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Unlikely Optimism: The Conjunctive Events Bias

Reading Time: 5 minutes

When certain events need to take place to achieve a desired outcome, we’re overly optimistic that those events will happen. Here’s why we should temper those expectations.

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Why are we so optimistic in our estimation of the cost and schedule of a project? Why are we so surprised when something inevitably goes wrong? If we want to get better at executing our plans successfully, we need to be aware of how the conjunctive events bias can throw us way off track.

We often overestimate the likelihood of conjunctive events—occurrences that must happen in conjunction with one another. The probability of a series of conjunctive events happening is lower than the probability of any individual event. This is often very hard for us to wrap our heads around. But if we don’t try, we risk seriously underestimating the time, money, and effort required to achieve our goals.

The Most Famous Bank Teller

In Thinking, Fast and Slow, Daniel Kahneman gives a now-classic example of the conjunctive events bias. Students at several major universities received a description of a woman. They were told that Linda is 31, single, intelligent, a philosophy major, and concerned with social justice. Students were then asked to estimate which of the following statements is most likely true:

  • Linda is a bank teller.
  • Linda is a bank teller and is active in the feminist movement.

The majority of students (85% to 95%) chose the latter statement, seeing the conjunctive events (that she is both a bank teller and a feminist activist) as more probable. Two events together seemed more likely that one event. It’s perfectly possible that Linda is a feminist bank teller. It’s just not more probable for her to be a feminist bank teller than it is for her to be a bank teller. After all, the first statement does not exclude the possibility of her being a feminist; it just does not mention it.

The logic underlying the Linda example can be summed up as follows: The extension rule in probability theory states that if B is a subset of A, B cannot be more probable than A. Likewise, the probability of A and B cannot be higher than the probability of A or B. Broader categories are always more probable than their subsets. It’s more likely a randomly selected person is a parent than it is that they are a father. It’s more likely someone has a pet than they have a cat. It’s more likely someone likes coffee than they like cappuccinos. And so on.

It’s not that we always think conjunctive events are more likely. If the second option in the Linda Problem was ‘Linda is a bank teller and likes to ski’, maybe we’d all pick just the bank teller option because we don’t have any information that makes either a good choice. The point here, is that given what we know about Linda, we think it’s likely she’s a feminist. Therefore, we are willing to add almost anything to the Linda package if it appears with ‘feminist’. This willingness to create a narrative with pieces that clearly don’t fit is the real danger of the conjunctive events bias.

“Plans are useless, but planning is indispensable.” 

— Dwight D. Eisenhower

Why the best laid plans often fail

The conjunctive events bias makes us underestimate the effort required to accomplish complex plans. Most plans don’t work out. Things almost always take longer than expected. There are always delays due to dependencies. As Max Bazerman and Don Moore explain in Judgment in Managerial Decision Making, “The overestimation of conjunctive events offers a powerful explanation for the problems that typically occur with projects that require multistage planning. Individuals, businesses, and governments frequently fall victim to the conjunctive events bias in terms of timing and budgets. Home remodeling, new product ventures, and public works projects seldom finish on time.”

Plans don’t work because completing a sequence of tasks requires a great deal of cooperation from multiple events. As a system becomes increasingly complex, the chance of failure increases. A plan can be thought of as a system. Thus, a change in one component will very likely have impacts on the functionality of other parts of the system. The more components you have, the more chances that something will go wrong in one of them, causing delays, setbacks, and fails in the rest of the system. Even if the chance of an individual component failing is slight, a large number of them will increase the probability of failure.

Imagine you’re building a house. Things start off well. The existing structure comes down on schedule. Construction continues and the framing goes up, and you are excited to see the progress. The contractor reassures you that all trades and materials are lined up and ready to go. What is more likely:

  • The building permits get delayed
  • The building permits get delayed and the electrical goes in on schedule

You know a bit about the electrical schedule. You know nothing about the permits. But you bucket them in optimistically, erroneously linking one with the other. So you don’t worry about the building permits and never imagine that their delay will impact the electrical. When the permits do get delayed you have to pay the electrician for the week he can’t work, and then have to wait for him to finish another job before he can resume yours.

Thus, the more steps involved in a plan, the greater the chance of failure, as we associate probabilities to events that aren’t at all related. That is especially true as more people get involved, bringing their individual biases and misconceptions of chance.

