Tag: Decisions

Preserving Optionality: Preparing for the Unknown

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.

Chesterton’s Fence: A Lesson in Second Order Thinking

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.

Externalities: Why We Can Never Do “One Thing”

No action exists in a vacuum. There are ripples that have consequences that we can and can’t see. Here are the three types of externalities that can help us guide our actions so they don’t come back to bite us.

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An externality affects someone without them agreeing to it. As with unintended consequences, externalities can be positive or negative. Understanding the types of externalities and the impact they have in our lives can help us improve our decision making, and how we interact with the world.

Externalities provide useful mental models for understanding complex systems. They show us that systems don’t exist in isolation from other systems. Externalities may affect uninvolved third parties which make them a form of market failure —an inefficient allocation of resources.

We both create and are subject to externalities. Most are very minor but compound over time. They can inflict numerous second-order effects. Someone reclines their seat on an airplane. They get the benefit of comfort. The person behind bears the cost of discomfort by having less space. One family member leaves their dirty dishes in the sink. They get the benefit of using the plate. Someone else bears the cost of washing it later. We can’t expect to interact with any system without repercussions. Over time, even minor externalities can cause significant strain in our lives and relationships.

The First Law of Ecology

To understand externalities it is first useful to consider second-order consequences. In Filters Against Folly, Garrett Hardin describes what he considers to be the First Law of Ecology: We can never do one thing. Whenever we interact with a system, we need to ask, “And then what? What will the wider repercussions of our actions be?” There is bound to be at least one externality.

Hardin gives the example of the Prohibition Amendment in the U.S. In 1920, lawmakers banned the production and sale of alcoholic beverages throughout the entire country. This was in response to an extended campaign by those who believed alcohol was evil. It wasn’t enough to restrict its consumption—it needed to go.

The addition of 61 words to the American Constitution changed the social and legal landscape for over a decade. Policymakers presumably thought they could make the change and people would stop drinking. But Prohibition led to numerous externalities. Alcohol is an important part of many people’s lives. Few were willing to suddenly give it up without a fight. The demand was more than strong enough to ensure a black-market supply re-emerged.

Wealthy people stockpiled alcohol in their homes before the ban went into effect. Thousands of speakeasies and gin joints flourished. Walgreens grew from 20 stores to 500, in large part due to its sales of ‘medicinal’ whiskey. Former alcohol producers simply sold the ingredients for people to make their own. Gangsters like Al Capone made their fortune smuggling, and murdered his rivals in the process. Crime gangs undermined official institutions. Tax revenues plummeted. People lost their jobs. Prisons became overcrowded and bribery commonplace. Thousands died from crime and drinking unsafe homemade alcohol.

Policymakers did not fully ask, “And then what?” before legislating. Drinking did decrease during this time, on average by about half.  But this was far from the hope of a total ban. The second-order consequences outweighed any benefits.

As economist Gregory Mankiw explains in Principles of Microeconomics,

In the presence of externalities, society’s interest in a market outcome extends beyond the well-being of buyers and sellers who participate in the market; it also includes the well-being of bystanders who are affected indirectly…. The market equilibrium is not efficient when there are externalities. That is, the equilibrium fails to maximize the total benefit to society as a whole.

Negative Externalities

Negative externalities can occur during the production or consumption of a service or good. Pollution is a useful example. If a factory pollutes nearby water supplies, it causes harm without incurring costs. The costs to society are high and are not reflected in the price of whatever the factory makes. Economists often view environmental damage as another factor in a production process. But even if pollution is taxed, the harmful effects don’t go away.

Transport and manufacturing release toxins into the environment, harming our health and altering our climate. The reality though, is these externalities are hard to see, and it is often difficult to trace them back to their root causes. There’s also the question of whether we are responsible for externalities or not.

Imagine you’re driving down the road. As you go by an apartment, the noise disturbs someone who didn’t agree to it. Your car emits air pollution, which affects everyone living nearby. Each of these small externalities will affect people you don’t see and who didn’t choose them. They won’t receive any compensation from you. Are you really responsible for the externalities you cause? If you’re not being outright careless or malicious, isn’t it just part of life? How much responsibility do we have as individuals, anyway?

Calling something a negative externality can be a convenient way of abdicating responsibility.

Positive Externalities

A positive externality imposes an unexpected benefit on a third party. The producer doesn’t agree to this, nor do they receive compensation for it.

Scientific research often leads to positive externalities. Research findings can have applications beyond their initial scope. The resulting information becomes part of our collective knowledge base. However, the researcher who makes a discovery cannot receive the full benefits. Nor do they necessarily feel entitled to them.

