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The Best-Case Outcomes Are Statistical Outliers

Reading Time: 3 minutes

There’s nothing wrong with hoping for the best. But the best-case scenario is rarely the one that comes to pass. Being realistic about what is likely to happen positions you for a range of possible outcomes and gives you peace of mind.

We dream about achieving the best-case outcomes, but they are rare. We can’t forget to acknowledge all the other possibilities of what may happen if we want to position ourselves for success.

“Hoping for the best, prepared for the worst, and unsurprised by anything in between.” —Maya Angelou

It’s okay to hope for the best—to look at whatever situation you’re in and say, “This time I have it figured out. This time it’s going to work.” First, having some degree of optimism is necessary for trying anything new. If we weren’t overconfident, we’d never have the guts to do something as risky and unlikely to succeed as starting a business, entering a new relationship, or sending that cold email. Anticipating that a new venture will work helps you overcome obstacles and make it work.

Second, sometimes we do have it figured out. Sometimes our solutions do make things better.

Even when the best-case scenario comes to pass, however, it rarely unfolds exactly as planned. Some choices create unanticipated consequences that we have to deal with. We may encounter unexpected roadblocks due to a lack of information. Or the full implementation of all our ideas and aspirations might take a lot longer than we planned for.

When you look back over history, we rarely find best-case outcomes.

Sure, sometimes they happen—maybe more than we think, given not every moment of the past is recorded. But let’s be honest: even historical wins, like developing the polio vaccine and figuring out how to produce clean drinking water, were not all smooth sailing. There are still people who are unable or unwilling to get the polio vaccine. And there are still many people in the world, even in developed countries like Canada, who don’t have access to clean drinking water.

The best-case outcomes in these situations—a world without polio and a world with globally available clean drinking water—have not happened, despite the existence of reliable, proven technology that can make these outcomes a reality.

There are a lot of reasons why, in these situations, we haven’t achieved the best-case outcomes. Furthermore, situations like these are not unusual. We rarely achieve the dream. The more complicated a situation, the more people it involves, the more variables and dependencies that exist, the more it’s unlikely that it’s all going to work out.

If we narrow our scope and say, for example, the best-case scenario for this Friday night is that we don’t burn the pizza, we can all agree on a movie, and the power doesn’t go out, it’s more likely we’ll achieve it. There are fewer variables, so there’s a greater chance that this specific scenario will come to pass.

The problem is that most of us plan as if we live in an easy-to-anticipate Friday night kind of world. We don’t.

There are no magic bullets for the complicated challenges facing society. There is only hard work, planning for the wide spectrum of human behavior, adjusting to changing conditions, and perseverance. There are many possible outcomes for any given endeavor and only one that we consider the best case.

That is why the best-case outcomes are statistical outliers—they are only one possibility in a sea of many. They might come to pass, but you’re much better off preparing for the likelihood that they won’t.

Our expectations matter. Anticipating a range of outcomes can make us feel better. If we expect the best and it happens, we’re merely satisfied. If we expect less and something better happens, we’re delighted.

Knowing that the future is probably not going to be all sunshine and roses allows you to prepare for a variety of more likely outcomes, including some of the bad ones. Sometimes, too, when the worst-case scenario happens, it’s actually a huge relief. We realize it’s not all bad, we didn’t die, and we can manage if it happens again. Preparation and knowing you can handle a wide spectrum of possible challenges is how you get the peace of mind to be unsurprised by anything in between the worst and the best.

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The High Price of Mistrust

Reading Time: 10 minutes

When we can’t trust each other, nothing works. As we participate in our communities less and less, we find it harder to feel other people are trustworthy. But if we can bring back a sense of trust in the people around us, the rewards are incredible.

There are costs to falling community participation. Rather than simply lamenting the loss of a past golden era (as people have done in every era), Harvard political scientist Robert D. Putnam explains these costs, as well as how we might bring community participation back.

First published twenty years ago, Bowling Alone is an exhaustive, hefty work. In its 544 pages, Putnam negotiated mountains of data to support his thesis that the previous few decades had seen Americans retreat en masse from public life. Putnam argued Americans had become disconnected from their wider communities, as evidenced by changes such as a decline in civic engagement and dwindling membership rates for groups such as bowling leagues and PTAs.

