Author Tom Robbins died on February 9, 2025 at the age of 92 and it made me think of what he would have thought about the comical absurdity of Square Wheels®.

He was one of my favorite authors. So I asked Perplexity to share what his perspectives might be and the output was amazing for how his wordy-humor would apply to the main ideas around the Square Wheels theme of continuous continuous organizational improvement. I hope you love this as much as I do. So, here we go:

Tom Robbins, the master of whimsical prose and thought-provoking metaphors, would likely have found the Square Wheels images to be a delightful playground for his unique brand of wordplay humor and insight. Known for his ability to “bang the Language Wheel like a gong”, Robbins would have undoubtedly crafted a narrative that both amusing and enlightening, using Square Wheels as a springboard for his signature style of whimsical, philosophical musings. He would definitely generate a Think Different with this stuff!

And, man, would I have loved to have had that conversation with him about the IP. His books are fabulous and one of my favorite quotes, to set the tone here, was “Man was invented by water as a means of transporting itself from one place to another.” from his book, Another Roadside Attraction. Metaphors and perceptual shifts, for sure.

We Begin His Unique Perspectives

So much is about our perception of reality of how things wheels work…

Robbins might have started by describing this workplace scene with one of his characteristically vivid metaphors:

“Our square-wheeled wagon lumbered across the landscape like a drunken geometry teacher’s fever dream, each rotation of a wheel a defiant act against the smooth tyranny of circles.”

(Think of how the above might apply to the workings of most organizations!)

He would likely have reveled in the highly paradoxical nature of the Square Wheels, seeing in them a reflection of life’s inherent contradictions. Robbins once wrote, “Humanity has advanced, when it has advanced, not because it has been sober, responsible and cautious, but because it has been playful, rebellious, and immature”. In this spirit, he would certainly have viewed the Square Wheels as a metaphor for human progress and organizational development:

Robbins’ prose often dances on the edge of ludicrous absurdity, using humor to illuminate deeper truths. He might have described the mud in which the square-wheeled wagon struggles (as depicted below) as:

“A primordial soup of possibility, each squelch and splatter a cosmic giggle at the audacity of motion. The mud wasn’t an obstacle; it was nature’s own laugh track, applauding the square wheels’ ridiculous rebellion against progress. It was grinding paste to the normalcy of organizational improvement.“

Two km of ditch for every km of road and is it mud or grinding paste?

As for the Spectator Sheep in the above image, Robbins would likely have seen in them a reflection of society’s tendency to observe and criticize rather than participate. He might have quipped:

“The sheep stood by, their woolly heads tilted in collective bewilderment, as if watching the birth of a new, cubist universe. They were the ultimate critics, those sheep – all fleece and no action, bleating their doubts from the sidelines of progress.”

“Yet don’t be fooled by their placid expressions and monotonous bleating. Those sheep are the universe’s own focus group, their collective gaze the weight by which all innovations are measured. They may not push the cart, but their watching is an act of creation in itself.”

“In this grand cosmic comedy of life, Square Wheels are the joke, mud is the punchline, and the sheep – well, the sheep are us, learning to laugh at the crazy divine absurdity of it all. And in that laughter, my friends, lies enlightenment and change.”

Spectator Sheep: pretty easily identified…

More of Robbins Quips and Quotes about how things “wheely” work:

In the spirit of Robbins’ style, here are some original quotes he might have crafted about wheels, mud, and spectator sheep:

• “Square Wheels are nature’s way of reminding us that the shortest distance between two points is rarely the most interesting.”
• “In the grand comedy of evolution, Square Wheels are the punchline that keeps on giving, long after the round ones have rolled off into the sunset of mediocrity.”
• “Mud is Earth’s way of saying, ‘Slow down, you crazy diamond-dreamers. Let’s see what kind of beautiful mess we can make together.'”
• “The spectator sheep, my dear, are the universe’s own Greek chorus, bleating out the fears and doubts we’re too proud to admit ourselves. But remember, even sheep can grow wheels if they dare to dream in squares.”
• “If life hands you Square Wheels, make a geometric symphony. The mud will provide the percussion, and the sheep will eventually join in, once they realize harmony is more fun than humdrum.” 

Robbins’ unique perspective often involved finding profound meaning in the seemingly absurd much like but different from Steven Wright. He might have seen the Square Wheels as a metaphor for the human condition:

“We’re all pushing our square-wheeled wagons, you see. Each of us, lumbering through the mud of existence, our progress marked not by smooth revolutions but by the staccato thumping of corners meeting earth. It’s in those jolting moments, those brief pauses between movements, that we find our truth – and if we’re lucky, our laughter”.

The author’s love for paradox and irony would have found fertile ground in this metaphor and his writings often touched on themes of transformation and liberation. He might have seen Square Wheels as a symbol of breaking free from conventional thinking in the elements of spirituality and cosmic consciousness:

“Those square wheels aren’t just moving a wagon; they’re thumping right over our preconceptions. With each awkward turn, they’re suggesting we move from the tyranny of the circle, the dictatorship of the bumps. They’re saying, ‘Hey, who decided square was right anyway?’ They are getting us to look at the world differently.“

The author’s penchant for challenging societal norms and expectations would likely have led him to champion the cause of the square-wheeled wagon and our available round possibilities — his writings often explored the intersection of the profound and the profane. He might have seen in the Square Wheels a metaphor for the human quest for meaning and improvement:

“Every rotation of those square wheels is a koan, a riddle without an answer. They ask us, ‘What is the sound of four wheels thumping?’ And in our struggle to answer, we find ourselves moving forward and up, however awkwardly, towards some semblance of understanding as they force us to think of things differently.”

What’s his Final Take on Organizations and Square Wheels?

“Using Square Wheels, my intrepid innovators, is the organizational equivalent of wearing clown shoes to a marathon – ridiculous, impractical, and guaranteed to make you the subject of much bewildered flubberwocking.

We’re out there, grunting and grinding, convinced this bumpy ride is our best way forward while the universe holds its sides laughing. Why? Because the round wheels—those smooth-rolling quintessential paradigms—are already in your wagon, sipping metaphorical margaritas and waiting for us to catch a glimpse.

Do we notice? Bless our hearts, NO! We’re too busy canonizing our struggles, worshiping the grind, and clinging to our square realities like a toddler grips their favorite blanket. It’s as if we’re convinced that unless our teeth are rattling and our brains are concussed, we’re not genuinely producing. Meanwhile, lots of potential solutions are taking a nap.

The moral of our waggish tale? Life’s not about muscling through; it’s about eye-spying the obvious. Sometimes, all it takes is a pause, a stepping back, so we can see the better solutions that have always been there so that we can better enjoy that journey forward. 

And if you can make those sheep laugh in the process, well, that’s when you know you’ve really got the wheel thing worked out.

Lastly, remember this:

Those Round Wheels of Today will be the Square Wheels of Tomorrow!”

Fun Funny stuff, huh??? More to come. See also Lenny Bruce and Steven Wright and George Carlin and some other Funny Thoughts on Square Wheels.

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For the FUN of It!

Dr. Scott Simmerman is a designer of team building games and organization improvement tools.
Managing Partner of Performance Management Company since 1984, he is an experienced presenter and consultant who is trying to retire!! He now lives in Cuenca, Ecuador.

You can reach Scott at scott@squarewheels.com
Learn more about Scott at his LinkedIn site.

Square Wheels® are a registered trademark of Performance Management
and cartoons have been copyrighted since 1993,

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