In Seeking Wisdom: From Darwin to Munger, Peter Bevelin writes:

A project is composed of a series of steps where all must be achieved for success. Each individual step has some probability of failure. We often underestimate the large number of things that may happen in the future or all opportunities for failure that may cause a project to go wrong. Humans make mistakes, equipment fails, technologies don’t work as planned, unrealistic expectations, biases including sunk cost-syndrome, inexperience, wrong incentives, changing requirements, random events, ignoring early warning signals are reasons for delays, cost overruns, and mistakes. Often we focus too much on the specific base project case and ignore what normally happens in similar situations (base rate frequency of outcomes—personal and others). Why should some project be any different from the long-term record of similar ones? George Bernard Shaw said: “We learn from history that man can never learn anything from history.”

The more independent steps that are involved in achieving a scenario, the more opportunities for failure and the less likely it is that the scenario will happen. We often underestimate the number of steps, people, and decisions involved.

We can’t pretend that knowing about conjunctive events bias will automatically stop us from having it. When, however, we are doing planning where a successful outcome is of importance to us, it’s useful to run through our assumptions with this bias in mind. Sometimes, assigning frequencies instead of probabilities can also show us where our assumptions might be leading us astray. In the housing example above, asking what is the frequency of having building permits delayed in every hundred houses, versus the frequency of having permits delayed and electrical going in on time for the same hundred demonstrates more easily the higher frequency of option one.

It also extremely useful to keep a decision journal for our major decisions, so that we can more realistic in our estimates on the time and resources we need for future plans. The more realistic we are, the higher our chances of accomplishing what we set out to do.

The conjunctive events bias teaches us to be more pessimistic about plans and to consider the worst-case scenario, not just the best. We may assume things will always run smoothly but disruption is the rule rather than the exception.

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What You Truly Value

Reading Time: 3 minutes

Our devotion to our values gets tested in the face of a true crisis. But it’s also an opportunity to reconnect, recommit, and sometimes, bake some bread.

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The recent outbreak of the coronavirus is impacting people all over the world — not just in terms of physical health, but financially, emotionally, and even socially. As we struggle to adapt to our new circumstances, it can be tempting to bury our head and wait for it all to blow over so we can just get back to normal. Or we can see this as an incredible opportunity to figure out who we are.

What many of us are discovering right now is that the things we valued a few months ago don’t actually matter: our cars, the titles on our business cards, our privileged neighborhoods. Rather, what is coming to the forefront is a shift to figuring out what we find intrinsically rewarding

When everything is easy, it can seem like you have life figured out. When things change and you’re called to put it into practice, it’s a different level. It’s one thing to say you are stoic when your coffee spills and another entirely when you’re watching your community collapse. When life changes and gets hard, you realize you’ve never had to put into practice what you thought you knew about coping with disaster.

But when a crisis hits, everything is put to the real test.

The challenge then becomes wrapping our struggles into our values, because what we value only has meaning if it’s important when life is hard. To know if they have worth, your values need to help you move forward when you can barely crawl and the obstacles in your way seem insurmountable.

In the face of a crisis, what is important to us becomes evident when we give ourselves the space to reflect on what is going to get us through the hard times. And so we find renewed commitment to get back to core priorities. What seemed important before falls apart to reveal what really matters: family, love, community, health.

“I was 32 when I started cooking; up until then, I just ate.” 

— Julia Child

One unexpected activity that many people are turning to now that they have time and are more introspective is baking. In fact, this week Google searches for bread recipes hit a noticeable high.


Baking is a very physical experience: kneading dough, tasting batter, smelling the results of the ingredients coming together. It’s an activity that requires patience. Bread has to rise. Pies have to cook. Cakes have to cool before they can be covered with icing. And, as prescriptive as baking seems on its surface, it’s something that facilitates creativity as we improvise our ingredients based on what we have in the cupboard. We discover new flavors, and we comfort ourselves and others with the results. Baked goods are often something we share, and in doing so we are providing for those we care about.

Why might baking be useful in times of stress? In Overcoming Anxiety, Dennis Tirch explains “research has demonstrated that when people engage more fully in behaviors that give them a sense of pleasure and mastery, they can begin to overcome negative emotions.”

At home with their loved ones people can reconsider what they value one muffin at a time. Creating with the people we love instead of consuming on our own allows us to focus on what we value as the world changes around us. With more time, slow, seemingly unproductive pursuits have new appeal because they help us reorient to the qualities in life that matter most.

Giving yourself the space to tune in to your values doesn’t have to come through baking. What’s important is that you find an activity that lets you move past fear and panic, to reconnect with what gives your life meaning. When you engage with an activity that gives you pleasure and releases negative emotions, it allows you to rediscover what is important to you.

