My Clever Use of Questions to Hide From Others

Why That’s No Longer Working For Me

There’s a question I’ve been asking myself of late:

What have I been hiding behind?

And the answer in recent weeks has become startlingly clear.

I’ve been hiding behind questions.

Not just the polite, get-to-know-you questions. No, I’ve mastered the art of deep, soul-piercing inquiry. The kind of questions that make people stop, tilt their head, and say, “Wow, no one’s ever asked me that before.”

It’s how I’ve built trust (or so I thought), formed friendships, and created the illusion of openness. But here’s the sobering truth: it hasn’t always been about connection. Sometimes, it’s been about deflection.

A few women friends have confided something to me over the years—sometimes playfully, sometimes with a tinge of exhaustion. “You know,” they’ve said, “so many men I meet only talk about themselves. They never ask me anything. It’s like we’re invisible.”

I took their words to heart because I never wanted to be that guy. So I built my identity around curiosity. I became the guy who asks. Who listens. Who digs deep. And for the most part, I believed I was doing it out of genuine care.

But in the quiet of my inner work, a different realization has emerged:

Asking questions has also been a form of protection.

In other words, if I’m the one asking, I’m not the one being seen. If I’m guiding the conversation, I’m not being asked about the parts of myself that feel uncertain, messy, or still unresolved.

This hit me hard recently while journaling after a meditation session. I had pulled a line from the Tao Te Ching, verse 33:

“Knowing others is intelligence; knowing yourself is true wisdom. Mastering others is strength; mastering yourself is true power.”

I realized I had spent so long knowing others, but in moments of intimacy, I still stumbled over the act of revealing myself—not in curated anecdotes, but in the raw, unscripted truths. I’ve been comfortable being seen as thoughtful, wise, compassionate. But what about being scared? Lost? Needy? Not so much.

Zhuangzi once asked:

“Am I a man who dreamt he was a butterfly, or a butterfly dreaming he is a man?”

For me, it’s felt like: Am I the curious interviewer, or a man terrified of being truly known?

There’s a subtle seduction in intellectualism. I’ve worn it like a cloak. It’s safe to ask existential questions about society, Taoism, or politics. But ask me what I’m grieving? Where I feel inadequate? Where I ache for love? That’s where my voice falters. That’s where I turn the spotlight back on you.

Even in writing this, I feel the reflex—the pull to pivot away, to quote another sage, to turn my essay into an impersonal lesson. But that’s not the point today.

Here’s the point:

I feel more comfortable sharing my vulnerability in an article like this—on Substack, in a space I control, in a format that feels spacious. It allows me to bleed a little without the awkwardness of direct eye contact. It lets me curate intimacy. And while there’s power in that, there’s also limitation.

So I’m going to experiment with something different.

I’m going to share more openly with others.

Not just parables or lessons from the I Ching. And not just on Substack. But my stories in the vulnerable presence of others—messy, hilarious, heartbreaking moments that let people experience me, not just my thoughts.

Moving forward, I want to share not as the “healer” or the “philosopher,” but as the man behind the curtain sharing his vulnerabilities while trying to figure things out like everyone else.

The I Ching reminds us in Hexagram 29, “The Abysmal,” that true power comes not from avoiding danger, but from learning how to flow through it with grace.

That’s my new task: not to navigate around vulnerability with clever questions, but to flow into it, to sit with it, and to offer it up as a bridge rather than a barrier.

This isn’t a rejection of my curiosity. That’s part of who I am. But I now see that curiosity becomes connection only when paired with courage. The courage to let others in—not just into my mind, but into my soul.

So the next time we talk, don’t be surprised if I tell you a story instead of asking you for one. Don’t be surprised if I let the silence linger a little longer. I’m learning that intimacy isn’t about collecting your answers. It’s about offering my truths.

And for once, I won’t ask a question to close this out.

I’ll just say: I’m here. Unfolding.

And maybe, just maybe, letting myself be seen in a raw, naked way will allow others to fully trust the authentic, high integrity person I truly am .

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