After years in your role, you start to learn the rhythm of things. That’s never a bad thing—your experience makes certain things second nature. Maybe you get to the point where you think, “man, I could do that with both hands tied behind my back!”
That kind of expertise is invaluable because it is built only through hands-on experience. You have to be in it. And these days, fewer and fewer people stick with their careers long enough to reach that level of know-how.
That’s not knocking the younger generation—work culture has changed—but I think being a “rare breed” of particularly seasoned professionals carries risks with its exclusivity.
Danger: Cognitive Entrenchment!
Researcher Erik Dane studied and named the phenomenon called cognitive entrenchment: the tendency for deep expertise in a domain to come with rigidity for you to process new information in that same domain.
The more competent you become at recognizing patterns, the more your brain leans on those patterns instead of looking at things with a proverbial fresh set of eyes.
Expertise isn’t bad, but it does cost us the longer we’re good at it: the ability to see and consider things without contextual and expert baggage influencing what we take in.
When Fundamentals Turn Into a Trap
My family’s business is in real estate, and it runs on fundamentals that really don’t change much over time. Cash flow, location, supply and demand, the math of a deal: they all stay basically the same. Those fundamentals have rewarded me for years, and they’ll reward the guy who comes after me, too.
The problem arises when the underlying principles stay the same: it’s easy to mistake “this still works” for “I don’t need to keep learning.”
We see these jokes play out on TV all the time: the businessman stuck in his 80s-era peak with pagers and fax machines, unable to move with the times. But real cognitive entrenchment is a lot more subtle than that caricature.
Smart, successful people who build wealth and businesses on sound principles stop updating the way they evaluate markets, use data, and think about risk.
The fundamentals never failed, but they began to assume the fundamentals were the end-all, be-all of their success.
How to Fight Against Cognitive Entrenchment
None of this means starting over or pretending years of earned judgment don't count. They do. But staying sharp takes more intention than it used to, especially once the basics start working well enough that you stop questioning anything else. Here's what I actually do about it.
I ask what would change my mind, before I need an answer. When something unfamiliar comes up, a new tool, a new way of underwriting a deal, a new read on a market, I force myself to name what evidence would actually move me before I react. If I can't answer that quickly, I'm not evaluating anything. I need those goalposts, those lynchpins, that don’t change based on feelings.
I keep at least one relationship with someone learning faster than I am. Usually, someone younger or newer to the business who hasn't built my shortcuts yet and notices things I've trained myself not to see. I don't need to agree with everything they say, but I make a point to hear them out before I make a decision.
I schedule exposure to things I have no expertise in at all. Outside of real estate and endurance training, entirely. It's a small thing, but practicing being a beginner in a low-stakes setting keeps the muscle available when I need it somewhere that matters.
You don’t even have to audit a university class for this. It can be as simple as picking a podcast on a topic you’re not familiar with, or picking a novel experience for your next date night.
Same Instinct, Different Outcome
The skill that built my career and the blind spot I wrestle with came from the same place.
Steady fundamentals and expertise are gifts that keep giving. But the minute we grow too comfortable, they can turn into a trap. Stay sharp!
What's your favorite way to keep your mind sharp and skills fresh? Let me know in the comments.