Change is stressful. But neither stress nor change have to be scary. If you think about it, you undergo moments of change every day because nothing in life is ever static. Our lives are a constant adaptation to a world that is always in motion.

All change brings opportunity. Some change gives us the opportunity to pause and ask what we can do better. How can we better connect to what has proven to be important? Connection is not an abstract intellectual exercise, but an experience that orients us to the values that provide us direction. If you look for opportunities in line with your values, you will be able to see a path through the fear and uncertainty guided by the light that is hope.

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Preserving Optionality: Preparing for the Unknown

Reading Time: 8 minutes

We’re often advised to excel at one thing. But as the future gets harder to predict, preserving optionality allows us to pivot when the road ahead crumbles.

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How do we prepare for a world that often changes drastically and rapidly? We can preserve our optionality.

We don’t often get the advice to keep our options open. Instead, we’re told to specialize by investing huge hours in our passion so we can be successful in a niche.

The problem is, it’s bad advice. We live in a world that’s constantly changing, and if we can’t respond effectively to those changes, we become redundant, frustrated, and useless.

Instead of focusing on becoming great at one thing, there is another, counterintuitive strategy that will get us further: preserving optionality. The more options we have, the better suited we are to deal with unpredictability and uncertainty. We can stay calm when others panic because we have choices.

Optionality refers to the act of keeping as many options open as possible. Preserving optionality means avoiding limiting choices or dependencies. It means staying open to opportunities and always having a backup plan.

An option is usually defined as something we have the freedom to choose. That’s a fairly broad definition. In the context of a strategy, it must also have a limited downside and an open-ended upside. Betting in a casino is not an option, for example—the upside is known. Losses and gains are both constrained. What about betting on a new tech startup? That’s an option—the upside is theoretically unlimited; the losses are limited to the amount you invest.

Options present themselves all the time, but life-altering ones often come up during times of great change. These options are the ones we have the hardest time capitalizing on. If we’ve specialized too much, change is a threat, not an opportunity. Thus, if we aren’t certain where the opportunities are going to be (and we never are), then we need to make choices to keep our options open.

Baron Rothschild is often quoted as having said that “the time to buy is when there’s blood in the streets.” That’s a misquote, however. What he actually said was “buy when there’s blood in the streets, even if the blood is your own.” Rothschild recognized that those are the times when new options emerge. That’s when many investors make their fortunes and when entrepreneurs innovate. Rothschild saw opportunity in chaos. He made a fortune buying during the panic after the Battle of Waterloo.

When we occupy a small niche, we sacrifice optionality. That means less freedom and greater dependency. No one can predict the future—not even experts—so isn’t it a good idea to have as many avenues open as possible?

The coach’s dilemma: strength vs. optionality

In Simple Rules: How to Thrive in a Complex World, Kathleen Eisenhardt and Donald Sull describe the experience of strength coach Shannon Turley. For the uninitiated, the role of a strength coach is to help athletes stay healthy and perform better, rather than teach specific skills.

Turley began his career working at Virginia Polytechnic Institute and State University. When he started, the football players there followed a strength program based on weightlifting alone. Athletes wore t-shirts listing their personal records and competed to outdo each other. The mantra was: get stronger by lifting more weight.

But Turley soon realized that this program was not effective because it left the athletes with limited optionality. Turley found no correlation between weightlifting prowess and competitive performance. Being able to bench press a lot of weight didn’t serve them well on the football field. As he put it, “In football if you’re on your back, you’ve already lost.” Keeping a record of what he saw, he began looking for different options for the athletes.

After gaining experience coaching in several sports, Turley realized that strength was not the most important factor for athletic success. What mattered for any type of athlete was staying free of injuries and good nutrition. Why? Because that gave athletes greater optionality.

An uninjured, healthy player could stay in each game for longer and miss fewer training sessions. It also meant less chance of requiring surgery, which many of his students faced, or of being forced to retire from competitive sports at a young age.

Turley began coaching football players at Stanford University. He implemented a program focusing on proper nutrition and flexibility exercises such as yoga—not weightlifting. He also focused on healing existing injuries that restricted athletes’ performance. One football player he worked with had ongoing back problems, so Turley designed a regime to improve that issue. It worked: the athlete never missed a game and went on to play in the NFL. Turley’s approach served to preserve optionality for his players. Even the best athlete will lose many competitions. So the more an athlete is healthy enough to participate in games, the greater the chances of those crucial successes. Turley’s experience illustrates the trade-offs between particular physical abilities and optionality.