Though aspects of Bowling Alone are a little dated today (“computer-mediated communication” isn’t a phrase you’re likely to have heard recently), a quick glance at 2021’s social landscape would suggest many of the trends Putnam described have only continued and apply in other parts of the world too.

Right now, polarization and social distancing have forced us apart from any sense of community to a degree that can seem irresolvable.

Will we ever bowl in leagues alongside near strangers and turn them into friends again? Will we ever bowl again at all, even if alone, or will those gleaming aisles, too-tight shoes, and overpriced sodas fade into a distant memory we recount to our children?

The idea of going into a public space for a non-essential reason can feel incredibly out of reach for many of us right now. And who knows how spaces like bowling alleys will survive in the long run without the social scenes that fuelled them. Now is a perfect time to revisit Bowling Alone to see what it can still teach us, because many of its warnings and lessons are perhaps more relevant now than at its time of publication.

One key lesson we can derive from Bowling Alone is that the less we trust each other—something which is both a cause and consequence of declining community engagement—the more it costs us. Mistrust is expensive.

We need to trust the people around us in order to live happy, productive lives. If we don’t trust them, we end up having to find costly ways to formalize our relationships. Even if we’re not engaged with other people on a social or civic level, we still have to transact with them on an economic one. We still have to walk along the same streets, send our children to the same schools, and spend afternoons in the same parks.

To live our lives freely, we need to to find ways to trust that other people won‘t hurt us, rip us off, or otherwise harm us. Otherwise we may lose something too precious to put a price tag on.

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No person is an island

As community engagement declines, Putnam refers to the thing we are losing as “social capital,” meaning the sum of our connections with other individuals and the benefits they bring us.

Being part of a social network gives you access to all sorts of value. Putnam explains, “Just as a screwdriver (physical capital) or a college education (human capital) can increase productivity (both individual and collective), so too can social contacts affect the productivity of individuals and groups.” For example, knowing the right people can help you find a job where your skills are well utilized. If you don’t know many people, you might struggle to find work and end up doing something you’re overqualified for or be unemployed for a while.

To give another example, if you’re friends with other parents in your local neighborhood, you can coordinate with them to share childcare responsibilities. If you’re not, you’re likely to end up paying for childcare or being more limited in what you can do when your kids are home from school.

Both individuals and groups have social capital. Putnam also explains that “social capital also can have externalities that affect the wider community, so that not all of the costs and benefits of social connections accrue to the person making the contact . . . even a poorly connected individual may derive some of the spillover benefits from living in a well-connected community.” A well-connected community is usually a safer community, and the safety extends, at least partly, to the least connected members.

For example, the more neighbors know each other, the more they notice when something on the street is out of the norm and potentially harmful. That observation benefits everyone on the street—especially the most vulnerable people.

Having social capital is valuable because it undergirds certain norms. Our connections to other people require and encourage us to behave in ways that maintain those connections. Being well-connected is both an outcome of following social norms and an incentive to follow them. We adhere to “rules of conduct” for the sake of our social capital.

Social capital enables us to trust other people. When we’re connected to many others, we develop a norm of “generalized reciprocity.” Putnam explains this as meaning “I’ll do this for you without expecting anything specific back from you, in the confident expectation that someone else will do something for me down the road.” We can go for the delayed payoff that comes from being nice without an agenda. Generalized reciprocity makes all of our interactions with other people easier. It’s a form of trust.

Putnam goes on to write, “A society characterized by generalized reciprocity is more efficient than a distrustful society, for the same reason that money is more efficient than barter. If we don’t have to balance every exchange instantly, we can get a lot more accomplished. Trustworthiness lubricates social life.” Trust requires that we interact with the same people more than once, or at least think that we might.

Generalized reciprocity as a norm also enables us to work together to do things that benefit the whole group or even that don’t benefit us personally at all, rather than focusing on ourselves. If you live in a neighborhood with a norm of generalized reciprocity, you can do things like mowing a neighbor’s lawn for free because you know that when you need similar help, someone will come through. You can do things that wouldn’t make sense in an “every person for themselves” area.