Blaise Pascal and Pierre de Fermat developed probability theory to solve a gambling dispute. Their work went on to inform numerous disciplines (like the field of calculus) and transform our understanding of the world. Probabilities are now a core part of how we think. Pascal and Fermat created a positive externality.

Someone who comes up with an equation cannot expect compensation each time it gets used. As a result, the incentives to invest the time and effort to discover new equations are reduced. Algorithms, patents, and copyright laws change this by allowing creators to protect and profit from their ideas for years before other people can freely use them. We all benefit, and researchers have an incentive to continue their work.

Network effects are an example of a positive externality. Silicon Valley understands this well. Each person who joins a network, like a marketplace app, increases the value to all other users. Those who own the network have an incentive improve it to encourage new users. Everyone benefits from being able to communicate with more people. While we might not join a new network intending to improve it for other people, that is what normally happens. (On the flipside, network effects can also produce negative externalities, as too many members can decrease the value of a network.)

Positive externalities often lead to the “free rider” problem. When we enjoy something that we aren’t paying for, we tend not to value it. Not paying can remove the incentive to look after a resource and leads to a Tragedy of the Commons situation. As Aristotle put it, “For that which is common to the greatest number has the least care bestowed upon it.” A good portion of online content succumbs to the free rider problem. We enjoy it and yet we don’t pay for it. We expect it to be free and yet, if users weren’t willing to support sites like Farnam Street, they would likely fold, start publishing lower quality articles, or sell readers to advertisers who collect their data. The end result, as we see too frequently, is low-quality content funded by page-view advertising. (This is why we have a membership program. Members of our learning community create a positive externality for non-members by helping support the free content.)

Positional Externalities

Positional externalities are a form of second-order effects. They occur when our decisions alter the context of future perception or value.

For example, consider what happens when a person decides to start staying at the office an hour late. Perhaps they want a promotion and think it will endear them to managers. Parkinson’s Law states that tasks expand to fit the time allocated to them. What this person would otherwise get done by 5pm, now takes until 6pm. Staying late becomes their norm. Their co-workers notice and start to also stay late. Before long, staying at the office until 6pm becomes the standard for everyone. Anyone who leaves at 5pm is perceived as lazy. Now that 6pm is the norm, everyone suffers. They are forced to work more without deriving any real benefits. It’s a lose-lose situation for everyone.

Someone we know once made an investment with a nearly unlimited return by gaming the system. He worked for an investment firm that valued employees according to a perception of how hard they worked and not necessarily by their results. Each Monday he brought in a series of sport coats and left them in the office. He paid the cleaning staff $20 a week to change the coat hanging on his chair and to turn on his computer. No matter what happened, it appeared he was always the first one into the office even though he often didn’t show up from a “client meeting” until 10. When it came to bonus time, he’d get an enormous return on that $20 investment.

Purchasing luxury goods can create positional externalities. Veblen goods are items we value because of their scarcity and high cost. Diamonds, Lamborghinis, tailor-made suits — owning them is a status symbol, and they lose their value if they become cheaper or if too many people have them. As Luca Lambertini puts it in The Economics of Vertically Differentiated Markets,

The utility derived from consumption is a function of the quantity purchased relative to the average of the society or the reference group to whom the consumer compares.” In other words, a shiny new car seems more valuable if all your friends are driving battered old wrecks. If they have equally (or more) fancy cars, the value of yours drops. At some point, it seems worthless and it’s time to find a new one. In this way, the purchase of a Veblen good confers a positional externality on other people who own it too.

That utility can also be a matter of comparison. A person earning $40,000 a year while their friends earn $30,000 will be happier than one earning $60,000 when their friends earn $70,000. When someone’s salary increases, it raises the bar, giving others a new point of reference.

We can confer positional externalities on ourselves by changing our attitudes. Let’s say someone enjoys wine but is not a connoisseur. A $10 bottle and a $100 bottle make them equally happy. When they decide to go on a course and learn the subtleties and technicalities of fine wines, they develop an appreciation for the $100 wine and a distaste for the $10. They may no longer be able to enjoy a cheap drink because they raised their standards.

Conclusion

Externalities are everywhere. It’s easy to ignore the impact of our decisions—to recline an airplane seat, to stay late at the office, or drop litter. Eventually though, someone always ends up paying. Like the villagers in Hardin’s Tragedy of the Commons, who end up with no grass for their animals, we run the risk of ruining a good thing if we don’t take care of it. Keeping the three types of externalities in mind is a useful way to make decisions that won’t come back to bite you. Whenever we interact with a system, we should remember to ask Hardin’s question: and then what?

