Here’s my interview with Ethical Systems. The beginning:
You say that many people who wish to philosophize with you are “estranged professionals.” What are the sorts of problems they typically face, and how do you tend to address them?
I would put the matter this way. Let’s say that it’s 2017, or sometime after that, since it was around this time that Silicon Valley “discovered” that I philosophize with technologists, founders, and executives. Since that time, a fair number of people with whom I’ve regularly conversed have come to the dawning and, for them, dramatic realization that they’ve done everything “right” and yet they’re, for reasons they know not, unhappy. They’ve worked hard, they’re now successful, they’ve accrued wealth and status, they have a charming family, and yet something in them is mysteriously off. Something remains unsatisfied or, as Hamlet once said, “out of joint.” How could it be that they’ve lived what they were told was the happy life at the same time that they know that something deep and seemingly unfathomable remains unasked and unconsidered? This is beyond puzzling.