Asia Adventures (Season 2)
Why I love Thailand, running a men’s retreat, taking a 10-day solo sabbatical, and lessons at 4 am in a strip club.
I LOVE Thailand.
There is a sense of boundless freedom here that I haven’t felt anywhere else in the world.
I rarely have to wear a shirt or shoes. I ride around shirtless on my moterbike with music playing through my AirPods through the mountains and in the sun. I only have to pay for gas once a week for $5. I spend my days popping in and out of cafes, dipping in the ocean, having a cappuccino, Coke Zero, or coconut, and writing and building.
Within 12 hours of landing in Bangkok, I felt at home. As I walked through the busy streets, saw street vendors at every turn, dodged motorbikes whipping around corners, and smelled the characteristic fragrances of cigarette smoke and marijuana, I was reminded of the boundless freedom I feel here that I haven’t felt anywhere else in my life.
When I’m in Thailand, it feels like all limiting beliefs, programs, and preconceived notions about how I “should” live life go out the window. Because no one knows who I am or has any preconceived notions of who I should be, there is a sense of limitlessness I feel here that I’ve never felt in the US. I could theoretically ride around the streets in only my underwear, blaring music out of a speaker, and no one would care. I probably wouldn’t, but the point is that I feel like I can truly do whatever I want.
When I’m here, I operate on no schedule. I eat when my body tells me to. I wake and sleep with the rhythms of my physical and creative energy. I workout when I feel inspired. I work with no constraints. Since no one from the Western world is awake during the day here, I enter a portal of timeless, creative flow. And if I stay up until 5am creating and building, for whatever reason, there is no guilt. I’m in Thailand. It doesn’t matter. It probably doesn’t in the US either, but the subconscious and societal programs seem to be stronger there.
It feels easier to stay healthy here too. I can order a smoothie at any time for $1. In the US, good luck getting a smoothie for less than $8. Same goes for paying for coffee, seafood, and all types of fruits. It’s simply much more affordable to eat whatever your body is calling for here. I don’t have to second-guess everything because of price like in the US.
Continuing on the health thread, the shining sun and constant humidity put me into a constant state of sweating, which makes me feel light, lean, and detoxified. It feels like I’m in a sauna all day. This makes me feel like I have to eat way less. I need to sleep less too and yet my energy still feels noticeably higher. It’s easy to stay vital and healthy here. The thought of eating shitty food while being on the beach in the sun simply doesn’t compute. I’d rather sip coconut water and coffee and eat ceviche and fruit. Going and dancing for a few hours is my peak form of exercise. I can also lift weights in the outdoor gyms in the sun without a shirt on. The saunas and ice baths scattered around the island also don’t hurt. And something about being here writing this article shirtless in a cafe just makes me want to eat less, eat clean, get tan, drink a lot of water, and just max out my health and vitality. It’s just a place where it feels good to be lean. I love it.
My Spirit Chose Thailand
It’s funny to think back to how I stumbled upon Thailand. I really didn’t choose it. Thailand chose me. Last May, when I was living in Austin, Texas, I knew I wanted to travel somewhere for the summer, but I didn’t know where to go. So I asked the Universe to guide me. From there, a number of synchronicities occurred. I picked up a book in a cafe and flipped open to a random page about Chiang Mai. I then got in an Uber, and the driver told me he lived in Chiang Mai for a few years. Then someone sent me an article on Twitter about Chiang Mai. Three felt like the magic number, so I trusted those signs and booked a one-way ticket to Chiang Mai last June. My life changed forever last summer.
Last summer, I found parts of myself I had yet to access in my life. These were the adventurous, exploratory, expressive, and feminine parts of myself. I had been a buzz-cut, football-playing, finance-type guy for my entire life. That summer in Thailand allowed me to discover the parts of myself I had never expressed in my first 22 years of life. Through ecstatic dance, cacao ceremonies, raves, psychedelic journeys, and a complete lack of a schedule, I allowed these new parts of myself to emerge out of the depths of my soul. I also learned to really trust God, let go of control, and open up to synchronicities. I learned to find peace in chaos in multiple situations, like having $3 of money accessible to me (due to some banking issues) and being completely cool with it. I felt I became much more antifragile last summer. I didn’t realize how reliant I was on structure and the system in the US until I stepped outside of it last summer.
