The Worst Case Scenario: Why It Helps to Prepare for the Worst

Critical Thinking
6 Minute
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Thinking about a worst case scenario takes me to a time I’d rather forget.

A family walk isn’t supposed to be the moment you regret not preparing for the worst. And yet, here I was standing in front of a plateau of bogy marshland with no clear path through it. It was getting dark and beginning to rain. We—my wife and two kids—were not prepared for this. With preparation, I may well have considered this outcome as our worst case scenario.

A thousand feet up, high above the village with no waterproof coats, torches, water, and no map or compass. The phone signal was non-existent, and the battery was running low. No one could have been more unprepared than we were.

Not only were we lost, but we were cold, wet, and scared.


What does worst case scenario mean?

Consider a situation where everything goes wrong. But rather than experience it, you imagine it—and capture it, hoping to avoid it in the future. This is the worst case scenario. A vision of the future you’d rather not have to experience.

Experience has taught us we can avoid the worst of outcomes.


“I am prepared for the worst, but hope for the best.”—Benjamin Disraeli


Considering the bad outcome offers opportunities.

We get to consider what might cause such a difficult situation. But we also get the chance to prepare for such an outcome, making its consequences easier to live with. We can, as Benjamin Disraeli said: "Prepare for the worst but hope for the best."

History offers us many ways to consider the prevention of such predicaments. One is a motto from the scouts, and the other is a business concept called the pre-mortem.


Be Prepared

The Scouts live by a famous motto: “Be Prepared”.

Being prepared means being ready for any potential outcome, both good and bad. Baden-Powell writes in Scouting for Boys: “by having thought out beforehand any accident or situation that might occur, so that you know the right thing to do at the right moment and are willing to do it.”

A good scout checks the weather before starting a walk. They will know whether a sun hat or a woolly hat and gloves need to be on the equipment list before they leave. Exposure to warm or cold weather is easily managed when you're prepared.

“There's no such thing as bad weather, only unsuitable clothing.” Said Alfred Wainwright.

The motto transcends life, as you might expect when such a phrase is taught to so many of us. From the girl guides to the scouts, the motto is a mantra we all remember. In practical terms, I found myself on my activities as scout where being prepared resolved many potentially bad situations.

Simple things, like carrying a first-aid kit in case someone had an accident saved many small cuts from turning septic.


The pre-mortem

Companies use a worst case scenario to help them avoid failure.

Post-mortems are the after-action reviews. They are deeply rooted in business culture and offer a means to look back at what happened. Regardless of the outcome, our biases will create narratives that change our view of the past. And of course, although learning after an event is good for the future, we have no means to correct the past.

What we can do is undertake a pre-mortem and consider a potentially critical situation.

Shreyas Doshi, a start-up advisor with experience from Stripe, Twitter, Google and Yahoo offers a great thread on the topic. He argues: “The best way to describe a pre-mortem is that if you do it right, you won’t need to do a tough post-mortem.”

A pre-mortem is an essential tool in a product manager's toolkit.

During a project, the team pauses and imagines it has failed. Working backwards, the team assesses potential causes highlighting flaws in the current project.

Armed with this information, they can prevent the project from failing in the future.


Lost—A Difficult Situation

Back on the hillside, we managed to get hold of mountain rescue.

Contrary to their advice, and after standing still and becoming colder by the second, we decided to try and retrace our steps. We had somehow looped around a secondary summit and as we walked down from it, so we found the path we had earlier been on.

Our relief was temporary.

The path was rocky, and with the falling rain walking was more like skating on black ice. We knew we had a tough walk ahead of us, and we knew we had no choice but to keep walking.

A shrill noise lifted our heads to look down the hill rather than at our next step. Torchlight punctured the mist and rain as the whistles grew louder.

It was one of the mountain rescue teams.

The lecture from the rescue leader was a painful ear bashing for me.

It’s why I’m writing this piece.

I was a scout for fourteen years. The motto, ‘be prepared’ could have been a tattoo on my soul—or so I thought. I dealt with potential worst case scenarios at work and planned to overcome them.

But here, with my family out on a walk in Snowdonia, I messed up.


Why You Need to Prepare for the Worst

We are all fallible.

Arrogance, along with a false belief in our talents lets us dodge the hard work of thinking. Extreme confidence prevents us from considering potential worst case scenarios. Impulsiveness is another.

It’s hard work contemplating a worst case scenario. It opens a window into uncertainty and forces us to dwell on outcomes we don’t want to experience. Our intuition says it knows better. It uses the stories we tell ourselves to believe in statements that, with a little inspection, show themselves not to be true.

Don’t expose yourself to the myth that planning is bad. It isn’t procrastination if it adds value.

If you don’t prepare for the worst, you may well end up having to deal with the dilemma it creates. To prevent yourself from ending up in such a situation is easy.

All it takes is planning.


The Essence of Good Planning

Planning gets a bad press these days. Urged to act now, we have to decide quickly and move fast. Planning is procrastination. It’s thinking about it, rather than doing it. This is all well and good, but sometimes, as I discovered, acting without planning can get you into lots of trouble. Benjamin Franklin once said: “Failing to plan is planning to fail.” He isn’t wrong.

Planning leads us to the future. It’s all about the goals we want and how we will achieve them. There is great comfort in undertaking planning as it offers a way for us to dodge the spectre of uncertainty. A future foretold is one wrapped in certainty—and plans give us this in spades.


“Imagining what could go wrong doesn’t make you pessimistic. It makes you prepared.”—Shane Parrish

Good planning goes further than preparing for success.

Good planning shows us the future we want but can also give us a sight of the future we don’t. It is the home of the worst case scenario. It is so easy to imagine a world where we are successful and realise our goals. But often this comes from avoiding the opposite.

Good planning lets you consider good and bad outcomes. Imagining both isn’t a flaw of a bias against optimism or pessimism—it is, as Shane says, good preparation.

Planning, it transpires comes in many forms.

Worst case scenario thinking occurs when we are prompted to plan. Whether it be a motto or a business process, both compel us to begin a process of critical thinking.

If it helps you avoid the worst, then that's all that counts.

Photo by Nathan Dumlao on Unsplash

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