The Cities Between the Plan

I was supposed to go to Montreal.

More specifically, I was supposed to board a twelve-hour train from New York — a route people kept describing as one of the most beautiful train rides in North America — to attend an Art of Hosting workshop that only happens a few times a year in this region.

Originally, I had planned to fly.

But because I booked too late, the flights to Montreal had become absurdly expensive.

So instead, I chose the train.

Slower.

Longer.

Slightly irrational.

But somehow, that already felt aligned with the spirit of the trip.

The timing was difficult.

I already had another trip to Portugal scheduled for the following week.

The entire North America trip would last only six to ten days at most.

Several people around me looked at the itinerary and said some version of the same thing:

“Is it really worth flying that far for such a short time?”

Especially because I booked the trip at a moment when flight prices were already climbing again.

But I’ve come to believe something else.

If I waited for the “perfect” amount of time,

the “perfect” schedule,

the “perfect” financial justification,

I might never go anywhere at all.

I’ve learned that life becomes smaller when it is built entirely around limiting thoughts.

It’s too expensive.

It’s too short.

It’s not practical enough.

It’s not efficient enough.

At some point, those thoughts quietly stop being temporary concerns and become a worldview.

And I think the opposite is also true.

The belief that I can leave when something meaningful calls me — even briefly, even imperfectly — has made my life feel far more abundant, expansive, and alive.

Sometimes, the belief that you can go — even briefly, inconveniently, imperfectly — changes your life more than waiting for the “right” conditions ever will.

If I only moved when everything became rational, optimized, and fully secured,

I think I would miss most of what has made my life feel alive.

So I went.

The Original Plan

The plan itself was simple.

Seoul → New York → Montreal → New York → Seoul.

Efficient. Tight. Structured.

I would spend a few days in New York first, then take the train to Montreal for the seminar.

The trip began in New York — a city that feels increasingly familiar to me.

And almost immediately, it reminded me why I had said yes to the trip in the first place.

I attended a Shabbat dinner with a group of Jewish people and found myself deeply moved by the way gratitude was woven naturally into shared food, conversation, and everyday rituals.

And on a beautiful sunny day, I spent hours walking across the city with Jan Dickey, who will soon join us as a guest host at Material Memory Studio in Seoul.

There were long conversations.

Unexpected meetings.

People who shifted something in me without trying to.

One evening, I watched a performance by a singer-songwriter whose work had been shaped by surviving cancer.

Something about the honesty of it stayed with me.

Not productive in the traditional sense.

But deeply alive.

The kind of conversations that quietly rearrange something internally.

At the time, I still believed Montreal was the destination.

New York was simply a stop along the way.

I didn’t realize yet that the trip had already begun changing shape.

The Missed Train

The morning I was supposed to leave for Montreal, everything seemed normal.

Then suddenly, all the roads were blocked.

I hadn’t realized that a major cycling event was happening across New York City that day.

Traffic completely froze on the way to the train station.

My Uber stopped moving.

Eventually, I found myself dragging two large suitcases through blocked streets, trying to reach the station on foot.

And slowly, it became obvious:

I was going to miss the train.

The train itself had already felt symbolic somehow —

a twelve-hour ride toward a gathering I had rearranged my life to attend.

Sitting in a nearby coffee shop for about an hour, it felt like a failure.

I was going to miss the workshop I had been excited to attend.

And now I was standing there with two large suitcases, no plan, nowhere to stay, and a strange amount of frustration.

For a while, all I could think was:

What now?

The Detour Became the Work

Then I did something impulsive.

Instead of trying to fix the situation and still find a way to Montreal, I bought a ticket for the next available train.

Boston.

I had no real plan there.

No clear reason to go.

I had never been there before.

I knew almost nothing about the city.

So I just left.

And strangely, something opened the moment I stopped trying to recover the original itinerary.

Boston felt slower.

Brick buildings.

River light.

Bookstores.

Museums.

Old-school restaurants.

I walked for hours without trying to optimize anything.

And somewhere during those walks, the trip stopped being about Montreal.

It became about perception.

And about allowing the trip to become something else.

And somewhere between those two cities, I realized that my artistic practice, my studio, and even my experiment with a Seoul-based nomadic life were all moving in a new direction.

Not because everything went according to plan.

But because the plan broke open enough for something else to enter.

By the second day in Boston, I no longer wanted to return to New York.

I felt full of energy — almost impatient to return to Seoul and begin building again.

New ideas.

New projects.

New spatial possibilities for Material Memory Studio.

So instead of returning to New York as planned, I changed my flight and flew directly from Boston back to Seoul.

The entire trip lasted less than a week.

And somehow, it still shifted something significant.

What looked irrational from the outside became deeply generative from the inside.

That trip eventually became part of what I now call Material Trips — research journeys where cities become less about tourism and more about attention, perception, texture, rhythm, and creative movement.

Not every meaningful trip gives you what you planned for.

Sometimes it gives you a different direction entirely.

A Small Reflection

I think many people quietly postpone movement until they feel fully ready.

More time.

More certainty.

More money.

A better schedule.

A clearer outcome.

But sometimes the real shift happens the moment you decide:

I am still allowed to go.

Even briefly.

Even imperfectly.

Even if the plan breaks apart halfway through.

Because once you begin living from that belief,

life starts becoming larger than the systems designed to contain it.

If this resonates with where you are right now, I offer 1:1 coaching for people navigating creative transitions, reinvention, and more expansive ways of living and working.

— Jay

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More field notes from these Material Trips will follow soon.