How People Make Big Decisions

We all go through psychological steps when we make big decisions. Some people call this the “existential cycle,” which really has four stages: doing, contemplating, preparing, and experimenting.

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Echoing Tolstoy on regret avoidance, Sebastian Bailey and Octavius Black write in Mind Gym: Achieve More by Thinking Differently:

These four stages are much like exercises in risk management. No one wants to look back on his or her life at some point and say I wish I would have or If only I had.

While there are other ways, the existential cycle helps us make life changing decisions — like who to marry, where to work, and where to live.

The first stage, “doing,” is where you spend most of your life: It is your settled, equilibrium position. The doing may be all sorts of things— writing emails, riding horses, reading books, washing up, going to meetings, listening to lectures, cooking, dancing, running, sharing stories with friends, telling jokes, or making love. Of course, these are not done all at the same time (not unless you’re really talented). Whatever the activity may be, and however enjoyable or dull it is, you are doing it and it tends to keep you occupied.

Sometimes we get to “contemplating,” where we consider whether or how things would be different. What would life be like if you move to California? (Hint: It won’t make you happier.)

Then occasionally we move to “preparing.”

You search on the web for real estate agents in San Diego or Key West, find out what property prices are, check weather patterns, possibly even visit your preferred destination on your next vacation. You have moved beyond imagining how things could be different to investigating the practical options for how to make them different.

Finally you make the change.

You leave your job, buy a house, and move all your possessions. This stage is called “experimenting.” After you’ve settled in and started the beachside bar you’d dreamed about, this becomes your normal way of living, and you are once again in a state of doing.

The process isn’t overly complicated or hard. The challenge becomes moving through it at the right pace in a way that aligns with your principles.

How-People-Make-Big-Decisions

The Doing Magnet

As you travel around your cycle, you will have conversations with yourself that stop you from moving on to the next stage and instead take you back to doing.

Sometimes these thoughts can be very sensible and prevent you from wasting time or following the wrong path. But sometimes, unfortunately, they prevent you from both spotting and taking opportunities that could dramatically improve your life. The trick lies in recognizing the internal conversations and being able to make an informed decision about whether to listen to them or to ignore them and move on.

When the Doing Magnet is Weak

Irrational exuberance are those people who are forever saying things like I wish I hadn’t rushed into that or If only I’d thought about it first. Rather than never crossing the Rubicon, they’re happy to head over far too easily— without ever considering the size of the army on the other side. In terms of the existential cycle, their doing magnet is relatively weak— the centrifugal momentum of the next new thing is stronger than the gravitational force of the status quo.

If you find that you can’t hold down a job, you can’t keep a relationship, you spend money on a whim, or you haven’t gotten around to making your home into a place you like living in, and you regret it, then you may be suffering from a form of irrational exuberance. The best advice in this situation is this: spend longer at the preparing stage before wading across your Rubicon.

For example, consider one of these choices:

  • Think through all the possible disadvantages of taking this course of action as well as the advantages— really make an effort to present the case for caution on this occasion.

  • Contrast the allure of the new situation with how your existing life might improve even if you don’t make this big change. People who are always moving on to new jobs often fail to consider how their current jobs could get better. A new job may be attractive, but it is wrong to assume the old one will stay the same. New possibilities could open up. What happens when your boss moves on?

  • Contemplate the bigger and better gains and pleasures you could have if you didn’t always go for instant gratification. Could the gratification get more gratifying?

  • Consider any decisions you made in the past that led to situations you later regretted. What can you learn from these that will help you make a wiser decision this time.

If you Want to Improve, you have to Cross the Rubicon

“Do. Or do not. There is no try.” — Yoda

You have a choice in how you run your life. There is no “can’t,” only “will” and “won’t.” The trick is knowing why you are, or aren’t, moving around the existential cycle and, in particular, crossing your Rubicon. Like we’ve said, the right thing isn’t to always cross or always not cross. The right thing is to understand why you want to cross or don’t want to cross, and then make your decision.

Nevertheless, none of us want to live our lives in a constant state of doing. I might not be in good enough shape today to swim 2.4 miles, but that doesn’t mean I won’t be in the future. Plus, our reasons for remaining in one state may not be strong. At some point, in certain aspects of our lives, if we want to progress, we must cross the Rubicon.

A decision to not cross the Rubicon based on the wrong reasons— when catastrophic fantasies rule our mind-sets— is what causes people to look back on their lives and think If only. … All of us who have looked back and been proud of what we have done have crossed the Rubicon at least once and maybe many times.

There’s a famous Latin maxim, carpe diem, which translated means “seize the day.” The question you have to ask yourself is, When it comes to crossing Rubicons, just how much of a Caesar am I prepared to be?