Tag: Thinking Tools

Your First Thought Is Rarely Your Best Thought: Lessons on Thinking

The best advice I've ever gotten about thinking came from a private-company CEO who has a thirty-year track record that's up there with Warren Buffett's. One day he said to me, “Shane, most people don't actually think. They just take their first thought and go.”

We're all busy. We've got meetings, phone calls, texts, kids, spouses, parents, friends, and of course the ever-present email. Busyness has become an end in itself, and nothing is more dangerous. What my CEO friend meant was that people are losing the ability to think through a problem.

Most people schedule themselves like lawyers. They work in five- to eight-minute increments, scheduled back to back. The best part of their day is when they manage to sneak away for a quick coffee with a friend before heading into the next meeting they haven't had time to prepare for.

I actually schedule time to think. It sounds ridiculous, I know, but I protect this time as if my livelihood depended on it because it does. Sometimes I'm in the office and sometimes I'm in a coffee shop. I'm not always thinking about a problem that I'm wresting with. I'm often just thinking about things I already know or, more accurately, things I think I know. Setting aside time for thinking works wonders, not only for me but also for most of the people I've convinced to give it a try.

The problem with not having time to think is nailed by William Deresiewicz, who said:

I find for myself that my first thought is never my best thought. My first thought is always someone else's; it's always what I've already heard about the subject, always the conventional wisdom.

Here's what Deresiewicz says does work:

It's only by concentrating, sticking to the question, being patient, letting all the parts of my mind come into play, that I arrive at an original idea. By giving my brain a chance to make associations, draw connections, take me by surprise. And often even that idea doesn't turn out to be very good. I need time to think about it, too, to make mistakes and recognize them, to make false starts and correct them, to outlast my impulses, to defeat my desire to declare the job done and move on to the next thing.

A lot of people see thinking more than a few minutes as a waste of time, but this viewpoint is shortsighted and flawed. While it might take me 30 minutes to come to the same conclusion that you come to in 5, I'll likely have a better idea of the nuances of the situation, including which variables matter the most. I'll know what to watch for and I'll know how to frame things for other people to appeal to their interests. Not only will collaboration take less time, but I'll make fewer mistakes. That's the real advantage.

Thinking time is non-linear. The time you spend thinking – walking around a problem in a three-dimensional way and exploring all of the various perspectives and mental models – pays you back tenfold in the end. The problem for those who are shortsighted is that this time will appear as a negative for a while because it looks like nothing is getting done. This situation is a great example of what I call first-order negative, second-order positive.

A lot of things in life are first-order positive and second-order negative. Heroin is an obvious one, sugar less so. We have trouble delaying gratification, so we do a lot of things that are first-order positive, second-order negative. We buy bigger houses than we need, only to find that rising interest rates make the mortgage payment untenable. We buy the sexy car only to discover later that it depreciates faster than the commuter car.

A real advantage is conferred on people who can do things that are first-order negative, second-order positive. Especially if these first-order negatives are very visible costs with no immediate benefit in the short term and a non-linear benefit at some future time.

Intuitively we know the value of delayed gratification. We tell our kids that they need to get an education, which is nothing more than preparation for life. And yet once we get out of school and start working full time, we are conditioned to think in terms of today and tomorrow, rather than months or years ahead. Suddenly, everything we do is supposed to provide an instant and visible benefit to the organization. At an individual level, this means that for your organization to value you more, you must run faster and faster. At a corporate level, this means you're ripe for disruption from a competitor willing to play the long game.

Making time to think is a great example of something that's first-order negative with some future payoff that's not easily visible. However, when you think through problems, you'll not only come to better decisions on the whole but you'll also avoid a lot of problems.

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Poker, Speeding Tickets, and Expected Value: Making Decisions in an Uncertain World

“Take the probability of loss times the amount of possible loss from the probability of gain times the amount of possible gain. That is what we're trying to do. It's imperfect but that's what it's all about.”

— Warren Buffett

You can train your brain to think like CEOs, professional poker players, investors, and others who make tricky decisions in an uncertain world by weighing probabilities.

All decisions involve potential tradeoffs and opportunity costs. The question is, how can we make the best possible choices when the factors involved are often so complicated and confusing? How can we determine which statistics and metrics are worth paying attention to? How do we think about averages?

Expected value is one of the simplest tools you can use to think better. While not a natural way of thinking for most people, it instantly turns the world into shades of grey by forcing us to weigh probabilities and outcomes. Once we've mastered it, our decisions become supercharged. We know which risks to take, when to quit projects, when to go all in, and more.