Now, a year and some change later, after returning to Thailand and running a retreat, it feels like I was always destined to end up in a place like this. My spirit always knew. It had been pulling me towards the sun, freedom, and adventure ever since I began listening to it around 20 years old. It also feels a part of my destiny to continue living in Thailand beyond this year. But first, I have a football season to complete in Chicago. More on that at the end of this letter (:
In this letter, I want to tell the story of my second year in Asia. I’ll share some lessons, some experiences, and how it changed me. The entire month will be condensed into this article, so it will be a bit long. If you want to read the articles from last year’s adventure, you can find them here.
This year, we’ll travel from my time building in Bangkok, to running the Thailand Expedition retreat in Chiang Mai, to spending 10 days alone in Koh Phangan.
Now, let’s begin.
Building In Bangkok
I came to Bangkok for a week before hosting the Thailand Expedition to build with my good friend Will (aka Thailand Bill). This first week, we lived the epitome of the “work-hard, play-hard” lifestyle. We’d build for 10-12 hours a day and then go out at night. I was probably consuming 4-6 units of caffeine a day (cappucinos, espressos, rebulls, etc), a handful of cigs, and a few zyns. It was a lot of masculine, fiery, GO energy. But we knew we were in a building energy for the week before chilling and decompressing during the retreat, so we wanted to go all out. No half measures. And I always find lessons are learned by taking things to their extremes.
It’s also been interesting to notice how my energy shifts in different cities.
Bangkok, a big city with lots of hustle and stimulation, brings forth a building/techno music/fiery/hardcore masculine energy out of me.
Pai, on the other hand, allows me to feel so comfortable, like all my needs are met between cafes, fitness, parties, people, and healthy food within a small radius. It can be peaceful and tranquil one day, and it can be an all-out ecstatic rave the next. The day of the week really doesn’t matter there. I can choose whichever energy I want to step into.
And Koh Phangan definitely gets me into a creative/watery/flowy/spiritual/healthy energy. I just flow from cafe to the ocean to a new cafe throughout the day and let inspiration take me wherever it wants me to go. In essence, Bangkok feels very masculine, Koh Phangan feels very feminine, and Pai can be whichever I want. From this information, I like to choose a creative project and intention based on the natural energy flow of the city I’m in. It’s like swimming downstream with the current vs. trying to fight it.
5 AM In The Red Light District
Now, back to Bangkok. On Saturday night, we went out to a few clubs, an electric techno rave, and ended up in the red light district at 4am. Not my choice and not my comfort zone, but I was going with the flow of the group. This place was not the typical rave scene I go to, where the focus is primarily on the music and dancing. Everyone was here for a different purpose:
Sex.
I felt out of place. I’ve never been the hookup type. Whenever I’ve tried it, I’ve hated it. And I’m also not the type to go out specifically for the purpose of hooking up. I like to be with my friends, dance, let loose, surrender into the music, and get into a deep flow state. If I meet someone, awesome, but it’s usually not my sole intention.
So yes, this scene was definitely a step out of my comfort zone. But I’ve learned there are ALWAYS lessons outside the comfort zone for me, so long as I stay in my center and don’t step out of integrity. So I decided to surrender into it and see what type of lessons may lie on the other side of the experience.
For the first 20 minutes, I floated around the perimeter of the club, dancing in my own energy and observing the scene. Then a cute girl and I locked eyes. There was an energetic magnetism across the room. I could feel it light up my body. I said to myself, “I’m here, f*ck it, why not,” went over to her, and started dancing. We had a magnetic chemistry. We were flowing and having a good time. But I was hesitant. I couldn’t tell if she was a hooker or not. So I asked. She didn’t speak English, so I pulled out my phone and asked on Google Translate. “What an interesting scenario," I thought to myself. She said yes, she was a hooker. That was a deal breaker for me. I told her (through Google Translate) that I was down to hang out and dance, but I wasn’t paying for anything. Her friend jumped in and started writing back to me, saying, “She doesn’t have a boyfriend,” and “She has to make money.” I told her, “Sorry, but it’s not for me.” I told her she was beautiful, thanked her for the dance, and walked over to my friend Will. I said to him, “Bro, I think every girl here is a hooker.” He said, “Yeah maybe,” and kept dancing with some girl. This guy is just built different, I guess.
I decided then I was going to vibe in my own energy. I didn’t care whether I ended up with a girl. I knew I was most definitely not going to pay for a hooker. I also decided I was going to have a good time dancing regardless of any external outcome. I was at a dope club at 5am in Bangkok with great EDM music and tons of pretty girls. Why would I choose any other way of seeing the situation?
