Jake Dobkin is a third generation New Yorker who lives in the same Park Slope brownstone he grew up in, just around the corner from his elementary school and his favorite childhood pizza joint. He went to high school and college in Manhattan, and as he likes to tell it, in his 42 years, he has never been away from the city for longer than 10 weeks. When he dies, he wants to have his ashes scattered on the Gowanus Canal, which is four blocks away from his home.
Though he has spent most of his life in a relatively small geographic area in Brooklyn, Dobkin is deeply familiar with all five boroughs of New York City. In his work as a documentary photographer, and as the co-founder and publisher of Gothamist, he has visited some of the most obscure corners of the city, sharing the stories of anonymous graffiti artists, endangered historic buildings, and unique neighborhoods. All of these life experiences and contradictions inform his first book, Ask a Native New Yorker, which was published in March.
During a recent walk around his childhood stomping grounds, including a visit to some of the historic buildings on the Gowanus that he and I photographed together a decade earlier, Dobkin reflected on how living in a constantly changing city led to his book.
“Scratch the surface of today’s New York, and you’ll see the heart and soul of the city remains in all its diversity, excitement, and challenges,” Dobkin writes. “New York actually gets better as you grow old.”
The idea for Ask a Native New Yorker goes back to 2013, as a series of sarcastic columns written by Dobkin for Gothamist. The earliest posts included humorous responses to questions like “Is It Normal For Roaches To Crawl Through My Hair At Night?” (answer: “Ask yourself what your hair is doing gentrifying his neighborhood”) and “When Am I A Real New Yorker?” (answer: “Call your mom in Philly and tell her you’re coming home”). Over the years, though, Dobkin’s columns evolved to become more thoughtful, reflecting a personal change in the author.
“I didn’t feel like being sarcastic carries you that far. It works in small doses,” Dobkin says. “If you want to say anything substantial about anything—and the city is a substantial topic—you must eventually be somewhat thoughtful, otherwise, what are you communicating?”
For the book version of Ask A Native New Yorker, Dobkin wrote entirely new responses to 48 questions, offering up deeply considered guidance that will be helpful to newcomers to the city. The questions he addresses range from where to live and work, how to find dates and raise children, and practical topics like whether it’s okay to urinate in the streets and whether to wash your hands after taking the subway. The chapters are relatively devoid of sarcasm, offering instead a positive and compassionate consideration of the many challenges that come with living in the city, somehow finding the silver lining in overcrowded subways, sidewalk grifters, real estate brokers, gentrifiers, and bedbugs.
Overall, Ask A Native New Yorker feels like a sometimes exasperated love letter to New York, which the author describes as “the greatest and most complex city this planet has ever produced.” His lifelong dedication to the city is apparent on every page. “There is no place more challenging and exhilarating to live … spend five years here, and you will you will discover things about yourself and about humankind that many people outside New York don’t learn in a lifetime,” writes Dobkin. “There is the feeling of awe knowing that the streets you are walking down are the very places where so much of American culture was born: hip-hop, graffiti, photography, virtually all the best American novels, poems, and plays.”
A recurrent theme throughout the book is that life in New York involves intense suffering, loss, and sacrifice, but that these challenges are coupled with numerous rewards, including a deeper understanding of self. Dobkin traces this philosophy back to his recent studies of Buddhist and Stoic texts, and interweaves his personal history into the book’s practical advice.
“Most of the people I know would not like to live in the New York that I grew up around, which was dangerous, which was chaotic, which was dirty,” says Dobkin, reflecting on his childhood in the 1980s and ’90s, when crime rates throughout the city were much higher. “It is funny in retrospect, but we had knives pulled on us, we had guns pulled on us. And some of the wisdom I think I have comes from suffering through those days.”
In the past four decades, Dobkin has lived through several different eras of New York history, which has led to a firm belief that change is the only constant in the city. “The true native New York perspective is that New York is constantly changing. In one lifetime, the city is completely recreated, to the point where the city that you grew up in, and were born in, is almost completely erased,” Dobkin told me during a conversation at Pino’s La Forchetta, the pizzeria of his childhood. “And you could see that as a terrible thing to worry about, but then you are going to be a very unhappy person, because it’s a fact of life that will never, ever stop.”
After the tumultuous decades of his childhood, and in the aftermath of 9/11, Dobkin began documenting the city as it entered into an era of rapid transformation, during the decade-long reign of Mayor Michael Bloomberg. In 2002, Dobkin began publishing his photographic work at a photoblog called Bluejake, amassing a collection of thousands of images from changing neighborhoods around the city. In 2003, he began publishing Gothamist, a website dedicated to the minutiae of city life. And in 2005, he started Streetsy, a collection of photographs of the ephemeral world of graffiti and street art.
It was during this era of the city’s history that I first met Dobkin, and from 2007 to 2010 we traveled across all five boroughs of the city to photograph endangered historic landmarks like the Domino Sugar Refinery in Williamsburg and the Samuel R. Smith Infirmary in Staten Island. Most of the buildings that we photographed in those years have since been demolished, to make way for a new landscape of residential towers built along the coastline of the city.
After the birth of his first child in 2009, Dobkin began to step away from his photography projects, and entered into a period of self-reflection, which eventually led to Ask a Native New Yorker. “When I was younger, I was just immature and self involved.… Having kids calms you down a little bit,” says Dobkin. “It gives you a different view of the city, and much more sympathy for all people, because parenting is so hard.”