Expected value refers to the long-run average of a random variable.

If you flip a fair coin ten times, the heads-to-tails ratio will probably not be exactly equal. If you flip it one hundred times, the ratio will be closer to 50:50, though again not exactly. But for a very large number of iterations, you can expect heads to come up half the time and tails the other half. The law of large numbers dictates that the values will, in the long term, regress to the mean, even if the first few flips seem unequal.

The more coin flips, the closer you get to the 50:50 ratio. If you bet a sum of money on a coin flip, the potential winnings on a fair coin have to be bigger than your potential loss to make the expected value positive.

We make many expected-value calculations without even realizing it. If we decide to stay up late and have a few drinks on a Tuesday, we regard the expected value of an enjoyable evening as higher than the expected costs the following day. If we decide to always leave early for appointments, we weigh the expected value of being on time against the frequent instances when we arrive early. When we take on work, we view the expected value in terms of income and other career benefits as higher than the cost in terms of time and/or sanity.

Likewise, anyone who reads a lot knows that most books they choose will have minimal impact on them, while a few books will change their lives and be of tremendous value. Looking at the required time and money as an investment, books have a positive expected value (provided we choose them with care and make use of the lessons they teach).

These decisions might seem obvious. But the math behind them would be somewhat complicated if we tried to sit down and calculate it. Who pulls out a calculator before deciding whether to open a bottle of wine (certainly not me) or walk into a bookstore?

The factors involved are impossible to quantify in a non-subjective manner – like trying to explain how to catch a baseball. We just have a feel for them. This expected-value analysis is unconscious – something to consider if you have ever labeled yourself as “bad at math.”

Parking Tickets

Another example of expected value is parking tickets. Let's say that a parking spot costs $5 and the fine for not paying is $10. If you can expect to be caught one-third of the time, why pay for parking? The expected value of doing so is negative. It's a disincentive. You can park without paying three times and pay only $10 in fines, instead of paying $15 for three parking spots. But if the fine is $100, the probability of getting caught would have to be higher than one in twenty for it to be worthwhile. This is why fines tend to seem excessive. They cover the people who are not caught while giving an incentive for everyone to pay.

Consider speeding tickets. Here, the expected value can be more abstract, encompassing different factors. If speeding on the way to work saves 15 minutes, then a monthly $100 fine might seem worthwhile to some people. For most of us, though, a weekly fine would mean that speeding has a negative expected value. Add in other disincentives (such as the loss of your driver's license), and speeding is not worth it. So the calculation is not just financial; it takes into account other tradeoffs as well.

The same goes for free samples and trial periods on subscription services. Many companies (such as Graze, Blue Apron, and Amazon Prime) offer generous free trials. How can they afford to do this? Again, it comes down to expected value. The companies know how much the free trials cost them. They also know the probability of someone's paying afterwards and the lifetime value of a customer. Basic math reveals why free trials are profitable. Say that a free trial costs the company $10 per person, and one in ten people then sign up for the paid service, going on to generate $150 in profits. The expected value is positive. If only one in twenty people sign up, the company needs to find a cheaper free trial or scrap it.

Similarly, expected value applies to services that offer a free “lite” version (such as Buffer and Spotify). Doing so costs them a small amount or even nothing. Yet it increases the chance of someone's deciding to pay for the premium version. For the expected value to be positive, the combined cost of the people who never upgrade needs to be lower than the profit from the people who do pay.

Lottery tickets prove useless when viewed through the lens of expected value. If a ticket costs $1 and there is a possibility of winning $500,000, it might seem as if the expected value of the ticket is positive. But it is almost always negative. If one million people purchase a ticket, the expected value is $0.50. That difference is the profit that lottery companies make. Only on sporadic occasions is the expected value positive, even though the probability of winning remains minuscule.

Failing to understand expected value is a common logical fallacy. Getting a grasp of it can help us to overcome many limitations and cognitive biases.

“Constantly thinking in expected value terms requires discipline and is somewhat unnatural. But the leading thinkers and practitioners from somewhat varied fields have converged on the same formula: focus not on the frequency of correctness, but on the magnitude of correctness.”

— Michael Mauboussin

Expected Value and Poker

Let's look at poker. How do professional poker players manage to win large sums of money and hold impressive track records? Well, we can be certain that the answer isn't all luck, although there is some of that involved.

Professional players rely on mathematical mental models that create order among random variables. Although these models are basic, it takes extensive experience to create the fingerspitzengefühl (“fingertips feeling,” or instinct) necessary to use them.