Over-specializing in one area is highly limiting, especially if it requires extensive upkeep. Like a football player, we can retain optionality by avoiding overtly damaging risks and ensuring we stay in the game for as long as possible—whatever that game is. That might mean lifting less metaphorical weight at any one time, while also working to keep ourselves flexible.

The tyranny of small decisions

Few people would deliberately lock themselves into an undesirable situation. Yet we often make small, rational decisions that end up removing options over time. This is the tyranny of small decisions. Economist Alfred Kahn identified the concept in 1966. Kahn begins the article with a provocative thought experiment:

Suppose, 75 years ago, some being from outer space had made us this proposition: “I know how to make a vehicle that could in effect put 200 horses at the disposal of each of you. It would permit you to travel about, alone or in small groups, at 60 to 80 miles an hour. But the costs of this gadget are 40,000 lives per year, global warming, the decay of the inner city, endless commuting, and suburban sprawl.” What would we have chosen collectively?

Put that way, the answer, of course, is no—we wouldn’t choose the advancement of transportation technology if we could immediately see the grievous cost. But we have said yes to that exact offer over time through a million small decisions, and now it is difficult to back out. Most of the modern world is built to accommodate cars. Driving is now the “rational” choice, no matter the destructive effect. Sometimes it feels as though we have no other option.

Kahn’s point is that small decisions can lead to bad outcomes. At some point, alternatives disappear. We lose our optionality. It is easy to see the downsides of big decisions. The costs of smaller ones can be more elusive. In a market economy, Kahn explains, change is the result of tiny steps. Combined, they have a tremendous cumulative effect on our collective freedom. Day to day, it is hard to see the path that is forming. At some point, we may look up and not like where we are going. By then it is too late. Kahn writes:

Only if consumers are given the full range of economically feasible and socially desirable alternatives in a big discrete bundle will misallocation of resources due to the tyranny of small market-determined decisions be broken.

The tragedy of the commons is another such instance of the power of small decisions. Garett Hardin’s parable illustrates why common resources are used more than is desirable from the standpoint of society as a whole. No one person makes a single decision to deplete the resources. Instead, each person makes a series of small choices that ultimately cause environmental ruin. In the original example where villagers are freely able to graze their animals on common land, having access to it gives everyone a lot of options for raising animals or farming. Once the pasture is exhausted from everyone putting too many animals out to graze, however, everyone loses their optionality.

Optionality can be a matter of perspective

As Seneca put it, “In one and the same meadow, the cow looks for grass, the dog for a hare, and the stork for a lizard.” Where some people only see blood in the streets, other people see a chance to succeed.

Preserving optionality can be as much about changing our attitudes as our circumstances. It can be about learning to spot opportunities—and to make them. Optionality is not a new concept. A portion of the Old Testament dating back to between 450 and 180 BCE declares:

Invest in seven ventures, yes, in eight; you do not know what disaster may come upon the land. If clouds are full of water, they pour rain on the earth. Whether a tree falls to the south or to the north, in the place where it falls, there it will lie. Whoever watches the wind will not plant; whoever looks at the clouds will not reap . . . Sow your seed in the morning, and at evening let your hands not be idle, for you do not know which will succeed, whether this or that, or whether both will do equally well.

In today’s world, optionality can be integrated into a number of different areas of our lives by looking for ways to prepare for a variety of possible events, instead of optimizing for the recent past.

Keeping our options open means developing generalist skills like creativity, rather than specializing in one area, like a particular technology. The more diverse the knowledge and skills you can draw on, the better positioned you are to take advantage of new opportunities.

It means not relying on a single distributor for your company’s product or having the supply chain for an entire industry dependent on one country. You can’t make your decisions solely on how the world was yesterday. Preserving optionality means you may take a short-term hit in sales by funding diversity, but the result is you will be much better positioned in the future to keep your business going when circumstances change.

It means not relying on a single energy source to power the vehicles that move us and the goods we need around. Building our society around oil—a finite resource—is limiting. Developing multiple forms of sustainable energy creates new options for when that finite resource is depleted.

Or consider the lean startup methodology. Building a minimum viable product means having the flexibility to pivot or change plans. No demand? No problem! Just try something else. Lean startups iterate until they find product/market fit. Many founders keep their teams as small as possible. They avoid fixed costs and commitments. They keep their options open.

The lean startup methodology recognizes that a new company cannot make a grand plan; it needs to adapt and evolve. As Steve Jobs understood, most customers don’t know they will want something until they have tried it. It’s hard to prepare for changing customer desires without optionality. If a company is flexible, they can adapt to the information they receive once a product hits the market.