Societies and groups with a norm of generalized reciprocity maintain that norm through “gossip and other valuable ways of cultivating reputation.”

When people are linked to each other, they know that news will spread if they deviate from norms. If one member of a bowling league cheats and another member notices, they’re likely to discuss it with others, and everyone will know to trust that member a little less. Knowing gossip will spread enables us to trust our perceptions of others, because if something were amiss we would have surely heard about it. It also nudges us towards behaving well—if something is amiss about us, others are sure to hear of that, too.

But with the decline of community participation comes the decline of trust. If you don’t know the people around you, how can you trust them? The more disconnected we are from each other, the less we can rely on each other to be good and nice. Without repeated interactions with the same people, we become suspicious of each other. This suspicion carries heavy costs.

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Rising transaction costs

In economics, a “transaction cost” refers to the cost of making some sort of trade within a market. Transaction costs are the price we pay in order to exchange value. They’re in addition to the cost of producing or otherwise providing that value.

For example, when you make a credit card purchase in a shop, the shop likely pays a processing fee to the card company. It’s part of the cost of doing business with you. Another cost is that the shop needs people working in it to ensure you pay. They can’t just rely on you popping the right money in the till then leaving.

Putnam explains later in the book that being able to trust people as a result of a norm of generalized reciprocity in our social lives leads to reduced transaction costs. It means we can relax around other people and not be distracted by “worrying whether you got back the right change from the clerk to double-checking that you locked the car door.” We can easily be honest if we know others will do the same.

With the decline of social capital comes rising transaction costs. We can’t rely on other people to treat us as they would like to be treated because we don’t know them and haven’t built the opportunities to engage in reciprocal relationships.

Much like trusting trustworthy people has great benefits, trusting untrustworthy people has enormous costs. No one likes being exploited or ripped off because they assumed good faith in the wrong person.

If we’re uncertain, we default to mistrust. You can see the endpoint of a loss of trust in societies and groups which must rely on the use or threat of force to get anything done because everyone is out to rip off everyone else.

At a certain point, transaction costs can cancel out the benefits of transacting at all. If lending a leaf blower to a neighbor requires a lawyer to set up a contract stipulating the terms of its use, then borrowing it doesn’t save them any money. They might as well hire someone or buy their own.

We don’t try new things when we can’t trust other people. So we have to find additional ways of making transactions work. One way we do this is through “the rule of law—formal contracts, courts, litigation, adjudication, and enforcement by the state.” During the period since the 1970s when Putnam considers social capital to have declined, the ratio of lawyers to other professions increased more than any other profession: “After 1970 the legal profession grew three times faster than the other professions as a whole.”

While we can’t attribute that solely to a decline in social capital, it seems clear that mistrusting each other makes us more likely to prefer to get things in writing. We are “forced to rely increasingly on formal institutions, and above all the law, to accomplish what we used to accomplished through informal networks reinforced by generalized reciprocity—that is, through social capital.”

***

The high price of mistrust

The cost of mistrust doesn’t just show up in the form of bills from lawyers. It poisons everything we do and further drives us apart.

Mistrust drives us to install remote monitoring software on our employees’ laptops and ask them to fill in reports on every tiny task to prove they’re not skiving off. It drives us to make excuses when a friend asks for help moving or a lift to the airport because no one was available last time we needed that same help. It drives us to begrudgingly buy a household appliance or tool we’ll only use once because we don’t even consider borrowing it from a neighbor.

Mistrust nudges us to peek at the search history of a partner or to cross-reference what a child says. It causes us to keep our belongings close in public, to double-lock the doors, to not let our kids play in the street, and a million other tiny changes.

Mistrust costs us time and money, sure. But it also costs us a little bit of our humanity. We are sociable animals, and seeing the people around us as a potential threat, even a small one, wears on us. Constant vigilance is exhausting. So is being under constant suspicion.

