Back That Month Up | Chiang Mai

Oh, no! We’re halfway there.

Having Hanoi as our first stop in Asia was, in my opinion, the scheduling equivalent of getting a pack of all orange Starbursts — it was the best possible scenario for everyone involved, obviously. After four weeks of learning to love the madness of Vietnam, I felt like I could handle anything SE Asia could throw at me.

I don’t know how else to describe it besides a feeling of confidence that you can overcome whatever cultural, language, or food barriers that are in your way. Although, maybe that’s just what happens after you’ve been traveling for six months.

Whatever the reason, I could feel the difference in my attitude and excitement from the minute we landed in Chiang Mai. Instead of feeling intimidated and apprehensive by the food situation like I was just a month earlier, I wanted to eat all of the things. Instead of feeling uneasy about getting around and following Mama Jen like a nervous duckling across the streets like I did on our first night in Hanoi, I was flagging down red trucks from the jump so that I could get to the nearest night market.

In short, I was beyond ready to spend the next month in Thailand.

The People

This month was fun because the majority of the krew lived throughout three apartment buildings in the same complex. You’d see people coming and going all day long throughout our cushy little bubble of apartment pools and cafes. This month was different than past months because it was probably the month that people used the workspace the least due to all of the amazing cafes nearby our apartments (not to mention the capped workspace space wifi 🙄). That, coupled with the fact that this was a big side trip month for a lot of people, meant that you didn’t see some of your pals for a while. That sounds like a bummer, but it also gives you the opportunity to hang out with people you might not normally spend as much time with, which is muy bueno.

Losing people in the group is inevitable, but that doesn’t make it any easier. Especially when they’re one of your best friends in the group. Our dearest Emmy Singh aka Mumsy (a nickname I bestowed upon her in Prague for literally no good reason yet somehow fully stuck) went back to Brisbane at the end of this month due to some changes with work at Microsoft, where she’s kiiiinda a big deal. We’re hoping she rejoins the group in the near future, whether that be to finish out the year in South America or just to visit.

This month I had my first visitor stay with me for two weeks. One of my best friends from back home, Ryan, flew over from Croatia after Yacht Week and met us in Koh Phangan for the Full Moon Party. It was really fun to finally have a friend from back home stay with me and hang out with my Kaizen friends. I’m typically awful at mixing groups of friends, but Ryan made it super easy for me and did a great job of blending in right away.

The Places



Chiang Mai is known as being a digital nomad hub and it’s very easy to see why. It is bursting at the seams with cafes and restaurants that cater to your westernized comforts from home. I consider myself a breakfast connoisseur and I feel confident in saying that they do American breakfast better than America does. Sadly, I don’t even think it’s that close.

Chiang Mai is much more than the embarrassingly addicting cafes, though. If you choose to venture outside of our Nimman neighborhood bubble, you can find some really authentic Thai experiences that remind you that no, you’re not actually back home.

From the countless night markets and street food stalls, to the fascinating and creative ladyboy cabaret shows, to the bajillion temples scattered throughout the city and the surrounding hills, there is a ton of stuff to discover.

In terms of RY, I think Chiang Mai has one of the best City Teams we’ve had this year (I feel like I say this about all of them, but Ton and Miao really are freaking great!).


  • Playing with, feeding, and bathing elephants at an elephant jungle sanctuary
  • Finally joining a crossfit gym after months of saying “next month is the month!” — my commute, a 40 min walk each way, was longer than the actual workouts, but that walk became a welcomed opportunity for some introverted pondering
  • Climbing up and down the famous sticky waterfalls on our track event
  • Going to see a ladyboy cabaret show and having a chance to hear some of the their stories about life as a ladyboy in Thailand (and having them pull Ryan on stage for a “Welcome to Kaizen” moment unlike we’ve had for any other visitor)
  • Cafe hopping on a daily basis — pretty sure I was the mayor of at least 10 different places on Swarm (💙Rustic & Blue 💙)
  • Hearing from three digital nomads at our Junction event who have made this their lifestyle… 🤔 💭
  • Taking a tour with Aashima to see Doi Inthanon, which was one of my bucket list items for my time in Chiang Mai
  • Discovering and binging the pure hilarity that is Rick and Morty
  • Eating an ungodly amount of 7-Eleven toasties — if you don’t know what they are, it’s worth the trip to Thailand for these alone


A bunch of Kaizens took side trips to Koh Phangan for a little beach action and for the infamous Full Moon Party, which was conveniently taking place in our second week of the month.

