This "post" is a work in progress. This rough draft will hopefully be finalized at a later date. Thank you to Perplexity for your help with the research and also forming my thoughts into this first draft. 

Why “Insightful” Is the New “Wise” (And How To Be a Philosopher)

Why “Wise” Feels Out of Reach

Have you ever been told to “be wise” or to “make wise choices”? If you’re like me, you’ve probably wondered what that actually means. The truth is, the word wise is slippery. It’s one of those words that everyone uses but few can define clearly. Ask ten people what it means to be wise, and you’ll get ten subtly different answers. For some, it means being cautious; for others, it’s about knowledge, experience, or even just not being foolish.

This ambiguity makes “wise” hard to pursue. If you can’t define it, how do you know if you’re becoming it? How do you teach it to your kids or measure it in your own life? The more I thought about it, the more I realized that wise is a word that, while noble, doesn’t give us practical handlebars for daily living.

The Power of Etymology: From “Wise” to “Insightful”

Digging into the roots of the word wise was eye-opening. The Old English wīs and the Proto-Germanic wissaz both mean “to see” or “to know”—but not just in a surface way. They imply “seeing into,” perceiving the heart of a matter. This is almost identical to our modern word insight, which literally means “seeing into.”

That’s when it clicked: insightful is a much more practical, actionable, and teachable word for what we usually mean by “wise.” It’s clear, precise, and gives us a way to measure and pursue growth. When I think about the choices I want to make—and the choices I want my kids to make—I don’t just want them to be “wise” in some vague sense. I want them to be insightful: to see beyond the surface, to understand deeply, and to make decisions that reflect that understanding.

Why “Insightful” Gives Us Access to Philosophy

Here’s where this new framing gets really exciting. If being insightful is the best way to be “wise,” then the pursuit of insight is something we can all access—not just scholars or sages. And this brings us to the word philosophy.

Most people think of philosophy as something abstract, academic, or reserved for university professors. But the word itself, from the Greek philosophia, simply means “love of wisdom.” If we update that to “love of insight,” suddenly philosophy isn’t just for the ivory tower—it’s for anyone who cares about understanding life and making good decisions.

The Story of Pythagoras and the Birth of Philosophy

Let me share a story that captures this spirit. Legend has it that Pythagoras, the famous Greek mathematician, was once asked if he considered himself a wise man (a “sophos”). He replied, “No, but I am a lover of wisdom—a philosopher.” In his view, no one could claim to possess wisdom fully, but anyone could pursue it, love it, and strive for it.

This story, whether fact or myth, gives us a powerful insight (pun intended): Philosophy is not about having all the answers—it’s about loving the process of seeking understanding. It’s about being curious, asking good questions, and letting that curiosity shape our lives and decisions.

Making Philosophy Practical: Insightful Judgment

So what does this mean for us? It means that wisdom isn’t some mystical quality reserved for a chosen few. It’s about practicing insightful judgment—the kind of decision-making that comes from seeing deeply, understanding fully, and acting thoughtfully.

Here’s how I define the process:

Wisdom is the process of asking to learn, learning to know, knowing to understand, and understanding to decide.

But if we want to make this even more actionable, let’s update it:

Insightful judgment is the process of asking to learn, learning to know, knowing to understand, and understanding to decide.

Or, if you prefer, “insightful decision-making” follows the same process.

Why This Matters for Everyone

By shifting from “wise” to “insightful,” we make the pursuit of wisdom accessible. We give ourselves and our children a clear path: slow down, ask questions, gather information, reflect, and then decide. This is something anyone can do, regardless of age, education, or background.

And by reclaiming the word philosopher as “lover of insight,” we invite everyone into the adventure of seeking understanding—not as a destination, but as a lifelong journey.

Final Thoughts

Words shape the way we live. By choosing “insightful” over “wise,” we move from ambiguity to action. We make the pursuit of wisdom something we can all strive for, not just admire from a distance. And in doing so, we become philosophers—not in the academic sense, but in the truest sense: lovers of insight, seekers of understanding, and people committed to making insightful decisions.

So the next time you’re faced with a choice, don’t just ask, “What’s the wise thing to do?” Instead, ask, “What’s the most insightful choice I can make?” In that moment, you’re not just being wise—you’re being a philosopher.