From this frame, I had an experience that reinforced my understanding of energetics, magnetism, non-neediness, and non-attachment - things I’d begun to understand last year through going to parties and raves in Thailand. I remembered how much I’d learn about myself and human nature at these scenes, much more than any book or psychology course. Here’s what played out:
There was another cute girl on the dance floor who stood out from the rest. She seemed especially free. She was dancing and playing with everyone. It seemed like every guy in the club was trying to dance with her. She’d play with them, but no dude could actually get through. I was monitoring the situation and watching this all play out. Of course, I wouldn’t mind dancing with her either. But how was I supposed to break through when the dozens of guys eyeing her couldn’t seem to get a second of her attention? I had an idea, and so I decided to run an experiment. The experiment was to see what would happen if I mainted interest in her, but I held my frame, stayed in my own energy, and practiced non-neediness and non-attachment. My hypothesis was that she would choose me out of every other guy there. So I ran the experiment.
Her and I started to catch eyes. But I wasn’t pursuing her like everyone else. Instead, I was vibing in my own energy, playing with my friends, smiling, and having a good time. I genuinely didn’t care if she liked me because I had come to an internal place where I was sure of myself and decided I didn’t care about getting with anyone. She began to feel this. Her energy began to shift. While she had been ultra-confident with other guys, she became shy with me. The game had flipped. While every guy had been chasing her, I chose not to chase, embodied my own frequency (while still maintaining interest), and she began to chase me. We ended up playing around like this for a while. To cut to the chase, she ended up liking me and we had a really fun time dancing and vibing together. But it only happened because I didn’t need it.
What you don’t need, you attract.
I tell this story not to convey myself as some pimp or f*ckboy. I’m actually quite hesitant to publish this story. But I feel the lesson is important to apply to all of life, and that the story is kind of an entertaining way to do so.
The lesson is that what you don’t need, you attract. Money. Business partners. Romantic partners. Job opportunities. Friendships. Respect. Followers. Admiration. Really everything you could desire follows this principle.
Whenever you need something, you push it away. When you want something, but remain neutral in your desire and avoid attaching your self-worth to the acquisition of that thing, the thing will naturally come into your awareness, where then you have the power to choose it or not. If you simply embody the frequency that the desired object would naturally gravitate to, and stay coherent to that frequency, it is only a matter of time before you will get what you want. The key is staying out of the frequency of need and staying in the frequency of knowing you already have it if you want it. From here, you just have to go out and choose it.
(It doesn’t matter, but it’s worth mentioning that I remember all of this so vividly because I was dead sober 99% of the night. There was one vodka redbull at 3am for the boost and the vibes but other than that I was just on just water and nicotine. Just to let you know :)
Life Path 5
Another reason I’m publishing this letter and more personal adventurous things is my newfound interest in numerology. In numerology, your life path number is a code for how you, as a unique soul, are likely to evolve throughout your life. You can learn a lot about yourself through this code, similar to human design, astrology, or gene keys. Each number 1-9 has a specific expression, and certain numbers like 11, 22, 33, and 44 are considered master numbers that don’t reduce. You can calculate your life path here. Your secondary number is then your date of birth reduced, so September 24 would be (2)+(4) = secondary number of 6. Once you know what each number means, each license plate you start to see, each road sign, or every time you look at the clock takes on a new flavor. Synchronicities never end. It can be quite jarring, but also quite enlightening, depending on your internal state.
I am a life path “5/3” in numerology. “5” is the number of the freedom seeker, adventurer, traveler, and explorer. “3” is the communicator, writer, speaker, and creator. The combination leads me to be a traveling writer. I have gone deeper into studying this life path 5 energy, and I realized many of the things I thought were just fun are actually a deeper part of my soul’s calling. The music, dancing, raves, parties, backpacking trips, nights out, and sidequest adventures are not distractions; they are aspects of myself that are meant to be explored and shared, and contain many lessons my soul is destined to learn.
The life path 5 energy is the reason I am even deciding to publish this letter. I feel a hesitancy around sharing the above story. But I know it is a part of my path to explore, adventure, push limits, experience new things, and come back with lessons. I also know it’s a part of my path to share these experiences (no matter who I’m worried about reading it).
