September 28, 2025
You’d think this would be easy. The hardest question should be something like “What’s the meaning of life?” or “Why is the cat staring at the wall like she’s seen a ghost?” But the truth is, the hardest questions aren’t usually cosmic or spooky, they’re personal.
I’ve been hit with questions that felt like sucker punches:
- “Are you happy, or just busy?”
- “What do you really want most in life?”
- “Why are you afraid to do the thing you dream about?”
Those questions are difficult because they cut through the noise. They don’t let you hide behind clever answers or quick deflections. They demand honesty. And honesty, at least the real kind, is rarely comfortable.
Kids are great at asking impossible questions too. My six-year-old once asked me why the moon “follows” our car. I gave my best dad-science answer, but he wasn’t impressed. He just kept asking “but why?” until I was out of explanations and left wondering if maybe I didn’t really understand the moon either.
The most difficult questions don’t care about trivia or being right. They care about revealing who you are. They make you pause, squirm, and sometimes even laugh nervously.
And maybe that’s the point. Life isn’t about nailing the perfect answer every time. It’s about letting yourself wrestle with the questions that matter, even when the answers never come neat and tidy.
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💬 Your Turn
So… what do you think is the most difficult question to answer?
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