Agnes Callard wasn’t happy with her answer to one of my interview questions. I asked what she thought of a remark by evolutionary biologist Richard Dawkins that existential “why” questions should never be asked because they’re unanswerable. Only “how” questions were proper in science. That evening, the University of Chicago philosopher put the question to her family at their recurring “Chautauqua.”

Callard’s three kids, ages 11, 16 and 21, plus her husband and ex-husband—who all live together—took part in the discussion. They traded ideas on science and metaphysics, the meaning of life and ethics, what is empirical and what isn’t. When one of her kids started talking about Wittgenstein, I couldn’t help feeling my own family conversations were sorely lacking. (Callard sent me a recording of the 25-minute discussion. You can listen to a 3-minute clip below.)

The intensity of the Callard’s dinner discussion epitomizes the philosopher herself. In our conversation about her new book Open Socrates: The Case for a Philosophical Life, she was as provocative as she was insightful.

Callard discovered Socrates in high school, and by the time she was a senior in college, she was obsessed. “I didn’t just want to interpret Socrates,” she writes. “I wanted to be Socrates.” She started hanging out on the front steps of the Art Institute of Chicago and would walk up to strangers and ask if they wanted to have a philosophical discussion. At first, they were intrigued, but then they just wanted to get away from her. “I’ve kind of spent my whole life since then trying to figure out how to do that but not make people run away from me,” she said with a laugh.

Our discussion about “rational love” and “philosophical dissatisfaction” in a marriage are representative of Callard’s prescription, via Socrates, for a meaningful life. Which, Callard believes, can only come about through conversation—and especially argument—with other people.

You recount a time in Leo Tolstoy’s life when he was going through a personal crisis. By his early 50s he was world famous and in a good marriage but was so unhappy that he was thinking about suicide. What happened?

He comes to realize he was looking away from some questions his whole life. “What can life mean in the face of eventual death?” “Why am I doing any of the things I’m doing?” “What does it matter whether or not I raise my children well?” They’re questions about the meaning of life. He can’t stop thinking about them. But at the same time, he finds them unanswerable and concludes the only real solution is suicide. But he also says he’s too much of a coward to commit suicide.

You say this is a cop-out and dub it “the Tolstoy problem.”

The reason why I think his move is a cop-out is because the questions are answerable. We have this fear that if we took a close look at the underpinnings of our lives, we would suddenly realize that it was all a sham. So, we don’t look closely. Tolstoy’s story is a vivid illustration of how that strategy just doesn’t work. Many people have moments in life where the questions break through to the surface.

I once had a contentious interview with Richard Dawkins who said there are no big “why” questions. There are only “how” questions such as “How did the universe begin or how did birds evolve wings to fly?” I pushed back, suggesting it’s worth asking existential questions like “Why are we here?” Even if they can’t be answered. How would you respond to Dawkins?

My reasoning goes the other way. We need to answer these questions. There’s a dialogue where Socrates is challenged by a Richard Dawkins kind-of-guy named Meno, who basically says, “I don’t think we can make progress on these questions.” Socrates gives an elaborate answer to explain why he thinks it does make sense to inquire into these questions. He’s saying I’m going to be a better person if I have the courage to try to make progress on this project—on which the value of human life hangs—without an advance guarantee that I’m going to succeed. Socrates puts it in a simple way: The unexamined life is not worth living.

“This is exhausting” is a response I get a lot.

You call these “untimely questions.” Most of us don’t want to think about the deeper meaning of our lives. We’ve got our careers, our children, our daily pursuits. As you say, “You put one foot in front of another, over and over again, right up to the moment when your journey is cut off by d