When I think back to my childhood, the strongest feeling I associate with that time is the freedom and joy of going bike riding.

Till this day, there haven’t been too many experiences that top it. A warm spring after-school evening. Racing to meet your friends at the park. Biking over to the neighborhood Hasty Market, which normally took way too long by foot. Zipping through the streets, cutting through the lawns of those unfortunate houses that lived on the corner. Flying down and feeling the rush of wind on your face on what felt like massive hills.

The joy and freedom of pedalling as hard and as fast as you wanted, with no one able to stop you.

I distinctly remember the times of going down a big hill, pedalling with all my might to go as fast as possible, heavy panting, and looking over and seeing a friend keeping up or going faster, both of you racing down the hill, both grinning and laughing.

Peak nostalgia.

The natural evolution of this, for boys, was the day we got our driver’s license.

Specifically, the holy grail. The province of Ontario called it the G2. It meant you could drive your car by yourself, and also on the highway.

Boy, did we do some reckless things.

There was one night, late in university. Probably around 1 in the morning. Our school was out in the middle of nowhere — Waterloo, surrounded by farms and country roads. We drove to a stretch of highway that was the literal end of the highway, where it felt like the edge of the universe, where no one would bother us. Fields on either side. No cops. No cars. We lined up all four of our cars right in the middle of the highway, one of us in the oncoming traffic lane, all of us on a 4-way speakerphone call. It felt like the Temu version of Fast & Furious. We counted down on the phone… 3… 2… 1… and slammed our almighty sedan’s pedal to the metal.

I remember hitting 150 km/h.

Exhilarated.

Looking over at the car next to you and feeling that same joy and freedom.

Peak coming of age.

This past Sunday, I woke up hungover.

My lovely Saturday night involved two clubs. Two VIP tables. First Shinjuku, then a 2 AM Uber ride across the city into Ginza, more sparklers, a bottle service Nobody Gets Out Sober sign that made me chuckle, and of course, more liquor.

The funny thing is, you don’t feel drunk at the club. You feel drunk when you leave.

Thinking back, I know we were definitely too loud in that Uber ride to Ginza. If I was sitting in the front seat, and I could hear the yelling from the second-row back seat, we were definitely drunk.

The one thing that never quite gets old is the walk down the stairs when you get to the club. Where we went in Ginza, well, anywhere really, it’s always the same. The same low bass you just slightly hear outside. You get your wristband. Go past coatcheck. The bass becomes more obvious. Escalator or a flight down the stairs and you forget just how drunk you were in that Uber a few minutes ago. And then when someone finally opens that door at the bottom of the stairs, the music becomes fully audible, and the movie starts all over again.

It wasn’t always like this.

When I was 19, the budget was a student budget. The cheapest vodka we could get, Polar Ice. $20.

When I was 22, we graduated. Slightly. Captain Morgan and Jack Daniel’s, $24.95.

At 25, I moved downtown for the first time. We’d chug a bottle of Crown Royal before going into the bar in an effort to save money. The bar tab would still end up being around $150. At that time, it felt like an embarrassingly shameful amount.

When I was around 28, 29, things really started adding up. Casa Amigos, Hennessy, three, four of them a night. The total damage next day, probably $300, $400 per mans. Honestly hurt.

When I hit 33, our business finally found its footing. We were making some serious bank. And this is when the Azuls first made their appearance. For reference, it’s quite possibly the most delicious drop of reposado you’ve ever had. It still doesn’t justify the $1000 price tag, more like $1200/$1300 after tax and grat. But there would be a certain itch we’d have when we went out. To enjoy this newfound freedom between me and my partners. A certain grin we’d give each other standing inside the booth at a club — ight, I guess we’re here. Guess we’re going in tonight, eh?

A few years ago, I went to Tulum for a close friend’s 35th birthday. That whole weekend was wild. But there was one particular night. For some reason, all of us subconsciously must’ve been on the same page. I think the night totalled thirty-three bottles for the whole lot of us. Thirty-three, I kid you not. It was non-stop. Non-stop sparklers. Non-stop signs. Just when you thought you were getting the hang of the night, you noticed the distinct flare and light up of the sparklers. After bottle number 10 it was pure bewilderment on all of our faces.

I’ve come to realize, it’s all the same.

That feeling of joy and freedom.

As a kid biking down the hill. At university, in the driver’s seat of a car too fast for an empty highway. And now, spending quite literally thousands of dollars at the club.

It’s all a feeling.

Here’s the thing about this feeling as well.

Of course it’s stupid. Riding full speed down a hill at nine was stupid. I’ve still got a scar on my right knee from it. Risking a dumb accident from racing on the highway. One mistake could’ve altered our lives.

I know.

But sometimes, the stupidity is the whole point.

That’s what the grin is. The grin is I know exactly what I’m doing and how dumb it is and I’m going to do it anyway. It’s the middle finger to the world for a second. The horsepower under you. The freedom of saying fuck it, we ball as you point to the Azul and ask for two. For a moment, you’re floating. You’re free.

Most people lose that feeling. They grow out of it. They get sensible. They get sober — not just from the booze, but from the whole thing.

I’m ok holding on to it.

Here’s what’s also true.

It’s slowing down. Basically over.

Most of my friends — most of my business partners — have kids now. Everyone’s settled. Everyone’s spread out. I’m in Tokyo. They’re not. Nights like Saturday don’t happen the way they used to. The frequency has dropped a lot.

The joy is the same. The frequency is not.

And one day it’ll stop entirely. One day, you’re too tired to go out. One day, the friends aren’t around to call. One day, you’re not around to call them.

The sign at the table was right.

Nobody gets out sober. Nobody gets out alive either.

Knowing that makes me want to ride the bike harder. Not slower.

I know there’s more to life. I’m banking on it. But I’m also banking on holding onto this while we go on this ride.

As I’ve gotten older, I’ve realized there are many things I’m unsure of. But the things that I’m sure of, I’m sure of.

The formula for a good life is one of those things.

Here it is. The first and most crucial step is to get good at something. Now, because you’re good, you can provide value. Because you provide value, people will pay you for it. Simple.

Now rewind. Before the most crucial step, it’s important to ask ourselves this.

How do you actually get good at something?

Well, either you were born with the talent. Or you weren’t. If you were, skip the rest of this, you lucky bastard. But if you weren’t, like the rest of us, you had to put in the time. Thousands of hours. Tens of thousands.

And how do you ensure you will put time into something?

Well, that means you just need to pick something you enjoy.

That’s it. That’s the whole formula.

Enjoyment → time → skill → value → enrichment.

In that order. No skipping.

I think about how beautiful this is a lot.

The world is actually set up so that if you find the thing you love, and you stick with it long enough to get good, it pays you back.

Imagine if it was the other way around. Imagine if the formula for a good life was built out of hate. Or cruelty. Or chasing a life you don’t actually want.

It isn’t.

The universe, in whatever way the universe works, is on our side. It’s conspiring with us, not against us. The reward for becoming yourself is a life you actually want.

You just have to stay in the game long enough to collect it.

I started being an entrepreneur at 21.

It took me 12 years to reach the intersection of stability and success. Twelve years.

I mean, I was making money the whole time. I landed my first wedding clients. I moved out downtown. On paper, I was fine.

However, the image of my bank account told a specific story. A story you might find frightening.

You see, from the ages of 22 to around 31, I had about a month of runway of money at any given time. Any time the number got above $5,000, if I even had that much, I spent it. Workshops. Flights to LA. Dinners with people smarter than me. New gear. New tools. New clothes. Paying off credit card debt. Things that pushed me towards the image of the man I had in my mind.

I wasn’t being irresponsible. I was doing the formula. I was playing multiple games. Skill set acquisition. Social skills development. Appearance development. Mental fortitude development.

Enjoyment → time → skill → value → enrichment.

I was deep in the time phase. The phase where you put every dollar back into becoming someone. The phase nobody takes photos of.

Then COVID hit.

The music industry I was managing artists in shut down. The weddings I was photographing stopped. That one month of runway evaporated. Toronto’s lockdown was the longest of any city in the world. It broke me in ways I’m still discovering.

I applied for CERB. The Canadian government sent me $2,000 a month. It wasn’t enough.

And then I texted my mom.

I didn’t call her. I couldn’t. I texted her and asked if I could borrow $5,000.

I was 30 years old.

She wrote back almost immediately. Two words.

How much?

I read them and sat with them for a while.

I’ll never know how she meant it. Maybe it was I’m here, tell me what you need. Maybe it was how much do I have to give you this time? The words can’t tell you which one. Only the tone does, and the tone of a text is whatever your guilt is.

My heart read it as the second one.

