Asking the Right Questions

There’s a funny thing about questions.

Most of the ones we ask are just loops.

They don’t actually lead anywhere. They circle around our assumptions, like a dog chasing its own tail and congratulating itself for the effort. We feel productive because we’re thinking, but nothing really changes.

We ask things like:

“How do I become successful?” instead of “What do I even mean by success?”

“Why am I unhappy?” instead of “Who is this ‘I’ that claims to be unhappy?”

“How do I fix myself?” instead of “What makes me believe I’m broken?”

On the surface, these sound like reasonable questions. Responsible questions. Even mature ones. But underneath them is an assumption that quietly goes unchallenged. And when the assumption is flawed, every answer built on it is flawed too.

That’s why real growth doesn’t begin with answers. It begins by dismantling the questions we’ve been taught to ask.

The Hidden Assumptions Behind Our Questions

Every question carries a belief.

When you ask, “How do I become successful?” you’re already assuming:

• Success is a clear, universal thing

• You don’t have it

• Someone else knows how to get it

When you ask, “Why am I unhappy?” you’re assuming:

• Unhappiness is a problem to be solved

• It belongs to a solid, permanent “me”

• There must be a cause you can identify and eliminate

  
  

When you ask, “How do I fix myself?” you’re assuming something even heavier:

• That you are fundamentally broken

Most of us never question these assumptions. We just rush straight to the answers. We read books. Watch videos. Follow advice. Try routines, frameworks, and morning habits—wondering why none of it quite lands.

It’s not because you’re doing it wrong.

It’s because you might be asking the wrong question.

How the World Trains Us to Ask Poor Questions

The modern world is very good at giving answers.

Google it. Search it. Watch a tutorial. Follow someone who “figured it out.”

From a young age, we’re trained to believe that wisdom lives somewhere else — inside experts, influencers, systems, or strategies. Curiosity gets outsourced. Thinking becomes consumption.

There’s a difference between information and insight.

Information adds more content to your mind. Insight removes what doesn’t belong there in the first place.

And insight almost never comes from collecting better answers. It comes from questioning the structure of the question itself.

Why Some Questions Can’t Take You Anywhere

Certain questions can’t be answered — not because they’re deep, but because they’re confusing.

Imagine asking:

• “How do I win a game I never agreed to play?”

• “How do I become someone other than myself?”

• “How do I get rid of a feeling that’s part of being human?”

  
  

No amount of effort will solve these, because the problem isn’t a lack of answers. The problem is the framing.

Some questions keep you trapped inside the very mindset you’re trying to escape.

They reinforce the idea that:

• You’re lacking

• You’re behind

• You’re unfinished

  
  

If you start from that assumption, every answer becomes another way to chase something just out of reach.

Great Doubt, Great Awakening

There’s a Zen phrase that cuts straight through this:

“Great doubt, great awakening. Little doubt, little awakening. No doubt, no awakening.”

This isn’t about skepticism or negativity. It’s about having the courage to question what you’ve always taken for granted.

You can only wake up from a dream if you realize you’re dreaming.

And most of us are dreaming inside inherited beliefs — about success, happiness, identity, purpose, and what a “good life” is supposed to look like.

So the invitation isn’t to question the world.

It’s to question the way you see it.

The Shift That Changes Everything

At some point, the questions begin to change.

Instead of:

• “How do I become someone better?”

  
  

  You start asking:

  
  

• “Who am I trying to become, and why?”

Instead of:

• “What’s wrong with me?”

  
  

  You ask:

  
  

• “Where did I learn to see myself this way?”

Instead of:

• “How do I get rid of this feeling?”

  
  

  You ask:

  
  

• “What happens if I stop fighting it?”

  
  

These aren’t questions that demand immediate answers. They slow you down. They interrupt momentum. They create space.

And in that space, something subtle happens.

You stop trying to escape yourself. You stop chasing imaginary finish lines. You start listening instead of fixing.

When the Question Falls Away

Eventually, some questions dissolve entirely.

Not because you answered them, but because you saw through them.

You realize the question was built on a misunderstanding. And once that misunderstanding is gone, the question has nowhere to stand.

That’s often how real clarity arrives. Quietly. Without fireworks. Without a breakthrough story to tell.

Just a simple recognition: Oh. That was never the right question.

And sometimes, the most powerful thing you can do isn’t finding the right answer.

It’s realizing the question never made sense in the first place.