Philosophy Not Working for You?
Perhaps You’re Not Making Enough Use of It. My Conversation with Agnes Callard
As with many good things in life, I first encountered
through ’s Conversations with Tyler podcast, where he interviewed her in 2018 around the release of Aspiration: The Agency of Becoming—a philosophical exploration of how people grow and change.Her latest book, Open Socrates: The Case for a Philosophical Life (2025), extends that inquiry, examining how Socratic questioning can sustain a life of ongoing reflection and moral development.
Callard teaches philosophy at the University of Chicago and has received a Guggenheim Fellowship, the Lebowitz Prize for Philosophical Achievement, and multiple teaching awards. She writes for The New York Times, The New Yorker, and The Point, cohosts the Minds Almost Meeting podcast with economist Robin Hanson, and co-leads the Night Owls public debate series.
I spoke with her about aspiration and the humanities. Check it out.
Aspiration is about how we come to value things we don’t yet fully understand or even appreciate. Can you use your own attraction to the topic as a way of explaining the phenomenon?
When I started working on the topic, I didn’t even know I was working on it. I wrote a dissertation on weakness of will, went on the job market, had my dissertation very effectively refuted by some of the best philosophers in the country, and over the course of that experience realized that my topic, all along, had been not weakness of will but aspiration. Sometimes you only know what you are doing towards the end of doing it!
“Sometimes you only know what you are doing towards the end of doing it!”
—Agnes Callard
What about the fact that we often want things while still acting against those wants? My mind jumps to St. Paul’s line: “I do the thing I hate.” It’s easy to see this failure as weakness, but that seems too simple; after all, there’s some part of us that does want the very thing we’re undermining. What’s happening here?
The idea that there’s some part of you that wants it is one way of theorizing weakness of will, so there’s no tension there. The deeper issue is: what does it mean for there to be parts of you? We are quick to use this metaphor and loathe to see that it needs to somehow be cashed out in non-metaphorical terms.
In Aspiration: The Agency of Becoming you describe people learning to love literature, music, and the arts. What role do you think the humanities play in the process of aspiration, sparking interest, maintaining interest, and so on?
Well the humanities contain some of the things we aspire towards—that is, we aspire to value literature, theater, music, philosophy, etc. In that sense they are just one example among many. But perhaps we can say something stronger, because I am struck by how often I am drawn to humanistic examples to explicate aspiration. Perhaps the humanities are a “shining example” of aspiration, in the sense that they make the phenomenon clearest.
How should we gauge the mimetic influence on aspiration? Do we really want what we think we want? How do we ensure we’re not simply aspiring to something because our friends are? Is that even bad?
Aspiration is not something that a person can do on her own, she needs help, and your friends are a source of that help. Of course your friends can also lead you astray, away from aspiration towards corruption. So mimesis has two faces. But there is no such thing as fully authentic aspiration; all aspirants are, in one way or another, being “pretentious.”
“There is no such thing as fully authentic aspiration; all aspirants are, in one way or another, being ‘pretentious.’”
—Agnes Callard
Do you see any harmony between your view of aspiration and St. Augustine’s view of the order of loves?
Augustine’s view is more substantive, the theory of aspiration is more formal, so no.
In what sense is aspiration self-perpetuating?
It’s not. It’s self-ending. It aims towards completion.
Turning to your new book Open Socrates, I’m struck by a possible tension. In Aspiration, you describe growth as moving toward a kind of end state, while the Socratic life seems to resist closure—staying open, unsettled, unfinished. How do you see those two projects as complementary rather than opposed?
I think the Socratic life moves towards knowledge, it’s just that that knowledge will take more than one lifetime. So the project will be finished, even if you and I don’t get to be there to see that.
How does that tension intersect with what you call the Fear of Never Arriving? (That’s the end state of all end states.)
I think there’s no tension.
In what sense is fiction a refuge in life?
In the sense that it allows you to inhabit a set of concerns that are not your own, and leave yours behind.
“[Fiction] allows you to inhabit a set of concerns that are not your own, and leave yours behind.”
—Agnes Callard
Besides Socrates himself, who’s the most Socratic character in literature (or film)?
Maybe Wallace Shawn in My Dinner with Andre?
It seems a lot of modern social and political conflict revolve around questions that don’t have good answers or end in policies that some large number of people will protest. How can Socrates better help us navigate social discord (that whole hemlock thing notwithstanding)? Or is social harmony a crummy aspiration to begin with?
Social harmony is not an end goal for a Socratic, but it is instrumental to creating a world in which we have better conversations, so it’s worth trying to attain. Socrates can help us by reminding us that we’re desperate, and other people are the ones doing us a favor by talking to us.
Does philosophy ever disappoint you? What is philosophy missing, if anything, for helping us navigate life?
I disappoint myself, all the time, for failing to be as philosophical as I know I could be. Philosophy is missing nothing, but we are missing something, namely the courage to make use of it more.
“Philosophy is missing nothing, but we are missing something, namely the courage to make use of it more.”
—Agnes Callard
What are the three best novels or films to understand the philosophical approach to life?
Here’s a novel, two movies and a play:
Robert Musil, The Man Without Qualities
Ingmar Bergman, Scenes from a Marriage or Winter Light
Sophocles, Oedipus Rex (by negation)
Final question: You can invite any three authors or conversationalists for a lengthy meal to discuss any philosophical question. Neither time period nor language is an obstacle. Who do you pick, why, and how does the conversation go?
Socrates, Immanuel Kant, William James
Is there progress in philosophy?
If I knew how the conversation went, I wouldn’t have to have it!
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I, too, wish that I could have a conversation with William James. He is a key figure in American intellectual life and seems to get so little attention now.
Surprisingly concise answers. Thank you Joel.