Paradoxes of Insight

“The whole problem with the world is that fools and fanatics are always so certain of themselves, and wiser people so full of doubts.”
Bertrand Russell

The game of innovation is a battle for insights that can be acted on quickly and effectively in a marketplace with constantly evolving requirements. It’s a journey of mastery requiring high energy for disciplined experimentation, savvy interpretation and novel reframing of possibilities.

Paradox as Statement

A terse statement that is seemingly contradictory, yet apparently true, is a paradox. For example, in design we sometimes hear “Less is more” which is rather puzzling until you realize that avoiding extraneous detail results in greater impact. Or in business we are sometimes exhorted to “Do more with less” which sounds nuts at first blush but means “get creative and work out how to get the job done with fewer resources.”

Paradox as Situation

Another take on paradox is that it can be a self-contradictory situation that at first seems true. For example, in the spirit of two-way communication and openness to listening, your new boss trumpets that “My door is always open!” yet that office door is always closed whenever you actually visit. You knock and are greeted with a gruff, “Can’t you see that my door is closed and that I’m busy?” Worse, if you foolishly point out the contradiction, you may have the paradox reiterated with “Yes, it is always open. Now please close it on the way out. I have important work to do.”

There are more things in heaven and earth, Horatio,
Than are dreamt of in your philosophy.
- Hamlet (1.5.167–8), Hamlet to Horatio

Virtually all managerial positions in the digital economy increasingly rely on data-driven decision making. Cutting-edge enterprises use analytics as the basis for creating value through managing key analytical processes and using the results of these processes as the basis for making informed, evidence-based decisions.

What is insight?

Insight is the phenomenon of apprehending or seeing into a situation, event or system with such penetration that you understand its fundamental workings or essence. With insight, you suddenly perceive a pattern that was previously hidden, unavailable or even invisible.

The state pathway of a cognitive system undergoing excitation and crossing a threshold for insight formation. The dots (current ideas, perceived events, recalled memories, etc) are joined into a new and meaningful whole.

The Expansion Paradox of Insight

In gaining insight about the dynamics of some deep mystery, the scope of that mystery may actually expand. It is as though the closer you get, the further away complete understanding becomes. Answers ignite yet more questions.

The more I understand what Heidegger is aiming at the more I see how much still escapes me.

— Leo Strauss, “Existentialism,” lecture given in February 1956

The more you come to appreciate, the less confident you become about totality of your understanding. What previously seemed finite, obvious, and concrete, becomes infinite, mysterious, and intangible. The safe shallows turn into murky depths and the fully graspable becomes fascinatingly evanescent.

The Temporal Paradox of Insight

Certain insights are experienced as realizations. You suddenly see into reality and its underlying structure so deeply that you cannot go back to a previous way of viewing the world. Once you have the insight, it feels completely silly or even unnatural to go back to the original way of seeing.

The Blindness Paradox of Insight

With insight there also comes a paradox of blindness. Insight is an occurrence of re-configuration whereby the previously unforeseeable sometimes comes to appear as inevitable. The new perception comes to dominate and sometimes blind you to yet other possible insights.

Once an insight is achieved, it tends to stay in place unless a new energetic stimulus again excites crossing another threshold to an even better insight.

Types and Levels of Insight

Algorithmic insight harvested from such computational extraction and scientific analysis can, and increasingly does, inform action-taking for maximizing product engagement, building brand loyalty, generating leads, driving traffic, and ultimately making good business decisions in general.

Photo courtesy of Aaron Strout
Another 4 line solution
A 3 line solution. Notice this one takes breaking out of 2 different boxes!



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James Milo

James Milo


Milo is the founder and Chief Education Officer of KnowledgePassion, Inc. Connect with him at