It’s Labor Day week, 2023, and Henry David Thoreau is the heart of our conversation. It’s not with him, but it’s driven by his example: American thinking at its best on the matter of how to make a living. John Kaag. Have no doubt that the gabby man-about-Concord in the 1850s was a worker: expert surveyor, gardener, as many trades as fingers, he said, not to mention the writer of Walden and Civil Disobedience, of course, and a life journal that came to two million words. We read Henry Thoreau anew for his insight into our work, not his: the often fruitless, driven, underpaid labor of the 2020s, and, oddly enough, our midnight anxiety that ChatGPT could take it all away. This is a conversation in the Harvard Bookstore with our friend the philosopher John Kaag, who co-wrote the pungent and personal handbook titled Henry at Work.