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Hole In My Life by Jack Gantos is the kind of book that feels really good to hold. The size is perfect for one-handed reading and the slightly textured cover feels like it was built to be passed on and on. The cover reminds me of the editions of Jack Kerouac books I spent all my money on in junior high. It took me a while to open this one up, and I savored the anticipation as much as I hoped to savor the story.

Jack Gantos won the Newbery Medal this year for Dead End in Norvelt. He’s written a number of children’s series including Joey Pigza, Rotten Ralph and the Jack Henry Adventures, as well as a few for older readers. Authors like Roald Dahl, Neil Gaiman and Maurice Sendak have made it impossible to apply any kind of stereotype to the person behind a children’s story. Still, prison is not the first place I would’ve guessed Mr. Gantos began to really write.

A Hole In My Life by Jack Gantos

Gantos skips over his childhood and begins the story of the hole in his life in high school when his father moved the whole family to St. Croix to follow a construction boom. Jack said a silent ‘Later, suckas’ to his classmates and moved to the island. But when the work fell through Jack returned to Florida alone to finish off his senior year at the same school, which just happened to be a former prison itself.

With little money, Jack found lodging at a dumpy, but harmless hotel with other misfits. Here the urge to write becomes an itch, but rather than get down to it he fell into smoking dope, hanging out and lucking out with no ladies:

I wanted girls to find me iteresting. But maybe it was my whiny Holden Caulfield imitation of a boy in need of carnal therapy that got me nowhere.

He graduates HS and wants to be a writer, but can’t think of what to write about. He does all the right and wrong things at once. Reading voraciously, he takes clues from Stephen Crane and Jack Kerouac (I knew it) and starts hunting for something to write about. This chase takes him from Hemingway’s house on Key West, to a Black Panthers’ headquarters after they’d called for white extermination on St. Croix.

It’s this same endearing mix of heedless curiosity and youthful disregard for risks that leads him to say ‘Yes’ when an easy-sounding, adventurous gig comes along. It involves a bit of hash (2000 lbs) and pays $10k. …

I read the rest of the book cringing and holding my breath and wanting so badly for things to work out different, but no. Gantos soon lands in federal prison fearing rape or brutal assault everyday.

It was this lottery of violence that haunted me.

Jack navigates prison like a grown character from one of his books, narrowly escaping violence and finding something to go after. Prisoners aren’t allowed to keep journals so he bargains for a pencil and begins to write down his fellow inmates’ stories in the margins and between the lines of Dostoevsky’s The Brothers Karamozov. Then one day he looked out a window and had to get out. He just:

knew life outside off prison was more interesting

This was when he first began writing his childhood memories and seeing value in his past. These memories would eventually become a mess of oddly smart and funny children’s books. And the prisoner would become the author he always wanted to be who can write about the dark years with honesty and humor.

You don’t have to like memoirs to enjoy this book. It has adventure, crazy mistakes and light because it’s told by someone who worked really hard to get himself where he wanted to be – even if it he took the long way round. I’m gonna go on a limb and guess Mr. Gantos would most definitely recommend aspiring authors to take another route.