One lesson we can take from Bowling Alone is that anything we can do to increase trust between people will have tremendous knock-on benefits. Trust allows us to relax, delay gratification, and generally be nicer to everyone. It makes for a nicer day-to-day existence. We don’t need to spend so much time and money checking up on others. Ultimately, it’s worth investing in trust whenever possible, as opposed to investing in more ways of monitoring and controlling people.

That’s not to say that there was ever a golden utopia when everyone trusted everyone. People have always abused the trust of others. And people on the fringes of society have always been unfairly mistrusted and struggled to trust that others would act in good faith. Nonetheless, whenever we go to install some mechanism intended to replace trust, it’s worth asking if there’s a different way.

The ingredients for trust are simple. We need to repeatedly interact with the same people, know that others will warn us about their bad behavior, and feel secure in the knowledge we’ll be helped when and if we need it. At the same time, we need to know others will be warned if we behave badly and that everything we give to others will come back to us, perhaps multiplied.

If you want people to trust you, the best place to start is by trusting them. That isn’t always easy to do, especially if you’ve paid the price for it in the past. But it’s the best place to start. Then you need to combine it with repeat interactions, or the possibility thereof. In the iterated Prisoner’s Dilemma, a game that reveals how cooperation works, the best strategy to adopt is tit for tat. In the first round you cooperate, then in subsequent rounds do whatever the other player did last.

How might that play out in real life? If you want your employees to trust you, then you might start by trusting them—while also making it clear that you’re not going to fire them suddenly and you want them to stick around.

Mistrust is expensive. But trusting the wrong people can sometimes seem too risky. The lesson we can take from Bowling Alone is that building trust is absolutely worthwhile—and that the only way to do it is by finding ways to get out there and engage with other people.

We can create trust by contributing to existing communities and creating new ones. The more we show up and are willing to have faith in others, the more we’ll get back in return.

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Why You Should Practice Failure

Reading Time: 3 minutes

We learn valuable lessons when we experience failure and setbacks. Most of us wait for those failures to happen to us, however, instead of seeking them out. But deliberately making mistakes can give us the knowledge we need to more easily overcome obstacles in the future.

We learn from our mistakes. When we screw up and fail, we learn how not to handle things. We learn what not to do.

Failing is a byproduct of trying to succeed. We do our research, make our plans, get the necessary ingredients, and try to put it all together. Often, things don’t go as we wish. If we’re smart, we reflect on what happened and make note of where we could do better next time.

But how many of us make deliberate mistakes? How often do we try to fail in order to learn from it?

If we want to avoid costly mistakes in the future when the stakes are high, then making some now might be excellent preparation.

***

Practicing failure is a common practice for pilots. In 1932, at the dawn of the aviation age, Amelia Earhart described the value for all pilots of learning through deliberate mistakes. “The fundamental stunts taught to students are slips, stalls, and spins,” she says in her autobiography The Fun of It. “A knowledge of some stunts is judged necessary to good flying. Unless a pilot has actually recovered from a stall, has actually put his plane into a spin and brought it out, he cannot know accurately what those acts entail. He should be familiar enough with abnormal positions of his craft to recover without having to think how.”

For a pilot, stunting is a skill attained through practice. You go up in a plane and, for example, you change the angle of the wings to deliberately stall the craft. You prepare beforehand by learning what a stall is, what the critical variables you have to pay attention to are, and how other pilots address stalls. You learn the optimal response. But then you go up in the air and actually apply your knowledge. What’s easy and obvious on the ground, when you’re under little pressure, isn’t guaranteed to come to you when your plane loses lift and function at 10,000 feet. Deliberately stalling your plane, making a conscientious mistake when you have prepared to deal with it, gives you the experience to react when a stall happens in a less controlled situation.

The first time your plane unexpectedly stops working in mid-flight is scary for any pilot. But those who have practiced in similar situations are far more likely to react appropriately. “An individual’s life on the ground or in the air may depend on a split second,” Earhart writes. “The slow response which results from seldom, if ever, having accomplished the combination of acts required in a given circumstance may be the deciding factor.” You don’t want the first stall to come at night in poor weather when you have your family in the cabin. Much better to practice stalling in a variety of situations ahead of time—that way, when one happens unexpectedly, your reactions can be guided by successful experience and not panic.

