The Trouble with Thinking
“The problem with the world is not that people know too little; it’s that they know so many things that just ain’t so.” — Mark Twain
Most folks go through life never really questioning their own thoughts. They carry their assumptions like an old, moth-eaten coat—full of holes, but too comfortable to toss away. We fancy ourselves rational creatures, yet we often defend our own nonsense with the stubbornness of a mule in a rainstorm. Small children know how to do it, and we forget… They Ask WHY?
Ah, the fine art of self-deception. We lie to ourselves better than any conman could. That’s where AI—our own mechanical lie detector—comes in handy. Not because it’s wise, but because it doesn’t much care for our flimsy excuses.
So, before you get too comfortable in your opinions, try these 10 hard-hitting ChatGPT prompts that will poke, prod, and rattle your thinking like a firecracker under a rocking chair. If used properly, they’ll lead you to insights you never expected—and if used improperly, well, at least you’ll be entertained.
1. “Ask me ‘why?’ repeatedly for each answer I give.”
Why it works:
People love their first excuse the way a cat loves a warm windowsill. But ask “why?” enough times, and you’ll see just how flimsy those excuses really are.
Example in action:
You: I don’t have time to start a business.
ChatGPT: Why?
You: Because I’m too busy with work.
ChatGPT: Why are you too busy?
You: Because I take on too much extra work.
ChatGPT: Why do you take on too much extra work?
You: Because I’m afraid to say no.
Insight: Turns out, the problem isn’t time—it’s fear of setting boundaries.
2. “Push me to justify every assumption.”
Why it works:
Most people’s logic is held together with chewing gum and wishful thinking. This prompt forces you to test whether your beliefs can stand on their own.
3. “Point out logical fallacies in my thinking.”
Why it works:
We love bad logic the way a dog loves chasing its own tail. This prompt helps you spot the circular reasoning, hasty generalizations, and good ol’ fashioned nonsense in your own mind.
4. “Keep questioning me until I reach complete honesty about what’s holding me back.”
Why it works:
We’re real clever at fooling ourselves. We say “I’m too tired,” when we mean “I’m too scared.” This prompt keeps drilling until you find the real truth.
5. “Help me create an actionable plan based on this newfound self-awareness.”
Why it works:
Knowing why you’re stuck is fine and dandy, but unless you do something about it, you might as well be a cat staring at a closed door, waiting for it to open itself.
6. “What would my biggest critic say about this decision?”
Why it works:
Most people are their own worst critics—but imagining what your biggest skeptic would say helps you prepare for real-world pushback.
7. “If a stranger looked at my life, what would they assume my priorities are?”
Why it works:
People say their priorities are one thing, but their actions tell a different story. This prompt forces you to match what you claim to care about with how you actually live.
8. “What is the worst-case scenario if I take this risk—and how likely is it really?”
Why it works:
Our minds love to make mountains out of molehills. This prompt helps you weigh risks logically instead of emotionally.
9. “If I had to explain my reasoning to a 10-year-old, would it still make sense?”
Why it works:
If you can’t explain your logic in simple terms, there’s a good chance it’s full of hot air.
10. “What would my future self, 10 years from now, tell me to do today?”
Why it works:
Your future self is just you, but with more regret or more wisdom. Which version would you rather listen to?
Conclusion: The Fool’s Choice and The Wise Man’s Move
Mark Twain once said, “Courage is resistance to fear, mastery of fear—not absence of fear.”
Now, after reading through these prompts, you have two choices:
- Do nothing.
You could set this article aside, let your old habits keep running the show, and stay exactly where you are. No harm, no foul—just another day in the same old rut. - Do something.
Use these prompts. Challenge yourself. Let AI give you the uncomfortable truths your friends are too polite to say out loud. Change how you think so you can change how you live.
If you want to think smarter, act bolder, and live better—start now. And ask WHY?
So, what’s it going to be?
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