Are You Asking the Right Questions — Or Just Worrying Out Loud?

I had a patient — I’ll call him Joshua — who came into session every week with a list. Not literally a list, though sometimes literally a list. Questions. Dozens of them. About his career. About his relationship. About whether he was making the right decisions, whether he was good enough, whether the world was about to fall apart.

He talked fast. He was intelligent. He could argue both sides of any dilemma with equal conviction. And after forty-five minutes of listening to him, I said something that surprised us both:

“Joshua, are you asking questions? Or are you just worrying out loud?”

He stopped. Mouth open. Mid-sentence. And for the first time in weeks, the room was quiet.

The Two Kinds of Questions

There’s a difference between a question born from curiosity and a question born from fear. They can sound identical. They can use the same words. But they lead to completely different places.

A question born from curiosity opens something up. It moves you forward. It’s the kind of question that, even if you don’t have the answer, changes the way you see the problem. “What would I do if I weren’t afraid?” That’s a curious question. It doesn’t demand an answer. It creates space.

A question born from fear is a circle. It goes around and around, masquerading as thinking. “What if I make the wrong choice?” “What if they leave me?” “What if it all falls apart?” These questions don’t want answers. They want reassurance. And reassurance, as anyone with anxiety knows, has a half-life of about twelve minutes.

ChatGPT will answer your question in 300 words. I’ll ask you one in five that changes your life. Because the problem isn’t that you don’t have answers. The problem is that you’re asking the wrong questions.

— Dr. John S. Tamerin

Joshua’s questions were almost entirely fear-based. He wasn’t exploring. He was circling. And the more he circled, the more anxious he got, which generated more questions, which generated more circling. He was drowning in a sea of his own words and mistaking the thrashing for swimming.

What AI Gets Wrong About Questions

This is where AI therapy fails most spectacularly. Not in its answers — its answers are often quite good. But in the question itself.

When you type a question into ChatGPT, it answers it. Immediately. Thoroughly. Confidently. It treats every question as legitimate. Every query gets the same earnest, helpful response.

But a good therapist knows that sometimes the most important thing you can do with a question is not answer it. Sometimes the question itself is the problem. Sometimes the question is a defense mechanism — a way of staying in your head to avoid what you’re feeling in your body. Sometimes the question is a trap, and answering it only tightens the snare.

With Joshua, I stopped answering his questions entirely. When he’d launch into his litany of “what ifs,” I’d interrupt him.

“Yes or no,” I’d say. “I’m not interested in anything else.”

He hated it at first. He wanted to elaborate. To qualify. To hedge. That was his defense — complexity as armor. If the question is complicated enough, you never have to arrive at an answer that scares you.

The Vague Problem

There’s a related issue that I see constantly and that drives me up the wall. Vagueness.

Patients come in and say things like: “I just feel off.” “Things aren’t great.” “I’m struggling with stuff.” And I say: “You’re very vague. You need to be a lot more specific. Vague doesn’t help.”

This is not cruelty. It’s the opposite. Vagueness is a hiding place. When you keep things general, you don’t have to confront anything specific. You can feel bad without ever pinpointing what’s actually wrong. And if you never pinpoint what’s wrong, you never have to do anything about it.

A good question is specific. “Why do I pour a drink every night when my wife goes to bed?” is a real question. “Why am I unhappy?” is not a question at all. It’s a mood wearing a question mark.

How do you feel about what I just said to you? That’s a question most therapists never ask. They interpret what you said. They reflect it back. But they don’t ask you to sit with your own reaction in real time. And that’s where the actual learning happens.

— Dr. John S. Tamerin

Pumping the Mind

One of the things I do at the end of nearly every session is ask: “What did you get out of this session?”

Patients are usually caught off guard. They expect to leave, not to be quizzed. But the question matters, because it forces a kind of processing that doesn’t happen automatically. You have to distill the experience. You have to name what shifted. You have to take ownership of the change rather than attributing it to me.

I call it pumping the mind. Like a pump that needs priming — sometimes you have to push the handle a few times before the water flows. The question creates the pressure. The answer creates the clarity.

And here’s the thing: sometimes the best answer is another question. “Should a good question result in more questions?” Yes. Almost always. Because a good question opens doors. It leads you somewhere you didn’t expect. It makes the landscape bigger, not smaller.

Anxious questions shrink the world. Curious questions expand it.

Teaching You to Fish

AI gives you fish. Very good fish, actually. Well-sourced, nutritionally complete, attractively presented. But you’re no better at fishing than you were before you asked.

Joshua, by the way, got better. Not because I answered his questions. Because I stopped letting him hide behind them. He learned to notice when he was worrying out loud versus genuinely exploring. He learned to catch himself mid-spiral and ask: “Is this curiosity or fear?”

That’s a skill no app can teach you. It requires a human being who is willing to interrupt you, challenge you, and sit with you in the uncomfortable silence after the question lands — the silence where the real answer lives.

If you’ve spent years asking questions and never feeling like you’ve arrived at anything real, the problem might not be the answers. It might be the questions themselves. And if you’d like someone to help you figure out which is which, that’s what I do.