I'm in your mother, I'm in your motherland. Show us around. Like, you know, what would you recommend? It's like, I like to go to these places. Now I'd be calling her before the trip and say, who do you know there who can show us around and can vouch for us, write a sponsor letter and just to make sure everything uh is taken care of when

What Comes Next And Defining Hope

Dr. Calvin Sun

we get there.

Danielle Elliott Smith

What trips do you have coming up?

Dr. Calvin Sun

I have just finished an upstate camping trip for my more local monsooners who don't like to travel internationally. And that was just upstate. So now we do a lot of domestic trips. The irony, we go travel the whole world just to realize where home is, which is right here. Um but that's the point. Like I didn't travel to get something different that I don't already have extern externally to internally. I travel externally to find what I already have internally. And that's what we're doing now. So a lot of camping trips, a lot of ski trips, all domestic, uh, West Coast, Vermont. It's on my website. Uh, and I have that Sudan trip because I always follow through my promises. I always follow through my promises. That person in Sudan has invited me, and I'm gonna try to go in January of 2027 if everything's stable. And I'll pick the next trip whenever I'll pick the next trip whenever someone invites me next. And I have an annual trip to Tomorrowland in Belgium, uh, a music festival, the largest electronic music festival every year, uh, because I have a special relationship where I get a lot of tickets and love to share that with people who have not been.

Danielle Elliott Smith

That is extraordinary. Calvin, how do you define hope?

Dr. Calvin Sun

I would say it is the in the face and presence of fear that something finds you the way out. Hope cannot exist in the absence of fear. You have to feel a feeling of fear, and hope is whatever isn't the action that is based on fear. Hope is the feeling and action that you make, that you think, that you envision when you take a step back, but you let you you you don't try to ignore the fear, you don't try to push it out, you don't try to suppress it, but you move through it or you let it pass through you. And out of that, just standing still, some thing arises, something comes out that reveals itself as the next step that feels far different than the initial feeling that you had when you had the fear. And that thing I would call hope.

Danielle Elliott Smith

I love that. Where can people find you?

Dr. Calvin Sun

Monsoon diaries.com, M-O-N-S-O-O-N-D-I-A-R-I-E-S dot com. You can also find me on social media, instagram.com slash monsoon diaries, or you can just google monsoon diaries, my name, and you'll eventually find it. I always say that the right trips choose the right people. So I we don't do any marketing or PR other than being asked like this and just going with the flow. So if you're meant to find it, the right trip will call to you. The algorithms be that may will get you to the right people, to the right place that'll lead you to a conversation with me. And hopefully I can take you wherever you want to go and have you come back with limitless and wonderful stories to tell your friends and family.

Danielle Elliott Smith

Kelvin, is there anything I didn't ask you about that you'd like to share?

Dr. Calvin Sun

No, I think you asked wonderful questions that brought up a lot of things I haven't thought of before and spoken to in a context that is very weird. Uh I was uh I was uh uh been going through I have been going through weeks and weeks of uncertainty regards to my family life and the the people around me. I'm in a hospital right now as a supporter rather than a physician, should clue you some of you in to I don't want to jinx anything, so that should be another clue of what is happening. Uh it's a one in out of 91 million case. Uh affects the people that I love. Uh it's kind of weird to not be in the driver's seat, uh, to be the thing that is happening to. I I'm a survivor of cancer three years ago, uh, where that was something similar to happened to me, but this is now happening to someone that is close to me. And I've been rack re uh reeling through that for the last five weeks. And so far, there's a lot of hope going out around, but uh, this is after a million false alarms and moments of fear. But hope cannot exist without fear.

Danielle Elliott Smith

We will send all kinds of love and hope your way. And I'm confident the community who's listening and watching will do the very same. It has been an absolute delight to have you on the podcast.

Dr. Calvin Sun

Thank you so much for having me. Thank you for letting me give this interview in a hospital. That's why you heard all the bells and whistles and distractions like right now.

Danielle Elliott Smith

That is okay. But it's it adds to the environment.

Dr. Calvin Sun

I hope that whoever's listening that there's hope in hopelessness. We are in a hospital because it's seen as a place of hopelessness for a lot of people, but also in that space, something arises and we call that hope.

Danielle Elliott Smith

Absolutely. There is so much hope in every piece of your story. There's hope and adventure and resilience. And I'm incredibly grateful for you spending time and friends for you joining into the podcast, whether you are listening or watching.

Where To Find Calvin And Share

Danielle Elliott Smith

It is so good for my heart to have these conversations and to be reminded of all the good and the the heartwork that goes on out there and the the adventure that people take and the way we put life into our life. I've learned so much during this podcast with Dr. Calvin's son, and I hope you have too. And that means I do hope that you will take this episode and share it with someone you know and you love. And do remember that Redefining Silver, our new app, is out. You can find that at studio.com/slash Dion Yo. And as always, I'm so grateful you're here. And I cannot wait to see you again next time. Take very good care of you.

Dr. Calvin Sun

Thank you, Danielle.

Danielle Elliott Smith

Naturally, it's important to thank the people who support and sponsor the podcast. This episode is supported by Chris Dulley, a trusted criminal defense attorney and friend of mine here in St. Louis, who believes in second chances and solid representation. Whether you're facing a DWI, felony, or traffic issue, Chris handles your case personally with clarity, compassion, and over 15 years of experience. When things feel uncertain, it helps to have someone steady in your corner. Call 314-384-4000 or 314-DUI HELP, or you can visit Dulilawfirm.com to schedule your free consultation. I'm thrilled to share that the Redefining Sober app is officially live. What began as questioning my own relationship with alcohol became a journey back to myself. And now I've created the support that I wish that I'd have. Redefining Sober is designed to help women explore, question, or change their relationship with alcohol while building self awareness, self trust, and a life that feels more aligned and fully their own. For a limited time, founding members can get a discount. Visit RedefiningSober.com today to learn more and begin your journey. I'm so excited to have you join us.