Here’s everything I’ve learned in my first 90 days in Japan.

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Living in Japan – There’s this room in the basement of my coworking space in Denver that’s designed for pregnant women. 

The walls are insulated so that the sounds of a crying baby won’t bother coworkers. There are toiletry-related items, a small trash bin with a lid, and a deadbolt on the inside so that people won’t accidentally walk in on somebody who’s feeding their kid. 

While the windows on the exterior of most other ‘call rooms’ are see-through, this one has frosted glass. And there’s a sign that you can flip over to indicate whether it’s ‘occupied’ or ‘vacant’. 

So I’m sitting down there, weeks before my scheduled departure out of LAX to Tokyo’s Narita airport, and I’m blubbering like a baby. I decided to move because my life was perfect and it was boring!

I’m not pregnant, but in the weeks leading up to that departure, I have the hormones of a pregnant woman.

I’ll start crying when I’m hungry or when my friend tells me that that Trader Joe’s doesn’t have my favorite flavor of La Croix. 

So, I used that room a lot in those last few weeks. I’d always wondered what it would be like if an actual pregnant lady knocked on the door, only to gaze upon my red, tear-soaked eyes.

Would she say, “Oh, I’m so sorry — I didn’t realize you were pregnant, too” maybe? 

The day before my departure, I’m sitting at a bar with my friend who’s had a long week, and I just start crying. 

I don’t know why, but I start crying my eyes out. 

The bartender is generally ignoring us because asking a crying person, “do you want another beer?” probably feels a little too on-the-nose. This is given the fact that I haven’t uttered a single full sentence for the past 30-minutes.

I’m crying, in part, because I’m leaving a beautiful city, dozens of beautiful friendships, and a life I love and adore for a life of complete uncertainty. 

It’s an experiment, with an uncertain outcome — and I’m scared, and it feels stupid. 

In the weeks before, I’d consulted with half-a-dozen different friends on whether or not I should follow through with it. In the end, I decided to simply do it, because, “fuck it, why not?” 

All of them echoed that sentiment because most of our friend-circles will consciously or unconsciously echo what they think we want to do, even if it seems dumb. 

And then, as soon as I get here, I’m thinking to myself, well, here it goes. 

Time for an adventure.

My first 90 days living in Japan

My first 90-days living in Japan have been an absolute dream!

I’ve gotten to ski in a foreign country, eat so much unforgettable food, visited some of my favorite cities in the world. I’ve taken hundreds of incredible photos, continued exploring my creativity, wrapped up some awesome client projects, and found several new ones.

I feel like I’ve been living in an alternate reality.

In short: Living in Japan is f**king awesome, and if the first paragraph made you feel even a little bit bad for me, you shouldn’t.

Most of my mornings these days start with some light jogging, meditation by the river or overlooking downtown Kyoto, and quiet journaling. 

During the day, I spend lots of time writing, recording videos, editing, working on other unrelated marketing projects, and generally just thinking.

My life is exactly what I had dreamed it would look like when I’d first thought about moving to Japan.

But it wasn’t always that way. 

And, for the first month or two, it was really strange, difficult, frustrating and full of anxiety.

Here’s everything I’ve learned in my first 90-days of living in Japan.

Lesson #1. Let go.

It is easy to tell yourself to “surrender” to experiences, and altogether something else entirely to do it. 

For the first month or two, I felt like I’d been effectively clenching my asshole. 

It was difficult for me to be present with new friends and in new experiences because I was constantly thinking to myself, shouldn’t I be doing more work? What should that work look like? What about my business? What about my client projects? What about my friends? What about my relationships back home?

In the past few weeks, I’ve focused as much as possible on letting go. I’m letting go of relationships that haven’t been serving me, businesses that weren’t working, and dictating my days based off of how I want to live, not based on what others want from me. 

I’ve effectively cut 90% of my workload out of my day-to-day. I started saying ‘No’ to just about every new project that people have brought to me and started spending a lot more time thinking.

This pandemic has helped accelerate a lot of those conversations, but they’ve always felt inevitable. 

