The Risk of Losing Curiosity
Reminding myself that while certainty is seductive, curiosity is what keeps leaders alive
Curiosity rarely dies in a dramatic fashion. It doesn’t collapse with a bang. Instead, it fades, quietly and almost politely, over time. You don’t notice it at first. Meetings get shorter, questions become more predictable, decisions feel routine. You’ve “seen it all before,” and the new ideas brought forward by your team strike you less as exciting possibilities and more as things to manage, filter, or dismiss.
Five years into my role as CEO of B:Side Capital, I’ve caught myself at times feeling more certain about things, less curious, and less excited to dig into the unknown.
That’s the trap. Certainty replaces curiosity. And while certainty feels safe, it’s also the first step toward stagnation. Leaders who stop being curious don’t just risk missing new opportunities—they risk losing their ability to lead.
History is full of this pattern. Nations, companies, even families that once thrived because of curiosity, ambition, and exploration eventually hit the wall of comfort. And when they did, decline was never far behind.
Certainty’s Seduction
It’s not hard to see why certainty feels so appealing. Certainty whispers that you’ve made it, that the hard part is over, that you’ve climbed the mountain and earned the right to coast. It tells you that you’ve earned the corner office, the accolades, the authority.
But leadership doesn’t work like that. The moment you lean back and decide you already know enough, the world begins moving past you. Competitors catch up. Markets shift. Teams lose their edge. And the leader—who once prided themselves on foresight—becomes reactive, clinging to past knowledge that no longer applies.
Certainty feels good in the short run. It’s warm, reassuring, and comfortable. But it’s also corrosive. Left unchecked, it hardens into arrogance. It blinds leaders to risk. It silences the impulse to ask “why” or “what if.” And it slowly erodes the habits that made them effective in the first place.
Curiosity, by contrast, is uncomfortable. It forces you to admit you don’t know. It puts you in situations where you ask questions and risk looking foolish. It compels you to listen longer than you’d like. But that’s the point. Curiosity is a guardrail against decline.
Leaders Who Kept Asking
The leaders who stand out in history are often those who never stopped asking questions.
Leonardo da Vinci is remembered as a painter, but his notebooks show a man consumed by questions. Why is the sky blue? How do birds fly? How does water move? He never settled for easy answers, and that endless curiosity fed every work of art and invention he left behind. His genius wasn’t just talent; it was the discipline of curiosity.
George C. Marshall, the U.S. Army Chief of Staff during World War II, is another example. Marshall was surrounded by subordinates who looked to him for answers. But he had a habit of asking questions, not just about tactics and strategy, but about people. Who was ready for more responsibility? Who could handle pressure? His curiosity about others allowed him to identify and promote Eisenhower, a relatively unknown officer at the time, into a role that changed the course of the war.
Contrast that with leaders who leaned into certainty. Napoleon’s early campaigns were marked by relentless curiosity, constantly studying his enemies, testing ideas, and pushing into new terrain. But as he consolidated power, certainty took over. He stopped asking questions and started issuing decrees. By the time he marched into Russia, his belief in his own certainty had replaced the curiosity that once made him brilliant. The result was disaster.
The Organizational Cost of Curiosity Lost
When leaders lose curiosity, their organizations follow. Teams stop experimenting because they know the boss has already made up their mind. Innovation stalls because new ideas are filtered out by leaders who think they already know the outcome.
Curiosity is contagious, but so is certainty. A curious leader creates a culture where it’s safe—even expected—to ask, test, and explore. A certain leader creates a culture where playing it safe is the norm.
This is why companies that were once titans can collapse in a single generation. Think of Kodak, which invented the digital camera but dismissed it because leadership was certain film would always reign. Or Blockbuster, certain that customers loved the store experience too much to embrace streaming. Certainty was their undoing.
Curiosity wouldn’t have guaranteed survival, but it would have kept them open to possibilities. It would have asked, “What if we’re wrong? What if the future looks different than the past?” Those questions could have changed everything.
Guardrails Against Decline
So how do leaders protect themselves from losing curiosity?
The first step is awareness. Recognize that curiosity doesn’t die all at once, it erodes. It slips when you stop asking follow-up questions in meetings. It dulls when you assume you already know the motives of your competitors. It fades when you stop reading outside your lane or engaging with people who don’t share your background. I’ve noticed these traits in myself and am working to catch myself before they take hold.
Second, build habits that force curiosity. Schedule time each week to read something unrelated to your field. Seek out dissenting voices in your organization. Invite people to challenge your assumptions and reward them when they do. Go into conversations with the intention of asking three questions before giving a single answer.
Third, embrace discomfort. Curiosity often leads to answers you don’t like. It might show you that your strategy is flawed or that your favorite project isn’t working. Certainty shields you from those truths. Curiosity forces you to face them. And in doing so, it gives you the chance to adapt before it’s too late.
The Personal Side of Curiosity
Curiosity isn’t just a professional tool; it’s a way of living. When people stop being curious, life shrinks. Days become repetitive. Conversations feel scripted. Challenges lose their edge. The world gets smaller.
But when curiosity is alive, even routine experiences take on depth. A curious person doesn’t just commute to work, they wonder why the city was designed the way it was. They don’t just talk to their kids about school, they ask about what they found surprising, confusing, or funny that day. Curiosity makes life bigger.
As leaders, it’s easy to forget this. We get so focused on outcomes and efficiency that we forget the value of simply wondering. But curiosity is what keeps us human. It’s what keeps us connected. It’s what keeps us learning, even when the world insists we should have it all figured out by now.
Certainty Kills, Curiosity Saves
The choice isn’t between curiosity and certainty, it’s between growth and decline. Certainty tells you the story is over. Curiosity keeps writing new chapters.
If you’re leading a team, building a business, or even just navigating life, the risk of losing curiosity is real. It won’t happen overnight, but it will happen if you don’t guard against it. And the cost isn’t just missed opportunities. It’s the slow erosion of your ability to adapt, connect, and lead.
The leaders worth following, the ones who leave something behind, are those who never stopped asking. They stayed curious, even when it was uncomfortable. Especially when it was uncomfortable.
Because curiosity, more than certainty, is what keeps us alive.