While reading the news during the summer of 2025, I was struck by how Vladimir Putin continues to pursue his war in Ukraine using what amounts to a time-worn strategy of attrition—grinding down the enemy through prolonged, resource-heavy engagement. It’s a tactic rooted deep in Russian military history, from Napoleon to World War II. But this isn’t 1942.
Despite the widespread use of drones, precision strikes, and AI-assisted targeting—and despite the mobilization and coordination demonstrated by the free world to counter his tactics—Putin remains committed to fighting the war he knows, not the one that is unfolding. It’s more than a strategic choice. It’s become part of his brand. His identity as a strongman, a student of Russian military tradition, and a leader who doesn’t blink under pressure is now inseparable from how he sees the path forward.
And that’s what makes his thinking so dangerous—not just to his enemies, but to his own cause.
What struck me is that I see echoes of this same mindset in many of the business owners I mentor.
A while back, I worked with a custom home builder who came to me for help in writing a business plan to secure a bank loan. His working capital was being squeezed, and he needed a line of credit to manage cash flow during construction cycles and the revenue lull he was experiencing. I suspected there might be a deeper issue, so I asked him about his marketing strategy.
“I’ve never needed marketing—my business is 100% referral,” he told me proudly.
He wore it like a badge of honor. And to be fair, that model had served him well for over two decades.
But when I asked how many leads he was getting this year versus last, he admitted,
“It’s been a bit slow lately, but I figure people are just being a little more cautious given the economy. It’ll bounce back—it always does.”
What he didn’t want to consider—and what many entrepreneurs resist—is that the world had changed around him. His core customer base was aging out. Younger buyers were searching online first. His once-reliable word-of-mouth engine was fading. But his belief in the “referral-only” model was so deeply ingrained that considering alternatives felt unnecessary—or even threatening.
Just like Putin clings to strategies rooted in a different era, this business owner had plenty of experience, but he was overly confident in his outdated experience. And that’s a pattern I’ve seen too often.
After years of working with entrepreneurs, I’ve learned this truth: the longer someone’s been successful with a single approach, the harder it is for them to question it. And while the Dunning-Kruger effect is often described as overconfidence in the inexperienced, there’s a subtler version that I see all the time: overconfidence in outdated experience.
That’s one reason why I consistently include teaching the Dunning-Kruger Effect in my workshops. It’s one of the most useful—and underused—mental models in entrepreneurship. I’ve seen firsthand how good people, running good businesses, can be led astray by overconfidence in outdated ideas. They mistake momentum for mastery. And when new evidence shows up, they often dig in deeper to defend their past decisions instead of reevaluating them.
When SEO Becomes an Identity, Not Just a Strategy
Let me share another story to illustrate this. A client of mine had been blogging about financial planning and retirement readiness for over a decade. Her writing was thorough, trustworthy, and full of practical advice. She had built a loyal audience by helping people prepare for retirement—everything from 401(k) rollovers to Social Security timing. Her core belief? “If I write valuable, evergreen content, readers will always find it.”
And for years, that belief held true. Her posts ranked well, and her audience grew steadily over the years. She didn’t need to chase trends because Google rewarded the depth and consistency of her content.
However, more recently, things began to change. Her organic traffic and engagement were dropping. The usual fixes—refreshing content, updating charts, improving formatting—were no longer moving the needle either.
When we looked at the situation together, I pointed out that Google’s AI-generated search summaries were providing users with answers directly—often using snippets from her own work—giving readers no reason to click through to her content to enable her to monetize her business by selling her products and services. Her revenues were eroding, and she was frustrated.
I asked her to consider a different lens: “What if your job isn’t just to write blog posts anymore to drive traffic? What if your true value lies in building trust, loyalty, and ongoing relationships through channels like newsletters, podcasts, or even short-form videos?”
That question hit hard. Her entire brand identity had been built on well-written long-form content optimized for search. Rethinking that model felt like walking away from the formula that made her successful. And understandably, admitting that might feel like acknowledging failure.
But here’s the truth I see time and again in my coaching sessions:
“When people anchor their identity to a belief, they stop questioning it—even when the evidence says it’s time to move on.”
The Psychology Behind Resistance to Change
That’s where Adam Grant’s book Think Again offers some hard-won wisdom. He explains that people often cling more tightly to ideas that are central to their identity. They don’t just believe something—they are that belief. And when that belief is challenged, it can feel like a threat to their very sense of self. Rather than calmly considering the new evidence, they argue more forcefully, not because the argument is stronger, but because their ego is now on the line.
This reflexive resistance isn’t just psychological—it’s neurological. Daniel Kahneman, in Thinking, Fast and Slow, describes how we rely on two systems of thinking: the fast brain and the slow brain. The fast brain is automatic, emotional, and instinctive. It’s closely tied to the more primitive, reptilian part of the brain—the same one responsible for fight-or-flight responses. So, when a core belief gets challenged, our fast brain interprets it as a threat. The result? A defensive reaction meant to protect the ego, not evaluating the argument.
Our slow brain—the more deliberate, logical part—could help us rethink. But under stress or identity threat, it gets overridden by the faster system. That’s why even intelligent and capable entrepreneurs, as well as world leaders such as Putin, continue to cling to outdated beliefs despite mounting evidence to the contrary.