The group I went with rented out what we eventually just started referring to as “dope ass villa”, because that’s literally what it was. It had three villas with bedrooms, an outside kitchen and living space, and a magical pool that went outside and into the kitchen area — there was even a little bridge! It was one of those times when you kind of screw yourself over by booking too cool of a place because you never want to leave it

Whenever we did finally manage to drag ourselves out of the pool and venture out, we did island-y things like snorkeling, getting beachside Thai massages, drinking out of coconuts, and eating a sh*t ton of Italian food. Oh, is that last one not typical Thai island behavior? Whatever. We really did have the best Italian food I’ve had outside of Rome, though. #noragrets

The Full Moon Party was the main event of our trip and I think it’s fair to say that it was the rare occasion where a huge party actually did live up to expectations unlike so many other big let downs (I’m looking at you, Every NYE Party Ever). Despite the fact that it started to monsoon within five minutes of us getting there, we didn’t let that dampen (lolz) our spirits. After paying probably too much to get our bodies painted and taking refuge from the rain in an Irish pub, we were able to meet up with the rest of the Kaizens and proceeded to have a great time. It all ended with watching the most beautiful sunrise from a secluded beach that you can only get to by boat.


Ryan and I had a weekend free for the two of us to go on a side trip while the rest of the group was in Bangkok to see the Chainsmokers. It was Monday and we were supposed to leave on Thursday, however, we still didn’t have a destination picked and we were having trouble deciding. That’s when we came up with the brilliant idea of putting a couple destinations in a hat and then letting fate decide for us.

The contenders were Bangkok, Ho Chi Minh City, Singapore, Cambodia, Cebu, Hong Kong, and Bali. Ryan ended up having the honors of picking and he pulled Singapore out of the hat. Within 10 minutes, we had our flights booked (PS: don’t use to book your flights 😠)

And just like that, Side Trip Roulette was born.

Singapore was a really interesting place, especially having just been in Vietnam and Thailand, which are both very affordable. Everything there was nice, clean, and modern. It was the most I’ve felt like I was back in the States probably since this trip started. It kind of felt like a mix of the cleanliness of downtown Austin and the big buildings of downtown Chicago.

We spent our first two nights in hostels in Chinatown, made some hostel friends, ate the cheapest Michelin star meal in the world, tried a Singapore Sling, and cringed whenever we had to pay for something (Singapore is expensive!).

“a glass of water costs how much?”

It was on our last full day in Singapore that we were laughing at breakfast about how damn expensive things were. Ryan had just ordered his drinks and realized that his bill was already up to 30 SGD and he hadn’t even ordered food yet. We hadn’t booked a place to stay that night, so we were discussing our options. I think I threw out the idea half-jokingly that we’ve already spent so much that we should probably just lean in and book a room at the Marina Bay Sands so that we can use that rooftop infinity pool all day.

What started out as a semi-joke suddenly took a very serious turn…


I don’t know that I’d say that we leaned in as much as we dove in — literally — as in, dove into the legendary rooftop infinity pool that was really the whole point of going. We spent the entire day and night at the hotel, basking in sun and happiness. It was a lot of money, but you only Singapore once, right? I regret nothing.

Bonus: The Chainsmokers performed at the F1 race in Singapore the night we we stayed at MBS, so we got to “see” them from the pool at night 😎.

The Things


Chiang Mai is home to dozens, maybe even hundreds, of insanely beautiful temples. They ranged from gold, to colorful elephant dragons being eaten by other dragons, to pagodas high up in the hills.

Pumping the breaks

While writing this blog, I realized that I really didn’t do many side trips this month compared to some of the previous months. I had a nice little morning routine going with crossfit and I loved my apartment, so I was perfectly content skipping the million trips to Pai and Bangkok to stay at home and get schwifty with Rick and Morty.

Cafe Food

Here is where I post gratuitous pictures of the delicious cafe food I keep talking about.

After a month in Chiang Mai, I can officially say that I get it. I get why expats flock to this place in droves.

This month was a nice break of sorts for me. The chaos-o-meter was dialed down a couple of notches from the prior month, which was a nice change of pace. While I wouldn’t say that I was absolutely dying for an “easy” month, it was nice to not have to bust out Google Translate to order breakfast every day.

While I am going to miss Thailand, it’s hard not to look ahead to Month 7 with the excitement of a kid on Christmas Eve. For me, it’s the most eagerly anticipated month of the year — so much so that I left Chiang Mai five days early to make sure I could spend as much time there as possible.

It’s time for Japan…

Chon Kaew, Chiang Mai!

Before you go, don’t forget to back these months up, too!