“Wealth is not about having a lot of money; it’s about having a lot of options.”

— Chris Rock

Ultimately, preserving optionality means paying attention and looking at life from multiple perspectives. It means building a versatile base of foundational knowledge and allowing for serendipity and unexpected connections. We must seek to expand our comfort zone and circle of competence, and we should take minor risks that have potentially large upsides and limited downsides.

Paradoxically, preserving optionality can mean saying no to a lot of opportunities and avoiding anything that will prove to be restrictive. We need to look at choices through the lens of the optionality they will give us in the future and only say yes to those that create more options.

Preserving your optionality is important because it gives you the flexibility to capitalize on inevitable change. In order to keep your options open, you need diversity. Diversity of perspective, thought, knowledge, and skills. You don’t want to find yourself in a position of only being able to sell something that no one wants. Rapid, extraordinary change is the norm. In order to adapt in a way that is useful, keep your options open.

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Chesterton’s Fence: A Lesson in Second Order Thinking

Reading Time: 8 minutes

A core component of making great decisions is understanding the rationale behind previous decisions. If we don’t understand how we got “here,” we run the risk of making things much worse.

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When we seek to intervene in any system created by someone, it’s not enough to view their decisions and choices simply as the consequences of first-order thinking because we can inadvertently create serious problems. Before changing anything, we should wonder whether they were using second-order thinking. Their reasons for making certain choices might be more complex than they seem at first. It’s best to assume they knew things we don’t or had experience we can’t fathom, so we don’t go for quick fixes and end up making things worse.

Second-order thinking is the practice of not just considering the consequences of our decisions but also the consequences of those consequences. Everyone can manage first-order thinking, which is just considering the immediate anticipated result of an action. It’s simple and quick, usually requiring little effort. By comparison, second-order thinking is more complex and time-consuming. The fact that it is difficult and unusual is what makes the ability to do it such a powerful advantage.

Second-order thinking will get you extraordinary results, and so will learning to recognize when other people are using second-order thinking. To understand exactly why this is the case, let’s consider Chesterton’s Fence, described by G. K. Chesterton himself as follows:

There exists in such a case a certain institution or law; let us say, for the sake of simplicity, a fence or gate erected across a road. The more modern type of reformer goes gaily up to it and says, “I don’t see the use of this; let us clear it away.” To which the more intelligent type of reformer will do well to answer: “If you don’t see the use of it, I certainly won’t let you clear it away. Go away and think. Then, when you can come back and tell me that you do see the use of it, I may allow you to destroy it.”

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Chesterton’s Fence is a heuristic inspired by a quote from the writer and polymath G. K. Chesterton’s 1929 book, The Thing. It’s best known as being one of John F. Kennedy’s favored sayings, as well as a principle Wikipedia encourages its editors to follow. In the book, Chesterton describes the classic case of the reformer who notices something, such as a fence, and fails to see the reason for its existence. However, before they decide to remove it, they must figure out why it exists in the first place. If they do not do this, they are likely to do more harm than good with its removal. In its most concise version, Chesterton’s Fence states the following:

Do not remove a fence until you know why it was put up in the first place.

Chesterton went on to explain why this principle holds true, writing that fences don’t grow out of the ground, nor do people build them in their sleep or during a fit of madness. He explained that fences are built by people who carefully planned them out and “had some reason for thinking [the fence] would be a good thing for somebody.” Until we establish that reason, we have no business taking an ax to it. The reason might not be a good or relevant one; we just need to be aware of what the reason is. Otherwise, we may end up with unintended consequences: second- and third-order effects we don’t want, spreading like ripples on a pond and causing damage for years.

Elsewhere, in his essay collection Heretics, Chesterton makes a similar point, detailed here:

Suppose that a great commotion arises in the street about something, let us say a lamp-post, which many influential persons desire to pull down. A grey-clad monk, who is the spirit of the Middle Ages, is approached upon the matter, and begins to say, in the arid manner of the Schoolmen, “Let us first of all consider, my brethren, the value of Light. If Light be in itself good—” At this point he is somewhat excusably knocked down. All the people make a rush for the lamp-post, the lamp-post is down in ten minutes, and they go about congratulating each other on their un-mediaeval practicality. But as things go on they do not work out so easily. Some people have pulled the lamp-post down because they wanted the electric light; some because they wanted old iron; some because they wanted darkness, because their deeds were evil. Some thought it not enough of a lamp-post, some too much; some acted because they wanted to smash municipal machinery; some because they wanted to smash something. And there is war in the night, no man knowing whom he strikes. So, gradually and inevitably, to-day, to-morrow, or the next day, there comes back the conviction that the monk was right after all, and that all depends on what is the philosophy of Light. Only what we might have discussed under the gas-lamp, we now must discuss in the dark.