When Confidence Becomes a Trap: Dunning-Kruger and Cognitive Tunneling
This neurological shortcut feeds directly into the Dunning-Kruger effect. When someone has a little experience or early success in a domain, their fast brain locks in that initial win as confirmation of mastery. They overestimate their ability because they haven’t yet developed the depth of knowledge required to see the complexity. And when that illusion of competence is threatened—say, by shifting market conditions or new data—it doesn’t trigger reflection. It triggers defense.
That defensive reaction becomes even more problematic under stress. Instead of expanding their awareness and reevaluating the situation, many business owners fall into cognitive tunneling—a mental state in which they hyper-focus on a familiar solution while ignoring new inputs. It’s the same kind of tunnel vision that prevents pilots from seeing warning signs in an emergency or causes a motorcycle driver to stare at a pothole in the road until they hit it.
In business, this means continuing to push a strategy that no longer works, simply because it’s what they’re used to. They stop scanning the horizon. They narrow their field of vision. And they double down on outdated assumptions.
These same business owners, instead of reevaluating their position, dig in—not because they’re being stubborn, but because their brain is doing what it thinks it needs to do to survive. That’s what makes rethinking such a powerful—and rare—skill in business leadership: it requires overriding not just old ideas, but deeply ingrained survival responses.
Tools for Thinking Again
The real test for any entrepreneur is not whether they were right the first time. It’s whether they’re willing to rethink when the landscape shifts.
In Think Again, Grant shares a decision-making tool I love. He suggests that whenever you’re evaluating a belief, strategy, or opportunity, you should build two lists:
What would have to be true for this decision to remain valid?
What would have to be false for this decision to fail?
This framing encourages scientific thinking. It puts you in the mindset of a detective—not a preacher defending tradition. It opens the door to consider that maybe, just maybe, what worked before isn’t working now because the assumptions underneath have eroded.
I’ve used this basic model with clients who are thinking about expanding to a second location, launching a new service line, or investing in new marketing tools. While I’ve used a similar approach for years, Adam Grant’s version helped make the idea more concrete and easier to communicate. I often pair it with first-principles thinking and the 5 Whys technique to help clients uncover the root of their assumptions—guiding them to their own realizations instead of just telling them outright. When we walk through the two lists together, it becomes painfully clear: their assumptions haven’t been tested in a long time.
Beliefs vs. Assumptions: What Are You Really Standing On?
Often, what they’ve treated as a belief is really just an unexamined assumption.
That’s the central idea of one of my blog posts: “Belief vs. Assumption.” A belief is something foundational, backed by experience, and tested over time. An assumption is a guess. When we treat an assumption like a belief, we risk building on sand. The structure might look solid, but one good storm—or one AI algorithm change—and the whole thing sinks.
Are You Coachable? What the Evidence Tells Me
So, here’s a question I ask myself when working with any client:
“Are they coachable, or are they stuck in their ways?”
Of course, I don’t ask this directly—I look for the evidence. Do they argue harder when presented with new data? Do they deflect or rationalize when their belief is clearly built on a crumbling foundation? Are they more focused on defending their original decision than exploring new possibilities?
These signs tell me what I need to know. Because the business owners who regularly question their past decisions—not out of insecurity, but genuine curiosity—are the ones who thrive. They aren’t constantly chasing shiny objects or pivoting for the sake of novelty. But they are willing to let go of what’s no longer working and lean into what might.
Rethinking Your Role in a Changing Landscape
Let’s go back to the financial blogger. While she doesn’t write about SEO, she has long relied on it—crafting well-optimized posts with the hope that Google would consistently send readers her way. SEO has quietly powered her visibility, and her content strategy was built around that assumption: “If I write quality, evergreen financial content, the traffic will come.”
But in a more adaptive future, she might recognize that SEO alone is no longer enough. She could begin repurposing her posts into short-form videos, start a newsletter to build direct relationships with her audience, or explore new channels like podcasts or webinars. The goal wouldn’t just be traffic—it would be connection.
Instead of relying entirely on search algorithms, she would start to see herself not just as a financial writer, but as a media creator and educator—someone who delivers value across platforms and touchpoints.
Her traffic? It might remain down from its peak—but her influence would likely rise. Her audience loyalty could be strengthened. And she’d be less dependent on forces beyond her control.
That shift could only happen if she’s willing to think again—to question old assumptions and embrace a more resilient, diversified identity.
Why Curiosity Wins
If you’re running a business today, the rules are changing faster than ever. Markets evolve. Algorithms shift. Customer behavior doesn’t sit still. What worked last year—or even last month—may not work tomorrow.
The only sustainable advantage is the willingness to question your own thinking.
So, as you go about your work this week, ask yourself:
What am I absolutely sure is true?
When was the last time I tested that?
What would I do differently if I weren’t so committed to what worked in the past?
It’s not easy to let go of a belief you’ve carried for years. But success doesn’t reward stubbornness. It rewards curiosity, humility, and adaptability.
That’s why I keep teaching the Dunning-Kruger effect in my workshops. Because most of us aren’t overconfident jerks—we’re just humans trying to navigate a fast-moving world with outdated maps.
The good news? You can always redraw the map.
But only if you are prepared to stop defending the route—and start questioning the terrain.
Are you clinging to a belief that once worked but may no longer serve you, or are you willing to rethink and adapt before the evidence forces your hand?