Earhart advises that in advance, the solution to many problems can be worked out on paper, “but only experience counts when there is no time to think a process through. The pilot who hasn’t stalled a plane is less likely to be able to judge correctly the time and space necessary for recovery than one who has.”

If you practice failing every so often, you increase your flexibility and adaptability when life throws obstacles in your way. Of course, no amount of preparation will get you through all possible challenges, and Earhart’s own story is the best example of that. But making deliberate mistakes in order to learn from them is one way to give ourselves optionality when our metaphorical engine stops in midair.

If we don’t practice failing, we can only safely fly on sunny days.

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We Are What We Remember

Reading Time: 7 minutes

Memory is an intrinsic part of our life experience. It is critical for learning, and without memories we would have no sense of self. Understanding why some memories stick better than others, as well as accepting their fluidity, helps us reduce conflict and better appreciate just how much our memories impact our lives.

***

“Which of our memories are true and which are not is something we may never know. It doesn’t change who we are.”

Memories can be so vivid. Let’s say you are spending time with your sibling and reflecting on your past when suddenly a memory pops up. Even though it’s about events that occurred twenty years ago, it seems like it happened yesterday. The sounds and smells pop into your mind. You remember what you were wearing, the color of the flowers on the table. You chuckle and share your memory with your sibling. But they stare at you and say, “That’s not how I remember it at all.” What?

Memory discrepancies happen all the time, but we have a hard time accepting that our memories are rarely accurate. Because we’ve been conditioned to think of our memories like video recordings or data stored in the cloud, we assert that our rememberings are the correct ones. Anyone who remembers the situation differently must be wrong.

Memories are never an exact representation of a moment in the past. They are not copied with perfect fidelity, and they change over time. Some of our memories may not even be ours, but rather something we saw in a film or a story someone else told to us. We mix and combine memories, especially older ones, all the time. It can be hard to accept the malleable nature of memories and the fact that they are not just sitting in our brains waiting to be retrieved. In Adventures in Memory, writer Hilde Østby and neuropsychologist Ylva Østby present a fascinating journey through all aspects of memory. Their stories and investigations provide great insight into how memory works; and how our capacity for memory is an integral part of the human condition, and how a better understanding of memory helps us avoid the conflicts we create when we insist that what we remember is right.

***

Memory and learning

“One thing that aging doesn’t diminish is the wisdom we have accumulated over a lifetime.”

Our memories, dynamic and changing though they may be, are with us for the duration of our lives. Unless you’ve experienced brain trauma, you learn new things and store at least some of what you learn in memory.

Memory is an obvious component of learning, but we don’t often think of it that way. When we learn something new, it’s against the backdrop of what we already know. All knowledge that we pick up over the years is stored in memory. The authors suggest that “how much you know in a broad sense determines what you understand of the new things you learn.” Because it’s easier to remember something if it can hook into context you already have, then the more you know, the more a new memory can attach to. Thus, what we already know, what we remember, impacts what we learn.

The Østbys explain that the strongest memory networks are created “when we learn something truly meaningful and make an effort to understand it.” They describe someone who is passionate about diving and thus “will more easily learn new things about diving than about something she’s never been interested in before.” Because the diver already knows a lot about diving, and because she loves it and is motivated to learn more, new knowledge about diving will easily attach itself to the memory network she already has about the subject.

While studying people who seem to have amazing memories, as measured by the sheer amount they can recall with accuracy, one of the conclusions the Østbys reach is “that many people who rely on their memories don’t use mnemonic techniques, nor do they cram. They’re just passionate about what they do.” The more meaningful the topics and the more we are invested in truly learning, the higher the chances are that we will convert new information into lasting memory. Also, the more we learn, the more we will remember. There doesn’t seem to be a limit on how much we can put into memory.

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How we build our narratives

The experience of being a human is inseparable from our ability to remember. You can’t build relationships without memories. You can’t prepare for the future if you don’t remember the past.

