Why You Should Question Everything

Embracing Curiosity, Conversation, and the Wisdom of Not Knowing

Some people collect souvenirs. Others collect accomplishments, credentials, or followers.

I collect conversations.

Not because I set out to interview people, but because I’ve never stopped being fascinated by the mystery of another human being. Put me in a neighborhood coffeehouse, a bustling bookstore, an airport terminal, or on a long train ride, and before long I will find myself talking with someone I met only moments before. More often than not, the conversation begins with a question.

“What are you reading?”

“Where did you spend your formative years growing up?”

“What has surprised you most about your life?”

These and other questions have become something of a spiritual practice for me. They are less about gathering information than about opening a doorway into another person’s world. Each answer reminds me that every passerby is carrying a story I could never invent on my own.

The older I become, the more convinced I am that curiosity may be one of the highest expressions of the Tao.

Every Stranger Is a Library

Years ago, I stopped thinking of strangers as strangers. Instead, I began seeing them as libraries whose shelves had simply not yet been explored.

That shift changed everything.

Whether I am reading before sunrise in a coffee shop in Fort Collins, wandering through a bookstore in Chicago, attending a conference in Las Vegas, or sitting beside someone on an airplane, I have learned that remarkable conversations rarely require extraordinary circumstances. They only require someone willing to ask a sincere question and someone else willing to answer it.

Some of these conversations last five minutes. Others stretch for hours.

Many of the people I have met eventually disappear back into the current of their own lives. I may never know what became of them, yet pieces of their stories remain with me.

A retired schoolteacher reminds me to never underestimate patience. An entrepreneur recovering from bankruptcy quietly teaches resilience. A young immigrant explains what courage actually looks like when your entire life fits inside two suitcases. A widower tells me how grief eventually learns to breathe again.

I never could have found those lessons in a search engine.They arrived because I asked.

Empty Enough to Listen

Lao Tzu repeatedly points us toward the usefulness of emptiness.

A cup serves us because it is hollow. A room becomes livable because of the space enclosed by its walls. A valley nourishes life because it rests below the mountain instead of competing with it.

Questions create that same kind of spaciousness.

Every sincere question empties us of the assumption that we already know. It creates room for someone else’s experience to enter our own.

That strikes me as profoundly Taoist.

Our culture celebrates certainty. Social media rewards opinions delivered with absolute confidence. Everyone seems expected to have a take before they have taken the time to understand.

Lao Tzu gently points in the opposite direction. He reminds us that the person who believes he already possesses all the answers has quietly closed the door to wisdom.

Humility is not thinking less of yourself. It is making enough room for reality to surprise you.

The Wisdom of the Butterfly

Zhuangzi takes this even further. His writing dances with uncertainty rather than trying to eliminate it.

His famous story of dreaming he was a butterfly has never struck me as a puzzle to solve. It feels more like permission to loosen my grip on certainty.

The world I inhabit is richer than my explanations of it. Each person is more complex than the labels I place upon them. Every conversation contains possibilities I cannot predict.

I often think Zhuangzi would smile at my habit of talking with strangers. Not because I am searching for answers, but because I am practicing the joyful art of not knowing.

Each conversation begins with the quiet admission that another person has something to teach me. There is enormous freedom in that.

The moment I believe I have someone figured out is usually the moment I stop seeing them clearly.

Curiosity keeps people alive. Certainty freezes them into caricatures.

Living in Wonder

Children ask questions almost effortlessly because the world still astonishes them.

Adults often stop asking because they assume they have already seen enough.

Growing wiser is not becoming more certain. It is recovering the wonder we slowly traded away.

Looking back, I realize that the most important teachers in my life have not always been famous authors or philosophers. Many have been baristas, rideshare drivers, booksellers, travelers, convention attendees, and fellow readers who happened to sit beside me at exactly the right moment. They expanded my world not because they intended to, but because they were willing to share a piece of themselves with someone genuinely interested in listening.

I have come to believe that asking thoughtful questions is one of the purest forms of generosity. It tells another person, “Your life matters. Your experience contains something worth discovering.”

In that sense, curiosity becomes an act of love.

The Tao is often described as the Way, but perhaps it is also a conversation. A continual invitation to meet the world without pretense, without rigid expectations, and without the need to always be right.

The older I become, the less interested I am in collecting answers. I would rather collect moments of genuine surprise.

I would rather leave every coffeehouse, every bookstore, every conference, and every chance encounter knowing just a little more about what it feels like to be someone else.

Because every meaningful question opens a door. And every person we meet may be another quiet sage walking beside us on the Way, waiting for someone curious enough to ask.

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