Getting It Right
I had three chances to get Tokyo right. Four if you count the hours between my return from Ishigaki and my flight home, wandering Haneda. But let’s say three.
Each one felt different—not just because of timing, but because of why I was there.
The first was with friends—everything shiny and new.
The second was the beginning of my photography workshop—the reason I came to Japan at all.
And the third was the in-between—after the workshop, just me, entering the final phase of my trip alone.
And somewhere within all those versions of Tokyo, my thoughts kept circling back to the same thing: purpose. Why was I doing this? Why was I here—now, in Japan—when I had such a big move ahead of me?
Purpose. A strange word for vacation. Should there be a purpose to travel?
But for me these days, there kind of is. Maybe it’s justification—for spending money I once thought I’d save for later. For choosing this version of my life before I fully know what comes next.
My first real experience of Tokyo came after Kanazawa, when I rejoined my friends. By then, they had already spent days exploring, so their final day was about returning to the things they had been eyeing all week.
Which meant… shopping.
Custom jeans that weren’t quite as custom as promised. Lindt chocolate—why does Japan get ten times the flavors we do in the U.S.? And our group favorite, Onitsuka Tiger, which I failed to buy—though my friends made up for it.
That evening, we stood in line for an overhyped pizza restaurant before walking along the Meguro River, glowing pink beneath hundreds of cherry blossoms just beginning to bloom. It was mesmerizing.
The next morning brought the granddaddy of overwhelm: Don Quijote. A sort of multi-story Temu. I was only there for 24 hours, but it was enough to leave an impression—bright, crowded, full of energy.
It felt familiar in a way I didn’t expect. A little like New York.
Sakura (cherry blossoms) lining the banks of the Meguro River – Tokyo, Japan
My second Tokyo began with the workshop.
I left my friends in Osaka and returned for the welcome dinner, joining a group of mostly strangers in the Shiba District, near Tokyo Tower—glowing orange and yellow at night.
Somewhere between my last photography workshop in Patagonia and this one in Tokyo, something in me had shifted. For the first time, I wasn’t overly concerned with what anyone thought—my camera, my experience, my work. I just wanted to be open. To learn. To see.
And I did see so much of Tokyo—the spiritual, the delicious, cherry blossoms lining rivers and street corners, and the chaotic beauty of Shibuya Crossing in the rain. Some of the best sushi of my entire trip was served piece by piece in front of us at Tsukiji Outer Market.
We moved through temples, markets, train systems (with robots), neighborhoods, and crowds. We ate constantly: sushi, ramen, yakitori, shabu shabu.
And within the group itself, I started noticing a different energy than I had experienced in Patagonia and Rapa Nui. Less communal, maybe. More individual. At the time, I mostly wrote it off as newness—different personalities, different dynamics, people still getting to know one another.
So by the time I returned to Tokyo for the third time, I didn’t want more. I wanted less.
Less noise.
Less pressure.
Less conversation.
I needed to decompress—to sleep, to wander quietly, to do something normal like getting my nails done, shopping for knives in Asakusa, or buying more Lindt chocolate in Shibuya.
I hadn’t looked at a single photo I had taken. Not one. Every night, I backed up the images and moved on to the next day. In my previous workshop, we shared images regularly—learning from each other, seeing through different perspectives. I missed that. I missed the sense of community.
And I realized something had shifted. Either in me—or in what I was willing to tolerate.
So… did I get Tokyo right?
I didn’t investigate every saved Instagram post or eat at every place I had planned. But looking back now, I’m satisfied. I saw so much of the city. A mix I probably wouldn’t have experienced on my own.
But I keep coming back to the same question: Did I actually experience Tokyo fully… or was I too focused on trying to capture it?