My mom had cleaned toilets for three dollars an hour in a new country so her son could have a better life. And her son was texting her at 30 asking to borrow money.

Humiliating.

It was the lowest point of those 12 years.

It was also the moment the formula looked most wrong, most likely to fail.

It wasn’t.

The formula works on a delay. It hurts hardest before you reach the cycle of accelerated returns. The years of unseen work feel thankless. You start doubting whether any of it is compounding. And then at some point the curve bends. The skills you built quietly start producing value loudly. The reps you did in the dark start showing up in the light.

The trick is you have to still be there when the curve bends.

Most people aren’t. Most people quit on day 3. Month 7. Year 2. They look at the bank account, they feel how far their dreams are, see no one around them clapping, and decide the formula is broken.

The formula isn’t broken. They’re still in the time phase.

Then they leave the phase, and never find out how good things start to get.

I used to coach myself through those years with a story.

If I could spend four years at the University of Waterloo for a degree I didn’t really want, tens of thousands of dollars on tuition, housing, textbooks, food, for a piece of paper that didn’t guarantee me a single thing, then why couldn’t I spend four years on something I actually chose.

Everyone around me accepted the first one as normal. Four years. Tens of thousands. No guaranteed outcome. For a degree. And then after this. A chance to begin, just begin, climbing up a company ladder. How much time was that going to take?

Whenever things started to feel long and unbearable, I looked around at the world. At reality. Artists, businessmen, athletes, people I admired. Stories I admired. The formula works. Stay in the game. Keep putting in the time.

It got me through.

Here’s the part I didn’t expect.

I came out the other side of those 12 years at 33. Stability, finally. Success I can feel, not just point at on paper.

But right now, at 36, I have completely started over. Again.

Seven months ago, I started building a personal brand. A YouTube channel. This Substack. I have 363 YouTube subscribers. 35 Substack followers.

I’ve spent over $50,000 on this endeavour.

Video camera. Lenses. My videographer. Flights. Hotels. Courses. Plugins. Tools. More gear. More flights.

Is it worth it right now, if you put it in a spreadsheet?

Absolutely not.

Am I going to keep going?

Yup.

What’s strange is that I know the formula.

I’ve lived through it. Photography took three years of invisible work before the first paid wedding. Which was only maybe $500, I think. The music industry took years of unpaid hours before the first platinum plaque. E-commerce took years of losses before it started feeding me instead of me feeding it. Tokyo took over 12 months of loneliness before it started feeling like home.

Every single time, the formula worked.

Every single time, it looked broken for the entire middle section.

Every single time, I was ready to quit about a month before it started working.

And yet here I am. Seven months into a new chapter. 363 subscribers. $50K in the hole. And a quiet voice in my head that still, occasionally, asks: is it actually going to work this time, or are you kidding yourself?

Lol.

Even after 12 years of proof, I have to remind myself. Constantly.

Maybe that’s part of the formula too. You don’t just do the reps once and graduate. You do them, you win, and then you go back to the starting line on the next thing and do them again. The belief isn’t a one-time install. It’s something you have to keep choosing.

I’m choosing it.

Today I’m at the desk again. 7 months in. New video uploading soon. This is only the second semester of a degree I picked for myself. The reps don’t show yet. They don’t have to. They just have to be happening.

One day, you take your shirt off and notice the body looks different. You didn’t see it happening. You were just showing up.

The world was set up for you to win.

You just have to stay in long enough to notice.

And then, when you start something new, you have to remember all over again.

My birthday is next month.

I hadn’t thought about it until this past Sunday. This marks my 2nd birthday ever spent in Tokyo.

In your 20’s, every year seems cool to celebrate and has a purpose of sorts. 23 — omg it’s your Jordan year. 26 — haha you’re over the hill. 27 — wait are you young or old? 28 — you start looking at 23-year-olds as little babies now. Even 29 has significance cause it’s one away from 30. But once you’re actually in your 30’s, only 30, 35, and 40 have any significance tbh.

I turn 37 next month. Even the numbers 3 next to 7 seem weird together and have little significance to me. Like a filler number. I think most guys are like this as well where they love doing something big for other people’s birthday, but rather not anything for themselves on their own.

I should just stay home and work away. We finally got back in routine and it feels so good.

Then a voice popped in my head.

Bro, you’re in Asia, and you’re single dafuq, go do something you’ll remember.

So I spent the rest of Sunday thinking about what to do for my birthday.

I started scrolling flights. Taiwan? Hong Kong? Back to Bangkok? I opened up some travel vlogs on YouTube to see if anything piqued my interest.

Should I just do something in Tokyo?

I started to get frustrated.

What do you really want, Derek?

Good question.

I closed my eyes. Nothing. Still nothing. Suddenly I saw it. Somewhere tropical and warm, with boats and jet skis, and loud speakers playing Drake’s “Honestly, Nevermind” album. Red cups. Laughter. I sat with it and asked myself the same question over and over.

Is this what I actually want to be doing? Is this what will bring me the most joy at this moment?

And then the absolute strangest thing happened. The answer came back clear — yes, definitively, yes, I would love for this to happen — but it felt hollow. Like a yes with something missing behind it. I dug deeper.

I would actually love to be on a boat, or on a jet ski, or somewhere vibey. That sounds like fun, yes I’ll do that. But why does the feeling feel incomplete? Ah yes, it’s because you are in Asia while your closest friends are in Canada, some 10,000 km away. On the other side of the world.

So why did we leave our friends again? You clearly want to be with them.

Hmmm. This is true. Why did I leave again? Ah yes, I optimized for growth. Not every day is your birthday — or else we’d all be optimizing our lives for a location with a palm tree, beach, friends, and a jet ski. I optimized for the other 364 days in the year.

So what is this feeling?

It’s not regret. It’s not loneliness. What is this weight? This payment?

Ah yes. This is a tax. Every form of growth has a tax. I see, now. This next chapter with 364 days of purpose, intention, and joy of building a new life in Tokyo will cost a day, or honestly probably a few more, of wishing I was back in Toronto.

Who else is paying taxes right now?

Ah yes, that recent trip to Bangkok I just mentioned. Two of our close friends back home just had a newborn. They weren’t able to make it out to the sauga city gathering aka the bachelor and bachelorette week and then the subsequent wedding in Krabi. They’d known for a year now that the timing was going to be tight. They watched the Instagram stories from the trip. The shenanigans. The fun. The group photos. It must’ve been bittersweet I imagined. Just having had the most incredible moment of their lives and simultaneously watched one of their closest friends get married through a phone screen.

They chose family and their next chapter. The tax was the trip.

I chose Tokyo. The tax is my birthday.

Where else has it been taxing lately?

I couldn’t stop pulling on this thread.

Ah yes, I will soon need to meet with multiple vendors who have been with our business for a decent amount of time to put those relationships to an end. Not because they did anything wrong. But because what I want for the business is bigger than what they can offer. We are choosing growth. The tax is the conversations, the relationships, the contract cancellations, and the pain of starting from scratch with someone brand new.

Do we have to pay this tax?

I felt like I heard myself talking to my accountant all of a sudden lol.

Why are we doing this again?

If I’m being honest, this question probably pops up in my mind every other week?

If the tax of the life I chose has me sitting alone in Tokyo scrolling flights trying to figure out my own birthday, why did I choose it? What am I building that's worth this?

Instantly, a list started forming:

I want an extraordinary life.

I want to look back and be proud of every evolution and chapter.

I want failures I can laugh at.

I want success I can point to.

I want people to praise me.

I want to be proud of myself.

I want my mom to see that her sacrifice was worth it.

I want to make enough money to take my friends anywhere in the world.

I want to be a role model for the family I’ll eventually have.

I want to be the man I clearly see in my mind.

I want complete financial freedom to create and to experience.

I want to lead by example and show my friends that even though it’s too late for them, they can push their kids to become entrepreneurs.

I want the world to know that this is how you win in life.

I want a beautiful wife.

I want a big house.

I want all the nicest things the world can offer, not because of materialism, but because I don’t think I’m less worthy than the ones who do get to experience them.

After my brain rattled out this list at rapid-fire speed, like emptying a magazine of honesty at a gun range, I realized something. Even though I had these thoughts bubbling around in my mind for a long time now, I had never once admitted it. Never once admitted it, let alone put it in writing. Something this concrete.

I’m not sure what your list looks like. But I know you have one. And whatever’s on it has a tax.

We’re all paying taxes whether we know it or not (the government wins again).

For now, the tax is a weekend scrolling flights with no good answer.

I’ll pay it.

The year is 2023. I’m sitting in my Range Rover in the Tim Hortons drive-through. Noise-cancelling speakers. Soft leather seats. It’s warm. It’s quiet. It’s mine.

