Boats, Jet skis, Red cups, and Laughter.

when im with my squad i cannot do no wrong

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.