EXAMPLES

UhOhology™ Examples:

Real-World Mistakes Through the Lens of Three Core Questions

Every UhOhology example starts with a simple idea:
you don’t have to make a mistake yourself to learn from it.

Below, you’ll see three core UhOhology questions — patterns that show up again and again in real-world business, operational, and leadership failures.

Under each question are three publicly reported Uh-Oh! mistakes, drawn from my book uh-oh! and past UhOhology newsletters. Each example is presented using the two-step UhOhology method:

(1) Observe & Understand — what actually happened, and why it mattered

(2) Think & Apply — how the same risk pattern could show up in your business

You can read these examples straight through, or jump to the question that feels most relevant to you right now. Each example is intentionally concise but complete — enough context to observe and understand what happened, followed by a prompt to think and apply the lesson to your own business.

Key Question #1:

“What is the one thing in my business that, if ever forgotten even once, could lead to disaster for me/us?”

Example 1 — The 10,000-Foot Fatal Freefall 

Observe & Understand:

Ivan McGuire was an experienced skydiver and cameraman filming a tandem jump. His role was to exit first, stabilize in freefall, and film the couple as they jumped behind him.

He exited the aircraft, positioned himself, and successfully captured the footage. Then he reached for his ripcord—and realized there was none. He had forgotten to put on his parachute before boarding the plane.

McGuire’s attention was focused on completing a secondary task — getting the shot — and the most basic requirement was assumed to be already handled.

Reference: uh-oh!  (book) Part Three → Epic-Fail Uh-Oh! Blunders → “The 10,000-Foot Fatal Freefall” (p. 91)

Think & Apply:
What is the equivalent “non-negotiable step” in your business—one that must never be skipped, even once?

Example 2 — Two Costly Lapses in Focus (Football + Airport)

Observe & Understand:

This example comes from two short reports in a recent UhOhology newsletter—one from a football game and one from an airport. In both, the mistake wasn’t lack of skill. It was a brief lapse in attention at the exact wrong moment.

In the NFL story, a player had a clear path to score. But before the play was fully finished, he relaxed—celebrating early—and the ball came loose before the score was secured. A near-certain touchdown flipped into a turnover.

In the airport story, a crew member working at the jetbridge made a routine-looking but high-consequence mistake and accidentally triggered an emergency slide deployment. The slide inflated, created damage and delays, and turned a normal ground operation into a costly, very visible incident.

Both stories share the same pattern: a moment of “autopilot” during routine action—followed by consequences that were anything but routine.

Reference: UhOhology Newsletter — October 2025

Think & Apply:
Where in your business do people (including you) tend to “relax early”—assuming the job is basically done—when one final step still carries real risk?

Example 3 — When One Extra Keystroke Risked $ Trillions

Observe & Understand:

This one is a “how is that even possible?” mistake: Citibank accidentally credited a customer’s account with $81 trillion—when the intended entry was $280. Not a scam. Not a cyberattack. A real transaction error—inside one of the world’s largest banks.

Here’s the part that matters most: the mistake was reviewed and approved—twice. It took a third employee, about 90 minutes later, to notice the amount was wildly wrong.

The transaction was reversed before any money left the bank—but the incident was still serious enough that Citi had to report it to regulators. Your point lands: this wasn’t “fancy tech failure.” It was a human-scale error with absurd-scale consequences.

Reference: UhOhology Newsletter — December  2025

Think & Apply
What’s the equivalent “$81 trillion vs. $280” risk in your business—where one digit, one default, or one unchecked field could turn a normal action into a catastrophic one (pricing, payroll, inventory, refunds, ad spend, wire transfers, tax payments, etc.)?

Key Question #2:

“If this mistake didn’t happen all at once, how did risk quietly build over time—and where could that same accumulation be happening in my business?”

Example 1 — When Small Assumptions Stack into a Big Loss: Hoover UK’s Free Flights Promotion

Observe & Understand:

In the early 1990s, Hoover UK ran a promotion offering free transatlantic flights to the United States to customers who purchased certain household appliances.

The problem wasn’t the idea itself—it was the economics. The actual cost of the airline tickets far exceeded the profit margin Hoover typically earned on each appliance sale. When demand surged, the promotion became financially disastrous.

No single assumption caused the failure. Instead, several “reasonable” assumptions stacked:

Demand would be modest

Redemption rates would be low

Fulfillment costs would stay manageable

Together, those assumptions quietly built risk until the promotion overwhelmed the business.