Flashback to highschool. Almost two decades ago, I was taking two buses in Mississauga just to get pho after school. The 61 South from Mavis and Bancroft to Square One, transfer, then the 35 to Pho 99 at Hurontario and Eglinton. It took about an hour and fifteen minutes each way for those delicious noodles.

I had to go back into Google Maps just now to remember the geography. That’s how long ago it was.

I always wanted to be the cool guy I used to see downtown in my early twenties. The guy who made me wonder how he did it. The clothes. The car. The confidence. But not just on the outside. Cool inside too. Character, real friendships, life stories, and wisdom. I made it a personal vow to do things the right way, which always meant the long road.

So I spent all of my twenties and my early thirties becoming him. Twelve years in total. Behind a camera first. 400 weddings photographed. Then managing an artist and bringing them a platinum plaque. Then, building e-commerce businesses from scratch. Start, fail, start, fail, start, figure it out. There was a good decade where I had nothing in the bank. Years where the smart move was to quit and get a job. I didn’t. Not because I was brave. Because I was stubborn. Maybe those are the same thing. Idk.

By 34, I finally reached the intersection of success and stability. I had the clothes, the car, the network, the reputation, and finally, some money. The kid who had nothing becoming the man who built everything. That was the dream.

And I was that. In the city I was born and raised in. I was grateful. Cloud 9 each and every morning I hopped in my Range to go to the gym. Cloud 9, even when sitting in traffic. Every part of me was filled with joy.

But even with all this, something was off.

Toronto had gotten smaller.

Not physically. Mentally. The conversations around me had shrunk to mortgage rates, settling down, and ironically, which new pho franchise just opened. The city that produced Drake. Where I watched someone who started from the bottom (no pun), become the biggest artist on the planet and thought, “if this city can make that happen, imagine what it can make happen for me.” That Toronto doesn’t exist anymore.

The affordability crisis had gutted the culture. The energy had drained out of the streets. I loved what Toronto was. But I couldn’t pretend it was still that.

And then something hit me that I wasn’t ready for.

My parents came from Hong Kong.

They disliked their conditions and feared the future there enough to restart their entire lives in a foreign country. Left everyone and everything they knew. Friends. Family. Missed birthdays. Missed weddings. Missed funerals.

My mom cleaned toilets for $3 an hour when she first came to Canada. Birthday cakes were too expensive, so my parents bought each other apple pies to celebrate. I have this image of my dad sitting in a plastic chair at city hall, holding a number, waiting to be called, surrounded by documents he couldn’t read. Not being able to ask for help because of his broken English. Most days, I still can’t comprehend how they built a foundation from that.

And from that, from literally nothing, they built a real life. A detached home in the suburbs. Living the Canadian dream. Church on Sundays. Taking the kids to swimming lessons and extracurricular math classes on weekdays. Eventually, sending both of their kids to university.

My entire life, the foundation of everything I’d built, wasn’t something I earned. It was something they suffered for. Every bus I took, every school I attended, every English word I spoke fluently without thinking — all of it was paid for in ways I was only beginning to understand.

Everything I’d accomplished was standing on their shoulders. The single greatest contribution to my life wasn’t something I did. It was being born in a Western country because two people gave up everything. I grew up with English. I had a real education. I grew up with a culture that told me to dream big and believe I could be anything. The toughest thing I had to do was study. Woop-di-doo. This life was off their backs. They built it. With $3-an-hour toilet cleaning and apple pies instead of birthday cakes.

I felt shame. Gratitude. Guilt. And then something stronger than all three.

I’d spent years calculating what I’d lose by leaving. I never once calculated what I was losing by staying.

If my parents could leave everyone they ever knew for a better life, how could I use “my friends live here” as an excuse to stay in a city that was shrinking?

How dare I.

At first, a loud voice said Los Angeles.

Made sense. I’d spent half my twenties there. Photography workshops, model shoots, music industry meetings at Interscope and Capitol Records (so cool, btw). I had friends there. The weather was perfect. And LA was the opposite of Toronto — a city where everyone thought big. In Toronto, only a handful of people dreamed at that level and most of them left. LA was the first place I’d ever been where ambition was the default, not the exception. It felt like the obvious next move.

I applied for the US work visa. A year of processing. Thousands in lawyer fees. And then, I got it. I’d gotten what millions of people around the world would give anything for. A legitimate path into the United States. The American dream, on paper, in my hands.

I remember sitting in my downtown apartment off Spadina the day the visa was approved, looking at apartments in West Hollywood on my laptop. I had a shortlist. I had a budget. I was ready to go. I couldn’t believe it.

Looking back, the LA voice was so loud because it was the safe version of being brave. Still optimizing for the least amount of loss, not the greatest amount of life.

And then a quieter voice said something I couldn’t unhear.

“Wouldn’t it be nice if we spent the second half of life in Asia?”

Around the same time, I visited Tokyo for the first time. Nine days.

I remember exploring Ginza, designer storefronts the size of buildings, hundreds of people moving in perfect silence around me. Nobody bumped into anyone. Nobody raised their voice. The entire city was moving like a single organism. The dark, luxury, interior lighting of the Alphard pulling up if we got lucky with the Uber.

I thought: this shit is actually mad.

Nine days in Tokyo was nothing. Everything I experienced was the surface. The tourist version. Behind the language barrier were conversations I couldn’t have, places I couldn’t find, and an entire culture I could see but couldn’t access. I was watching through glass.

One night I got lost walking back from a convenience store in Shinjuku. Wrong turn somewhere. Ended up on a residential street I’d never seen. No tourists. No English. Just houses, power lines, and a row of vending machines humming in the dark. I bought a hot Boss coffee from one of them, stood on the sidewalk, and drank it. No idea where I was. Didn’t care. My phone was at 4%. I remember thinking, this is the calmest I’ve felt in years. Standing on a street I can’t pronounce, drinking canned coffee, completely lost. Meanwhile, back in Toronto I used to white-knuckle the steering wheel on the Gardiner doing 20km/h in traffic, quietly speaking affirmations to calm me down. “You are blessed. You are in a Range Rover. You will not let Toronto traffic disturb you.”

When I came back to Toronto, I started taking Japanese lessons.

And that’s when everything connected.

Japanese and Cantonese share overlapping sounds, words, and kanji — the traditional writing system of both Hong Kong and Japan. Through learning Japanese, I reconnected with my own heritage. A language I should have known better. A culture I should have understood deeper. It came through the back door of a completely different country.

A homecoming disguised as an adventure.

I’d found a city where everything was done with intention. Not in a flashy way. In an honest way.

Growing up, I’d find maybe one or two people who carried themselves at this level. The guy who had the style, the work ethic, the quiet confidence. In Tokyo, it’s not one or two people. It’s the whole city. The ramen shop owner who’s been perfecting the same recipe for 30 years. The barber who treats a haircut like surgery. The convenience store clerk who bags your egg sando and Pocari Sweat like it matters. Shit, even some salaryman in their 50’s and 60’s had this oldman swagger that would peak even the coolest kids on Queen West. Everyone here takes their craft seriously. Not for attention. Because that’s the standard.

The loud voice had said Los Angeles. The quiet voice had said Tokyo.

The quiet voice was right.

The first year and a half was brutal.

I knew nobody. I couldn’t read a menu. I couldn’t ask for directions. Trying to explain to a barber how I wanted my fade was the absolute worst. I sat in my apartment some nights and thought: Derek... what have you done.

One night I went to a yakiniku spot near my apartment. Sat down. The menu was entirely in Japanese. I pointed at something that had a picture of what I was pretty sure was beef. It was not beef. I don’t know what it was. Some kind of organ, maybe intestine, grilled to a texture I would describe as “aggressive.” I ate every piece with the signature move you learn as a kid — a mouth stuffed with rice to hide the taste, and swallowing before things were fully chewed — just because the chef was watching me from three feet away and I’d rather die than send it back in a language I didn’t speak. I walked home and ate a 711 onigiri at midnight like a man who had just been humbled by a menu.

There’s a loneliness that comes with starting over that nobody warns you about. Not the kind where you miss people. The kind where you realize that every piece of identity you built — your reputation, your network, your place in a city — means nothing here. You’re nobody. You’re starting from actual zero.

Some nights I’d think about my dad in that plastic chair at city hall. At least I had Google Translate.

Whenever I came back to Toronto and saw my mom, she would always ask how it’s going. I never had the nerve to tell her a shred of negativity about my experience. She always worried too much about me. The last thing I wanted to do was cause her any more concern. She had already done so much for both of us.

