Overthinking…or underthinking?

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The author reflects on the concept of overthinking, arguing that underthinking can be just as dangerous, if not more so. The author shares a personal story about homeschooling their sons and noticing that one of them tends to mistake action for progress, particularly in the realm of mathematics. The lesson imparted is that clear thinking and strategic problem-solving are crucial before diving into action. The author criticizes the notion of "imperfect action," highlighting the importance of correct thinking that strikes a balance between overthinking and underthinking. The article emphasizes the need for careful consideration and precision, especially in leadership and decision-making, and challenges the prevailing cultural emphasis on hasty action. The author concludes with a maxim: "Doing nothing is preferable to doing things without understanding," suggesting that thoughtful understanding is essential for effective execution.

Overthinking…or underthinking?


Overthinking gets a bad rap.  Underthinking is just as dangerous, perhaps more, but you don’t tend to hear people criticize that.

Here’s a story to illustrate what I mean, and it’s relevant to much of what I currently find lacking in the coaching/consulting/mentoring space today.

Both of my sons are homeschooling this year.  It’s the first time we’re trying this.  COVID shook up a lot of related structure and practices of course - without that I doubt we’d have any concept of doing this.  Challenges and opportunities in every new thing that comes down the road, on every scale.

We have found that one of our sons has a way of self-directing his productivity in a manner that is very effective.  He’s also on his second year of homeschooling.

The other, trying it for the first time this year, is still getting used to the initiative demanded by this freedom and independence, and has required some guidance to get off the ground a bit.

I helped the second with his math last night and made some observations.  What I noticed is that he often mistakes action with progress, laboring under the misconception that completing the task is sufficient.  As you and I know, mathematics is about accuracy and precision (at the level of middle school pre-algebra at any rate).  If you get half of the problem set wrong you’re not benefiting anyone, no matter how much action you take to get there.

I taught him to slow down, read carefully, think even more carefully, and strategize his problem solving efforts.  And I left him with a maxim that I improvised just for this situation, but which has the ring of truth to me…

“Doing nothing is preferable to doing things without understanding.”

Now, if you’re familiar with my work you likely know that I also say it’s impossible to do nothing.  Our participation in what I call the Realm of ACTION demands constant activity from which it is a metaphysical impossibility to abstain.

So you can’t do nothing.  You just end up doing something else (like sitting, pacing, thinking, scrolling on your phone, etc.)

But, once we’ve resolved to purposefully solve our problem, clear thinking is an essential part of formulating a strategy.  It always is, in all times and places.  And in this way our ACTIONs become ordered, efficient, and effective within our limited spacetime.

My son was demonstrating the dangers of underthinking, that is getting into ACTION too quickly without first properly strategizing.

Many coaches speak of “imperfect action”.  And I understand this.  Sometimes that is indeed what is needed.  Our insecurities and fears motivate us to analyze and second-guess endlessly, which paralyze and preclude us from ever taking the ACTIONs that our visions demand.

Sometimes you need to brainstorm, get creative, take things less seriously, start building momentum, even before you’re sure you’re doing the right thing.  This is the problem of overthinking.  And it’s a real problem.

But just as often, and perhaps more frequently, I observe the opposite problem, revealed when people think that forward momentum is all they need, and thus sacrifice the rational clarity that is so essential to structuring our efforts efficiently and effectively.

I find a crucial and reliable part of the process through which I guide leaders, creatives, and visionaries, is picking up on the embryonic elements of their visions and helping them think through all the components, implications, and ramifications, carefully watching for logical contradictions and fallacies as we examine each pertinent component of the system we are constructing.

I even suspect that “overthinking” is a fashionably overused buzzword whose time has come and gone.  And I think it’s an incredibly short-sighted criticism.

What’s necessary is correct thinking, which splits the difference between “overthinking” and underthinking.

What does it mean to overthink, exactly?

I remember a couple years ago when a friend of mine shared a very philosophical podcast on Facebook.  The episode involved an intricate and complex discussion about a particularly challenging moral and ethical question, which I found quite stimulating.  The first comment on his post disheartened and annoyed me: “These guys think too much.”

I was like “Huh?!”  How could you navigate such a topic without deep thought and consideration of all relevant facets and nuances?  How could we build an effective self-driving car, design a sustainable system of government, or systemize a multinational corporation without similar cognitive commitment.


Did Aristotle overthink?  How about Thomas Jefferson or Henry Ford?  Martin Luther King Jr.?  Their abundant pages and creations positively brim with the evidence of copious and nuanced thought processes.  Can any of these luminaries be accused of overthinking???!!!  Or did people such as these see exactly where thinking was needed and thus apply it in precise and correct measure?  You can probably guess my answer to that question.


While overthinking may be a problem for some, I find underthinking to be a far more insidious plague to challenging leadership situations, and one that is particularly destructive to successful execution.


Yes, sometimes we need to get moving.  Sometimes we need to generate ideas and see them more clearly.  And this stage of the process demands spontaneity, agility, a breathless pace of creativity to shake up entrenched patterns.


But, once we know what we want, we need to discard notions of overthinking and conversely shift our guard against underthinking, which is likely not the problem you are watching for, given the prevailing cultural mantra of “imperfect action”. It has its place, but not as wide a place as many people seem to think.


Examine your results.  If you are reasonably clear on your vision and your reality fails to meet it, you likely need to think more, not less, and to do so with greater clarity and precision.

Otherwise we get sloppy, and return incorrect responses to half of the problem set, which doesn’t do anyone any good.


“Doing nothing is preferable to doing things without understanding.”  Our son is learning.  And so can the rest of us.

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The advice I would give to my kids if they asked today