Following a four-year stint in Toronto, Canada, for university, photographer Kaitaro Kobayashi retraced his steps and returned to the city where he grew up — Tokyo.

For Kaitaro (or Kai, for short), the move home felt natural. Tokyo is where his family lives, the place where opportunity was waiting — and that opportunity came in the form of a job at an advertising agency.

In Toronto, he fulfilled his dream of living abroad, having immersed himself in another city and culture. His desire to live somewhere else still exists, but upon his move home to the largest city in Japan, he discovered a sense of responsibility — something he took away from his time in Canada.

“I feel that the photographer community is huge in Tokyo, but it’s not as tight as in other cities,” Kai says. “I used to join more photographer gatherings in Toronto, and in Tokyo it seems like people are less connected to one another physically.”

Kai is determined to help change this and, in the process, reconnect with the city he spent four years away from.

In Tokyo, Kai pushes himself outside as often as possible, continuing to do what drew him to photography in the first place: urban exploration. His itch to capture skyscrapers and cityscapes was inspired by New York-based photographer Humza Deas whose epic rooftop photographs caught Kai’s eye immediately. The day he first came across Deas’ photos, Kai took to the rooftop of his own building, the tallest residential building in North America.

“The view was unforgettable — I was hooked.”

Nowadays, much of his admiration falls upon “traditional film photographers” such as Allan Schaller and Vivian Maier, but he still holds true to his first love: wandering the streets of his favorite Tokyo neighborhoods like Shinjuku and Ueno.  

It’s here, walking through the streets, camera in hand, that Kai feels the most at home. He’s able to let the city — with its fascinating originality — come to him, rather than forcing the shot himself.

Living in a city with over 13 million people, Kai captures scenes that many have come to associate with major cities. There are shots of crawling intersections and giant skyscrapers. But what comes as a surprise is the calming nature of his photographs — even the ones filled with people. There’s a subtleness to them. Mixed with the bustle is a single umbrella in an empty alley, or a lone onlooker by a foggy pond. With chaos flooding in from all directions, his pictures isolate Tokyo’s simple beauty.

Kai doesn’t label himself with a specific style, but his photographs still seem intent on standing out.

“I focus on the individual lives in a busy city,” he says. “In Tokyo, the Japanese traditional culture is heavily integrated with this huge modern city and it is truly original. The crowded intersections, tiny back alleys, and huge neon signs — they are very special to me and I feel like these things really make up the complete image of Tokyo.”

The Japanese capital boasts an unparalleled blend of old and new, but, like most developing cities, it’s leaning more and more toward the latter.

As the city continues to change, Kai holds the city close, aware that the days of the shining nuances he so often trains his lens on may be numbered.

“Tokyo is changing rapidly, especially in recent years because the Olympics are happening,” he says. “Many of the locations I like are being replaced with modern skyscrapers, and the true colors of the Tokyo are disappearing.”

Despite the change though, Kai is determined to keep pushing forward, digging deeper into the city that has helped shape him and his art, holding out for the like-minded.

“Because of photography, everywhere I go I could meet someone and connect with them. That’s really amazing and I am thankful for that.”

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Brad Donaldson is a writer and editor proudly based out of Halifax, Nova Scotia. Although his roots are in Canada, his desire to see more of the world frequently takes him away from home. His work, both as an editor and writer, has appeared in local newspapers and publications, most recently showcased through the co-founding of his former university's inaugural creative writing journal.