Every time I came back to the city as well, I’d do my best to organize dinners and hangouts with literally everyone. But each time, I could feel the list of “who to catch up with” and the list of “what to catch up on” getting heavier and heavier. To the point both sides probably felt like, “what’s the point?” You can catch up for hours and hours and still feel like you’re drifting apart. I’m not saying I’d change the decision. I’m saying the decision changed things I can’t get back. Those are different sentences.

It’s the biggest decision I’ve ever made.

Not just externally. Internally. Moving here cracked open something I didn’t know was closed.

The pride of doing what my parents did — going to a foreign country, filling out forms in a language I barely understood, anxiety at 100, starting from zero. I finally understood what they went through. Not intellectually. But physically. Sweat dripping from confusion and embarrassment on my body (it doesn’t help it’s always so poorly ventilated at any city hall). The loneliness of the first year. The fear that maybe this was a mistake. And the slow, quiet realization that it wasn’t.

My appreciation for my parents went from something I said to something I felt. Having lived even a fraction of what they went through, I want to give them more. My mom, especially. More of the world. More of what’s possible. Because I finally understand what it cost them to give me everything. I need to show her it was all worth something.

My parents didn’t have a framework. They didn’t have a pros and cons list. They didn’t read a book about cognitive bias. They had a vision for a larger life and a country that was closing in on them, and so they bought plane tickets. They didn’t overthink it. They couldn’t afford to. I could. And that was the problem. Comfortable people make the worst decisions because they have the luxury of making none at all.

This move made me a better entrepreneur. A better son. A better human. It also made me a 36-year-old who just learned how to properly order coffee in Japanese. But hey, that’s part of it.

Toronto gave me everything I needed to start. Tokyo is giving me everything I need to become.

I still get lost and wander my neighbourhood on some random evenings. Order a hot milk tea from the vending machine. I look around and think. It’s warm. It’s quiet. It’s mine.

I’ve photographed over 400 weddings. And the one thing I know for sure: planning a wedding and planning your life are the same problem.

Most people get lost in the details of both.

Flower arrangements. Seating charts. What kind of cut the dress should be. Will we get featured in a magazine? Will the centrepieces match the napkins? Will the napkins match the bridesmaids? Will the bridesmaids match each other? I’ve seen this conversation last two hours. Two hours.

It never ends. And the further into the details you go, the further you get from the only question that actually matters.

What is this day supposed to be about?

Is it bringing together friends and family from opposite sides of the world who have never been in the same room? Is it throwing a party so good people talk about it for years? Is it making a childhood dream come true?

These are all different weddings. They require completely different plans. But most couples never sit with that question long enough to answer it clearly. They start planning before they start thinking. And then they wonder why nothing feels right.

Sound familiar? Yeah.

Stress is when you want two opposing things at once.

I watched this play out hundreds of times. A couple wants a low-key, casual wedding. Then the bride starts micromanaging the placement of every candle on every table. A couple wants intimate sunset portraits, golden hour, just the two of them, the kind of photos you frame. But they also want to personally greet all 150 guests during cocktail hour. You can’t do both. The sun doesn’t wait for your thank-you rounds.

Same thing happens in life. Exactly the same.

You want to build a business but you also want every Friday night out with your friends. You want financial freedom but you also want the security of a paycheck. These aren’t problems. They’re conflicts. And conflicts don’t get resolved by working harder. They get resolved by choosing.

With anything in life you can have more. You just need to increase your sacrifice. Or reduce your desire. Those are the only two levers. There isn’t a third one. I know because I spent a decade looking for it.

I’ve seen things at weddings. Things.

I once hung a bride’s dress by the hotel window to photograph it. Standard shot. Every wedding photographer does it. While I was adjusting the train, the bride’s sister walked up and said, casually, almost like she was commenting on the weather: “I honestly don’t know why she’s marrying him.”

I said, “well if you don’t know why, I wouldn’t know why either.” And I went back to photographing the dress.

But for the rest of that day, every time I raised my camera, a small part of me was somewhere else. Taking candids of the first dance, I wondered what the backstory was. Shooting the toasts, I wondered how things had led to this moment. Photographing the couple walking through a shower of sparklers, I wondered whether these photos would be cherished for decades or end up in a trash bin. Deleted. Forgotten.

That’s a strange thing to carry while your job is to make everything look beautiful.

I’ve had a groom and his best man get into an actual fistfight the night before the ceremony. The best man missed the ceremony entirely. Missed the portraits. Showed up at the reception with a black eye. Nobody talked about it. Everyone just pretended it was normal.

I’ve watched a bride and her sister, the maid of honor, get into a full shouting match during the portrait session. In front of me. In front of the makeup team. I just kept shooting. What else was I supposed to do. Because nobody said what they actually needed until it was too late.

I get it though. It’s most of these people’s first time planning something this big. First time getting married. You’re filled with advice from friends, Pinterest boards, family, all telling you what you need and what you don’t. You’re pulled in every direction. In-laws want this. Parents want that. The budget can only handle so much. And you’re supposed to make the biggest commitment of your life while managing all of it. On the same day.

But here’s the thing. Life is the same way. Just longer.

But some couples get it right.

I’ve seen it enough times to know what it looks like. No formula. No pattern.

It’s not about budget. Some of the best weddings I’ve shot were in backyards. Some were in ballrooms. The venue didn’t matter. The flowers didn’t matter. The napkins — I promise you — never mattered.

What mattered was something you could feel the moment you walked into the room.

Both people were grounded. Not emotionless. Not robotic. Grounded. They were in the air from the joy of the day but both feet were planted in the ground together. When they said their vows, you believed them. Not because the words were poetic. Because there was a balance of emotion and honesty behind them. Enough self-awareness to counterbalance the high of the moment. Most people say their vows from pure emotion. These couples meant theirs.

It showed in how they treated everything else too. They weren’t swept up in it. They enjoyed the day without being consumed by it. They made decisions without agonizing. They handled problems without spiraling.

But the ones where you walked away thinking — love is real, their love is real, their commitment is real — those couples all had the same thing.

Clarity.

Not certainty. Clarity. They knew what the day was about. They knew what mattered. And they let everything else be imperfect without it ruining anything.

I’ve been thinking about this a lot lately. Not about weddings. About thinking.

For most of my career I didn’t have a tool for thinking clearly. I had real examples. 400 of them. I watched couples implode and I watched couples glow. I saw what happened when people knew what they wanted. And when they didn’t. I learned by watching other people’s decisions play out from behind a lens.

But not everyone gets 400 front-row seats to how decisions shape outcomes.

As I get older I keep arriving at the same place. Better thinking leads to clarity. Clarity leads to confidence. Confidence leads to the outcome you actually wanted. The couples who got it right didn’t get it right because they were luckier or more in love. They got it right because they thought clearly about what mattered before they started planning. The thinking came first. Everything else followed.

That’s why I’m building Clarity.

Not an app that tells you what to do. A thinking partner. Built on first principles, Socratic reasoning, and the best mental models from the sharpest minds in history. Marcus Aurelius for staying grounded. Charlie Munger for making decisions. Naval Ravikant for figuring out what you actually want.

One tool. Built to help you think clearly enough to trust yourself.

Because the couples who got it right and the people who get it right in life have the same thing in common. It’s not luck. It’s not a formula. It’s not even confidence, at least not at first.

It starts with clarity. The confidence follows.

We’re building it right now. Join the waitlist at getclarity.tokyo

I was nine years old the first time I made a real decision.

Not the kind adults hand you. Not “what do you want for dinner” or “which shirt do you want to wear.” The kind where the safe option is to stay quiet and you choose not to.

I grew up in a house where noise was dangerous.

An accidental laugh. A dish placed too hard on the counter. A door closed too loud. Any of it could set my father off. Beatings. Screaming. Two-hour lectures inches from your face, rage behind his eyes. It didn’t matter where we were. Our living room. The middle of Home Depot. He would berate us without a second thought. And never, in all the years I can remember, a single apology.

I noticed what it was doing to everyone.

I noticed it in myself. The way I had to shake off the morning’s episode before I could show up at school and look normal. I noticed it in my brother, the way he would disappear into television and video games after it happened. And I noticed it in my mom. She kept a Gatorade bottle by her bed. I knew it wasn’t Gatorade. I knew it was wine. I knew she needed it to fall asleep.

So I called a family meeting.

I was nine, maybe ten. I stood in our living room, trembling, tears running down my face, and I told my father: you are a bad father. You are doing things to this family that are taking us in the wrong direction.

I’m sure I didn’t say it that cleanly. I’m sure I looked like a kid crying about being hit. But somewhere underneath the tears, I knew something. I could see where one person’s actions were dragging an entire family. And I decided that staying silent was more dangerous than speaking up.

