Writing a book about failing to write a book?

Jason Diamond reads from his book at Politics and Prose while Amber Sparks asks him questions


By: Laura Saini

For as long as Jason Diamond could remember, he was obsessed with John Hughes movies. From Ferris Bueller’s Day Off to The Breakfast Club to Home Alone, Hughes’ films are famous for capturing the teenage experience. Diamond, growing up in the same Chicago suburbs the movies were filmed in, always imagined himself as a Hughes’ character. Facing a rocky childhood, the films provided Diamond solace in his teenage years.

Diamond loved the films so much that he decided he would write Hughes’ biography. Without any qualifications or connections, he moved to New York to become a writer. While working as a barista and a guard to support himself, he spent years trying to write the biography.

However, Hughes had already passed away, and no close friends or colleagues would talk to Diamond. Years later, he knew he could not write this biography.

Still, Diamond knew he was a good writer. Instead of writing the biography, he used his experiences to write a memoir, “Searching for John Hughes.” Diamond writes his book like a Hughes’ movie- describing his journey of chasing his dream and failing. Diamond moved to New York, worked odd jobs and called every person who knew Hughes for interviews. Still, he was no closer to writing Hughes’ unofficial biography.

“I didn’t pay attention to all the signs that said ‘you should not be writing this book,’” Diamond said at Politics and Prose on Friday.

When he did realize the signs, he said it was time to let go of his dream to write this biography. He didn’t want to chase something he couldn’t achieve. But he also didn’t want to give up on something he loved: writing and Hughes. Instead, he turned his failure into a story about a man’s coming-of-age.

The memoir details Diamond’s life from his childhood in Chicago to a writer in New York. The first few chapters of the book discuss what it’s like to be a teenager.

“When I was a kid, I was like just let me be this ball of sadness,” Diamond said. I would go listen to the Smiths or something. My parents always wondered what was wrong with me.”

Diamond faced numerous problems growing up. He had ADHD, his parents were divorced and constantly fighting, and his father was abusive. For a while he was homeless, sleeping on friends’ couches.

“It’s a book that I really admire because it seems so effortless, but it must have been really difficult to write,” said Amber Sparks in regards to Diamond’s childhood. Sparks was interviewing Diamond; she is known for May We Shed these Human Bodies, a collection of stories and essays.

Throughout all his problems, Diamond latched on to Hughes’ movies. They was his coping mechanism.

“I like that Hughes’ movies always had a happy ending and wrapped up nicely,” he said.”It made me feel grounded.”

Diamond felt a kinship to two of Hughes’ films as a child: Ferris Bueller’s Day Off and Home Alone. He lived close to the house where Home Alone was filmed, a movie that looks at what happens when a family goes for a vacation and accidentally leaves a child at home.

Ferris Bueller’s Day Off is also based in Chicago, and Diamond sees it as Hughes’ homesick movie. Hughes lived in Northbrook, Illonois, a suburb in Chicago.

“The movie is like a love letter from Hughes to Chicago,” Diamond said.  It features many famous landmarks in Chicago, including the Sears Tower and the Art Institute of Chicago.

The other half of the book discusses Diamond’s coming-of-age as he struggles to writes the biography for years. Diamond is not shy about admitting his failures, but he also reflects on how he learned from it.

“I personally love it when people talk about failure,” he said. “I don’t think people talk about it enough.”

Diamond told a story of one particularly embarrassing moment he had while trying to write Hughes’ biography. As he was sitting in the bar with a friend , Ally Sheedy, a lead role in the Breakfast Club, walked in and sat near them. Having failed to interview any of Hughes’ stars or coworkers, Diamond tried to gain Shetty’s attention.

Asking his friend to call his cell phone, Diamond started talking very loudly about his interview with Paul Gleason. Since Gleason was a fellow actor with Sheedy in “The Breakfast Club,” Diamond hoped this would get her attention.

Instead, another man at the bar asked Diamond about his interview with Gleason. Apparently, the man was Gleason’s neighbor. He told Diamond that Gleason died three months ago.

“I felt like a failure,” Diamond said. “What was I doing trying to write a biography about John Hughes and not knowing that one of his star actors just died?”

Diamond thinks people tend to gloss over their failures, but that it’s the failures that really shape people and push them to the point of reaching success. He emphasized that failure should not stop people from pursuing their dreams.

“You should try to make every day ‘one perfect day,’” he said, drawing from Ferris Bueller’s words in the movie. “It’s important to live in the present and stop worrying about the future so much.”



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