Michael Miller Monkey

Cultural Skydiving: The Fastest Way To Adapt To A New Culture

What do gambling, lady-boy bars, and drinking in gas station parking lots have to do with rapid culture adaptation?

Keep reading and find out.

Today is the day that I’m deciding to unleash my new rapid culture adaptation method, Cultural Skydiving.

Sounds fun and a little dangerous, right?

Well, it can be… but I wouldn’t ask that you take it to the extremes that I have.

So what is Cultural Skydiving?

Very simply, it’s jumping headfirst into different cultural situations to help you better understand the new country, culture and local people. It will improve your confidence, ability to communicate with locals, and overall comfort in your new country.

In this post I’m going to take you through some of my past experiences, give you a couple to try on your own and tell you how to completely change your life in 30 days. It’ll take about 10 minutes to read… but it’s going to be an entertaining 10 minutes.

So let’s start with a couple stories that sparked this method.

Becoming “The House” at a Maui Thai kickboxing match in Thailand

On my way home from my expat assignment in China, I decided to stop for a 2-week vacation in Thailand with a few friends.

Now, whenever I visit a new country I go out of my way to experience the food, local pastimes, culture and especially meet locals. This Thailand trip was no different and one of the things on our “to-do” list was to go see a live Maui Thai kickboxing match.

So when we were out wandering around we asked the locals where the best fights would be and were directed to a small arena on the other side of town. So that night we got a Tuk-Tuk and headed over.

The arena was a little smaller than expected, with a musky smell to match the old wooden bleachers. It seemed somewhat cozy to me and actually reminded me of the small Vermont gymnasiums I grew up playing basketball in.

The small crowd was excited, cheering for the two fighters already in the ring. I immediately noticed two distinct seating areas, three sides of the ring were filled with tourists and one was full of rowdy locals.

The locals were all screaming in Thai, money in hand, excited to bet on the next match. The tourists that were closest to that section were terrified. (which was really amusing to me)

So I did the only thing that felt natural, broke out my hypothetical parachute, and said, “Let’s bet on the next match”. So we walked over to the local section to make a bet.

The bookie (person that takes bets) smiled when I approached, ready to take an American tourist’s money.

“We each want to bet 1000 Bhat on the blue fighter.” I said, as I handed him the bills. That is only about $33 USD… but it was a decent sized bet for the small arena we were at.

He smiled, excitedly took the money and turned back to the locals to take their bets.

We got our seats, got comfortable and got ready for the first fight. Now, if you’ve never been to a live fighting event, I would suggest it. It’s a super intense event showcasing amazing athleticism and you will never be bored. This fight was no different. The battle raged back and forth, kick for kick, punch for punch, for many rounds.

Finally, it came down to a judges decision. We sat on the edge of our seats until the judge announced the winner… and it was BLUE! WE WON!

Here’s a flattering picture of me posing with our waitress and some of our winnings.

Maui thai kickboxing winnings

We were pretty happy. In fact, we were so happy that on the next fight we decided to make the original bet plus all of our winnings.

And guess what happened?


Then again, and again, and again.

We started jiving with the local crowd a little bit because they were a little upset that we had won so much money. That’s about the time the bookie, through a number of broken English sentences and hand gestures, decided to ask us to be “the house”. (people make bets with us and we pay out if we lose)

We decided to continue the experience and honor the bookie’s request.

So in the matter of about 2 hours, we had went from “stupid American tourists” to being completely accepted by the locals and having a blast!

All kinds of locals were making bets with us, salivating over the money they could win.

For the next fight, every single local bet on Red and we again bet on Blue. They were screaming things at the fighters before the fight started and we assumed it was just “words of encouragement”.

Before we knew it, the fight had ended… and we won again! We laughed, decided to call it a day and went on to the next adventure.

In retrospect, could the bookie or locals have easily taken advantage of us and rigged a fight? Could they have screamed at us to get out of their area?


But they didn’t. Just like I always believe, they were just people trying to enjoy life. Because of this and our confidence to approach locals, we built new relationships and experienced the culture in a way none of the other tourists could.

This next experience may make you raise your eyebrows a little but stick with me.

Going to a lady-boy bar with a Australian businessman in Shanghai

To answer your first question; NO. I had no idea we were going to a lady-boy bar.

To answer your second question; yes, I followed the Australian businessman because I constantly seek out cultural adventures and am occasionally a little crazy.

And to answer your third question, yes, it was weird as hell and I was shocked! You should have seen all the expat businessmen with lady-boys on their laps! Now, if that’s your thing I have nothing against you, people should do whatever they want, but it’s definitely not a common site for an American kid from Vermont.

