CHAPTER 6

Adventures in Mental Time Travel

Let Marty McFly run into Marty McFly

Thanks to the success of the three Back to the Future movies, our go-to source on the rules of time travel is more likely to be Doc Brown than Dr. Stephen Hawking. The first rule, emphasized by the trilogy and repeated by nearly every time-travel movie since, is “Whatever you do, don’t meet up with yourself!” Doc Brown (Christopher Lloyd) explains to Marty McFly (Michael J. Fox) in Back to the Future: Part II (1989) that “the encounter could create a time paradox, the results of which could cause a chain reaction that would unravel the very fabric of the space-time continuum and destroy the entire universe. Granted, that’s the worst-case scenario. The destruction might, in fact, be very localized, limited to merely our own galaxy.”

“Don’t meet up with yourself” has become an unquestioned element of the “science” of time travel. In Timecop (1994), because “the same matter can’t occupy the same space at the same time,” Jean-Claude Van Damme’s character destroys the villain by pushing his past and future versions together. The villain turns into a liquefied blob and disappears from existence.

In real-life decision-making, when we bring our past- or future-self into the equation, the space-time continuum doesn’t unravel. Far from turning us into a liquefied blob, a visit from past or future versions of us helps present-us make better bets. When making decisions, isolating ourselves from thinking about similar decisions in the past and possible future consequences is frequently the very thing that turns us into a blob, mired by in-the-moment thinking where the scope of time is distorted. As decision-makers, we want to collide with past and future versions of ourselves. Our capacity for mental time travel makes this possible. As is the case with accountability, such meetings can lead to better decisions: at the moment of the decision, accountability to our group can pop us briefly into the future to imagine the conversation about the decision we will have with that group. Running that conversation will often remind us to stay on a more rational path.

Just as we can recruit other people to be our decision buddies, we can recruit other versions of ourselves to act as our own decision buddies. We can harness the power of mental time traveling, operationalizing it, encouraging it, and figuring out ways to cause that collision of past, present, and future as much as possible. Present-us needs that help, and past-us and future-us can be the best decision buddies for the job.*

Poker players have unique decision challenges that get them thinking a lot about how to get this collision of past-, present- and future-self to occur at the moment of making a decision and executing on it. Because decisions in poker are made so quickly, players don’t have the luxury of time in coordinating their rational, long-term, strategic plans with their decisions at the poker table. And all those decisions made under severe time constraints have immediate consequences expressed as an exchange of poker chips. The constant exchange of chips reminds players that there is risk in every decision. Of course, the direction in which the chips flow in the short term only loosely correlates with decision quality. You can win a hand after making bad decisions and lose a hand after making good ones. But the mere fact that chips are changing hands is a reminder that every decision has consequences—that all those execution decisions you make along the way really matter.

Away from the poker table, we don’t feel or experience the consequences of most of the decisions we make right away. If we are winning or losing to a particular decision, the consequences may take time to reveal themselves. If we make a losing eating decision, like substituting SnackWell’s for apples, there’s no immediate outcome that lets us know there might have been a cost to that choice. If we repeat that kind of decision enough, there will be consequences, but they take time to play out. In business, if a leader ignores the ideas of an intern because “What does an intern possibly know?” it could take years for that intern to become a successful competitor before that mistake becomes obvious. If the trajectory of that business suffers because of the poverty of new ideas, the owner of the business might never realize the effect of that attitude.

The best poker players develop practical ways to incorporate their long-term strategic goals into their in-the-moment decisions. The rest of this chapter is devoted to many of these strategies designed to recruit past- and future-us to help with all the execution decisions we have to make to reach our long-term goals. As with all the strategies in this book, we must recognize that no strategy can turn us into perfectly rational actors. In addition, we can make the best possible decisions and still not get the result we want. Improving decision quality is about increasing our chances of good outcomes, not guaranteeing them. Even when that effort makes a small difference—more rational thinking and fewer emotional decisions, translated into an increased probability of better outcomes—it can have a significant impact on how our lives turn out. Good results compound. Good processes become habits, and make possible future calibration and improvement.

