He Wanted to Go Back Home to the Hamptons. Could He Afford It?

Ryan Sherman’s first job was picking up cigarette butts outside the restaurant where his mom worked. He was 12. A year later he started changing kegs and polishing silverware. “I was a hustler,” he said. “I always worked hard.”

So did the people around him. While his mother managed restaurants, his father built single-family homes. Most of his friends had two working parents, and most of his friends worked — summers, after school, whatever they could squeeze in. “Everybody who lives in this town is hardworking,” he said. “You have to be.”

But for Mr. Sherman and many like him who grew up in East Hampton, N.Y., hard work is rarely enough to make it in their hometown.

“Everybody’s getting eaten alive by that same monster that is the housing beast,” he said. “This is the struggle for everyone trying to make it out here. I don’t care if you’re in construction, landscaping, retail — whatever it is, you’re not making enough money to live here.”

Mr. Sherman moved back in 2019. After living on the West Coast and traveling throughout Europe, he wanted to reconnect with the place that had shaped him: “I missed home and wanted to experience it again.”