Nothing changed. Not immediately. The house didn’t get quieter. But something changed in me.

I felt light.

Not because the situation improved. Because the weight of carrying hundreds of mental notes, building a case inside my own head, rehearsing what I would say, all of that released the moment I opened my mouth. The backlog cleared. And even though I couldn’t change my father, I realized I could change myself. I could change my environment. I could start building my own independence.

That was the first decision I ever made. I was nine.

That moment set the pattern for everything that came after. Most people wait their entire lives for the courage that nine-year-old had.

Up until 31, I never kept more than $5,000 in my bank account.

I was building. Photography first. 400 weddings, editorial work, magazine shoots. Then artist management. Then e-commerce. Every dollar above the bare minimum went right back in. Workshops. Flights to LA for meetings and shoots. Better gear. Dinners with people passing through Toronto.

I decided early that I would tie my identity to my growth, not my bank balance. That security could wait.

There were months where income arrived late, expenses lived on my credit card, and the next deposit was a complete mystery. Confidence was the only thing keeping me moving forward.

But I kept deciding. Deciding to stay an entrepreneur when the smart move was to get a job. Deciding to reinvest when the safe move was to save. Deciding to try again when the reasonable move was to quit.

Then the pandemic hit. And everything stopped.

Both businesses died overnight. Photography and music management. Gone.

A decade of reinvesting in myself meant a decade of having nothing in reserve. I went into debt. I applied for CERB, the government’s pandemic funding. And then I did something I never thought I’d have to do. I called my mom and asked to borrow money.

I remember hanging up the phone and sitting on the edge of my bed, doing the math on a decade. Ten years of work. Ten years of risk. And I was borrowing money from the woman who used to keep wine in a Gatorade bottle just to get through the night.

That was the lowest point. Not financially. Financially I’d been low before. But mentally, the math hit different this time. I’d worked for a decade and had no bank statement to show for it. All the momentum I’d been building, years of it, evaporated in weeks.

I thought about quitting. Seriously. Getting a job. Letting the whole thing go. The voice in my head that had been quiet for years suddenly got very loud: this was stupid. You should have played it safe. You should have built something more stable.

But I didn’t quit. Not because I was brave. Because by that point, deciding was the only thing I knew how to do. The muscle was too built to break. Even at the bottom, I kept making small decisions. Adjusting. Pivoting. Looking for the next door.

And eventually, a business took off. Beyond anything I’d ever built before. The same decade of investing in skills, network, and self that had left me broke was also the reason the opportunity existed. Everything I’d invested in for a decade finally compounded. And the return was bigger than anything I could have planned.

That’s what people miss about risk. The cost of playing it safe compounds just as quietly as the cost of betting on yourself.

But not every decision I made was the right one. And worse, not every decision I avoided was harmless.

I managed a music artist for years. I believed in him. The talent was real.

Early on, I called in a personal favor to get him a press opportunity. The kind of thing you don’t get twice. I used a relationship I’d spent years building, put my name on the line, and set it up.

He didn’t show up on time. Then he decided not to come at all. Told me to handle it.

I sat in that interview looking like a clown. I’d told them we needed fifteen more minutes, fifteen minutes ago. Then I had to make up an excuse they clearly didn’t believe. I didn’t look like the manager. I looked like a failed babysitter.

That was the moment I knew. Not in my head. In my gut.

I should have had the conversation immediately. The honest one. The one where you sit down and say “this isn’t working and here’s why.”

I didn’t.

I waited. I rationalized. I told myself it would get better, that the tension was temporary, that the work would speak for itself. And the longer I waited, the wider the gap grew. By the time I finally had the conversation, it was too late. Not because the problems were unsolvable, but because the silence had compounded into something neither of us could undo.

I learned a phrase during that time: honest conflict is better than dishonest harmony.

I wish I’d learned it sooner. I live by it now.

The cost of avoiding that decision wasn’t just a failed partnership. It was years of my life spent inside a situation I knew wasn’t right, performing a version of peace that didn’t exist. The avoidance felt safe in the moment. In hindsight, it was the most expensive choice I made.

Most people are carrying a version of this right now. A conversation they know they need to have. A truth they keep swallowing because the silence feels safer than the conflict.

I moved to Tokyo.

The first year was quiet in a way I didn’t expect. I knew nobody. I spent my days wandering the city, sitting in cafes where I couldn’t read the menu, ordering by pointing at pictures. Some days the only person who heard my voice was a convenience store cashier.

Every morning I’d walk among thousands of people my age, mid-thirties, all heading to the same job in the same clothes. Same lunch. Same commute home. Same conversations.

And something shifted.

The gap between my life and theirs wasn’t about culture. It wasn’t about East versus West. It was about decisions. A decade of them. Every time I’d chosen to invest in a skill instead of saving the money. Every time I’d said yes to something uncomfortable. Every time I’d walked through a door that scared me. Those decisions had compounded across every domain of my life. Health. Wealth. Relationships. Identity. We were the same age, breathing the same air, walking the same streets. But the lives we were living were separated by a thousand small choices made over a thousand ordinary days.

Your life is not the result of one big moment. It’s the compound interest of every small decision you made when nobody was watching.

That’s when the pattern clicked.

Every good thing in my life came from a decision. The photography career. Leaving the artist. Surviving the pandemic. Moving to Tokyo. Every one of those chapters started the same way. Not with a plan. Not with certainty. Not with feeling ready. With a decision.

And every regret? Those started the same way too. With avoidance. With waiting. With telling myself I needed more time before I could act.

The decisions didn’t always lead where I expected. Some of them led to failure. Some to pain. But the ones I never made? Those cost me more than any failure ever did. Because failure teaches you something. Avoidance just takes your time and gives you nothing back.

I think about this every day. Not as philosophy. As practice.

I decided to learn Japanese and Mandarin at 34 because the investment would compound for decades. I decided to build a personal brand because the skills and stories I’d accumulated over fifteen years were worth more shared than stored. I decided to build Clarity because I’d lived the cost of indecision long enough to know that most people aren’t stuck because they lack options. They lack a way to think through them.

Every one of those decisions felt too early. None of them felt ready. That’s the point.

If you’ve read this far, you recognized something in these stories. Not my details. Yours.

The conversation you’ve been avoiding. The move you’ve been researching for months. The idea sitting in your notes app. The version of your life you can see clearly but haven’t started building.

You already know what the decision is. You’ve known for a while.

More time won’t make it easier. It won’t give you clarity you don’t already have. It will just make you older by the time you finally do what you were always going to do.

I learned this at nine years old, standing in my living room, trembling, telling my father the truth. Nothing changed that day except me. And that was enough.

It’s always enough.

Not because deciding guarantees the right outcome. But because the weight of not deciding is heavier than any failure you’ll ever face. The lightness that comes from finally acting, from saying the thing, walking through the door, that lightness is real. I felt it at nine. I felt it booking a flight to Tokyo. I feel it every time I stop rehearsing and start doing.

Your decisions are the only thing that will ever change your life. Not your circumstances. Not your timing. Not whether you feel ready.

Somewhere right now, there’s a version of you standing in a living room, trembling, knowing exactly what needs to be said.

Say it.

They say when you’re born, you look like your parents. And when you die, you look like your decisions.

About a year ago, I heard through a friend that someone close to me had said our relationship changed. That the reason it changed was money.

My first instinct was to be hurt. But I sat with it. And I started asking myself questions. Because that’s what I do when something bothers me more than it should. If it stings, there’s something underneath worth looking at.

So I asked: is it true? Did the money change me?

I had to be honest with myself. My lifestyle looks different now. The trips, the clothes, the dinners. From the outside, the before and after is obvious. So I can understand why someone would draw that line. Money arrived, Derek changed. Simple.

But is that what actually happened?

I went back further. What came before the money? A decade. Trying, failing, trying again. Businesses that didn’t work. Ideas that went nowhere. Years where I had nothing to show for the path I chose except the fact that I was still on it. The money didn’t arrive and turn me into someone new. The money arrived because of who I’d already become through a thousand small decisions nobody ever saw.

So the real question isn’t “did the money change me?” The real question is: what do people see when they look at your life, and are they seeing the cause or the output?

They were seeing the output. And calling it the cause.

That realization led me somewhere deeper. I asked: why did this bother me so much? If I’m confident in my decisions, why does one person’s misread sting?

Because it revealed a gap. Not between me and this friend. Between what I know to be true about my own path and someone else’s ability to see it. That gap is lonely. And no amount of being right about your own life makes that less true.