Those methods involve a lot of mental time travel, and those poker players could teach Marty McFly and Doc Brown a thing or two.

Night Jerry

For all the scientific research on the battle between our immediate desires and long-term goals, a particularly succinct explanation comes from Jerry Seinfeld, on why he doesn’t get enough sleep: “I stay up late at night because I’m Night Guy. Night Guy wants to stay up late. ‘What about getting up after five hours of sleep?’ ‘That’s Morning Guy’s problem. That’s not my problem. I’m Night Guy. I stay up as late as I want.’ So you get up in the morning: you’re exhausted, you’re groggy. ‘Oooh, I hate that Night Guy.’ See, Night Guy always screws Morning Guy.”

That’s a good example of how we struggle in the present to take care of our future-self. Night Jerry is always going to want to stay up late and, if Morning Jerry has no say in the decision, Night Jerry will get his way regardless of what’s in Jerry’s longer-term best interest. When we make in-the-moment decisions (and don’t ponder the past or future), we are more likely to be irrational and impulsive.*

This tendency we all have to favor our present-self at the expense of our future-self is called temporal discounting.* We are willing to take an irrationally large discount to get a reward now instead of waiting for a bigger reward later. An example of temporal discounting among adults includes a study from the military drawdown in the 1990s that led tens of thousands of military employees to choose lump-sum retirement payments at drastically discounted rates instead of guaranteed annuity payments. The men and women of the U.S. military took lump-sum payments worth $2.5 billion, a 40% discount compared to the present value of the annuity payments they would have received. (For additional sources on temporal discounting, see the Selected Bibliography and Recommendations for Further Reading.)

When Night Jerry stays up late, it’s because it benefits him now; he discounts the benefits that come later from going to bed. Saving for retirement is a temporal discounting problem: the gratification of spending discretionary income is immediate. Putting it away for retirement means we have to wait decades to get enjoyment from that money. We are built for temporal discounting, for using the resources that are available to us now as opposed to saving them for a future version of us that we aren’t particularly in touch with in the moment of the decision. Time traveling can get us in touch with that future version of us. It can get future-us to remind present-us, “Hey, don’t discount!” Or at least, “Don’t discount so much!”

When we think about the past and the future, we engage deliberative mind, improving our ability to make a more rational decision. When we imagine the future, we don’t just make it up out of whole cloth, inventing a future based on nothing that we have ever seen or experienced. Our vision of the future, rather, is rooted in our memories of the past. The future we imagine is a novel reassembling of our past experiences. Given that, it shouldn’t be surprising that the same neural network is engaged when we imagine the future as when we remember the past. Thinking about the future is remembering the future, putting memories together in a creative way to imagine a possible way things might turn out. Those brain pathways include the hippocampus (a key structure for memory) and the prefrontal cortex, which controls System 2, deliberative decision-making. It is our cognitive control center.* By engaging those pathways, Night Jerry can access memories like oversleeping and missing appointments or dozing off during morning meetings that he can use to imagine how tired Morning Jerry will be or what’s going to happen to Morning Jerry’s schedule when he doesn’t want to get up or how his day will go when he can’t pay attention.

Wouldn’t it be great if Morning Jerry could travel back in time and tap Night Jerry on the shoulder to tell him to go to bed? As it turns out, there’s an app for that.

From advancements in photo techniques and virtual reality, there is software that can show you a prediction of what you will look like decades into the future. If you feel, like most adults, bad about seeing your parents age, these images of future-you can be unsettling, like looking into a sadist-designed funhouse mirror. Fortunately, they’ve found ways to put this age-progression technology to more productive uses than just making us stare into the void of our own mortality.

