Why Great Questions Don’t Have Easy Answers
Why do you believe what you believe? Try asking someone that at a dinner party. The room gets quiet—not because it’s rude, but because it’s risky. Great questions unsettle us. They force us to confront how much we’ve accepted without examination. And that’s exactly why they matter.
So what makes a question really great? Three things come to mind—though you might add a few of your own. Great questions challenge assumptions, invite introspection or re-evaluation, and resist one-size-fits-all answers. When I write these blog posts, I often find myself digging into my own assumptions—challenging how I see things, so I can better understand how you might see them.
That’s why really great questions have difficult answers. You can’t just look them up in a textbook or find a tidy answer on a trusted website. The best questions ask something about us—and we are a complicated subject.
Easy Answers Are Often Unsatisfying
There are times when we genuinely need an easy answer—like when we’re solving a problem on the spot. But more often, we reach for easy answers out of comfort. We want reassurance. Or we fall into confirmation bias, looking for validation instead of truth. And while that feels good in the moment, it can stunt our growth and keep us from facing harder, more important truths. Our beliefs become part of who we are—and letting go of them often feels like letting go of a piece of ourselves.
I talk more about this in my post on perspective, where Vinny explains to his young cousin that by demonstrating the card’s flatness, he can disprove the idea that it’s a brick. And that’s okay—sometimes we need a visual, a new angle, or even a silly example to begin to understand something differently. It’s even okay to ask, “Wait—is that a brick or not? What makes it a brick? What should I do with this new understanding?”
The difficult answers enable — and often force — us to explore our thoughts in the environment of our current status, our upbringing and history, and the influences of others in our lives. We often find that life is a test, and it becomes a real challenge when you’ve studied for a multiple-choice and true/false test, only to find that the teacher is assigning an essay exam.
The Nature of Great Questions and Hard Answers
Why do we resist seeking or accepting hard answers? Because we’re wired for efficiency—our brains are built to conserve energy for survival. But thanks to the long arc of human progress, most of us now live with enough comfort that we can afford to spend that energy thinking. That doesn’t mean we want to. Still, hard answers often require trade-offs. You might have to give up comfort, convenience, or even a piece of your identity to reach for something more meaningful. Hard answers can also bring pain or loss—like letting go of a relationship that’s no longer working. They might force you to hold yourself accountable or dig deep for the courage to act or change. And even then, they rarely offer a tidy resolution. What feels like the “right” answer today might not hold forever. As you grow, the answer often changes, too.
Many years ago, at a job I truly enjoyed, my supervisor reprimanded me for wasting time—spending it on things that weren’t part of my role. The harsh feedback stung. But a long drive home gave me the space to reflect. And he was right. It was hard to admit, but facing that truth—and changing my behavior—shifted everything. When he saw that I was trying to add value, he began investing in me. Over time, that reprimand became the turning point in one of the most rewarding work experiences I’ve ever had.
Why the Hard Answers Matter Anyway
Hard answers shape us—because they ask something of us.
When you hold a belief that you’ve worked for, wrestled with, and examined from every angle, that belief means something. Maybe it changes you. Maybe it confirms what you already knew—but now it’s anchored. Either way, you weren’t formed by default. You were formed by effort.
Great questions don’t hand out answers. They hand out mirrors, and chisels, and roadmaps with missing sections. They make us think—really think. And you can’t solve them with flashcards or clever acronyms. There’s no mnemonic for ethics. No cheat sheet for love. No bullet-point plan for legacy.
You have to sit with the question. Struggle with it. Sometimes for years.
That’s why it matters. Not because it’s hard—but because it’s honest.
Living with Great Questions
You won’t always find an answer to a really great question. That doesn’t make the question any less valuable. Often, the real worth lies in the journey—not the destination.
Once you accept the question, you start to notice its fingerprints everywhere. Bits of insight appear in ordinary moments, casual conversations, and quiet realizations you weren’t even looking for.
As the poet Rainer Maria Rilke wrote:
“Live the questions now. Perhaps then, someday far in the future, you will gradually, without even noticing it, live your way into the answer.”
Your Turn
Think about a great question in your life, and ask yourself: Am I reaching for an easy answer, or am I willing to dig deeper? Writing about it in a journal can help a lot, and it can help you find threads and connections you might otherwise miss. I don’t want you to disclose your great questions in the comments below, but if something resonated with you, the Comments section follows the Related Posts block.
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