I’ve never shared this before. But for all of my twenties, I never kept more than $5,000 in my bank account. Not because I didn’t earn more. Because I chose not to hold it.

Every dollar above that line went back into the life I was building. Photography workshops. Flights to LA to shoot and take meetings. Better gear. Dinners with people passing through Toronto who I wanted to learn from, build with, stay connected to. I decided early that I would run lean and not tie my confidence or my identity to a bank balance. That I would over-index on growth and under-index on security.

It was nerve-wracking. There were months where income I was counting on arrived late and expenses lived on my credit card. But I knew my life was a startup. And I felt confident, from the amount of work I was putting in, that eventually it would pay off.

Nobody saw that decision. Not the friend who said money changed me. Not anyone. They saw what came after. They never saw the years I deliberately kept myself at zero so I could invest in becoming someone worth betting on.

So what does that mean about everyone else? If my life reflects my decisions, what does anyone’s life reflect?

I had to ask it honestly. If someone’s life looks like the default, like what you’d end up with if you never actively chose anything at all, does that mean they didn’t choose? That they followed? That they took what was handed to them and called it theirs?

I’m not asking that as a judgment. I’m asking because the same logic has to apply to everyone, including me. If my decisions built my life, then the absence of decisions built someone else’s. That’s not good or bad. It’s just the clearest way I know how to see it.

When you’re young, this is invisible. You and your friends can be completely different people, but your lives look the same. Same routines, same starting line. The differences are happening underneath, in what you choose to do with your time, what you give up, what you say no to when nobody’s watching.

I felt this early. Up until graduation, I had one friend group. Close friends from high school who grew super tight throughout university. But when I graduated and decided not to use my degree, I was suddenly exposed to the full world. I started building friendships in photography, in the music industry, downtown Toronto, different cities entirely.

And I remember noticing something. Whenever we’d go out as a group downtown Toronto, to Montreal, LA, wherever, I knew people in those cities. I had connections, conversations, rooms I could walk into. Not because I was special. Because I had been making a decision, over and over, to keep growing my world while it would have been easier to keep it the same size.

I couldn’t name it at the time. But I could feel a gap forming. Not in status. Not in money. In range. In the breadth of experiences, conversations, and knowledge that comes from choosing to keep expanding when nothing is forcing you to.

Then I asked myself the hardest question: what do I actually want this friend to understand?

Not that I’m right. Not that they’re wrong. Just that the money was never the thing. The decisions were always the thing. They were the thing when nobody could see them, they were the thing when everything was failing, and they’re still the thing now. The money is just what it looks like from the outside when a decade of decisions finally compounds.

And if I’m being fully honest, the question I keep coming back to isn’t about this friend at all.

It’s: am I still making decisions? Or am I starting to coast on the ones I already made?

Because the same principle that got me here can work against me if I stop. The moment I stop actively choosing is the moment my life starts drifting toward the default. Doesn’t matter what’s in the bank account. Doesn’t matter what the last decade looked like.

Your life looks like your decisions. It always has. The only question worth asking is: are you still making them?

There’s a specific kind of self-deception that humans are remarkably good at.

Not the big lies we tell other people. The quiet ones we tell ourselves — with complete conviction, while the evidence sits right in front of us.

Here’s the most relatable version: the crush.

Someone asks about a person you’ve been seeing. You go one of two ways — you admit it, or you play it cool. “I mean, they’re cool. It’s not that serious.”

And then you go home and spend forty-five minutes cleaning your bathroom.

I learned something about myself somewhere in my thirties. I can gauge exactly how I feel about someone by what I do before I see them. Not what I tell my friends — what I actually do.

The baseline: tidy the room, take out the trash, make the bed. Solid 6/10 interest.

Car wash before pickup? Something real is happening.

But recently in Tokyo, before seeing someone I'd been telling myself I was "on the fence" about — I steamed my clothes. Scrubbed the shower. Wiped the dust off my full-length mirror. Vacuumed every corner. Emptied every trash bin in the apartment. Sprayed room scent inside the shoe closet. And genuinely considered getting on my hands and knees to check under the TV console.

I thought about it. I want to be clear about that.

You can tell yourself you’re not that interested. But you cannot say that while filling a mop bucket that hasn’t been touched since move-in day. At some point, your actions stop cooperating with your narrative.

Once I noticed it in myself, I started seeing it everywhere.

Over the course of shooting more than four hundred weddings, I had a front-row seat to one of the most honest displays of human behaviour imaginable. Weddings are extraordinary because the stakes feel enormous — and yet how people actually behave in those hours reveals everything.

I’ve watched brides spiral over centerpieces while their partner stood quietly to the side, waiting to be seen. I’ve watched grooms refuse to step outside for a fifteen-minute sunset shoot — the one part of the day the bride had mentioned wanting for months — because it was either too hot outside or they were more comfortable at the bar with their friends. Nobody was being malicious. They weren’t thinking about what their actions were communicating. They were just doing what came naturally.

And what came naturally, in some cases, wasn’t presence. It wasn’t attentiveness. It was protecting their own comfort on a day that was supposed to be about something else entirely.

That gap — between what people say they feel and what their behavior quietly reveals — it’s one of the most human things I’ve ever observed.

You see it in parents too.

My father loved us. I don’t doubt that. He said it, and somewhere underneath everything, I believe it was true.

But love was also the word he used to explain the beatings. The discipline that came without patience, without teaching, without a single apology in all the years I can remember. He genuinely believed that because the intention was love, the experience of it must be love too.

What I received and what he believed he was giving were two entirely different things. And the gap between them couldn’t be discussed, because in his mind, there was no gap.

That’s the quietly devastating version of this. Not malice. Just a man who never learned to read the distance between what he felt and what he showed.

And then there are the people with the idea — or in some cases, already living it.

I managed a music artist for years who genuinely believed he was going to be great. And maybe he could have been. The talent was real. The vision was vivid. When he talked about where he was headed, you almost believed it alongside him.

But he missed soundchecks. He missed rehearsals. He wanted to grow his brand but refused to spend money on events, music videos, or any kind of promotion — every conversation circled back to finding a sponsor, finding someone else to carry the cost. He wanted to work with the best producers in the industry, and then balked at every fee that came with actually doing so.

The dream was real. I believed him every time he talked about it. But somewhere between what he said he wanted and what he was willing to do to get it, the truth was already visible — to everyone around him, and probably to some quiet part of himself he wasn’t ready to hear yet.

That’s the thing I kept coming back to across all of it — the apartment I cleaned, the sunset shoot that never happened, my father’s silences, the missed rehearsals. In every case, something was being communicated. Clearly, consistently, without a single word.

Actions are a language. They’ve always been a language. We just don’t get taught how to read them.

We’re taught to listen to what people say. To take words at face value. To believe the story someone tells about themselves — including the story we tell about ourselves. But words are easy. Words cost nothing. Words can be assembled to say almost anything, and they often are.

Actions are different. Actions have weight. They require something — time, energy, sacrifice of some other option. And because of that, they tend to be honest in a way that words rarely are.

Once you start reading actions the way you read words — in others and in yourself — something shifts. You stop being surprised when people behave exactly as they’ve been showing you they would. You start noticing when your own behavior is quietly telling a different story than the one in your head.

It’s not about judgment. It’s about clarity.

What story are your actions telling right now?

Not the story you’d like them to tell. Not the story you’d give if someone asked. The story a stranger would piece together if they followed you around for thirty days and never heard you say a word.

That story is already being told. It’s being told every day, whether you’re paying attention or not.

The only question is whether you’re one of the people listening.

Around 100,000 years ago, something shifted in the human brain that no other species could match.

Homo sapiens developed a cognitive edge — unique to us, absent in Neanderthals and chimpanzees — that didn’t make us stronger or faster or better hunters. It made us something far more dangerous.

It gave us creative self-awareness. The ability to think in the abstract.

And on the surface, that might not sound like much. Abstract thinking. Creative self-awareness. They sound like things you’d put on a LinkedIn profile or read about in a business book. But what they actually unlocked was something that no other species in the history of this planet had ever done before.

They made us able to believe in things that didn’t exist.

To understand what I mean, picture this. An early human reaches down and picks up a seashell from the sand. It has no nutritional value. It can’t shelter you, protect you, or keep you warm at night. By every practical measure, it’s worthless. And yet somehow — through nothing more than collective agreement, with no physical proof and no authority forcing the decision — a group of strangers decides this shell has worth. That you can trade it. That someone across the valley who has never met you, who owes you nothing, will accept it in exchange for something real.

That’s not just the origin of currency. That’s the origin of civilization. Every company, every government, every religion, every stock market that has ever existed — all of it built on the same foundation. The ability to take an abstract idea and make it real enough that other people will act on it together.