As simple as Chesterton’s Fence is as a principle, it teaches us an important lesson. Many of the problems we face in life occur when we intervene with systems without an awareness of what the consequences could be. We can easily forget that this applies to subtraction as much as to addition. If a fence exists, there is likely a reason for it. It may be an illogical or inconsequential reason, but it is a reason nonetheless.


“Before I built a wall I’d ask to know
What I was walling in or walling out,
And to whom I was like to give offence.”

— Robert Frost, “Mending Wall”

Chesterton also alluded to the all-too-common belief that previous generations were bumbling fools, stumbling around, constructing fences wherever they fancied. Should we fail to respect their judgement and not try to understand it, we run the risk of creating new, unexpected problems. By and large, people do not do things for no reason. We’re all lazy at heart. We don’t like to waste time and resources on useless fences. Not understanding something does not mean it must be pointless.

Take the case of supposedly hierarchy-free companies. Someone came along and figured that having management and an overall hierarchy is an imperfect system. It places additional stress on those at the bottom and can even be damaging to their health. It leaves room for abuse of power and manipulative company politics. It makes it unlikely that good ideas from those at the bottom will get listened to.

However, despite the numerous problems inherent in hierarchical companies, doing away with this structure altogether belies a lack of awareness of the reasons why it is so ubiquitous. Someone needs to make decisions and be held responsible for their consequences. During times of stress or disorganization, people naturally tend to look to leaders for direction. Without a formal hierarchy, people often form an invisible one, which is far more complex to navigate and can lead to the most charismatic or domineering individual taking control, rather than the most qualified.

It is certainly admirable that hierarchy-free companies are taking the enormous risk inherent in breaking the mold and trying something new. However, their approach ignores Chesterton’s Fence and doesn’t address why hierarchies exist within companies in the first place. Removing them does not necessarily lead to a fairer, more productive system.

Yes, doing things the way they’ve always been done means getting what we’ve always got. There’s certainly nothing positive about being resistant to any change. Things become out of date and redundant with time. Sometimes an outside perspective is ideal for shaking things up and finding new ways. Even so, we can’t let ourselves be too overconfident about the redundancy of things we see as pointless.

Or, to paraphrase Rory Sutherland, the peacock’s tail is not about efficiency. In fact, its whole value lies in its inefficiency. It signals a bird is healthy enough to waste energy growing it and has the strength to carry it around. Peahens use the tails of peacocks as guidance for choosing which mates are likely to have the best genes to pass on to their offspring. If an outside observer were to somehow swoop in and give peacocks regular, functional tails, it would be more energy efficient and practical, but it would deprive them of the ability to advertise their genetic potential.

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All of us, at one point or another, make some attempt to change a habit to improve our lives. If you’re engaging in a bad habit, it’s admirable to try to eliminate it—except part of why many attempts to do so fail is that bad habits do not appear out of nowhere. No one wakes up one day and decides they want to start smoking or drinking every night or watching television until the early hours of the morning. Bad habits generally evolve to serve an unfulfilled need: connection, comfort, distraction, take your pick.

Attempting to remove the habit and leave everything else untouched does not eliminate the need and can simply lead to a replacement habit that might be just as harmful or even worse. Because of this, more successful approaches often involve replacing a bad habit with a good, benign, or less harmful one—or dealing with the underlying need. In other words, that fence went up for a reason, and it can’t come down without something either taking its place or removing the need for it to be there in the first place.

To give a further example, in a classic post from 2009 on his website, serial entrepreneur Steve Blank gives an example of a decision he has repeatedly seen in startups. They grow to the point where it makes sense to hire a Chief Financial Officer. Eager to make an immediate difference, the new CFO starts looking for ways to cut costs so they can point to how they’re saving the company money. They take a look at the free snacks and sodas offered to employees and calculate how much they cost per year—perhaps a few thousand dollars. It seems like a waste of money, so they decide to do away with free sodas or start charging a few cents for them. After all, they’re paying people enough. They can buy their own sodas.

