The Pivot Paradox

Why constant reinvention is both vital—and a sign you may have no idea what you're doing

Once upon a time, to pivot meant something rather graceful. Dancers did it. Basketball players did it. Generals, occasionally, did it—sometimes with disastrous consequences. In business, however, the pivot arrived late, as Silicon Valley’s polite euphemism for “We got it wrong but would prefer not to say so.”

The term entered the managerial bloodstream sometime after the 2008 financial crisis, gaining prestige through Eric Ries’s 2011 book The Lean Startup. There, pivoting was rebranded as the scientific method in action—a bold manoeuvre rather than a flailing course correction. Where once failure was something to be hidden in a footnote, now it became validated learning, which sounds better on a slide deck. The pivot, in this telling, was not desperation. It was enlightenment in hoodie form.

Suddenly, everyone was pivoting. Messaging apps became workplace tools. Grocery delivery startups became “dark kitchen platforms.” Dating apps for pets turned into “AI-enabled pet wellness ecosystems.” Entrepreneurs discovered that with enough abstraction and enough pitch decks, any product could become a platform, and any pivot could be called “strategic repositioning.” Like overenthusiastic philosophers, they kept changing their ontology while hoping no one would notice the epistemological mess.

But as Nassim Nicholas Taleb might remind us, what the Silicon Valley set calls “pivoting,” the rest of the world might call optionality, or—less charitably—fragility in disguise. A robust system does not require constant change to remain viable. A truly antifragile one thrives under volatility because its core assumptions are built on skin in the game, not just slideware.

As Taleb puts it:

“If you see fraud and do not say fraud, you are a fraud.”

He might have added: if you see a business change its core model every quarter and still call it visionary, you may be looking at someone who is playing roulette with other people’s chips. Optionality is not the same as directionlessness. The former allows for adaptation under uncertainty. The latter is simply indecision dressed in Patagonia fleece.

This is the pivot paradox. In an era where permanence is suspect and flexibility is a virtue, the ability to shift gears is essential. But too much pivoting becomes a symptom of chronic insecurity, or worse, of building a business on a foundation so vague it can support anything—except revenue.

The confusion arises, in part, from a misreading of evolution. Startups like to fancy themselves as agile organisms in a Darwinian landscape. But biological evolution works through selection, not constant mutation. Organisms don’t try a new strategy every week. They double down on what works, and quietly go extinct when it doesn’t. Markets, unfortunately, aren’t so merciful.

Founders, meanwhile, are taught to treat every failed prototype as “feedback.” This leads to a peculiar strain of corporate existentialism: the belief that meaning will emerge from iteration alone. But this is how you end up with a series of disconnected experiments rather than a coherent company.

A good pivot is like a chess move. It’s calculated, directional, and based on new information. A bad pivot is like playing Twister blindfolded, hoping the next awkward stretch will somehow land you on “scale.”

The irony, of course, is that the businesses that don’t pivot are often those built on old-fashioned, inconveniently unscalable things like real revenue, genuine customer need, and unit economics that don’t require heroic assumptions. But such models rarely win TechCrunch Disrupt. They do, however, tend to endure.

So yes, pivot. But before you do, consider whether your wheel is attached to anything. As Taleb might say, the road to robustness is paved with exposure, not experiments. Strip away the jargon, and sometimes a pivot is just another word for flailing. Or, worse, fundraising.

Choose your movements wisely. After all, if you pivot long enough, you may find you’ve done a full circle—and landed right back where you started. Only this time, with more debt.