Neanderthals couldn’t do this — at least not at the same scale. Their brains were wired for the immediate and the concrete. What’s in front of me right now. What I can see, touch, hunt, use. They were extraordinary at that. But the moment you need to coordinate with strangers around an idea — something invisible, something agreed upon, something imagined — that’s where Homo sapiens left them behind.

We didn’t win because we were stronger. We won because we could think in the abstract.

And 100,000 years later, that same edge is still the most underrated advantage a person can have.

I think about this a lot in the context of my own career. Because the pattern keeps showing up.

I spent over a decade as a photographer — 400+ weddings, magazine shoots, editorial work. Then I moved into artist management in the music industry. Then start-up e-commerce companies. And now I’m building a personal brand. On paper, these look like completely different industries. Different skills, different markets, different languages.

But here’s what I noticed: the frameworks are always the same.

When I moved into artist management, I wasn’t starting from zero. I understood visual storytelling — so I could creative direct shoots, build assets, speak fluently with photographers and videographers we hired. The aesthetic instinct I’d built behind the camera transferred directly into how we built an artist’s identity, their brand, the visual world around their music.

When I started ecommerce companies, the same thing happened. Product photography, brand direction, the way a campaign feels — I wasn’t outsourcing that and hoping for the best. I understood it at a level most founders don’t because I’d built it from the ground up in a completely different context.

The skill didn’t change industries. I did. And I took the abstract understanding of how it worked with me.

That’s what abstract thinking actually is. It’s not a personality trait or some mystical creative gift. It’s the ability to look at a framework in one place and recognize it somewhere else. To see the bones of something — the underlying structure, the principle at work — and apply it somewhere it’s never been applied before.

Here’s the most powerful example I keep coming back to: the path to mastery.

Every athlete, every artist, every entrepreneur who has ever gotten genuinely good at something has taken a different journey to get there. Different starting points, different obstacles, different timelines, different breakthroughs.

But abstractly? The journey is always the same.

You develop some ability. You build momentum. You hit a ceiling. The ceiling frustrates you — emotionally, psychologically. Your performance dips. You reassess. You find new perspective, a new teacher, a new framework. You climb again. Repeat.

The specifics are always unique. The structure is always identical.

Once you see that pattern abstractly, you stop panicking when you hit the ceiling. You recognize it. You know what it means and what comes next. And that recognition alone gives you an edge over everyone around you who is experiencing it for what feels like the first time.

This is why all self-help is essentially the same advice. Because at an abstract level, all human growth is the same journey. The packaging changes. The lessons underneath don’t.

Creativity is the same way.

Most people think of creativity as something reserved for artists — a talent you either have or you don’t. But creativity is just abstract thinking in action. It’s the muscle you use when you’re figuring out how to take your partner on a date that actually means something. How to land a meeting with someone who has no reason to take it. How to position yourself in a market that’s already crowded. How to solve a problem at work that nobody has solved yet because nobody has thought to look at it from a different angle.

Every one of those things is a creative act. And like any muscle, it gets stronger the more you use it — and weaker the more you default to what’s familiar and automatic.

The people who consistently outperform their peers in business, in relationships, in life — they’re rarely the smartest in the room or the most talented. They’re the ones who’ve trained themselves to see connections that other people miss. To take a framework from one world and apply it to another. To stay curious enough, and uncomfortable enough, that their thinking never stops expanding.

That’s the edge. It’s always been the edge.

It’s the same edge that separated us from the Neanderthals 100,000 years ago. The ability to look at a shell and see a financial system. To look at a framework and see a possibility. To look at what is, and imagine what could be.

Use it.

Everything you have right now — your job, your relationships, your income, where you live, how you carry yourself in a room — is a direct result of three things.

What you know, who you know, and a third thing I’ll tell you at the end.

Think about that seriously for a second, because it sounds simple until you actually pull on the thread.

You know how to get dressed for work. You know how to do your job. You know how to talk to someone you’re interested in. Every single thing you’ve figured out how to do — no matter how small — expanded what was possible for you. And every single thing you still don’t know is a door you haven’t opened yet. A version of your life you haven’t accessed.

What you know has gotten you exactly here. The question worth sitting with is: if you knew more, where would you be?

Let me give you a small example.

I’ve been working out at the same gym in Roppongi since I moved to Tokyo. It’s fine. It does the job. But it’s not the kind of place that makes you excited to show up — limited equipment, limited variety, limited everything. I’d just accepted it as the best option in the area.

Then only just yesterday I’m in the locker room, making small talk with someone I’d seen around, and I mentioned offhand that it was basically the biggest gym around. He looked at me and very casually told me there was actually a new place that had just opened around the corner — bigger, better equipped, cleaner, the kind of gym that actually makes you want to train.

I had no idea it existed.

I walked over the next day, and just wow. It was everything he described. I’ve been training there ever since.

Here’s the thing — it’s not really about a gym.

If I hadn’t been talking to that person. If I hadn’t asked the question. If I had just gotten dressed and left like I normally would — I’d still be at the old gym right now, still assuming it was the best I could do, still operating inside a smaller version of what was available to me.

The better gym existed the whole time. I just didn’t know about it.

This is how most of life works.

The job opportunity, the connection, the relationship, the version of your life that’s genuinely better than the one you’re living — so much of it is sitting just at the edge of your reach. Not hidden. Not locked away behind some impossible barrier. Just one conversation, one question, one new person away from becoming real.

But you have to be in motion to find it. You have to be talking, asking, engaging, exploring. Because the world is far bigger than what any one person can see from where they’re standing. The question is never whether it’s out there. The question is how much of it you’re willing to go looking for.

So often we forget this.

I’ve fallen into loops — watching the same shows, listening to the same music, having the same conversations — and noticed how my world shrank. Not dramatically. Not in any way I could point to on a given day. But over time, the edges closed in. The picture stayed the same size.

Think about what that actually costs.

Every year spent in the same loop with the same people and the same information is a year where the picture doesn’t grow. Where the opportunities that exist just outside your reach stay exactly there — just outside your reach — because you never moved far enough to find them.

Progress isn’t just a nice idea. It’s the thing that gives life meaning. Growth, expansion, understanding more than you did yesterday — this is the work of being human. It doesn’t require grand gestures. It requires something much simpler and much harder at the same time.

I think about this one moment from junior high. We’d just started biology — first real textbooks, first assigned readings that actually demanded something from you. I was sitting with this one chapter, and I’d read it four times. Four. My brain was processing the words, I understood the words individually, but the actual meaning kept slipping past me. I was tired and frustrated, and when I get frustrated I tend to speed-read even faster — which obviously makes it worse. To this day I still have to catch myself, take a breath, and go slow.

But that night I read it a fifth time. And it clicked. The whole concept just opened up, like it had been waiting for me to stop fighting it.

That’s what expanding your world actually looks like most of the time. Not some dramatic leap into the unknown. Just one more pass at the thing you don’t yet understand, when every part of you wants to quit and call it good enough.

Because somewhere at the end of one of those threads is a door. And behind that door is a version of your life you didn’t know existed.

The gym was there the whole time.

So is everything else you haven’t found yet.

But here’s the thing nobody talks about.

Knowing the gym existed meant nothing until I walked through the door.

That’s the third thing. And it’s the one that actually separates the people who talk about changing their lives from the people who do. Because you can know all the right things and be connected to all the right people — and still stay exactly where you are. Still go back to the old gym. Still have the same conversations. Still live inside the smaller version of your life because acting on what you know requires something that knowledge and connections alone can never give you.

It requires a decision.

I have a condition called pectus excavatum. It’s where the chest cavity is sunken in — happens to about 1 in 500 people, mostly boys. Mine is mild, but when you’re skinny growing up, mild doesn’t feel mild.

I remember changing in the locker room in grade school and one of the boys asking me if someone had punched me too hard in the chest when I was young. I remember my girlfriend in my early twenties — kindly, sweetly — saying there was a place in my chest where she could rest her head. Both moments landed in the same spot. Both reminded me that my body looked like something that needed explaining.

I knew for years that building muscle and improving posture could reduce how visible it was. I’d done the research. I had the information. And for a long time, I didn’t do anything with it.

Then at twenty-seven I decided to start. I hired a personal trainer. Four sessions a week. Eight years later, twenty pounds of muscle later, close friends have asked me how I “fixed” it. I take my shirt off at the beach without thinking twice now. Confident. Not because the condition disappeared — but because I finally acted on what I already knew.

That’s the gap. That’s where most people’s lives stall out. Not at the knowing. At the doing.

