“You catch me in my frailty and my weakness as an increasingly older dude,” actor and comedian John Hodgman says. The former Daily Show with Jon Stewart contributor, who now hosts the Judge John Hodgman podcast and contributes a weekly column under the same name for the New York Times Magazine, where he arbitrates real-life problems, has dropped the clean-shaven, brainy persona he used to deliver fake news, to write about his life in Vacationland: True Stories from Painful Beaches (Viking, Oct.). “I had written a thousand pages of fake facts that contained every joke and story I needed to tell. And now I was out of material,” Hodgman says, referring to his Complete World Knowledge trilogy (Dutton): The Areas of My Expertise (2005), More Information Than You Require (2008), and That Is All Maine (2011).

Two years ago, Hodgman found new inspiration in the basement performance space below Union Hall, a popular bar in Brooklyn, N.Y. There he held court once a week while he developed a one-man show called Vacationland. “None of it was written down, except in very broad strokes as a series of notes,” Hodgman says. “Over time, I would talk it out on stage until it filled the shape that I wanted it to.”

Hodgman spent nearly a year adapting the show into a book of the same name. Instead of fake facts, Vacationland taps into his genuine memories of his 20s and 30s in western Massachusetts and his middle-aged move to a family vacation home in Maine. “Maine is called ‘Vacationland,’ which is something of a cruel joke because the beaches are so painful and the water wants to kill you,” Hodgman says. “But if you are someone who naturally believes they don’t deserve happiness in the first place, then Maine is a great place to vacation. It definitely promotes contemplation of mortality in a very amusing way.”

Mortality and family legacy are major themes of the book, which also captures the bruising effect middle age has had on the author’s comedy mojo. Hodgman recalls how one of his jokes recently fell flat at his local coffee shop. “Nice dad joke,” the barista had scoffed.

At that moment, Hodgman realized he had crossed the invisible borderland of cultural relevancy that separates the young and the old. “I had never heard that term before,” he says, laughing. “But I heard it loud and clear in that moment. That’s how I died. In that moment. I died. Now you are talking to a ghost.”

Today, 9:45–10:45 a.m. John Hodgman will appear on a panel, “Do I Amuse You?,” Downtown Stage.

Today, 4–5 p.m. Hodgman will sign galleys at the Viking booth (1921).