Blank writes that, in his experience, the outcome is always the same. The original employees who helped the company grow initially notice the change and realize things are not how they were before. Of course they can afford to buy their own sodas. But suddenly having to is just an unmissable sign that the company’s culture is changing, which can be enough to prompt the most talented people to jump ship. Attempting to save a relatively small amount of money ends up costing far more in employee turnover. The new CFO didn’t consider why that fence was up in the first place.

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Chesterton’s Fence is not an admonishment of anyone who tries to make improvements; it is a call to be aware of second-order thinking before intervening. It reminds us that we don’t always know better than those who made decisions before us, and we can’t see all the nuances to a situation until we’re intimate with it. Unless we know why someone made a decision, we can’t safely change it or conclude that they were wrong.

The first step before modifying an aspect of a system is to understand it. Observe it in full. Note how it interconnects with other aspects, including ones that might not be linked to you personally. Learn how it works, and then propose your change.

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Using Models to Stay Calm in Charged Situations

Reading Time: 6 minutes

When polarizing topics are discussed in meetings, passions can run high and cloud our judgment. Learn how mental models can help you see clearly from this real-life scenario.

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Mental models can sometimes come off as an abstract concept. They are, however, actual tools you can use to navigate through challenging or confusing situations. In this article, we are going to apply our mental models to a common situation: a meeting with conflict.

A recent meeting with the school gave us an opportunity to use our latticework. Anyone with school-age kids has dealt with the bureaucracy of a school system and the other parents who interact with it. Call it what you will, all school environments usually have some formal interface between parents and the school administration that is aimed at progressing issues and ideas of importance to the school community.

The particular meeting was an intense one. At issue was the school’s communication around a potentially harmful leak in the heating system. Some parents felt the school had communicated reasonably about the problem and the potential consequences. Others felt their child’s life had been put in danger due to potential exposure to mold and asbestos. Some parents felt the school could have done a better job of soliciting feedback from students about their experiences during the previous week, and others felt the school administration had done a poor job about communicating potential risks to parents.

The first thing you’ll notice if you’re in a meeting like this is that emotions on all sides run high. After some discussion you might also notice a few more things, like how many people do the following:

Any of these occurrences, when you hear them via statements from people around the table, are a great indication that using a few mental models might improve the dynamics of the situation.

The first mental model that is invaluable in situations like this is Hanlon’s Razor: don’t attribute to maliciousness that which is more easily explained by incompetence. (Hanlon’s Razor is one of the 9 general thinking concepts in The Great Mental Models Volume One.) When people feel victimized, they can get angry and lash out in an attempt to fight back against a perceived threat. When people feel accused of serious wrongdoing, they can get defensive and withhold information to protect themselves. Neither of these reactions is useful in a situation like this. Yes, sometimes people intentionally do bad things. But more often than not, bad things are the result of incompetence. In a school meeting situation, it’s safe to assume everyone at the table has the best interests of the students at heart. School staff and administrators usually go into teaching motivated by a deep love of education. They genuinely want their schools to be amazing places of learning, and they devote time and attention to improving the lives of their students.

It makes no sense to assume a school’s administration would deliberately withhold harmful information. Yes, it could happen. But, in either case, you are going to obtain more valuable information if you assume poor decisions were the result of incompetence versus maliciousness.

When we feel people are malicious toward us, we instinctively become a negatively coiled spring, waiting for the right moment to take them down a notch or two. Removing malice from the equation, you give yourself emotional breathing room to work toward better solutions and apply more models.

The next helpful model is relativity, adapted from the laws of physics. This model is about remembering that everyone’s perspective is different from yours. Understanding how others see the same situation can help you move toward a more meaningful dialogue with the people in the meeting. You can do this by looking around the room and asking yourself what is influencing people’s approaches to the situation.

In our school meeting, we see some people are afraid for their child’s health. Others are influenced by past dealings with the school administration. Authorities are worried about closing the school. Teachers are concerned about how missed time might impact their students’ learning. Administrators are trying to balance the needs of parents with their responsibility to follow the necessary procedures. Some parents are stressed because they don’t have care for their children when the school closes. There is a lot going on, and relativity gives us a lens to try to identify the dynamics impacting communication.

After understanding the different perspectives, it becomes easier to incorporate them into your thinking. You can diffuse conflict by identifying what it is you think you hear. Often, just the feeling of being heard will help people start to listen and engage more objectively.

Now you can dive into some of the details. First up is probabilistic thinking. Before we worry about mold levels or sick children, let’s try to identify the base rates. What is the mold content in the air outside? How many children are typically absent due to sickness at this time of year? Reminding people that severity has to be evaluated against something in a situation like this can really help diffuse stress and concern. If 10% of the student population is absent on any given day, and in the week leading up to these events 12% to 13% of the population was absent, then it turns out we are not actually dealing with a huge statistical anomaly.

