The first time I interviewed the famed author and journalist Richard Rodriguez, it was a formal occasion: I came to his apartment in San Francisco with a list of questions on the subjects he’s accustomed to speaking about (immigration and education, chiefly). At a table, I struggled to find some space between back issues of the Financial Times and a pile of manuscripts, while he sat across from me, in front of a wall of books. On the second occasion, two years later, in the summer of 2012, I assumed it would be no different. I came to his place with another list and the same voice recorder, but, to my surprise, he greeted me at the gate and offered to buy me some coffee.

As we walked to a café a couple blocks away, he started asking about what I had been doing since we’d last spoken. I was studying investigative reporting across the bay at the Berkeley Graduate School of Journalism. In a few weeks I’d be on a plane to Tanzania for a reporting trip. Inevitably, when you start telling people about your soon-to-be career in journalism, they have warnings to offer you, and this time was no different: jobs are scarce, the field is changing, he said. Best to carve out some sort of niche expertise, as he had done. And of course all that was stacked upon the usual litany of bad news for America’s twentysomethings, we both agreed, from a Himalayan range of debt to the diminishing value of a college degree. Had our nation become more difficult to live in or just more complicated? I wondered. It was nice to have someone successful interested, for a few minutes, in what I was doing.

Then we sat down, back to business. But as we talked about the big-picture questions about the fate of Western civilization, somehow the talk kept steering back to those more pressing questions about the future of my generation, and about journalism. So it was that I found myself in a discussion that was part interview, part friendly chat. I put my questions aside for another day.

—Alex Park

[“WHY AM I LEARNING ABOUT SHAKESPEARE?” AND OTHER QUESTIONS WORTH ASKING]

RICHARD RODRIGUEZ: I...