My name is Graham, and I’ve spent my career collecting, re-shaping and applying stories. I’m also an engineer with almost two decades of experience. There’s more overlap there than you might suspect.

Stories help us make sense of a vast, weird, and frequently overwhelming world. They aren’t just passive aids to understanding. The stories we tell each other and the ones we tell ourselves actively shape the way we operate. They are alive.

Even the technical realm is subject to this influence. Product decisions are made by people, for people, and so to make the right calls we need to properly understand competing perspectives while maintaining the right level of trust in our own story.

In 2016, Apple decided to drop the venerable 3.5mm headphone jack from the iPhone 7. To say this led to some pushback would be an understatement. Tech journalists fumed while droves of outraged customers signed doomed petitions. Somehow the option of buying a jack-restoration dongle ($29) did little to calm the discourse.

Another company might have looked at the response to the early rumours and had second thoughts. Apple doubled down, with then-marketing chief Phil Schiller invoking the c-word:

“[The decision to remove the headphone jack] comes down to one word. Courage. The courage to move on and do something better for all of us.”

The derision that followed showed that that courage was necessary. By removing a key aspect of how users interacted with their phones, Apple risked not just significant backlash to a key product launch but to the ‘it just works’ consumer narrative that they’d been nurturing with barely a hiccup for the better part of 15 years.

Interfering with their users’ headphones was no mere hiccup. Headphones are one of the few gadgets that can rival Apple’s lineup for raw affection, and suddenly the two were at war. Apple’s explanations for their decision — more space for cameras and batteries, improved water resistance — were fair enough, but also felt a little forced.

This is because they were. The death of the headphone jack wasn’t really about engineering tradeoffs. It was instead a natural consequence of the consumer narrative we discussed earlier. Because with every customer seduced into Apple fandom and every wildly successful product launch, their internal story was gaining momentum:

“We know what the future looks like, and we’re going to take you there.”

The lesson seems obvious. Over its period of unmatched success, Apple earned the confidence to placidly defy not just its critics but its own consumers. In retrospect they were obviously right. Wired headphones are more or less extinct, AirPods are ubiquitous, and absolutely nobody is clamouring for the return of the headphone jack. Apple made a bold call, stuck to their guns, and their bet paid off.

But what if it hadn’t? No matter how considered their decision-making process, every company makes mistakes. What interests me most about the launch of the iPhone 7 isn’t the success but the potential for failure. There must have been internal discussions about the signals that might tell them their call was wrong. What were they? What would it have taken to shake Apple’s courage?

The gamble on jack removal was perhaps not quite as risky as it looked to outsiders, since Apple would have had some idea about the improving reliability of Bluetooth, the quality of the incoming AirPods, and so on, but there was still some possibility of serious failure, no matter how small. Apple didn’t let that stop them. When you’re betting on the future, some appetite for risk is a given, and the probabilities would have felt comfortable.

But ideas do not succeed or fail in purely probabilistic terms. The standard language of risk management — tolerance, chance, etc — can elide an important mechanism for thinking about how they do fail: falsifiability.

When is the risk of failure actually realised? And how do you recognise that moment? Apple have every right to be confident and locked in on their vision of the future, but as anyone unfortunate enough to have used a butterfly keyboard will tell you, even the most well-earned confidence can prove misplaced.

Every decision-maker will think about risk and the consequences of being wrong. Every decision-maker is equally alert for signs of success. It is far less common and much more difficult to identify and actively seek out the signals of failure. Refusal to lay down the groundwork of falsifiability, however, means that when failure comes — and it will — the courage that wears victory so lightly might look more like denial.

Because the stories we tell ourselves are all to some degree wrong. Working out how they might be wrong and when they might be wrong matters more than the mere fact of wrongness; the foundation of sustained success lies in identifying, admitting, and fixing mistakes. Turns out “kill your darlings” isn’t just writing advice.