The memories we hold on to early on have a huge impact on the ones we retain as we progress through life. “When memories enter our brain,” the Østbys explain, “they attach themselves to similar memories: ones from the same environment, or that involve the same feeling, the same music, or the same significant moment in history. Memories seldom swim around without connections.” Thus, a memory is significantly more likely to stick around if it can attach itself to something. A new experience that has very little in common with the narrative we’ve constructed of ourselves is harder to retain in memory.

As we get older, our new memories tend to reinforce what we already think of ourselves. “Memory is self-serving,” the Østbys write. “Memories are linked to what concerns you, what you feel, what you want.”

Why is it so much easier to remember the details of a vacation or a fight we’ve had with our partner than the details of a physics lesson or the plot of a classic novel? “The fate of a memory is mostly determined by how much it means to us. Personal memories are important to us. They are tied to our hopes, our values, and our identities. Memories that contribute meaningfully to our personal autobiography prevail in our minds.” We need not beat ourselves up because we have a hard time remembering names or birthdays. Rather, we can accept that the triggers for the creation of a memory and its retention are related to how it speaks to the narrative we maintain about ourselves. This view of memory suggests that to better retain information, we can try to make knowing that information part of our identity. We don’t try to remember physics equations for the sake of it, but rather because in our personal narrative, we are someone who knows a lot about physics.

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Memory, imagination, and fluidity

Our ability to imagine is based, in part, on our ability to remember. The connection works on two levels.

The first, the Østbys write, is that “our memories are the fuel for our imagination.” What we remember about the past informs a lot of what we can imagine about the future. Whether it’s snippets from movies we’ve seen or activities we’ve done, it’s our ability to remember the experiences we’ve had that provide the foundation for our imagination.

Second, there is a physical connection between memory and imagination. “The process that gives us vivid memories is the same as the one that we use to imagine the future.” We use the same parts of the brain when we immerse ourselves in an event from our past as we do when we create a vision for our future. Thus, one of the conclusions of Adventures in Memory is that “as far as our brains are concerned, the past and future are almost the same.” In terms of how they can feel to us, memories and the products of imagination are not that different.

The interplay between past and future, between memory and imagination, impacts the formation of memories themselves. Memory “is a living organism,” the Østbys explain, “always absorbing images, and when new elements are added, they are sewn into the original memory as seamlessly as only our imagination can do.”

One of the most important lessons from the book is to change up the analogies we use to understand memory. Memories are not like movies, exactly the same no matter how many times you watch them. Nor are they like files stored in a computer, unchanging data saved for when we might want to retrieve it. Memories, like the rest of our biology, are fluid.

“Memory is more like live theater, where there are constantly new productions of the same pieces,” the Østbys write. “Each and every one of our memories is a mix of fact and fiction. In most memories the central story is based on true events, but it’s still reconstructed every time we recall it. In these reconstructions, we fill in the gaps with probable facts. We subconsciously pick up details from a sort-of memory prop room.”

Understanding our memory more like a theater production, where the version you see in London’s West End isn’t going to be exactly the same as the one you see on Broadway, helps us let go of attaching a judgment of accuracy to what we remember. It’s okay to find out when reminiscing with friends that you have different memories of the same day. It’s also acceptable that two people will have different memories of the events leading to their divorce, or that business partners will have different memories of the terms they agreed to at the start of the partnership. The more you get used to the fluidity of your memories, the more the differences in recollections become sources of understanding instead of points of contention. What people communicate about what they remember can give you insight into their attitudes, beliefs, and values.

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Conclusion

New memories build on the ones that are already there. The more we know, the easier it is to remember the new things we learn. But we have to be careful and recognize that our tendency is to reinforce the narrative we’ve already built. Brand new information is harder to retain, but sometimes we need to make the effort.

Finally, memories are important not only for learning and remembering but also because they form the basis of what we can imagine and create. In so many ways, we are what we remember. Accepting that our vivid memories can be very different from those who were in the same situation helps us reduce the conflict that comes with insisting that our memories must always be correct.

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“Jootsing”: The Key to Creativity

Reading Time: 5 minutes

Creativity can seem like a mysterious process. But many of the most creative people understand that you can actually break it down into a simple formula, involving what researcher Douglas Hofstadter calls “jootsing.” Here’s how understanding systems can help us think more creatively.