Now, most of my days are spent quietly writing, workshopping new ideas, and testing new video concepts. 

Like, this one: 

Or, this one: 

I’m becoming increasingly protective of my free time, and want to spend as little of it as possible helping others build their dreams. 

Lesson #2. Try to eliminate things that make you unhappy.

The sad reality for most people is that, until Universal Basic Income becomes a thing, most people will be forced to complete some sort of work or obligation that they ultimately find unfulfilling or unrewarding. 

While a good chunk of my client projects is incredibly rewarding and gives me full creative control, others aren’t so much.

And I’ve found that often the projects that I struggle with the most, where clients seem to be the least happy, and in which I often lose money executing on are the ones in which clients can’t seem to let go. 

So, in the past few weeks — due to several unrelated circumstances, like a lack of communication, COVID-related declines, and so on — I basically took an ax to each of my client relationships and projects and eliminated close to 90% of them. 

In one instance, I sent out a client email that looked, uh, similar to this: 

What I thought would happen? Some of our clients might try to angrily sue to collect their money back from services that they’d paid for that we simply weren’t able to deliver on anymore, but that wasn’t the case. 

What happened. A few clients were disappointed. One was pretty mad and felt kinda cheated and screwed, and the others simply ignored the email and went on with their lives. 

Having these difficult conversations is hard, but wildly important — it’s one thing to do work out of love, admiration, and respect for your clients and their businesses. 

But our editing service — clients would hire us on a monthly retainer to edit their videos — simply wasn’t working how I’d planned. In trying to develop a process that worked, I became increasingly frustrated. 

That, and communication with my business partner had effectively fallen off the map and I wasn’t willing to continue to provide the business with CPR.

So, I was keeping something afloat that was neither A. Working and B. Something that I cared about anymore. 

And frankly, I discovered that pretty early on in the process but continued to go with it because I thought, maybe, just maybe I can figure out how to make this something I care about.


It didn’t matter. 

And now, I have an infinite amount of more time to say Yes! to great opportunities when they present themselves, like the podcast I’m guest-hosting, the healthcare worker care package I’m promoting throughout May, and so on. 

So? If you’re in a situation in which you find yourself continually working on things that are neither bringing you happiness nor personal fulfillment, one of the quickest ways to increase your day-to-day happiness is to trouble-shoot that situation. 

Whether it be a job, business opportunity, a partnership, or maybe even a relationship that’s dragged on for far, far too long. Chances are, there’s a reason it’s making you unhappy, and maybe you’ve tried to figure out why but haven’t been able to do that. 

And now is perhaps your best opportunity ever to, at the very least, start to think critically about why you’re feeling discontent with that situation and what you might be able to do to fix it in the short-term. 

And if not? 

Figure out a plan for transitioning away from whatever role you find yourself in. 

Lesson #3. Be patient.

There’s always this moment when I try something new where I say to myself, “WHERE THE FUCK IS THE MASSIVE, LIFE CHANGING THING THAT WAS SUPPOSED TO HAPPEN?!”

This was my thought-process every new day that I’d been liviin Japan. 


Each day, I took a few minutes through apps like Memrise and TinyCards to study Japanese. 

Within a month or two, I was speaking semi-coherent sentences.

And then I stopped. I’d become frustrated in the learning process, and felt like Japanese was too hard for me. 

Every new learning process or new experience has this initial moment of ‘YAY! THIS IS AWESOME!’ followed by a long period of, “I WANT TO KILL MYSELF” then a long while after thinking, “THIS IS COOL!” 

Moving to Japan, learning Japanese, learning video, and everything else I’m doing in life — I’ve always experienced that.

It is impossible at the moment to remind yourself to be patient — that you’re an ice cube, and that ice cubes don’t melt until they hit 32 degrees Fahrenheit. 

In that period from 29 to 32 degrees, you’re saying to yourself, “wow, I’m such a piece of shit stubborn block of ice that I haven’t made any progress.” 

And yet, you’re warming up. You’re getting there.

One day, bang! You start melting. 

Into the experience. 