Then you can evaluate the anecdotes with the model of the Law of Large Numbers in mind. Small sample sizes can be misleading. The larger your group for evaluation, the more relevant the conclusions. In a situation such as our school council meeting, small sample sizes only serve to ratchet up the emotion by implying they are the causal outcomes of recent events.

In reality, any one-off occurrence can often be explained in multiple ways. One or two children coming home with hives? There are a dozen reasonable explanations for that: allergies, dry skin, reaction to skin cream, symptom of an illness unrelated to the school environment, and so on. However, the more children that develop hives, the more it is statistically possible the cause relates to the only common denominator between all children: the school environment.

Even then, correlation does not equal causation. It might not be a recent leaky steam pipe; is it exam time? Are there other stressors in the culture? Other contaminants in the environment? The larger your sample size, the more likely you will obtain relevant information.

Finally, you can practice systems thinking and contribute to the discussion by identifying the other components in the system you are all dealing with. After all, a school council is just one part of a much larger system involving governments, school boards, legislators, administrators, teachers, students, parents, and the community. When you put your meeting into the bigger context of the entire system, you can identify the feedback loops: Who is responding to what information, and how quickly does their behavior change? When you do this, you can start to suggest some possible steps and solutions to remedy the situation and improve interactions going forward.

How is the information flowing? How fast does it move? How much time does each recipient have to adjust before receiving more information? Chances are, you aren’t going to know all this at the meeting. So you can ask questions. Does the principal have to get approval from the school board before sending out communications involving risk to students? Can teachers communicate directly with parents? What are the conditions for communicating possible risk? Will speculation increase the speed of a self-reinforcing feedback loop causing panic? What do parents need to know to make an informed decision about the welfare of their child? What does the school need to know to make an informed decision about the welfare of their students?

In meetings like the one described here, there is no doubt that communication is important. Using the meeting to discuss and debate ways of improving communication so that outcomes are generally better in the future is a valuable use of time.

A school meeting is one practical example of how having a latticework of mental models can be useful. Using mental models can help you diffuse some of the emotions that create an unproductive dynamic. They can also help you bring forward valuable, relevant information to assist the different parties in improving their decision-making process going forward.

At the very least, you will walk away from the meeting with a much better understanding of how the world works, and you will have gained some strategies you can implement in the future to leverage this knowledge instead of fighting against it.

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Finite and Infinite Games: Two Ways to Play the Game of Life

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If life is a game, how do you play it? The answer will have a huge impact on your choices, your satisfaction, and how you achieve success.

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James Carse, the Director of Religious Studies at New York University, wrote a book, Finite and Infinite Games, that explores the difference between approaching life as a game with an end, or a game that goes on forever. According to Carse, playing to win isn’t nearly as satisfying as playing to keep the game going.

For starters, what do you do after you win a finite game? You have to sign yourself up for another one, and you must find a way to showcase your past winnings. Finite players have to parade around their wealth and status. They need to display the markers of winning they have accumulated so that other players know whom they are dealing with. Carse argues that these players spend their time in the past, because that’s where their winning is.

Infinite players, in contrast, look to the future. Because their goal is to keep the game going, they focus less on what happened, and put more effort into figuring out what’s possible. By playing a single, non-repeatable game, they are unconcerned with the maintenance and display of past status. They are more concerned with positioning themselves to deal effectively with whatever challenges come up.

Thus, how you play the game of life will define the learning you pursue. Finite players need training. Infinite players need education. Why? According to Carse, “to be prepared against surprise is to be trained. To be prepared for surprise is to be educated.” If you play life as a finite game, you train for the rules. If life is instead an infinite game, you focus on being educated to adapt to unknowns.

“What will undo any boundary is the awareness that it is our vision, and not what we are viewing, that is limited.”

Whether you choose the finite or infinite game will also determine how you define success, and what you need to achieve it. Finite players need power. Power gives them the best chance to win in each successive contest. Infinite players need endurance. They need attributes to keep them going. Carse explains, “let us say that where the finite player plays to be powerful, the infinite player plays with strength.”

Ultimately, approaching life as a finite game or infinite game impacts your daily attitude. Carse asserts that “the finite play for life is serious; the infinite play of life joyous.” Considering your life through this frame helps you determine if you are making the right choices to be successful at the kind of game you want to play.

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