Overcoming painful perplexities is one of the most rewarding parts of my work as a strategic designer.
Perplexity is incapacity to understand a difficulty, so thorough that the difficulty cannot even be expressed negatively as a problem or question. As I’ve said millions of times over the last thirty years, perplexities induce intense mysterious anxiety in people. It is not “discomfort” with “ambiguity”. It is excruciating and disturbing, and it makes people behave atrociously.
If we are to believe Wittgenstein, perplexities are essentially philosophical problems: “A philosophical problem has the form: ‘I don’t know my way about.’”
But the majority of people are unphilosophical. They lack all awareness of the existence of the phenomenon of perplexity and the language to recognize and diagnose it — much less methods, skills and mindset required to overcome perplexity.
And people are not merely unphilosophical. They are aggressively unphilosophical. Philosophical thought annoys people. It is socially acceptable to disrespect it and anyone who does it. Even open-minded “good listeners” stop listening and tune out if they detect philosophy in a line of thought. And if you press it further, the resistance presses back even harder. The trajectory is very much hemlockward.
Here is the problem: one of the horrors of my job is the everpresent risk of being trapped in a collective perplexity with collaborators who are unwilling to confront and grapple with it for what it is. In such situations, one is a participant in an emergent collective being who transcends each individual person. Each person is immersed in the pain that has gripped the group, but is entirely powerless to overcome it alone.
Overcoming the perplexity requires a concerted and coordinated effort.
But many perplexed people behave like drowning swimmers. Instead of cooperating with the lifeguard’s attempt to rescue them, they instead try to climb over the lifeguard’s body to get oxygen. This is why most of lifeguard training is learning break-holds. Often a lifeguard must subdue a drowning person in order to rescue them. If the drowning person gets control of the lifeguard, everyone drowns.
Perplexed people who lack awareness of perplexity instinctively flail and grope for whatever control over the situation they can get, but whatever control they exert only defers and amplifies the confusion and anxiety. Instead of finding a better way to conceptualize the difficulty so it can be framed as a problem, people desperately try to ignore or bypass the perplexity or bludgeon it with mismatched techniques and expertise — and everyone drowns together.
Being is scalar.
Collective being is just as real as individual being.
Collective beings can be perplexed.
Collective beings can also be depressed, anxious, delusional and psychotic.
Entire classes and societies can go mad. Nietzsche said it: “Madness is rare in individuals — but in groups, parties, nations, and ages it is the rule.”
Leadership differs from management in that management treats only systematized parts of organizational life. Leadership participates in the collective being of an organization, addressing its personhood from within — as a part.
I would dearly love to work at an organization that would acknowledge and value my philosophical work. My best work is unappreciated, unsupported, unacknowledged and uncompensated at best. If I speak about what I do and how I think about it, the best I can expect is tolerance, but the usual response is vapid or jocular dismissal and disrespect. “There he goes again.”
Nothing, however, is more respectable and more valuable. I know this even if nobody else does.
This whole age is convulsed in perplexity. People will fight wars before confronting and resolving a perplexity.




