Ask why until you hit bedrock
Good morning! Let’s continue talking about critical thinking! This is part of my Critical Thinking series of essays – you can find the link to my other essays in the comments! Let’s go!
Essay 19: The Questions That Actually Matter
I’m going to tell you the most useful critical thinking skill I’ve learned, and it’s going to sound too simple to work.
Ask “why?” five times.
That’s it. That’s the Socratic method stripped down to its core. Keep asking why until you get to the actual foundation of a claim.
Someone says “we need to ban TikTok.” Why? “Because it’s a national security threat.” Why is it a national security threat? “Because China could access user data.” Why is that different from other companies accessing user data? “Because China is our adversary.” Why does data access from an adversarial government create national security risks that other data access doesn’t?
You’re not being obnoxious. You’re getting to the actual argument.
Most political positions collapse after three or four “whys” because they’re not based on thought-out reasoning. They’re based on slogans that sound good but don’t have much underneath them.
This works on yourself too. Take something you believe strongly. Ask yourself why you believe it. Then ask why that reason is true. Then ask why that matters.
If you can’t get to bedrock – to some foundational principle or evidence that holds up under questioning – you might be believing something for bad reasons.
The Socratic method isn’t about winning arguments. It’s about figuring out what you actually think and why.
Socrates annoyed the hell out of people by doing this constantly. He’d go around Athens asking people questions about justice, virtue, courage – concepts they used all the time but couldn’t define clearly when pressed.
They’d give him an answer. He’d ask a question that showed their answer didn’t work. They’d revise. He’d ask another question. They’d revise again. Eventually they’d realize they didn’t actually know what they were talking about.
This made him extremely popular. (It didn’t. They executed him.)
But the method works because it forces you to examine the foundations of your beliefs instead of just asserting them.
I use this when I catch myself having a strong reaction to something. Instead of just staying in the reaction, I ask: why does this bother me? What principle does it violate? Is that principle consistent with my other beliefs? What would change my mind about this?
Sometimes the answer is “this violates my core values and I’m right to be bothered.” Sometimes the answer is “I’m reacting emotionally to something that doesn’t actually matter.” Either way, questioning it helps.
The questions aren’t about doubt for doubt’s sake. They’re about understanding.
“What do I actually believe and why?” That’s the first question. But here are the others that matter:
What would falsify this? If I’m right, what evidence would prove me wrong? If I can’t think of anything that would change my mind, I’m not holding a belief – I’m holding a prejudice.
What’s the strongest version of the opposing view? Can I state it in a way the other side would agree with? If I can’t, I probably don’t understand the disagreement well enough.
What am I assuming? Every argument rests on assumptions. Can I identify mine? Are they warranted?
What am I ignoring? Selection bias is real. What evidence or perspectives am I not seeing because I’m not looking for them?
Who benefits from me believing this? This isn’t about conspiracy thinking. It’s about recognizing that beliefs have consequences and some people benefit from others holding certain beliefs.
These questions are uncomfortable. They’re supposed to be. Comfort is the enemy of clear thinking.
If you ask yourself these questions and all your beliefs stay exactly the same, you’re probably doing it wrong. Real questioning should change some things. Maybe not your core values, but at least how you apply them or what policies you support.
I’ve changed my mind on things. Not because someone convinced me – people are terrible at convincing each other directly. Because I questioned my own reasoning and found it lacking.
That’s the point. Not to win arguments. Not to prove you’re smart. To actually think clearly about what you believe and why.
The questions aren’t magic. They don’t give you answers. They just force you to do the work of thinking instead of relying on slogans and emotional reactions.
Try it on something you believe strongly. Ask why until you hit bedrock. If the bedrock holds up, great – now you understand your own position better. If it doesn’t, you just learned something important.
Most people never question their beliefs this way because it’s uncomfortable and time-consuming and sometimes you discover you were wrong.
But being confidently wrong is worse than being uncertainly right.
Ask why. Keep asking. Don’t stop at the first answer that sounds good.
The foundation of critical thinking isn’t having the right answers. It’s asking the right questions.