One of the more surprising lessons that comes with age and experience is that expertise and curiosity often pull in opposite directions. Experience teaches us what works. Curiosity asks whether it still does.
To be clear, this is not a post that argues against experience. In fact, my intention is almost the opposite. Most of what we know has been earned through years of trial and error, successes and failures, observations and lessons learned. Experience matters. Wisdom matters. Process matters. But there is a difference between relying on experience and becoming captive to it.
Some of the most successful people I know possess an unusual combination of confidence and humility. They have developed convictions through years of practice, but they remain willing to revisit those convictions from time to time. They understand that asking questions is not a sign of weakness. It is a sign of intellectual curiosity… and intellectual honesty.
Curiosity is often misunderstood. It is not the belief that everything old is broken or that every new idea is automatically better. In fact, many of the traditions, principles, and processes we rely on have survived precisely because they work remarkably well. The goal is not to replace everything that came before. The goal is to periodically examine it – the value lies in the evaluation itself. Sometimes you uncover something that needs attention. Other times you gain confidence that the existing structure remains sound.
The same principle applies to how we think, work, invest, and live. In investing (and providing overall financial advice), there is a temptation to become attached to familiar narratives. We develop views about markets, asset classes, economic relationships, or portfolio construction and eventually begin treating those views as permanent truths. Yet markets have a way of reminding us that permanence is often an illusion. The most successful investors are rarely those who abandon their principles every six months in pursuit of the latest trend. They are also not the investors who refuse to adapt under any circumstances. Instead, they occupy the middle ground. They maintain a disciplined framework while remaining open to new information.
A healthy investment process asks questions.
Does this assumption still hold?
Has something fundamentally changed?
Are we solving today’s problem with yesterday’s solution?
Sometimes the answer leads to meaningful adjustments. Other times it reinforces the original conclusion. Both outcomes are valuable. The same is true in life. Relationships benefit from curiosity because people change. Careers benefit from curiosity because industries evolve. Personal growth depends on curiosity because the person you are today is not the person you were ten years ago.
The challenge is that certainty feels comfortable. Once we find a method that works, it is tempting to place it on a shelf labeled “Solved Forever.” The wisest among us seem remarkably comfortable saying, “I don’t know,” or perhaps more importantly, “I haven’t thought about it that way before.” Those phrases are not admissions of ignorance; rather, they are invitations to learn. There is also a practical benefit. When we stop assuming we have all the answers, we become far better at finding them. Perhaps wisdom is not the accumulation of certainty but the cultivation of curiosity. It is the willingness to periodically inspect our assumptions, challenge our conclusions, and view familiar problems through fresh eyes. And if we’re fortunate, curiosity keeps us from becoming the person who finds themselves often saying “we’ve always done it this way.” History would suggest that sentence rarely appears immediately before a breakthrough.
The good news is that we do not have to choose between experience and curiosity. Experience provides the foundation. It gives us judgment, perspective, and a framework for making decisions. Curiosity keeps that foundation from becoming rigid. It helps us test assumptions, adapt to changing circumstances, and remain open to new possibilities. The strongest investors, advisors, and lifelong learners are rarely those who possess the most certainty. They are often those who have learned to balance conviction with curiosity. They trust what they know, while remaining willing to explore what they do not. That balance creates a powerful advantage.
So, I/we keep learning (artificial intelligence – I am looking right at you), keep asking questions, and keep challenging assumptions… including my own. Not because everything needs to be reinvented, but because growth requires occasional examination. And every now and then, after asking the questions and exploring the alternatives, you may discover that the way you have been thinking about a problem or opportunity was actually the right way all along. There is value in that answer, too. After all, curiosity is not about finding a different answer every time. Sometimes its greatest gift is confirming that the wisdom you’ve earned still deserves a seat at the table.