What you know opens the door. Who you know shows you where the doors are. But what you do — that’s the only thing that actually walks you through one.

Most people get stuck at the first two and call it bad luck. They have the information. They have the awareness that something better exists. And they still don’t move. Because knowing is comfortable. Doing is not.

The door is already there. You already know where it is. The only thing left is to walk through it.

The greatest thing that ever happened in our lives had nothing to do with us. It wasn’t a deal we closed, a skill we built, or a decision we made. It happened before we were old enough to have an opinion about it.

Our parents left.

Some left for opportunity. Some left because there was no opportunity. Some left because of war, civil unrest, or governments that had made it clear their families had no future there. The reasons were different, but the decision was the same — they looked at where they were, decided it wasn’t good enough, and chose to do something drastic about it.

They left their language. Their family. Every familiar thing they’d ever known. They arrived somewhere new with no connections, no network, no guarantee that any of it would work out. They built something from nothing — not because it was easy, but because the alternative was staying somewhere they knew was wrong for them.

We are the result of that decision.

So here’s the question I’ve been sitting with. And I want you to actually sit with it too, not just read past it.

What is the hardest thing you have ever done?

Not the hardest thing that was done for you. Not the sacrifices your parents made, or the opportunities that were handed to you as a result of their courage. I mean you, specifically — what have you done that was hard? What have you genuinely sacrificed, of your own choosing, for a future you decided you wanted?

For most of us — and I include myself in this — the honest list is shorter than we’d like to admit.

We went to university for four years. We applied to jobs. We worked, saved, maybe scraped together a down payment. We gave up some free time when we started a family. These are real things. Nobody is saying they aren’t.

But if you stood in front of everyone you respect — your parents, your grandparents, the people whose sacrifices made your life possible — and you listed out the hard things you’ve done, the things you chose for yourself, the risks you took on your own terms because you believed in something better... how long would that list actually be? And how many of those things did you choose, versus how many were just the expected next steps that everyone around you was also doing?

Go to school. Get a job. Buy a car. Get a house. Complain about the Trudeau’s government.

Is that it?

Because here’s the irony that I can’t stop thinking about.

Our parents saw their situation clearly. They didn’t romanticize it. They didn’t tell themselves it wasn’t that bad, or that things would eventually improve, or that leaving would be too hard because their friends and family were there. They saw reality for what it was, made a ruthless decision, and acted on it.

And we — their children, born into the opportunity they bled for — have become so comfortable inside that opportunity that we’ve lost the very instinct that created it.

The comfort they sacrificed everything to give us has become the reason we don’t sacrifice anything.

Since COVID, if you’re from Toronto, you already know. You don’t need me to explain it. You felt it — the slow hollowing out of a city that used to have a pulse. The businesses that didn’t make it. The spots that meant something, gone. The cost of everything going up while the quality of everything went down. And the conversations — god, the conversations. Every dinner, every catch-up, every group chat eventually collapses into the same thing. The city isn’t what it was. Something got lost and it’s not coming back.

And yet most people are still there. Still having the same conversations. Still complaining. Still not leaving.

When I brought up moving, the response was almost always the same: “Yeah, but — my family is here. My friends are here.”

I want to sit with that for a second.

Your parents didn’t have family where they were going. There were no friends waiting on the other side, no familiar face at the airport, no safety net of people who knew their name. They arrived somewhere foreign and built all of that from scratch — the community, the friendships, the family network that you are now using as your reason to stay.

Everything you’re holding onto was built by someone who had nothing to hold onto.

We inherited the fruits of their bravery and quietly used it to construct a life comfortable enough that we no longer need to be brave ourselves. We are standing on the shoulders of giants — and when the view from up there shows us something worth moving toward, we freeze.

We tell ourselves it’s love. It’s loyalty. It’s roots.

But sometimes comfort just sounds like those things when you say it out loud.

And in the quiet underneath all of it — underneath the excuses and the familiarity and the life we’ve carefully arranged to require as little disruption as possible — there’s a question we’re all avoiding.

Don’t miss the meaning of your life by trying to avoid suffering.

I’m not saying everyone needs to leave Toronto (although I’d bet you never regret that decision).

I’m asking something harder than that.

When did you last make a decision that actually cost you something? When did you last look at your life with the same clear eyes your parents used when they looked at theirs — and ask honestly whether where you are is truly the best you can do with what you’ve been given?

Most of us don’t ask that question. Not really. Because asking it seriously means you might have to do something about the answer. And doing something about it is uncomfortable. And we have been very, very well trained to avoid discomfort.

Our parents didn’t have that luxury. That’s exactly why we’re here.

Our parents left everything so that we’d have the freedom to answer that question honestly.

The least we can do is actually answer it.

Not the comfortable answer. Not the answer that lets you go back to your life without changing anything. The real one. The one that costs you something just to admit.

What have you actually sacrificed for the future you say you want?

And if the answer is thin — what are you going to do about it?

I’ve been sitting on my answer for a while. And it came from an unlikely place.

Every so often, someone reaches out and asks to pick my brain over coffee. I usually say yes. This time it was a young entrepreneur passing through Tokyo. We met up in my neighborhood in Azabu-Juban and just started walking — talking about everything from Meta Ad daily spends to what consumer behavior in Japan actually looks like up close. At some point we found ourselves sitting on the steps in the middle of the neighborhood, and he turned to me and asked: what’s the highest leverage skill you’ve ever had?

I gave him some answer in the moment. Honestly, I don’t even remember what I said. But the question stuck with me longer than I expected — and sitting with it more, my real answer is photography.

Photography was the first skill that gave me real freedom. It was the first thing I was good enough at that someone would pay me well for it — which meant I could survive on my own terms, be my own boss, and take risks in life knowing I always had something to fall back on.

Over ten years, 400+ weddings, magazine shoots, editorials — photography wasn’t just a job. It was my foundation. And it still is. Even now, it shows up everywhere. In how I shoot my Instagram stories, in how I document my journey, in the photos you’ll see throughout this Substack that give you a more intimate look at my life and what I’m thinking about.

But let me give you a concrete example of what I mean — because this is where it gets interesting.

When I transitioned into artist management, I noticed something pretty quickly. A lot of my peers were smart, hardworking, well-connected. But they were dependent. They’d have to brief a photographer and hope for the best. They’d struggle to articulate a creative vision to a director. They’d look at a photo and know something felt off but couldn’t tell you why.

I didn’t have that problem.

Because of my background, I could creative direct a shoot from scratch. I could build the assets myself when the budget didn’t allow for a full team. When we hired photographers and videographers to create content for our artists, I could speak their language — not as a client guessing at what they needed, but as someone who’d been on the other side of the lens for a decade.

And the aesthetic standard I brought to everything — the eye for light, composition, story, mood — gave our artists a visual identity that stood out. That taste level isn’t something you can fake, and it isn’t something you can just hire. It has to live in you.

That edge has followed me into everything I’ve built since. Every ecommerce brand I’ve founded since 2020 has benefited from it. The product photography, the creative direction, the brand aesthetic, the way we tell a visual story — that’s not a department I hand off and hope for the best. I’m deeply involved because I can be. Because I built that foundation years before I ever knew I’d need it.

That’s what I mean by a first freedom skill.

It’s the skill that gets your hands dirty. The one where you’re actually making something — a photo, a piece of code, a design, a piece of furniture, a paragraph that moves people. Think photography, coding, design, copywriting, carpentry, painting. Skills where you’re the one producing the thing, not just managing the people who do. That hands-on foundation is what gives you your first shot at independence — your first client, your first service-based business, your first “I don’t need to ask anyone for permission” moment.

And here’s what most people miss: those foundational skills are what make every other skill you pick up later actually land. When you understand how something is made, business strategy clicks differently. Sales comes more naturally. Networking has more substance behind it. You’re not just learning to talk about the work — you understand it from the inside out. The tertiary skills are built on top of something real.

But what makes a first freedom skill truly special isn’t just that it pays the bills early on. It’s that it compounds. It doesn’t just get you started — it grows with you. It bleeds into everything. A designer sees the world differently. A copywriter communicates differently. A photographer notices light, composition, and story in rooms most people walk straight through without a second glance. These skills don’t stay in a box labeled “career.” They shape your relationships, your businesses, the way you think, the way you see.

That’s what separates a first freedom skill from just a job. A job you leave at the door. A first freedom skill — you carry it with you forever.

So if you’re early in your journey and trying to figure out where to put your energy, I’d ask you this: what’s the skill that could give you your first taste of freedom? Not the most impressive skill. Not the trendiest one. The one that could make you dangerous — first financially, and then in every room you walk into after that.

Find that skill. Go deep on it. The rest compounds from there.