A player needs to make correct calculations every minute of a game with an automaton-like mindset. Emotions and distractions can corrupt the accuracy of the raw math.

In a game of poker, the expected value is the average return on each dollar invested in the pot. Each time a player makes a bet or call, they are taking into account the probability of making more money than they invest. If a player is risking $100, with a 1 in 5 probability of success, the pot must contain at least $500 for the bet to be safe. The expected value per call is at least equal to the amount the player stands to lose. If the pot contains $300 and the probability is 1 in 5, the expected value is negative. The idea is that even if this tactic is unsuccessful at times, in the long run, the player will profit.

Expected-value analysis gives players a clear idea of probabilistic payoffs. Successful poker players can win millions one week, then make nothing or lose money the next, depending on the probability of winning. Even the best possible hands can lose due to simple probability. With each move, players also need to use Bayesian updating to adapt their calculations. because sticking with a prior figure could prove disastrous. Casinos make their fortunes from people who bet on situations with a negative expected value.

Expected Value and the Ludic Fallacy

In The Black Swan, Nassim Taleb explains the difference between everyday randomness and randomness in the context of a game or casino. Taleb coined the term “ludic fallacy” to refer to “the misuse of games to model real-life situations.” (Or, as the website logicallyfallacious.com puts it: the assumption that flawless statistical models apply to situations where they don’t actually apply.)

In Taleb’s words, gambling is “sterilized and domesticated uncertainty. In the casino, you know the rules, you can calculate the odds… ‘The casino is the only human venture I know where the probabilities are known, Gaussian (i.e., bell-curve), and almost computable.’ You cannot expect the casino to pay out a million times your bet, or to change the rules abruptly during the game….”

Games like poker have a defined, calculable expected value. That’s because we know the outcomes, the cards, and the math. Most decisions are more complicated. If you decide to bet $100 that it will rain tomorrow, the expected value of the wager is incalculable. The factors involved are too numerous and complex to compute. Relevant factors do exist; you are more likely to win the bet if you live in England than if you live in the Sahara, for example. But that doesn't rule out Black Swan events, nor does it give you the neat probabilities which exist in games. In short, there is a key distinction between Knightian risks, which are computable because we have enough information to calculate the odds, and Knightian uncertainty, which is non-computable because we don’t have enough information to calculate odds accurately. (This distinction between risk and uncertainty is based on the writings of economist Frank Knight.) Poker falls into the former category. Real life is in the latter. If we take the concept literally and only plan for the expected, we will run into some serious problems.

As Taleb writes in Fooled By Randomness:

Probability is not a mere computation of odds on the dice or more complicated variants; it is the acceptance of the lack of certainty in our knowledge and the development of methods for dealing with our ignorance. Outside of textbooks and casinos, probability almost never presents itself as a mathematical problem or a brain teaser. Mother nature does not tell you how many holes there are on the roulette table, nor does she deliver problems in a textbook way (in the real world one has to guess the problem more than the solution).

The Monte Carlo Fallacy

Even in the domesticated environment of a casino, probabilistic thinking can go awry if the principle of expected value is forgotten. This famously occurred in Monte Carlo Casino in 1913. A group of gamblers lost millions when the roulette table landed on black 26 times in a row. The probability of this occurring is no more or less likely than the other 67,108,863 possible permutations, but the people present kept thinking, “It has to be red next time.” They saw the likelihood of the wheel landing on red as higher each time it landed on black. In hindsight, what sense does that make? A roulette wheel does not remember the color it landed on last time. The likelihood of either outcome is exactly 50% with each spin, regardless of the previous iteration. So the potential winnings for each spin need to be at least twice the bet a player makes, or the expected value is negative.

“A lot of people start out with a 400-horsepower motor but only get 100 horsepower of output. It's way better to have a 200-horsepower motor and get it all into output.”

— Warren Buffett

Given all the casinos and roulette tables in the world, the Monte Carlo incident had to happen at some point. Perhaps some day a roulette wheel will land on red 26 times in a row and the incident will repeat. The gamblers involved did not consider the negative expected value of each bet they made. We know this mistake as the Monte Carlo fallacy (or the “gambler's fallacy” or “the fallacy of the maturity of chances”) – the assumption that prior independent outcomes influence future outcomes that are actually also independent. In other words, people assume that “a random process becomes less random and more predictable as it is repeated”1.

It's a common error. People who play the lottery for years without success think that their chance of winning rises with each ticket, but the expected value is unchanged between iterations. Amos Tversky and Daniel Kahneman consider this kind of thinking a component of the representativeness heuristic, stating that the more we believe we control random events, the more likely we are to succumb to the Monte Carlo fallacy.