Saving for retirement is a Night Jerry–versus–Morning Jerry problem. If Night Jerry isn’t even thinking ahead to tomorrow morning, he’s certainly not thinking ahead several decades to retirement. Retirement planning involves a series of decisions in which our present-self can act to the detriment or benefit of our future-self. When we set retirement goals, we are necessarily thinking about our future-self’s goals—how much we need to save for that older version of us to live comfortably. Our spending decisions, however, don’t seem to be particularly focused on what’s best for our seventy-year-old-self. In fact, a quick Google search on the topic quickly reveals that our retirement savings are dangerously low. According to one study by the Center for Retirement Research at Boston College, “roughly half of today’s working households will not be able to maintain their standard of living in retirement.” Depending on which estimate you read, the shortfall could be $6.8 to $14 trillion.

Several organizations and companies with an interest in encouraging retirement planning have resources that allow clients to “meet” their future-selves as they make retirement decisions. In the simplest versions of these tools, clients plug in their age, income, savings practices, and retirement goals. The apps then show the client the financial situation and lifestyle their future-self can expect, compared with the present.

Prudential Retirement, AARP, and others have versions of these apps that emphasize the consequences of retirement planning by visually introducing us to our future-self. Bank of America Merrill Lynch in 2012 (for web-access computing) and 2014 (for mobile devices) introduced Merrill Edge, which includes a tool called “Face Retirement.” Customers upload a picture of themselves and get to see, according to the press release, “a life-like 3D animation of their future self, enabling them to envision every wrinkle they could encounter at retirement age—and beyond.” Night Jerry gets a glimpse of what Morning Jerry looks like without enough sleep to function.

This idea that seeing our aged future-self could help us make better allocation decisions is based, in part, on research by Jeremy Bailenson and Laura Carstensen of Stanford University’s Freeman Spogli Institute for International Studies. They used immersive virtual-reality technology in a lab setting to demonstrate how a visit from Morning Jerry will help Night Jerry make better decisions. Subjects entered a virtual-reality environment, after which they were asked to allocate $1,000 among accounts for various purposes, one of which was a hypothetical retirement account. Subjects seeing a digital representation of their present-self in the mirror allocated on average $73.90 to the retirement account. Other subjects looking in that mirror saw an age-progressed version of themselves. This latter group of subjects, on average, allocated $178.10 to the retirement account. This is a startling example of how future-us can act as an effective decision buddy for present-us.

Bringing our future-self into the decision gets us started thinking about the future consequences of those in-the-moment decisions. Fundamentally, Morning Jerry and Night Jerry are living the same life, and getting Morning Jerry into Night Jerry’s face will remind him of that. Seeing our aged-self in the mirror, along with a spreadsheet showing us how future-us has to struggle to get by, is a persuasive reminder to put aside some discretionary spending money for retirement. It’s that tap on the shoulder from our future-self. “Hey, don’t forget about me. I’m going to exist and I’d like you to please take that into account.”

We’re not perfectly rational when we ponder the past or the future and engage deliberative mind, but we are more likely to make choices consistent with our long-term goals when we can get out of the moment and engage our past- and future-selves. We want Night Jerry and Morning Jerry colliding on the decision of when to get some sleep. We want all those Marty McFlys to get the additional perspective of all the other Marty McFlys. And we want our aged, wrinkly self colliding with us when we decide between spending more money now on something like a nicer car versus saving more money for retirement.

Moving regret in front of our decisions

Philosophers agree that regret is one of the most intense emotions we feel, but they have argued about whether it is productive or useful. Nietzsche said that remorse was “adding to the first act of stupidity a second.” Thoreau, on the other hand, praised the power of regret: “Make the most of your regrets; never smother your sorrow, but tend and cherish it till it comes to have a separate and integral interest. To regret deeply is to live afresh.”

