The Problem of Certainty

Hello loyal readers and subscribers. As always, thank you for your continued encouragement and support of this newsletter. Today’s article begins a new experiment: every Monday, Wednesday, and Friday I am going to publish a mini-essay as part of a weekly theme. Taken together, these three pieces will explore a single idea in problem solving, from concept, to method, to application.

So, here we go:

The moment you are certain, you stop seeing a problem clearly

We tend to think of confidence as a strength in problem solving. And often, it is. Confidence allows us to act, to decide, to move forward when uncertainty would otherwise paralyze us. But there is a quieter, more dangerous form of confidence. It is the overconfidence that does not accelerate progress toward a solution, but prevents it. It is the undeserved confidence of premature understanding.

Certainty in problem solving is often mistaken for understanding. But when you assume you understand a problem, you stop examining it. And when you stop examining it, you stop learning.

Overconfidence does not accelerate solutions; it distorts them. Before you attempt to solve a problem, question whether you understand it at all.

In past newsletters, I have emphasized the importance of understanding the problem as well as possible before attempting to solve it. That means defining the problem and understanding its root cause. Furthermore, the system in which the problem developed should be thoroughly examined. Finally, make sure you really have a problem that can actually be solved, that is, one that has a real solution.

I often cite the classic movie Groundhog Day, in which the main character Phil Connors finds himself reliving the same day over and over again. At first, he treats the situation as a problem to be solved quickly. He assumes he understands what is happening, or at least how to respond to it. So he experiments repeatedly to fix the situation, but only within the narrow confines of his own assumptions. And so he fails. Repeatedly. Not because he lacks intelligence. Not because he lacks effort. But because he misunderstands the problem itself.

This is where many of us find ourselves in our own lives. We encounter a problem, whether at work, in relationships, or in our personal life, and we move too quickly to solutions. We rely on past experience. We trust our instincts. We assume we “get it.” But what if we don’t?

What if the problem we think we are solving isn’t the real problem at all?

Hubris (false pride in our own ability or excessive overconfidence) in problem solving is not arrogance in the traditional sense. It is much more subtle than that. It is the quiet and mistaken belief that our current understanding is sufficient. That we have seen this before. That we already know enough to act. But every problem exists within a system. And if we misread that system, if we misidentify the variables, the relationships, and the underlying structure, then every action we take, no matter how well-intentioned, simply reinforces the problem. We become, in a sense, trapped in our own version of a loop. Same assumptions. Same actions. Same results.

Progress in problem solving does not begin with better answers. It begins with better questions. Sometimes, the most powerful question you can ask is this:

What if I don’t understand this problem as well as I think I do?

That question does something important. It creates space. Space to observe. Space to reconsider. Space to see the problem, not as you assumed it was, but as it actually is.

Before you try to solve your next problem, pause.

Resist the urge to act. Resist the urge to decide. Instead, re-examine your understanding. Because the most dangerous Problem Solver is not the one who doesn’t know. It is the one who believes they already do.

Well, that concludes this newsletter. Wednesday, I will continue on with this theme in…

Breaking the Problem of Certainty: The “I Might Be Wrong” Method

I hope readers enjoy this shorter format as an alternative to longer-form content, which, though enjoyable for me to write, takes a little more time to read.

Happy Problem Solving!

Evan