Stephen Shepard nearly retired. It was 2004, he was 65, and he had been the editor of BusinessWeek for 20 years — making him one of the longest-serving weekly magazine editors in history. Shepard had steered BusinessWeek through the trading scandals of the 1980s and the dot-com boom of the ’90s, transforming it, in the process, into a prestigious title. He had guided BusinessWeek’s first forward-looking steps toward digital distribution. So when 2004 came along, he was in a position to end his career at the best place one possibly can: its height.

Instead of retiring, though, Shepard started afresh at the place he had come from: the City University of New York, his alma mater. He accepted a job as the founding dean of an upstart new journalism school being established under CUNY’s auspices — one aimed at serving students who couldn’t afford the pricey programs at nearby Columbia and NYU, and one that would, it was hoped, “increase the number of minority journalists in a profession sorely lacking them.” The school, its dean proudly points out, offered the first publicly supported masters program in journalism in the Northeast. Its goal was nothing less than creating “a new school for a new era.”

Shepard explores that new era and the many that preceded it in “Deadlines and Disruption.” The book is in part a memoir, a tale of a life lived at the height of print journalism when print journalism itself was at its height. But it is also an analysis, an examination of the new challenges facing an old industry as it ambles and occasionally sprints its way into the digital age. “My personal passage,” he notes, “is, in many ways, a microcosm of the larger struggle within the journalism profession to come to terms with the digital reckoning.”

“Deadlines and Disruption” treads familiar ground: the debates about who, ultimately, counts as a journalist. The questions of how to encourage the kind of vital investigative reporting so essential to a democracy. The all-important matter of financing. Shepard treats those journalistic questions journalistically, bringing a reporter’s sensibility — curiosity, an eye for detail, an impulse to analyze and synthesize — to his assessment of his profession. His conclusion is learned and passionate and just a little bit romantic. “I believe,” he writes, “in the smithy of my soul, that even if the medium ultimately changes — and it will — the human need, the intellectual need, for thoughtful journalism will never, ever go away.”

‘Deadlines and Disruption: My Turbulent Path from Print to Digital’ by Stephen Shepard (McGraw-Hill)

But the journalism itself will have to evolve. News outlets that produce digital news — which is to say, all news outlets — will need to reconsider the comparative advantage they enjoy in a world where the amateur expert has access to the same tools as the professional. “We need,” Shepard says, “to emphasize editorial value — what we can bring to the party.” And that will mean reemphasizing not just original reporting but also skilled writing, smart analysis and “the highest ethical values.” It will mean being open to conversations with audiences — journalism as a process as well as a product — and to new ways of presenting civically relevant information, whether through databases or calendars or multimedia. There’s Web video to explore, Shepard points out. There are apps. There are e-readers. There are platforms that are, at the moment, only gleams in the eye of an upstart entrepreneur.

And there are, crucially, new funding methods to invent. In an age of digital upheaval — the now-cliched idea that the sheer scale of the Internet has reduced “print dollars to digital dimes” — it is the funding question that supersedes everything else. Every year, Shepard gathers CUNY’s incoming class of journalism students for a screening of “All the President’s Men.” And follow the money, in the context of CUNY, takes on a new relevance: Shepard is teaching the next generation to follow the money not just to find stories, but also to find the business models that will ensure they can keep telling them.

So Shepard’s fledgling program at CUNY has focused on finance, emphasizing entrepreneurship and the creation of new funding models. The school recently opened the Tow-Knight Center for Entrepreneurial Journalism, which, among other things, awards seed funding for news-related projects developed by students. “The results won’t be known for many years to come,” Shepard notes, “but the still-young CUNY J-School has put a stake in the ground. With a little luck, we will train students who go on to make a difference — coming up with ideas that will help reinvigorate the profession we all care deeply about.”

It’s this commitment that makes Shepard’s story so compelling. And it is made even more so by the fact that he is the consummate embodiment of the halcyon days of the media. His résuméincludes stints at Product Engineering, Newsweek, the Saturday Review and Columbia’s Graduate School of Journalism. He has served as president of the American Society of Magazine Editors. Photos featured in the book show Shepard not only as a boy posed with his parents in the Bronx but also as a man posed with presidents Ronald Reagan, George H.W. Bush and Bill Clinton. His circle of friends and associates has included not only fellow journalists but also politicians and business-world leaders such as Michael Bloomberg, Alan Greenspan, Andy Grove and Bill Gates. He was taught to use a computer mouse by Steve Jobs.

All of which makes the path Shepard took in the encore of his career — founding a graduate school, immersing himself in the digital journalism that has proved so disruptive to his profession and craft, and generally doubling down on an unknown future — even more remarkable. Starting a school is no easy task. There were program requirements to be determined, students to be recruited, money to be raised, a building to be restored. (When the first class arrived at CUNY’s journalism school in August 2006, Shepard recalls, “wires hung from walls, some of the computers weren’t hooked up, and almost as many construction workers were on site as faculty members.”)

The new school was and is a start-up, in almost every sense of the word. It has been driven, as most start-ups are, by the impulse to create something that could achieve anything from making money to changing the world. Ideally, both. Its products are journalistic careers — careers that will be everything, and nothing, like Shepard’s own. “On most days,” he writes, “I’m optimistic.”

Megan Garber is a staff writer at the Atlantic.


My Turbulent Path From Print to Digital

By Stephen B. Shepard

McGraw Hill. 338 pp. $28