The problem isn’t so much whether regret is an unproductive emotion. It’s that regret occurs after the fact, instead of before. As Nietzsche points out, regret can do nothing to change what has already happened. We just wallow in remorse about something over which we no longer have any control. But if regret occurred before a decision instead of after, the experience of regret might get us to change a choice likely to result in a bad outcome. Then we could embrace Thoreau’s view and harness the power of regret because it would serve a valuable purpose. It would be helpful, then, if we could get regret to do some time traveling of its own, moving before our decisions instead of after them. That way, regret might be able to keep us from making a bad bet. In addition, it wouldn’t, as Nietzsche implied, rear its head later by causing us to make a remorse-fueled second mistake.

Morning Jerry regretted Night Jerry’s decision to stay up late, but it was too late for him to do anything about it. When we see the retirement-savings shortfall in this country, there is no doubt that many of the future, retired versions of us are going to regret the financial allocation decisions that younger-us made, after it is too late to fix it. The age-progression imaging works to address this issue of regret occurring when it’s already too late. By giving us a look at the retirement-aged version of ourselves, it gives us a chance to experience some regret that we didn’t plan adequately for retirement before we’ve made inadequate plans. That was one of the purposes of my loss limit in poker. Because of the loss-limit agreement I had made with myself and my group, I ran the conversation in my head that I’d be forced to have when I explained why I kept playing beyond my limit. It gave me a chance to regret the decision before I bought more chips.

One of our time-travel goals is to create moments like that, where we can interrupt an in-the-moment decision and take some time to consider the decision from the perspective of our past and future. We can then create a habit routine around these decision interrupts to encourage this perspective taking, asking ourselves a set of simple questions at the moment of the decision designed to get future-us and past-us involved. We can do this by imagining how future-us is likely to feel about the decision or by imagining how we might feel about the decision today if past-us had made it. The approaches are complementary; whether you choose to travel to the past or travel to the future depends solely on what approach you find most effective.

Business journalist and author Suzy Welch developed a popular tool known as 10-10-10 that has the effect of bringing future-us into more of our in-the-moment decisions. “Every 10-10-10 process starts with a question. . . . [W]hat are the consequences of each of my options in ten minutes? In ten months? In ten years?” This set of questions triggers mental time travel that cues that accountability conversation (also encouraged by a truthseeking decision group). We can build on Welch’s tool by asking the questions through the frame of the past: “How would I feel today if I had made this decision ten minutes ago? Ten months ago? Ten years ago?” Whichever frame we choose, we draw on our past experiences (including similar decisions we may have regretted) in answering the questions, recruiting into the decision those less-reactive brain pathways that control executive functioning.

In poker, because the decisions are all made in the moment and the consequences are big and immediate, routines like 10-10-10 are a survival skill. I recognized in poker that in the same way that I was not the best judge of how I was playing after losing a certain amount of money, I was also not the best judge of the quality of my poker after about six to eight hours of play. Just as we can convince ourselves we are sober enough to drive, it is easy for poker players to convince themselves that they are alert enough to keep playing after many hours of intense, intellectually taxing work. In my more rational moments, away from the tables, I knew I would be better off if I played just six to eight hours per session. When I reached that point in a session and considered continuing past that time limit, I could use a 10-10-10-like strategy to recruit my past- and future-self: How have I felt when I kept playing in the past? How has it generally worked out? When I look back, do I feel I was playing my best? This routine of asking myself these questions helped mitigate the in-the-moment risk that, as I was losing my mental edge, I might try to convince myself that the game was so great that I had to keep playing.

Moving regret in front of a decision has numerous benefits. First, obviously, it can influence us to make a better decision. Second, it helps us treat ourselves (regardless of the actual decision) more compassionately after the fact. We can anticipate and prepare for negative outcomes. By planning ahead, we can devise a plan to respond to a negative outcome instead of just reacting to it. We can also familiarize ourselves with the likelihood of a negative outcome and how it will feel. Coming to peace with a bad outcome in advance will feel better than refusing to acknowledge it, facing it only after it has happened.