“Art is limitation; the essence of every picture is the frame. If you draw a giraffe, you must draw him with a long neck. If in your bold creative way you hold yourself free to draw a giraffe with a short neck, you will really find that you are not free to draw a giraffe.” —G.K. Chesterton

We can break the creative process down into the following three steps:

  1. Gain a deep understanding of a particular system and its rules.
  2. Step outside of that system and look for something surprising that subverts its rules.
  3. Use what you find as the basis for making something new and creative.

It may not be simple to do, but it is reliable and repeatable.

In Intuition Pumps and Other Tools for Thinking, philosopher Daniel C. Dennett describes this process of understanding a system in order to step outside of it as “jootsing,” using a term coined by Douglas Hofstadter. “Jootsing” means “jumping out of the system.”

Dennett explains that jootsing is the method behind creativity in science, philosophy, and the arts: “Creativity, that ardently sought but only rarely found virtue, often is a heretofore unimagined violation of the rules of the system from which it springs.” The rules within a system could be things like the idea that a painting must have a frame, a haiku must only have seventeen syllables, or a depiction of landscape must have a blue sky. But galleries hang paintings without frames all the time. Haiku without seventeen syllables win international contests. And landscape paintings don’t need to contain a sky, let alone a blue one.

***

Creativity, as Dennett describes it, is not about pure novelty. The concept of jootsing shows us that constraints and restrictions are essential for creativity.

Breaking rules you don’t know exist is not a statement. It’s a common refrain that much of modern art could be the work of a five-year-old. Yet while a five-year-old could produce a random combination of elements that looks similar to a famous work of modern art, it would not be creative in the same way because the child would not be jootsing. They wouldn’t have an understanding of the system they now sought to subvert.

Limitations are essential because they give us a starting point and a shape to work against.

While amateurs may attempt to start from scratch when trying to make something creative in a new area, professionals know they must first get in touch with the existing territory. Before even contemplating their own work, they take the time to master the conventional ways of doing things, to know what the standards are, and to become well-versed in the types of work considered exemplary. Doing so can take years or even the best part of a career. Dennett summarizes: “It helps to know the tradition if you want to subvert it. That’s why so few dabblers or novices succeed in coming up with anything truly creative.”

***

Understanding a system first is necessary for creativity for two reasons. First, it provides something comprehensible to use as a starting point, and second, it makes it possible to come up with something more interesting or useful. If you try to start a creative effort from nothing, you’ll end up with mere chaos.

Dennett writes: “Sit down at a piano and try to come up with a good new melody and you soon discover how hard it is. All the keys are available, in any combination you choose, but until you can find something to lean on, some style or genre or pattern to lay down and exploit a bit, or allude to, before you twist it, you will come up with nothing but noise.”

Creativity often begins with accidents that end up showing a new possibility or reveal that violating a particular rule isn’t as harmful as expected. Elsewhere in the book, Dennett suggests that any computer model intended to generate creativity must include mistakes and randomness, “junk lying around that your creative process can bump into, noises that your creative process can’t help overhearing.”

***

Most of us say we want to be creative—and we want the people we work with and for to be creative. The concept of jootsing reveals why we often end up preventing that from happening. Creativity is impossible without in some way going against rules that exist for a good reason.

Psychologists Jacob Getzels and Phillip Jackson studied creativity in the 1950s. Their findings were repeated across many studies and described what was termed as the Getzels-Jackson effect: “The vast majority—98 percent—of teachers say creating is so important that it should be taught daily, but when tested, they nearly always favor less creative children over more creative children.”

Kevin Ashton, in How to Fly a Horse, explains why. Teachers favor less creative children “because people who are more creative also tend to be more playful, unconventional, and unpredictable, and all of this makes them harder to control. No matter how much we say we value creation, deep down, most of us value control more. And so we fear change and favor familiarity. Rejecting is a reflex.” Ashton notes that the Getzels-Jackson effect is also present in the organizations we are a part of in adulthood. When the same tests are applied to decision-makers and authority figures in business, science, and government, the results are the same: they all say they value creation, but it turns out they don’t value creators.

