Why Most Plans are Terrible. And How to Improve Them.

It’s Time to Get Comfortable with Uncertainty.

Jake Wilder
Sep 11, 2018 · 7 min read
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“If you fail to plan, you are planning to fail,” was the advice of Benjamin Franklin and every sanctimonious boss that ever lived. Yet what happens when our very plans set us up for failure?

We’ve all heard about the importance of planning. It’s an easy thing to preach, which probably explains why so many people drone on about it. Yet for all of this diatribe, it doesn’t seem as though we’re getting any better at finishing things on time. Whether it’s a new development project, a kitchen remodel, or the time that it should take me to write this article, we’re constantly underestimating the time needed to do our work.

Despite the push to schedule every aspect of our day — and create endless checklists of trivialities — we continue to repeat these same mistakes. Maybe it’s time to try something different. Or just consider whether any of us really know what we’re doing.

“We must become more comfortable with probability and uncertainty.” — Nate Silver

Imagine that we have a bag filled with red and white marbles. Which of the below choices would you prefer to gamble on?

A. Draw a red marble from a bag of 50% red marbles and 50% white marbles.

B. Draw seven red marbles in a row from a bag containing 90% red marbles and 10% white marbles.

C. Draw at least one white marble in seven tries from a bag containing 90% red marbles and 10% white marbles.

As psychology professor Maya Bar-Hillel found out, the majority of people choose B, then A, then C. Yet the actual likelihood runs in the opposite direction, C (52%) — A (50%) — B (48%).

In multiple studies similar to this one, people repeatedly overestimate the probability of conjunctive events and underestimate the likelihood of disjunctive events.

When we consider the likelihood of drawing seven red marbles in a row, we start with the initial probability of 90%. While we all inherently know that probability decreases with compounding events, we rarely adjust to fully account for this impact.

Conversely, we see the 10% likelihood of drawing a white marble and extend this probability across each subsequent opportunity. As with any type of anchoring bias, we struggle to sufficiently adjust from our starting point, skewing our final position and giving us an inaccurate perspective of future probabilities.

So why should you care? Well, not only does this example give you a piece of trivia that’s sure to earn eye rolls at parties, but it also helps show why most of our plans are doomed from the start. We fail to plan for disjunctive events.

“The unexpected always happens — the unexpected is indeed the only thing one can confidently expect. And almost never is it a pleasant surprise.” — Peter Drucker, The Effective Executive

Nothing new is easy. Or simple. Most projects — whether it’s a new product development or an organizational change — contain hundreds of different events that all need to occur for the overall project to succeed.

Each of these projects represents a series of conjunctive events. If a project has 100 different tasks, each with a likelihood of success at 99%, it stands to reason that the overall project will finish on time.

Yet, the probability of these 100 conjunctive events all succeeding is less than 37%. As the total number of events increases, our overall likelihood of success drops significantly.

We rarely know where the problem will occur or which event will fail to happen as planned. And this often causes us to put together success-based plans that don’t account for any deviations. But even though the probability of each event is small, the likelihood that something will go wrong is high. And we ignore this probability at our peril. Or as the great J.R.R. Tolkien pointed out,

“It does not do to leave a live dragon out of your calculations, if you live near him.”

In 1911, two teams of explorers set off to be the first people in history to reach the South Pole. One expedition was led by the Norwegian explorer Roald Amundsen, the other by British naval officer Robert Falcon Scott. Both developed plans and provisions for their trip, yet one ended in success while the other cost the lives of everyone he led.

Amundsen studied the methods of the Eskimos and experienced Arctic travelers to determine the best method to transport his team’s equipment and supplies was by dogsled. He assembled a team of expert skiers and dog handlers and planned a schedule that limited the daily travel to 15–20 miles over a six-hour period, making sure people had plenty of time for rest and recovery. Amundsen stocked supply depots along the way so that his team didn’t need to carry everything throughout the entire trip. He gave his people the best gear possible so they could adapt into different conditions and better handle any issues.

Scott, in contrast, elected to use motorized sledges that ended up breaking down five days into the trip. As a result, his team needed to haul all of their own supplies, exhausting everyone. He also stocked supply depots, but failed to bring extra reserves and his team was constantly short on food and water. Their gear proved to be inadequate for the Antarctic environment and it wasn’t long before every team member had frostbite. One man reportedly needed an hour every morning just to get his boots onto his swollen, gangrenous feet.

When Scott’s team eventually did reach their destination on January 17, 1912, they were greeted by the Norwegian flag and a letter from Amundsen, letting them know that the other team had beaten them by five weeks. Amundsen’s team was well-prepared to deal with the harsh Antarctic environment and they returned safely to their base camp — the worst thing that happened was one team member got an infected tooth that needed to be removed. Scott, on the other hand, failed to prepare his team for the unexpected difficulties they experienced. The elements ultimately became too much for them on the return trip and they died 150 miles from their base camp.

We know Scott’s story from his diary, with some of his last words being, “We took risks, we knew we took them; things have come out against us, and therefore we have no cause for complaint, but bow to the will of Providence, determined still to do our best to the last.”

Scott died blaming the environment for his failure. Yet it was his own preparation and inability to respond to changing situations that cost him and his team their lives.

“In preparing for battle I have always found that plans are useless, but planning is indispensable.” — Dwight D. Eisenhower

In the life-and-death situations surrounding a trek to the South Pole, it’s easy to recognize the importance of accounting for the unexpected. Yet our daily work brings this same need.

Failures are, by definition, unpredictable. The predictable failure never occurs.

If I told you the exact manner by which your project would fall apart, you’d change plans and protect yourself against that risk.

Thus it’s those struggles that we don’t anticipate which ultimately become our downfall — the unknown unknowns that seemingly come out of nowhere to foil our carefully laid plans.

The answer then, I think, isn’t to double down on our obsession with plans. That route only leads to more rigidity. And more misplaced confidence in our perceived chances of success.

Instead, we need to recognize that we don’t have all the answers. Assume that we don’t have a perfect map and prepare ourselves to deal with those surprises — whatever form they take — that will eventually come up.

The purpose of planning then isn’t to develop plans, but options. Options that set us up to adapt to the changing circumstances that are sure to happen.

Challenge your assumptions. Give yourself extra time and resources to manage the unexpected. And ask yourself, what will I do if things don’t go as planned?

As Dylan Evans wrote in Risk Intelligence: How to Live with Uncertainty, describing the essential skill of understanding the limits of our knowledge and using that insight to improve our decision-making,

“Our ability to cope with uncertainty is one of the most important requirements for success in life, yet also one of the most neglected. We may not appreciate just how often we’re required to exercise it, and how much impact our ability to do so can have on our lives, and even on the whole of society.”

There are always more possibilities before us than we can imagine. The best we can do is be ready to change and adapt with them.

A huge thank you to Adam Holownia for animating a previous post of mine, Never Stop Exploring. Choose to be Curious. on his YouTube channel The Art of Improvement. I encourage everyone to check it out as well as the rest of Adam’s fantastic animations and inspirational messages. Cheers!


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Jake Wilder

Written by

Enemy of the Status Quo.


A network of business & tech podcasts designed to accelerate learning. Selected as “Best of 2018” by Apple. Mission.org

Jake Wilder

Written by

Enemy of the Status Quo.


A network of business & tech podcasts designed to accelerate learning. Selected as “Best of 2018” by Apple. Mission.org

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