After college, Alson says he found it difficult to forge a career as a writer.

“When I graduated, everyone was going into careers, and I was trying to become a writer,” he recalls. “For me, writing was and continues to be a brutal struggle. I have a love-hate relationship with it.”

Alson’s travails with writing compelled him toward unconventional jobs. He drove an ambulance at one point and, at another, helped to repossess cars in somewhat unsafe neighborhoods in New York.

“I quit after someone fired a shot at us,” he says.

When his friend offered him the opportunity to work as a bookie, Alson accepted.

“It’s not so extraordinary for a young writer to want to soak up new experiences,” he says.

In his memoir, Alson indicated that the allure of a rebellious lifestyle played a large role in attracting him to bookkeeping.

“Professional gamblers—even those who gambled legally—had an outlaw mentality,” Alson writes. “They were people who had chosen to live their lives outside the socially accepted boundaries, to thumb their noses at the world. I admired them for that.”

Alson had previously acquired some familiarity with gambling, having written a profile piece about one of the world’s most succesful poker players, and having enjoyed some success at the poker table.

Still, throughout his book, he stresses the differences between himself and his thuggish “colleagues.”

Describing his relationship with another bookie, Alson writes, “we were like two aliens, two beings from different galaxies who had somehow ended up in the same small room.”

Post Confessional

To date, Confessions has been Alson’s most prominent work, although he has also published pieces in Playboy, Esquire, and other periodicals.