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If you want people to be creative, you can’t complain or punish them when they question a system that is “typically so entrenched that it is as invisible as the air you breathe,” as Dennett says. You need to permit a lot of exploration, including ideas that don’t work out. Not everything outside of a system proves worth pursuing. And often the rules that are most beneficial to break are those that seem the most load-bearing, as if meddling with them will cause the whole system to collapse. It might—or it might make it much better.

You also need to permit the making of mistakes if you want to foster creativity, because that often ends up leading to new discoveries. Dennett writes, “The exploitation of accidents is the key to creativity, whether what is being made is a new genome, a new behavior, or a new melody.” Most accidents never end up being profitable or valuable in a measurable way. But they’re necessary because they’re part of the process of developing something new. Accidents fuel creativity.

In the book Loonshots, Safi Bahcall explores, among other ideas, how to nurture and develop those seemingly crazy ideas that turn out to be paradigm-shifting innovations. He gives many examples of now ubiquitous technologies that were initially laughed at, rejected, or buried. He notes that it’s not easy to immediately buy in to radical developments, and if we want to have environments where creating is possible, then we have to give creativity space and understanding. “It’s worth keeping in mind,” he says, “that revving the creative engine to fire at higher speeds . . . means more ideas and more experiments, which also means, inevitably, more failed experiments.”

As individuals, if we want to be creative, we need to give ourselves space to play and experiment without a set agenda. Amos Tversky famously said that the secret to doing good work is being a little unemployed so you always have hours in the day to waste as you wish. During that wasted time, you’ll likely have your best, most creative ideas.

If your schedule is crammed with only room for what’s productive in an obvious way, you’ll have a hard time seeing outside of the existing system.

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The Best of The The Knowledge Project 2020

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One of the best ways to learn is a good conversation.

While there are many advantages to a good conversation, perhaps the best is that you can benefit from the lessons that other people have already paid the price for. Of course, that’s not all. Good conversations can also offer a new way to interpret your past experiences, discover something new, and remind us of something we already know.

A good conversation updates the software in your brain. But not all updates are the same. Learning more isn’t simply a matter of having more conversations, but rather getting more out of each conversation that you are apart of. Deep conversations with ‘people that do’ offer the richest source of learning. Conversations that skim the surface, on the other hand, only offer the illusion of learning.

With that in mind, we’d like to invite you to join us in the top conversations we had on The Knowledge Project in 2020.

It’s time to listen and learn.

  • Episode 82: Bill Ackman: Getting Back Up — Legendary activist investor, Bill Ackman talks about lessons he’s learned growing up, raising a family, what drives him forward and back up from failure, consuming information and ideas, and facing criticism.
  • Episode 94: Chamath Palihapitiya: Understanding Yourself — Founder and CEO of Social Capital, Chamath Palihapitiya sits down with Shane Parrish to chat about what it means to be an observer of the present, how to think in first principles, the psychology of successful investing, his thoughts on the best public company CEOs and much more.
  • Episode 74: Embracing Confusion with Jeff Hunter — CEO of Talentism, Jeff Hunter, teaches how to rewrite damaging narratives that hold us back, how to give and receive helpful feedback, and why confusion can be a good thing.
  • Episode 80: Developing the Leader in You with John Maxwell — Leadership expert John Maxwell breaks down the four traits every successful person possesses and how to awaken the leader within you, no matter what your job title says.
  • Episode 85: Bethany McLean: Crafting a Narrative — Best-selling author of The Smartest Guys in the Room and All the Devils are Here, Bethany McLean, discusses how to write a story, the behaviors of CEO’s, visionaries and fraudsters and so much more.

Honorary mention to Derek Sivers: Innovation Versus Imitation [The Knowledge Project Ep. #88], who was only 131 downloads away from making the list.

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In other news this year, we released a TKP youtube channel with full-length videos of our conversations so you can see the guest, as well as a “Clips” channel, where we are building the world’s best repository of nugget-sized information you can use in work and life.

If you’re still curious, check out the 2019 list.

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