Philosophy doesn’t begin in a seminar room. It begins when a question arrives that won’t let you go–when the life you’ve been living suddenly insists on being contemplated.

The Art of Inquiry: Meditations on Living Wisdom, I trace the movement from existential confusion to living wisdom — from the moment philosophy arrives uninvited to the unimaginable clarity that ensues. Drawing on fifteen years of inquiry with hundreds of people across four continents, I show what it actually means to philosophize: not as a diversion but as an invocation.

Part essay collection, part philosophical manual, part memoir, The Art of Inquiry is grounded in the Socratic and Daoist traditions, yet alive to the particular pressures of our time. It closes with a piece of performance art: a live dialogue with Claude that reveals, with precision and unexpected poignancy, what genuine inquiry demands — and what even the most capable AI cannot yet provide.

Through his art of inquiry, Andrew has shown me how to question, observe, discern, and contemplate freely—without ego, without armor. Turning inward, I learn to embrace life, love, meaning: all of it. It’s a way of living without the crud in your gut. — Ilan Weiss, Portfolio Manager, BAM

Andrew introduced me to a kind of inquiry I didn’t have a name for — and didn’t know I needed. What he showed me: the offness that’s been tugging is not brokenness. It’s the beckoning signal. His questions were sharp, warm, faithful to the full descent. I came in confused. What I left with doesn’t leave. —Daniel Young, AI Humanist, Google

My conversations with Andrew Taggart always take me to a place I didn’t expect, to lands I’d never before seen. He’s filled with wisdom, humor, and a deep, palpable affection for people and life. —Jed Cairo, Founder, Juxtapose

Andrew’s inquiries helped me see the truth behind my unhappiness and suffering. I’d been living inside walls I didn’t know were there. Without them, I’m home. This has been the most valuable practice of my life. —Entrepreneur

Preface

Around the time I deposited my Ph.D. dissertation in early January 2009, the weather in Madison, Wisconsin, was positively Siberian, with temperatures sometimes falling to -10 or -19 degrees. One late afternoon while the wan sun was falling, I walked up Bascom Hill and handed my bundle of papers to some quiet bureaucrat. Seven years spent thinking about the nature of the good life in the modern world, and here was the anticlimax.

That winter I often sat in the kitchen like Whistler’s mother. I looked up at a bird feeder that, wrapped in layer upon layer of ice, was dangling from a distressed hanger attached precariously to the gutter. It swayed, and I swayed.

What slowly came through was the recognition that I wasn’t cut out to be an academic despite the fact that I’d poured the last 11 years of my life into becoming a professor. It was all over now–and I had no idea what I was going to do.

The irony wasn’t lost on me. Even though I’d written my dissertation on the nature of the good life, I realized that I didn’t know how to live. My perplexity–perhaps it was a plea–was met by grace: having stumbled upon the works of the French philosopher Pierre Hadot, those in which he argued that philosophy was “a way of life,” an ongoing pursuit of wisdom, I began to take seriously a life devoted to inquiry. A philosopher committed to what Hadot termed “spiritual exercises” would seek to be wise.

I was moved, and my heart assented. Eight months later, I left for New York City, trained as a practical philosopher, and started philosophizing with others. Here was the soft volta.

* * *

We start off in blindness since almost none of us know what we’re doing here. A philosophical grownup admits what the rest of us deny. Knowing that we don’t know what we’re doing here entails throwing ourselves into the pursuit of self-knowledge. I don’t mean that there aren’t mysteries in life–though that is certainly true. I’m referring to the recognition that, in modernity, life itself has no preset meaning, no determined shape, no built-in direction, and certainly no compass, and so it comes to feel as though life itself were up for grabs. It’s as if we fell into a strange world whose whispered aim was to suss out how to do something more than merely survive. The entire enterprise–a life lived well–hangs on making contact with this moreness.

The more we contemplate, the more we accept that we never come with answers in hand. Where once we inquired of objects, now we turn the question back on the subject. After all, how can I avoid inquiring into myself once I see life as a great, open mystery? What is it all about? What am I doing here? And how do I make sense of these sometimes nearly unbearable existential questions? Life, thus, is cracked open.

* * *

I wrote the original Art of Inquiry in the summer of 2012partly as a hedge: if I failed to be a genuine teacher, at least I could hand the students something. A few months prior, my late friend Pete Sims (1981-2021) had invited me to teach at Kaos Pilots, a social entrepreneurship-meets-art school in Denmark. Given my academic background, I was accustomed to a scholarly approach to teaching: reading books, scrutinizing arguments, sticking with the topic. Yet this “folk high school” (højskole) style of education was grounded in experience: the classroom was a performance space, and for eight hours each day we were invited to learn through what was unfolding between us.

That was 14 years ago. During that time, I’ve inquired with teenagers, artists, Sufis, Buddhists, Catholics, the spiritual but not religious, social entrepreneurs, scientists, CEOs, portfolio managers, fathers, mothers, private investors, and more. And they’ve all shared the same character trait: open-mindedness, an eagerness to take up questions they’ve never seen before, questions whose answers they now yearn to discover.

What makes for the beginning and the end of any philosophical inquiry? The basic coordinates spelled out in The Art of Inquiry: Meditations on Living Wisdom are existential confusion and existential clarity, the movement from the first to the second. Once I was perplexed, and then perplexed again, and now I am much clearer.

Of course, we shouldn’t make the mistake of regarding the art of inquiry as a linear process so much as an iterative, often highly textured one. Unlike “conversion stories” in which a character is transformed once and for all, inquiry into the heart of one’s existence offers a truthful account of the process of self-transformation. As Socrates knew, self-examination is ongoing and increasingly nuanced and, with practice, self-knowledge becomes deeper, sharper, more refined.

In The Examined Life: Philosophical Meditations, Robert Nozick once likened leading an examined life to painting a self-portrait. Such is not the work of a day, Nozick thought, and the task can’t be undertaken without attending closely to those features—the angle of the jawline, the shape of the forehead—that are uniquely our own. Each dab of paint indicates a decision, possibly a new direction; each etching more than hints at the settled habits of age. Over time, the figure on the canvas comes to represent the artist’s earnest desire, despite his many doubts and reservations, to perceive himself clearly. If after years of self-examination we manage to avoid filling up our lives with half-finished canvases, with self-caricatures and cardboard morality plays, then we may end up with a lifework—an unflinchingly honest self-portrait—that satisfies almost as much as the most penetrating Rembrandt painting.

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