The first half of this trip, I was really feeling the energy of the 5. I had a breakthrough idea to include music from my favorite rap artist Lil Uzi Vert in the marketing for a new project. I got my hair braided for the first time in my life by a Thai woman I met through a friend in Bangkok. This “5” energy carried perfectly into the next leg of the adventure, which was running the Thailand Expedition Retreat, where I led a group of guys through the mountains, riding motorbikes, dancing at parties, and working with psilocybin.
The Thailand Expedition
Now, the retreat. The Thailand Expedition was a 10-day group adventure through the northern parts of Thailand. These 10 days were some of the most fun and impactful of my life. The retreat was f*cking epic.
The group of guys there was so special. Every single dude was unique, gifted, talented, successful, and hilarious in his own way. I learned a ton from every single guy there and have carried lessons with me beyond the retreat. Jak’s warrior spirit, esoteric knowledge, and devotional application. Bjorn’s mental precision, aesthetic sense, writing abilities, and philosophical takes. Will’s “I-don’t-give-a-f*ck” attitude, willingness to step up and lead, and provide deep spiritual insights (without needing to convey himself as spiritual). Donnel’s devotion to surrender to every twist and turn life has in store for him, and do so gracefully. Nicholas’s mental precision, articulation, and INSANE comedy unlocked a humerous/ bro/ playful side of myself I hadn’t accessed in a while. He also inspired me to make sobriety a bigger emphasis in my identity. Every single guy was so special in his unique ways. The amount of inside jokes that developed over the 10 days was actually mind-boggling. I feel this humor coming through not only in my writing but in my overall approach to life. And it’s so refreshing to take everything a whole lot less seriously.
This is the beauty of retreat settings. We are mimetic creatures, meaning we adopt the behaviors of and imitate those around us. If your 5 best friends are billionaires, you’ll probably be the 6th. If your 5 best friends are alcoholics, you’ll probably also be the 6th. Who we surround ourselves with impacts us in more ways than we consciously recognize. When you get a group of people together in the context of a retreat, everyone brings unique insights, knowledge, experiences, and wisdom to the group. You pick up on subtle things from the others that you could never really learn through a book or the internet. And when everyone there is striving for a higher version of themselves, everyone in the group elevates because of it.
I’m not going to go into crazy detail with stories, as there are too many to put into one article, but essentially over the course of the 10 days, we swam and wrestled in a river, hiked in a jungle on psylocibin mushrooms, went to an incredible ecstatic dance, danced at a few late night raves, meditated with Buddhist monks, did some deep inner reflection, met one of my good friends and favorite writers Paul Millerd, and laughed our asses off for hours every single day. On the mushroom journey and hike, when we were walking back to our motorbikes, I thought to myself, “Yeah, this is definitely the Thailand EXEPEDITION. This sh*t is more than a retreat. And so many people would f*cking love this experience.” So trust me when I say there will be more. We’re aiming for March 2026 for the next one in the South of Thailand, just as a heads up. You can sign up for the early bird pricing here. (:
I feel transformed in many ways from this expedition. First, I feel I deepened into the identity of creator and leader of retreats. There was a lot of fear, insecurity, and self-doubt in the first retreat I ran last November. It decreased significantly during the second retreat in January. And it was essentially non-existent this time. I realized I really just have to show up and be myself. I don’t have to perform in any way or impress anyone. Naturally, I will hold space, organize a plan, and come up with activities because it’s in my nature. But I don’t have to force it or prove to anyone (or myself) that I can do it. There is simply an embodied knowingness now.
There is also a knowingness that retreats will be something I will double down on going forward. I find them so fun, so energizing, and so transformational that I can’t imagine a life where I’m not hosting retreats. Was this one profitable? No. None of them have been so far. But I wouldn’t change a thing because of how much I’ve grown as a man through hosting them and how I’ve seen them impact lives. I’d much rather lose money in the short run learning how to run retreats and lead men than build some marketing agency or even work a marketing job. I’ve tried, and it kills my spirit. But hey, that’s just me. I have faith these types of containers and retreats will grow over time. And it’s why I will continue to do this work for decades to come!
Aligning In Koh Phangan
After the retreat, I spent one night in Chiang Mai, recorded a podcast with Paul Millerd, and took a flight down to the island of Koh Phangan to spend 10 days with myself before heading back to Chicago.
The 10 days were just pure freedom. I barely wore shoes or a shirt. I rode around the island on my motorbike listening to music in my AirPods. I hopped from writing in a cafe to reading on the beach to swimming in the ocean to building again from a new beachside cafe for the entire 10 days. I went to a few parties, dances, and an incredible cacao and sound healing ceremony. I felt so aligned, inspired, creative, and healthy in Koh Phangan. It is another place I will definitely return to beyond this year.