After-the-fact regret can consume us. Like all emotions, regret initially feels intense but gets better with time. Time-travel strategies can help us remember that the intensity of what we feel now will subside over time. And that helps reduce the emotion we feel in the moment, making it less likely that we will prove Nietzsche right and add a second act of stupidity to the first.

A flat tire, the ticker, and a zoom lens

Imagine you are standing on a narrow strip of concrete on the shoulder of the highway. Behind you is your car, hazard lights flashing. The rear tire on the driver’s side is shredded. It is fully dark and the drizzle has turned into a cold, heavy downpour. You’ve called roadside assistance, twice, and both times (after long hold times) spoken with operators who’ve told you someone will arrive “as soon as they get there after responding to your call.” You decide to change the tire yourself, only to discover you have no jack. You’re soaked to the skin and cold.

How does it feel? It likely feels like the worst moment of your life. You are likely bemoaning how unlucky you are, wondering why these things always happen to you. You are miserable and you can’t imagine feeling any other way.*

That’s how it feels in the moment. But if the flat tire had happened a year ago, do you think it would have an effect on your happiness today, or your overall happiness over the past year? Not likely. It likely wouldn’t cause your overall happiness to tick up or down. It would probably have faded to a funny story (or a story you try to make sound funny) told at cocktail parties.

In our decision-making lives, we aren’t that good at taking this kind of perspective—at accessing the past and future to get a better view of how any given moment might fit into the scope of time. It just feels how it feels in the moment and we react to it. We want to create opportunities to take the broader perspective prior to making decisions driven by the magnified feelings we have in the moment. A 10-10-10 strategy does that, getting us to imagine the decision or outcome in the perspective of the past and the future.

The flat tire isn’t as awful as it seems in the moment. This kind of time-travel strategy calms down the in-the-moment emotions we have about an event, so we can get back to using the more rational part of our brain. Recruiting past-us and future-us in this way activates the neural pathways that engage the prefrontal cortex, inhibiting emotional mind and keeping events in more rational perspective. This discourages us from magnifying the present moment, blowing it out of proportion and overreacting to it.

This overestimation of the impact of any individual moment on our overall happiness is the emotional equivalent of watching the ticker in the financial world. We make a long-term stock investment because we want it to appreciate over years or decades. Yet there we are, watching a downward tick over a few minutes, consumed by imagining the worst. What’s the volume? Is it heavier than usual? Better check the news stories. Better check the message boards to find out what rumors are circulating.

A stock like Berkshire Hathaway reveals why ticker watching isn’t a particularly productive endeavor when you are investing for the long run. Look at this chart of Berkshire’s performance since 1964:

Now zoom in on a random day in late January 2017. The upticks and downticks look large and potentially frightening. You can imagine sitting at the low point around 11:30, feeling like your losses are spiraling.

If you zoomed in on the performance of Berkshire Hathaway stock during the banking crisis, September 2008 to March 2009, you would feel terrible most days:

Yet we know from the first chart, the big picture, that all those minute-to-minute and even day-to-day changes had little effect on the investment’s general upward trajectory.

Our problem is that we’re ticker watchers of our own lives. Happiness (however we individually define it) is not best measured by looking at the ticker, zooming in and magnifying moment-by-moment or day-by-day movements. We would be better off thinking about our happiness as a long-term stock holding. We would do well to view our happiness through a wide-angle lens, striving for a long, sustaining upward trend in our happiness stock, so it resembles the first Berkshire Hathaway chart.

Mental time travel makes that kind of perspective possible. We can use our past- and future-selves to pull us out of the moment and remind us when we’re watching the ticker, looking at our lives through that lens on extreme zoom.

