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In A Literary Journey to Jewish Identity, published in 2018, Shepard explores his encounters with several Jewish-American writers who inspired him and influenced his sense of what it means to be Jewish. He writes of the great flowering of Jewish-American fiction in the post-war era – the golden age of Saul Bellow, Bernard Malamud, Philip Roth, Isaac Bashevis Singer, Arthur Miller, Cynthia Ozick, and others.

What, he wondered, did it mean to be a Jewish-American writer? Was there such a thing as a Jewish-American novel? And even more basic: Why did he care so much about these books? 
Along the way, he describes the anti-Semitism directed at Bellow; details the literary feud between Roth and Malamud, muses about the "Jewish" John Updike; contemplates anew the horror of the Holocaust through the writing of Ozick; and sheds light on Miller's unwillingness to admit that Willy Loman, the famous protagonist of Death of a Salesman, was actually a Jewish character. 
Through these writers, he was able to think more deeply about what it means to be Jewish -- coming to terms with his own place in the Jewish firmament. He writes as an enthusiastic reader, a fan watching his team play.

Deadlines and Disruption is Shepard's book about journalism at a time of radical disruption, written as a memoir by someone who lived through it. The book is fundamentally a tale of transition. It is the transition of a working class kid from the Bronx who rises to the top of the magazine world. It is the story of how he built BusinessWeek into one of the best and most lucrative magazines, only to see it later succumb to the imperatives of the Internet age. It is the saga of how, at age 65, he launched a new graduate school of journalism for a new era, struggling himself to understand the topsy-turvy forces at work -- and to accept them. And, ultimately, it is the transformation of journalism itself as it tries to find new business models for the digital age.