You start to become one with the experience — you were just getting acclimated to the environment or the learning process or the whatever.

(Thank you James Clear for this ice cube analogy.) 

So, I have to remind myself, every morning — why I’m here, what I’m trying to learn about myself, and why I should just chill the heck out. 

Or, warm the heck up.

Lesson #4. Assume you know nothing and respect the damn culture.

A few weeks ago, back when going to Aikido class was cool because you wouldn’t instantly ingest a potentially deadly virus, I joined my first Aikido classes alongside a friend.

For the first few classes, I arrived late. 

I assumed that with my exhaustive one and a half years of experience in BJJ, receiving numerous stripes on my white belt, that this would be a cake-walk. 

Boy was I wrong. 

One class I arrived late, knocked over a loud piece of wood onto the floor, and as the rest of the class silently stared at me I thought to myself, You know that magic trick I learned as a kid where I just go poof into thin air?! Can that work, now, please, God?!

I’m not religious by any stretch of the imagination, but even slightly mortifying social situations make me question my agnostic beliefs. 

And so, each week I’d be taught a new lesson about a culture that I was wildly unfamiliar with: 

1. Show up on time. In the U.S., in Jiu-Jitsu, I’d gotten so used to showing up late to class that it almost became a running meme. Our teachers didn’t care so long as we weren’t an hour late, because it was easy enough to slot yourself in and just the act of showing up felt significant enough.

2. Be respectful of the teachers. In BJJ, I would often hover over my teacher trying to absorb every small movement and action, telling myself, “this is how you learn HARDER!” In Aikido, they ask you to sit down, thank your teacher after they’ve taught you a movement, and generally stay out of your teacher’s way. It was strange the first few times.

3. Clean up after yourself. This was perhaps the most interesting part of my brief foray into Aikido-ism — that after every class, everybody — including the teacher — takes part in the process of cleaning up the dojo. People wipe down the mats, sweep hair, dust and other particles from the edges, and put everything back in a neat, organized fashion. 

Throughout that process, in addition to feeling completely out-of-my-element with all of the often intense Aikido movements, I learned a lot about mutual respect, the Japanese martial arts culture, and other things that I can’t recall at this moment. 

Learning new things is always wildly uncomfortable, and I felt humbled to continue to do that stuff. 

Lesson #5. It will all start to come together.

On Sunday afternoon, I asked one of my housemates — “hey dude, do you wanna cook steaks tonight?” 

And he said, “not tonight, but what about tomorrow?”

And then I thought to myself, what about Steaknight Japan?!

You see, in the U.S., I’d often hosted this thing called Steaknight.

It’s just a fun get together with friends. I call it Steaknight because why the hell not?!

And I thought to myself, “NOW IS THE TIME, LET’S DO THIS!”

It’s funny, but a dream of mine that I’d always had before I left for Japan was to host a STEAKNIGHT IN JAPAN and now that dream has finally been realized and I can die happy.

This is what that looked like:

Seriously — in the last few weeks alone I’ve had more life highlights than I can ever recount but this was easy TOPS. 

The last few months have been exhausting — mentally, emotionally, physically. 

Mentally because I think that anytime you’re living through a global pandemic, it’s a mind-fuck. 

Emotionally, because I’ve had to have about a dozen really difficult conversations with friends, business partners, clients, etc. 

Physically, because I’ve been running every day and my body hurts but it’s one of the only ways I stay sane.

And yet, I’m incredibly happy — every day, I journal at the end of the day using the app Day One and rate my days, and my last few weeks look roughly like this: 

You get the point.

Progress happens gradually. 

And while I recognize that life won’t always be a walk-in-the-park and that I’ll probably go through days and weeks where I’m at, like, a 2/5 or a 1/5 and I want to kill myself that day because life feels impossibly painful, I still have so, so much gratitude.

A lot of people around the world are suffering right now — I understand that, and I empathize with their challenges, which is why I’m trying to do as much as I can to give back and to connect with the community around me. 

But it will get better. 

I honestly believe that — or else I wouldn’t be here, right now. 

I just wouldn’t.

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