I will be writing another article about the power of solo hiatuses and diving much deeper into my experience in Koh Phangan in that letter. Also, here is the podcast I recorded with Paul:
Eden
I visited many “third places” over the course of this trip in Thailand, specifically in Pai and Koh Phangan, that continue to inspire the vision of what I wish to build.
These places were crosses between wellness centers with saunas and ice baths, cafés with lots of space for coworking and coffee chats that served incredible espresso and cacao, and community spaces for things like ecstatic dances and sound healing ceremonies. Each time I go to one of these facilities, I always leave lighter and in a higher vibration. And each time I go, it becomes more clear that I would love to create something similar.
We lack these type of third places in the West. Everything is overly commercialized, commoditized, and optimized, and there are very few places for true community connection and spiritual growth.
My Northstar, above any other creative project, is to build a community center called Eden - likely in Thailand. All other projects in the Transcendence Universe feed into this one. Of course, to build something like this, a large amount of money is required, money that I do not have yet. If the vision of this inspires you and you would like to be an investor and help create it, send me an email.
Switching Seasons - Entering The Arena
I’m about to enter into a completely different season energetically and environmentally than I was just in. I’m going from the absolute freedom backpacking lifestyle in the islands and mountains to going back to college, living in the suburbs with my family, and playing quarterback on a college football team. The transition feels quite strange and sometimes surreal. I am really integrating two seemingly polar opposite worlds. But I’m beginning to understand the overlap between them.
The spiritual world has helped me connect to my intuition, read people and situations energetically, and detach my self-worth from anything I do externally. Those aspects of my development will all be used on the football field.
Football has taught me leadership, discipline, accountability, brotherhood, community, and the power of a shared mission. These things all translate over to everything I am building with Transcendence, Sovereign Creators, and retreats.
The two worlds combine two parts of myself that fuse to encapsulate all of me. I am an athlete. I am a warrior. I am a leader. But I am also a creative, explorer, and adventurer. I am ambitious and disciplined, yet I am also one of the most woo-woo people I know. I used to think I had to choose between these two sides of me. But I’ve learned that these different expressions are ALL me. These next five months feel like the ultimate side quest to integrate the two sides and catapult me into the next evolution of my life.
Our first game is September 7. Am I nervous? Yeah, a bit. I haven’t played football competitively in 4 years, and I haven’t played quarterback in 6 years. But I know this is another growth edge for me. Can I step into the arena with full conviction, full confidence, and full embodiment? Can I still trust my intuition in the heat of the fire? Can I play freely from creativity, passion, and love without attaching my self-worth to my performance? I feel fear and uncertainty in my body as I write this. Just being a traveling writer living on the beach feels a lot calmer than playing quarterback in the heat of battle. But I know love, passion, joy, and excitement are the other side of the coin of those not-so-ideal emotions. I also know this is a part of my soul’s path, and these are my trials.
To prepare for this season, I want to LOCK TF IN for a month before the season. I want to invite you to lock in with me in a group cohort for 30 days. This 30-day personal transformation cohort will be called the “Transcendence Sprint.” We will have daily accountability, personal and community challenges, live drop-in calls each week, a few guest masterclasses from top health and performance creators, and a content bank for you to digest at your own pace. The cohort is $222 and starts July 30. I would love to work with you in the next month to take every aspect of your life to the next level.
Join the Transcendence Sprint here.
Throwing today with my good friend and incredible wide receiver Alex Siebens (remember this name).
I will definitely be back to Thailand, and I believe I will also likely explore more of Asia in the years to come. I imagine I will be back come January, barring unforeseen circumstances with the advancement of my football career. But time will tell, and I have an entire season to play out before any decision needs to be made. For now, my aim is to be as present as possible, have as much fun as possible, and be the best quarterback, teammate, and leader as possible over these next five or so months. I know Thailand will be there when it is time for me to return.
If you made it to the end, thanks a ton for reading. It’s always special to hear that someone would actually read these stories in their entirety! And I hope you got something out of it, be it an insight, an idea, or inspiration to take your own adventure.
With that, I’m grateful for your attention, and I will see you in the next article. 🛸
With love,
<3 Jack
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so when are you moving!? ;)
omg absolutely LOVED reading this!