On Uncertainty, the Perks of Impostor Syndrome and Other Thoughts on Change, Elephants and Tortoises (Post 1 of 3)
On the impossibility of certainty and why that’s liberating.
In 1910, two Cambridge philosophers set out to prove that 1+1=2.
Not approximately. Not intuitively. Prove it, from pure logic, with absolute certainty, so that no reasonable person could ever doubt it again.
It took them 362 pages. The project consumed a decade. Bertrand Russell later admitted he used to stand on a footbridge near Oxford, watching trains pass, thinking about stepping in front of one.
Why would anyone do this?
Because Russell wanted certainty — and that’s an addiction, the way some people want faith. Mathematics, clean and undeniable, might be the one place where humans could finally know something for sure.
Here is what happened next:
Having constructed an elephant upon which the mathematical world could rest, he found the elephant unstable. So he built a tortoise to keep it from falling. But the tortoise was no more secure. Twenty years later, he concluded there was nothing more he could do to make mathematical knowledge indubitable.
Elephants all the way down.
I think about this often. Not because I worry about mathematical proofs, but because I have spent twenty years in banking, an industry that builds elephants professionally.
And this story calms me down. I surrender at the gate and accept the beautiful chaos as given, letting go of any need to control.
Every risk model is an elephant. Every compliance framework is a tortoise beneath the previous elephant. Every strategic plan is another layer, meant to create the certainty regulators demand, boards expect, and executives need to sleep at night.
And then 2008 happens. Or a pandemic. Or a war.
I was CIO of a bank in Ukraine when Russia invaded. The risk models did not have a line item for “tanks crossing the border.” We had built our elephants carefully, professionally, and expensively.
They shook anyway.
Twenty years after Russell and Whitehead published their proof, Kurt Gödel proved something devastating: Any system complex enough to do basic arithmetic will contain true statements that cannot be proven within that system.
Not “might contain.” Will contain. Mathematically guaranteed. Russell project was impossible from the start. You cannot create a system that is both complete and self-validating.
Russell’s response was remarkable: “Dr. Gödel’s great ability makes me think it highly probable that many of his criticisms of me are justified.”
The desire for total control is not ambitious. It is impossible.
Every layer of controls creates new uncertainties. Every model that “captures risk” freezes a moment while reality keeps moving. This is not pessimism. This is the beginning of something better.
Russell said the value of philosophy is found largely in its uncertainty. The person without philosophy goes through life imprisoned by assumptions. Unfamiliar possibilities are rejected.
In that sense, the tower of AI is built on its own hierarchy of tortoises and elephants, above mathematics and theory. Before AI comes for our brains, it first has to understand itself — and that seems not to be a trivial task.
Russell wrote this as fascism rose across Europe. His observation from 1933: “The fundamental cause of the trouble is that in the modern world the stupid are cocksure while the intelligent are full of doubt.”
Sound familiar?
The paradox of leadership: the people most attuned to uncertainty are least likely to project the confidence that organizations demand. We promote the cocksure. We celebrate the decisive. We build cultures where admitting you don’t know feels like weakness.
And then we puzzle why our elephants shake.
Many successful leaders carry private doubts that they rarely voice in public.
Not impostor syndrome. Something more honest. The awareness that they are making consequential decisions with incomplete information, under time pressure, while pretending more confidence than they feel.
Seneca wrote that no wind is favorable to the sailor who doesn’t know which port he sails toward. True. But Russell has a darker version: sometimes we don’t even know we’re on a ship.
The most dangerous knowledge in transformation is the knowledge you think you have. The budget you “know” is accurate. The competitor you “know” is two years behind.
Like Taleb’s turkey, or Russell’s chicken, fed every day of its life. Each day, confidence in the farmer grows. On the day when confidence reaches its maximum, the farmer cuts its neck. The crisis of 2008, and many current events, are chicken-neck-cutting events.
So what does this mean?
Humility is a strategic advantage, not a weakness to hide.
Building organizations that adapt when elephants shake matters more than building elephants that seem stable.
Leaders who create safety for people to say “I don’t know” will outperform leaders who demand certainty.
Whitehead, Russell’s collaborator, developed a philosophy of process — reality as events, becoming, continuous change. He said the art of progress is to preserve order amid change, and to preserve change amid order.
Both. Simultaneously.
And he offered this warning, written in 1927:
“The major advances in civilization are processes which all but wreck the societies in which they occur.” The advances and the destruction are inseparable. The question is not how to avoid the wreck but how to navigate it.
Each transformation is a condition, not a project. I don't know what will emerge. Anyone who tells you they know is, at best, unaware of their limitations.
What I do know is that the leaders who acknowledge uncertainty — who hold their plans lightly, who listen for signals that their assumptions are wrong — will navigate better than those who insist on certainty.
The elephants will shake. That is not a prediction; it is a mathematical fact about complex systems.
….continue to part 2
On Uncertainty, the Perks of Impostor Syndrome and Other Thoughts on Change, Elephants and… was originally published in DataDrivenInvestor on Medium, where people are continuing the conversation by highlighting and responding to this story.