Magnitude over Frequency

Steven Crist, in his book Bet with the Best, offers an example of how an expected-value mindset can be applied. Consider a hypothetical race with four horses. If you’re trying to maximize return on investment, you might want to avoid the horse with a high likelihood of winning. Crist writes,

The point of this exercise is to illustrate that even a horse with a very high likelihood of winning can be either a very good or a very bad bet, and that the difference between the two is determined by only one thing: the odds.”2

Everything comes down to payoffs. A horse with a 50% chance of winning might be a good bet, but it depends on the payoff. The same holds for a 100-to-1 longshot. It's not the frequency of winning but the magnitude of the win that matters.

Error Rates, Averages, and Variability

When Bill Gates walks into a room with 20 people, the average wealth per person in the room quickly goes beyond a billion dollars. It doesn't matter if the 20 people are wealthy or not; Gates's wealth is off the charts and distorts the results.

An old joke tells of the man who drowns in a river which is, on average, three feet deep. If you're deciding to cross a river and can't swim, the range of depths matters a heck of a lot more than the average depth.

The Use of Expected Value: How to Make Decisions in an Uncertain World

Thinking in terms of expected value requires discipline and practice. And yet, the top performers in almost any field think in terms of probabilities. While this isn't natural for most of us, once you implement the discipline of the process, you'll see the quality of your thinking and decisions improve.

In poker, players can predict the likelihood of a particular outcome. In the vast majority of cases, we cannot predict the future with anything approaching accuracy. So what use is expected value outside gambling? It turns out, quite a lot. Recognizing how expected value works puts any of us at an advantage. We can mentally leap through various scenarios and understand how they affect outcomes.

Expected value takes into account wild deviations. Averages are useful, but they have limits, as the man who tried to cross the river discovered. When making predictions about the future, we need to consider the range of outcomes. The greater the possible variance from the average, the more our decisions should account for a wider range of outcomes.

There's a saying in the design world: when you design for the average, you design for no one. Large deviations can mean more risk-which is not always a bad thing. So expected-value calculations take into account the deviations. If we can make decisions with a positive expected value and the lowest possible risk, we are open to large benefits.

Investors use expected value to make decisions. Choices with a positive expected value and minimal risk of losing money are wise. Even if some losses occur, the net gain should be positive over time. In investing, unlike in poker, the potential losses and gains cannot be calculated in exact terms. Expected-value analysis reveals opportunities that people who just use probabilistic thinking often miss. A trade with a low probability of success can still carry a high expected value. That's why it is crucial to have a large number of robust mental models. As useful as probabilistic thinking can be, it has far more utility when combined with expected value.

Understanding expected value is also an effective way to overcome the sunk costs fallacy. Many of our decisions are based on non-recoverable past investments of time, money, or resources. These investments are irrelevant; we can't recover them, so we shouldn't factor them into new decisions. Sunk costs push us toward situations with a negative expected value. For example, consider a company that has invested considerable time and money in the development of a new product. As the launch date nears, they receive irrefutable evidence that the product will be a failure. Perhaps research shows that customers are disinterested, or a competitor launches a similar, better product. The sunk costs fallacy would lead them to release their product anyway. Even if they take a loss. Even if it damages their reputation. After all, why waste the money they spent developing the product? Here's why: Because the product has a negative expected value, which will only worsen their losses. An escalation of commitment will only increase sunk costs.

When we try to justify a prior expense, calculating the expected value can prevent us from worsening the situation. The sunk costs fallacy robs us of our most precious resource: time. Each day we are faced with the choice between continuing and quitting numerous endeavors. Expected-value analysis reveals where we should continue, and where we should cut our losses and move on to a better use of time and resources. It's an efficient way to work smarter, and not engage in unnecessary projects.

Thinking in terms of expected value will make you feel awkward when you first try it. That's the hardest thing about it; you need to practice it a while before it becomes second nature. Once you get the hang of it, you'll see that it's valuable in almost every decision. That's why the most rational people in the world constantly think about expected value. They've uncovered the key insight that the magnitude of correctness matters more than its frequency. And yet, human nature is such that we're happier when we're frequently right.

Footnotes
  • 1

    From https://rationalwiki.org/wiki/Gambler’s_fallacy, accessed on 11 January 2018.

  • 2

    Steven Crist, “Crist on Value,” in Andrew Beyer et al., Bet with the Best: All New Strategies From America’s Leading Handicappers (New York: Daily Racing Form Press, 2001), 63-64.