Ok, so I answered those three questions up front because they get asked every single time I tell this story and I want to get them out of the way.

The question you should actually be asking is “Why does this seem strange to me and why was Mike so shocked?”

Well, my opinion is that there is a lack of culture education in the world. No one has any idea what is going on in other countries let alone their own country. (I’ll explain in my next story about the state of Georgia)

The “lady-boy” culture is not that common in China or in American (and a lot of other people), however, we met plenty of businessmen in Asia that felt very comfortable in it.

Does this make them immoral, weird or “just wrong”?

No. They just have different views and beliefs. The Australian was very successful and a really nice guy.

Personally, I have no desire to go back to a bar like that but at the same point, I respect that guy’s choice to do what makes him happy.

In the end I consider this a valuable Cultural Skydiving experience because it helped me realize how very little I truly know about the world and the massive variety of cultures.

Drinking beers in a parking lot in Southern Georgia

I’m not sure who has lived in the “Deep South”, but it’s a different place. Don’t get me wrong, I loved my time there and all the people I met… but it’s a vastly different culture than what I was used to.

One aspect of society in that area that was extremely different to me was the racial divide that seemed to exist. Derogatory terms were used often and groups of people rarely seemed to be mixed-race. (these are just my feelings and own personal experience)

So based on that description, I want you to picture this: 23-year-old Mike, in Khakis and a preppy polo, drinking a beer next to my shiny red convertible… in a gas station parking lot alongside 15 African-American Georgian’s.

So how did I get there?

Well, I became friends with a guy at work who invited me out for a beer and told me to meet him at said parking lot.

Did I think we were going to stay there for the beer?


Did I feel out-of-place at first?

A little bit… but they all warmed up to me really quickly.

Did a cop sit across the road watching me the entire time because he didn’t understand what was happening?

Of course.

So why was I invited into this typically closed culture and upon entering, accepted?

Well, one of the biggest reasons is because I also treat every encounter like the person could change my life or become a lifelong friend. I keep an open mind and understand that the outside view may not always be correct. I also try to avoid all preconceived notions, ideas that have been drilled into our minds from a young age.

I can honestly say that they were all great guys and I’m glad to have met them. Funny side note; the English accent they had was easily the hardest I’ve ever had to decipher. The dialect of English they speak is like nothing you’ve ever experienced.

Had I been timid or introverted, I would never have experienced this culture within my own country.

Do you have to become an extrovert to go Cultural Skydiving?

Yes, but you don’t have to change who you are as a person.

I have not always been an extrovert and I’ve had to force myself to do a lot of things that made me scared or uncomfortable. I know that fear is what keeps people from learning or doing great things.

Have I been scared to speak to complete strangers? Speak a new language? Try a new food? Go to a local event?

Yes. Heck, I still get scared.

Anyone that has been skydiving knows the tight chested, mix of fear and excitement, when they are sitting over the edge of the door about to jump from 10,000 feet. There’s no other feeling in the world like it… other than jumping headfirst into a new cultural situation.

If you are able to push through this fear and “skydive” into vastly different cultures, you will adapt faster. The new experiences will educate you, open your mind and make you a stronger person.

Cultural Skydiving will allow you to feel comfortable in your new country, build more relationships, and lead a successful life.

How can you learn Cultural skydiving?

So at this point, you may be thinking, “This guy is crazy. There is no way I’m doing anything like this.”

Well, I don’t expect you to do such intense activities. In fact, I’m actually testing a 30-Day Cultural Skydiving Challenge with my H-1B Institute class right now. We start with relatively easy stuff and each day gets progressively more difficult. The goal of the challenge is to completely change student’s mindsets and build their confidence beyond anything they imagined. They will also learn the valuable lessons I have about overcoming preconceived notions, being open-minded and valuing human interaction.

Each day I give the students a new challenge to complete that will help them reach their personal and professional goals. They are enjoying the exercises and some are already seeing the benefits.

For instance, the Day 1 Challenge is just to start small talk with one random person. This skill is extremely beneficial to your professional career and social life.

So if you read this entire epic post, I think you should try this challenge today. I promise he won’t bite you and you will probably never see him again.

Here are just a few possible lines you can try today.

Weather: “It’s beautiful out today. Do you know of any great outside activities around here?”
Sports: “Did you catch the ______ game last night? Amazing game, huh?”
Current events: “Did you hear that ______? How cool/crazy/strange is that?”
Entertainment: “Have you seen the new _____ movie yet? I wonder if it’s any good.”

After you’re done, write a comment about your experience.

If you’re interested in learning more or getting more fun challenges, sign up for the mailing list here.