The book version of Ask a Native New Yorker was written during another period of upheaval, one that also greatly reshaped the landscape of New York media. While working on its chapters, Dobkin sold Gothamist to Joe Ricketts, the billionaire owner of hyperlocal news outlet DNAinfo. This ill-fated decision was soon followed by both Gothamist and DNAinfo being shut down after a majority of both companies’ employees voted to unionize. In the aftermath, Dobkin was widely criticized in the press for his role in the sale and shutdown (which one former reporter characterized as “textbook union-busting stuff” to The New Yorker). Gothamist has since been resuscitated in a partnership with WNYC. (DNAInfo was not part of that partnership.)
As Dobkin makes clear in the final pages of Ask A Native New Yorker, the challenges of this self-described “fiasco” helped to shape the reflective tone of his book. “Sooner or later, if you live here long enough, you’re going to have one of these years—when your job or personal life or health lurches into a seemingly uncontrollable, fiery tailspin, and I hope you will be as comforted by New York City as I have been,“ writes Dobkin in the concluding paragraph of the book. “It’s a hard city, sometimes, but it’s worth it. Don’t ever leave.”
Dobkin grew up on this quiet, tree-lined street in Park Slope. After living in other parts of the city for 19 years, he returned here five years ago. He now lives in his childhood home with his wife, children, and parents. “When I was growing up in Park Slope, it was a much more normal-class place,” says Dobkin, who remembers there being only a handful of businesses in the neighborhood. Over the past 40 years, the neighborhood has been completely transformed, with property values skyrocketing and hundreds of businesses now lining its streets.
Dobkin’s elementary school, P.S. 321, is just around the corner from his home, in a neighborhood now filled with children. “I’ve asked my kids, and so far they want to stay in New York. It’s nice—they see this as a special place,” says Dobkin. “I love the idea of raising more native New Yorkers, and that somebody could be a fourth generation.”
Across the street from P.S. 321 is Pino’s La Forchetta pizzeria, a local landmark that opened in 1962, and which has served generations of Park Slope kids. In Dobkin’s childhood, he remembers it being one of the only restaurants in the neighborhood.
The Community Bookstore, which opened in 1971, is another local landmark. “This was the only bookstore we had,” says Dobkin, who had never visited the Strand Bookstore in Manhattan until 2018. “When I first saw my book here, I felt like, ‘Ah, I’ve arrived.’”
A few blocks from the Community Bookstore is the Carroll Street Bridge on the Gowanus Canal, one of Dobkin’s favorite haunts as a teenager. “This place was like three blocks from where I grew up, and I didn’t know about it until I was in high school. It had a magical kind of reality to me,” says Dobkin. Today, a new residential tower has completely changed the landscape next to the bridge, but Dobkin recalls that when he was growing up, “it was all abandoned factories, and a few coffee roasters, and sewage and dead bodies.”
Raw sewage and oil slicks still pollute the waters of the Gowanus, although a Superfund cleanup is now underway here, after centuries of neglect. “I look around and I still see a lot that hasn’t transformed,” says Dobkin.
But this part of the Gowanus may soon be transformed, with the city planning a rezoning project that will build residential towers all along the banks of the toxic canal. “From Dutch New Amsterdam to today, each generation has transformed the city, leaving it vastly different by their grandchildren’s time,” writes Dobkin. “The city is like a phoenix, always burning down and rising from its ashes.”
South of the Carroll Street Bridge, a few vestiges of the old Gowanus still remain, including a last pocket of graffiti. “Talk about lost urban fabrics,” says Dobkin. “It’s only for the documentarians that we even have any idea of what graffiti used to be.”
Another historic remnant along the canal here is the Central Power Station of the Brooklyn Rapid Transit Company, aka The Batcave. Built in 1896, the building has remained in a ruinous condition for most of Dobkin’s life. It is now being renovated by owner Joshua Rechnitz, and redesigned by Herzog & de Meuron, to become the Powerhouse Arts center.
In the early 2000’s, the Batcave was a notorious squat and graffiti mecca, and during his years as a photoblogger, Dobkin visited its interior to document its graffiti and architecture. “To get inside, we had to jump three fences, and climb to the second story. It was a hassle,” says Dobkin, seen here in 2007, inside the Batcave. “When we did our work there, the roof was gone, and it was going to collapse.”
“There are people who are angry that this is no longer an aging ruin that they found beautiful. It offends them that there is any change at all,” says Dobkin. “If this can be turned into anything good for the neighborhood, or for the city at large that can be productive, whether it’s artists spaces, housing, or really anything other than a giant decaying wreck, that’s a plus for the city that we should all get behind.”
The author, photographing demolished warehouses along the Gowanus in 2009. Despite having spent so much time documenting the area, Dobkin is surprisingly unsympathetic towards the idea of preserving most of the industrial landscape here. “Of all the factories and industrial buildings, I can only think of five that are architecturally significant and historically significant enough to save,” says Dobkin. “I don’t feel romantic about 1960s warehouses that are just being used to store stuff.”
However, Dobkin is highly critical of the plans to build more residential towers on the banks of the Gowanus, especially as sea levels continue to rise. “I don’t love this idea of building all rich rental apartments in a flood zone. That does not strike me as being particularly good policy,” says Dobkin. “If it was me, I would make a park for at least a block on both sides, because we need the absorption.”
“I actually think that it will be pretty interesting to live here in 100 years,” says Dobkin, reflecting on how New York City will be affected by climate change and sea level rise. “Does New York have a future three generations from now? Because I’ve been here three generations, and I think that it does. I am actually more optimistic than most people.”
Nathan Kensinger is a photographer, filmmaker, and curator who has been documenting New York City’s abandoned edges, endangered neighborhoods, and post-industrial waterfront for more than a decade. His Camera Obscura photo essays have appeared on Curbed since 2012. His photographs have been exhibited by the Museum of the City of New York, the Queens Museum, the Brooklyn Museum, the NYC Parks Department, and inside the Atlantic Ave-Barclays Center subway station.