Wisdom Won’t Find You
You Must Seek It Out
Wisdom never just arrives. It doesn't politely knock on your door or wait patiently in your inbox. It doesn't automatically come with age, experience, or even success. Instead, wisdom is something you must chase down, wrestle with, and continuously cultivate throughout your life. The uncomfortable truth is that wisdom isn't passive—it's an active pursuit.
Too often, we believe simply getting older or accumulating experiences equals wisdom. But experience alone, without thoughtful reflection and intentional effort, is just a collection of unexamined events. Real wisdom demands something more: deliberate effort and a relentless hunger to learn and grow.
The Deliberate Practice of Reading
I recently read "What You're Made For: Powerful Life Lessons from My Career in Sports" by George Raveling, one of the most insightful leaders in sports history. In this compelling book, Raveling credits much of his growth to his relentless pursuit of knowledge through reading. For Raveling, books aren’t just passive objects to collect; they are mentors, guides, and conversation partners. The act of reading, particularly reading intentionally, is a cornerstone habit of wise leaders.
Like Raveling, I've always been deeply passionate about reading. For me, books aren't just sources of entertainment—they’re doorways into other worlds, other minds, and other experiences. I genuinely believe in Harry S. Truman’s famous observation: "Not all readers are leaders, but all leaders are readers." Reading gives you the incredible ability to download the experiences, thoughts, and insights of people who’ve navigated paths you’ve never walked. It’s a chance to absorb decades of wisdom in hours or days, to learn from others' successes and mistakes without having to repeat them yourself.
Reading intentionally means choosing your books thoughtfully, marking them up, taking notes, and actively engaging with the material. It means reading not just to confirm what you already know but to challenge your beliefs, assumptions, and biases. This method transforms books from passive experiences into active dialogues that shape your thinking and decision-making.
For leaders who want to grow, adopting this deliberate practice of reading is essential. Start by setting aside dedicated daily time for reading. It might be fifteen minutes or an hour—whatever fits your schedule. Choose books outside your comfort zone, from biographies of leaders in unrelated fields to books about psychology, philosophy, or even fiction. Then, as you read, jot down questions, reflections, and insights in the margins or a separate notebook. This approach turns each book into a living source of wisdom, continuously shaping your understanding and actions.
Capture Your Thoughts: The Power of Journaling
If reading provides the raw material, journaling is the refinery. Journaling isn't just a diary or a place to record daily events. Instead, think of journaling as a workspace for your mind—a place to distill insights, explore ideas, and crystallize lessons from your experiences.
Personally, I keep a commonplace book—a dedicated notebook where I capture quotes, ideas, insights, and reflections from the books I read and experiences I have. A commonplace book isn't a journal in the traditional sense; it’s more of an organized collection of knowledge and wisdom you find valuable. Historically, commonplace books were widely used by great thinkers and leaders. Figures such as Marcus Aurelius, Leonardo da Vinci, and Thomas Jefferson all famously maintained commonplace books to consolidate their thoughts and guide their actions. Keeping a commonplace book allows you to organize your thoughts, revisit your insights, and continuously refine your thinking.
Make journaling a daily practice. Even five or ten minutes each evening can yield powerful results. Reflect on what you've learned, where you succeeded or stumbled, and what actions you might take differently tomorrow. Over time, you'll build a deep reservoir of insights tailored uniquely to your own leadership journey.
Surround Yourself with Different Perspectives
Wisdom grows in diversity, not uniformity. It thrives in environments where ideas collide, perspectives clash, and assumptions are routinely questioned. Surrounding yourself only with people who echo your beliefs creates a bubble that stifles growth. To seek wisdom actively, you must deliberately engage with people who see the world differently.
This doesn't mean seeking conflict for its own sake. It means thoughtfully engaging in conversations with people from varied backgrounds, industries, and perspectives. If you're in finance, talk regularly with people in creative industries. If you're leading a large corporation, seek insights from small business owners or entrepreneurs. Each interaction offers fresh perspectives and unexpected insights, fostering genuine wisdom.
But before you can fully benefit from these exchanges, you need to prepare your mind. Enter each conversation with humility, acknowledging that your own viewpoint is limited and could be improved. Cultivate genuine curiosity, asking open-ended questions and listening deeply rather than simply waiting to respond. This mindset helps you not only hear different perspectives but truly process and possibly integrate them into your own thinking. Over time, this openness to challenge and new ideas will expand your understanding and help you develop deeper, richer wisdom.
Lean into Discomfort
True wisdom rarely feels comfortable. In fact, discomfort often signals that you're on the verge of a significant insight. It's human nature to seek comfort, but growth and comfort rarely coexist. Wise leaders learn to lean into discomfort, recognizing it as a sign of learning and growth.
George Raveling, reflecting on his own career, noted that his greatest leaps in understanding came during moments of profound discomfort. From navigating racial tensions during his college days to feeling out of place among tech entrepreneurs in his eighties, each uncomfortable experience offered significant learning opportunities.
Leaders seeking wisdom must regularly ask themselves uncomfortable questions: Where might I be wrong? What biases am I ignoring? How can I approach this situation differently? These questions invite introspection, challenge assumptions, and unlock deeper levels of understanding.
Make Wisdom-Seeking a Daily Habit
Finally, wisdom requires consistency. It’s not a one-time event or something you achieve and then coast on. It’s an ongoing pursuit that needs nurturing every day.
Establish daily rituals that reinforce your commitment to seeking wisdom. Combine intentional reading, journaling, diverse conversations, and embracing discomfort into a sustainable routine. Protect this time fiercely, recognizing that wisdom-seeking is not just beneficial—it's essential.
Each small daily action compounds, gradually shaping you into a wiser, more effective leader. Wisdom doesn’t come all at once, nor does it announce itself dramatically. Instead, it quietly accumulates through consistent effort, thoughtful reflection, and deliberate pursuit.
Wisdom Is Waiting—Go Find It
Wisdom won’t seek you out. It won’t show up spontaneously, no matter how experienced or accomplished you are. But it's there, waiting patiently for you to find it. All it requires is your active participation, intentional curiosity, and a willingness to engage deeply with the world around you.
Don't wait passively for wisdom to arrive. Chase it deliberately. Make it part of your daily routine. Read intentionally, journal thoughtfully, engage diverse perspectives consistently, and lean into discomfort whenever you encounter it. Do these things, and you'll find that wisdom is never far away—because you're actively creating the conditions for it to flourish.