Reference: uh-oh! (book) Part Three → Epic-Fail Uh-Oh! Blunders → “The Free_Flight Giveaway that Crashed a Company” (p. 95)

Think & Apply
Where in your business do individually reasonable assumptions—about demand, cost, usage, or behavior—quietly stack in ways that could flip a good idea into a bad outcome as volume grows?

Example 2 — When Risk Accumulates and No One Stops the Process (Identity errors that should have triggered a halt—but didn’t)

Observe & Understand:

In two unrelated but strikingly similar real-world cases, funeral homes mixed up bodies—resulting in the wrong person being cremated or buried.

In each case, small breakdowns appeared early: paperwork mismatches, unclear handoffs, missing confirmations, or assumptions that someone else had already verified identity. None of these issues, on their own, seemed catastrophic.

But instead of triggering a mandatory stop for verification, the process kept moving forward.

Once the body was transferred, prepared, and ultimately cremated or buried, the mistake became permanent. What began as a manageable discrepancy turned into an irreversible outcome—not because no one cared, but because the system allowed uncertainty to compound without intervention.

These failures weren’t about a single dramatic error. They were about risk accumulating quietly over multiple steps, with no designed point where the process had to pause and confirm correctness.

Reference: UhOhology Newsletter — February 2025 

Think & Apply
If this mistake didn’t happen all at once, but built up step by step, where could risk be quietly accumulating in your business—and where should a hard stop exist, but doesn’t?

Example 3 — When Small Conditions Quietly Stack Until Failure (Risk accumulation you don’t notice until it’s too late)

Observe & Understand:

Every Thanksgiving, fire departments respond to house fires caused by deep-frying turkeys. These fires aren’t triggered by one dramatic error.

Instead, they happen when multiple small risk factors quietly align:
the oil is overheated,
the turkey isn’t fully thawed,
the fryer is placed too close to a structure,
or the pot is slightly overfilled.

Any one of these might be survivable. Together, they create a predictable ignition point. Once the turkey is lowered into the oil, the outcome unfolds in seconds—and there’s no meaningful chance to intervene.

The mistake isn’t reckless intent. It’s normalizing risk step by step until conditions cross a threshold.

The UhOhology lesson is that many business failures unfold the same way: not from a single bad decision, but from a series of small compromises, assumptions, or “we’ll fix that later” choices that quietly stack the odds against you.

Reference: UhOhology Newsletter — November 2025

Think & Apply
Where in your business are small shortcuts, temporary fixes, or unresolved assumptions quietly accumulating risk—without a clear moment where someone is required to stop and reassess

Key Question #3:

“If someone sensed something was wrong but didn’t stop the process here, where could that same hesitation exist in my business—and what’s at stake if it continues?”

Example 1 — When No One Stopped the Show – The 2017 Oscars: Wrong Best Picture Announced

Observe & Understand:

At the end of the 2017 Academy Awards ceremony, the presenters opened the envelope for Best Picture and announced the wrong winner. La La Land was named—when in fact Moonlight had won.

Almost immediately, signs of a problem were visible. The La La Land producers hesitated. People on stage looked confused. Behind the scenes, others realized the wrong envelope had been handed to the presenters.

But for several long moments, no one stopped the process.

The acceptance speeches continued. The mistake unfolded live on television before the announcement was finally interrupted, corrected, and reversed in front of a global audience.

This wasn’t a failure of talent or preparation. It was a failure to intervene decisively once something felt wrong, in a high-pressure, public moment.

Reference: uh-oh! (book) — Part Three: Epic-Fail Uh-Oh! Blunders → “The Do-Overs that Shocked The Entertainment World” (p. 84)

Think & Apply
Where in your business might someone recognize that “this doesn’t seem right”—but hesitate to interrupt momentum because the moment feels too visible, too fast, or too awkward to stop?

Example 2 — When No One Stopped the Launch – The Challenger Disaster

Example 3 — When a Known Risk Isn’t Stopped in Time — The Francis Scott Key Bridge Collapse

UhOhology Newsletter Library

Below is an archive of every UhOhology™ newsletter published to date, listed with the most recent issue first. Each issue examines a real, publicly reported mistake and applies the UhOhology method to surface transferable lessons for founders and small business owners.

You can scan the summaries, open the full issue, or return anytime when a new example catches your attention.