When we view these upticks and downticks under the magnification of that in-the-moment zoom lens, our emotional responses are, similarly, amplified. Like the flat tire in the rain, we are capable of treating things that will have little effect on our long-term happiness as having significant impact. Our decision-making becomes reactive, focused on off-loading negative emotions or sustaining positive emotions from the latest change in the status quo. We can see how this can result in self-serving bias: fielding outcomes to off-load the negative emotions we feel in the moment from a bad outcome by blaming them on luck and sustaining the positive emotions from good outcomes by taking credit for them. The decisions driven by the emotions of the moment can become a self-fulfilling prophecy, degrading the quality of the bets we make, increasing the chances of bad outcomes, and making things worse.

“Yeah, but what have you done for me lately?”

Watching the ticker doesn’t just magnify what has happened in the very recent past. It distorts our view of it as well. To understand the additional element of distortion, the casino is a great place to look.

Imagine that you go to a casino for an evening of blackjack with your friends. In the first half hour, you go on a winning streak and are ahead $1,000. You keep playing because you and your friends are having such a good time. For the next hour and a half, it seems like you never win a hand. You lose back the $1,000 and break even for the night. How are you feeling about that?

Now imagine that you lose $1,000 in the first half hour and stick around playing with your friends because they are having a great time. In the next hour and a half you go on a winning streak that erases the early loss, and you end up breaking even for the night. How are you feeling about that?

I’m guessing you are pretty sad and morose about starting off with the big win, only to break even. In the second example, you’re probably so happy that the drinks are on you. While you took a different path to get there, in both cases you didn’t win or lose a dime at the end of the two hours. But in one case you are really sad about the result and the other really happy.

As they say in the infomercial world, “But, wait! There’s more!”

Imagine you go up that same $1,000 in the first half hour but now, over the next hour and a half, you can’t seem to win a hand and lose $900 back, ending the night with a $100 win. How does that feel? Now imagine that you lost that same $1,000 in the first half hour but then went on a winning streak to end the night down only $100. How does that feel? Most likely, you’re pretty glum about the $100 win but still buying drinks for everyone after recovering from that terrible start to only lose $100. So you’re sad that you won $100 and happy that you lost $100.

The way we field outcomes is path dependent. It doesn’t so much matter where we end up as how we got there. What has happened in the recent past drives our emotional response much more than how we are doing overall. That’s how we can win $100 and be sad, and lose $100 and be happy. The zoom lens doesn’t just magnify, it distorts. This is true whether we are in a casino, making investment decisions, in a relationship, or on the side of the road with a flat tire. If we got a big promotion last week and have a flat tire right now, we are cursing our lives, complaining about how unlucky we are. Our feelings are not a reaction to the average of how things are going. We feel sad if we are breaking even (or winning) on an investment that used to be valued much higher. In relationships, even small disagreements seem big in the midst of the disagreement. The problem in all these situations (and countless others) is that our in-the-moment emotions affect the quality of the decisions we make in those moments, and we are very willing to make decisions when we are not emotionally fit to do so.

Now imagine if you had gone for that night of blackjack a year ago. When you think about the outcomes as having happened in the distant past, it is likely your preference for the results reverses, landing in a more rational place. You are now happier about the $100 win than about the $100 loss. Once we pull ourselves out of the moment through time-traveling exercises, we can see these things in proportion to their size, free of the distortion caused by whether the ticker just moved up or down.

This is a constant challenge in poker. While the moving scoreboard has the upside of reminding players that all their decisions have consequences, there is also a downside. The scoreboard, like a stock ticker, reflects the most recent changes, creating a risk that players get caught up in ticker watching, responding emotionally and disproportionately to momentary fluctuations. Poker players think about this problem a lot.

Tilt

Surfers have more than twenty terms to describe different kinds of waves. The reason is that the type of wave, the way it breaks, the direction it’s coming from, the bottom depth, etc., create differing challenges for surfers. There are closeouts (waves that break all at once) and double-ups (a type of wave created when two waves meet to form one wave) and reforms (a wave that will break, then die down, then break again). Non-surfers just call all of these “waves.” On rare occasions when we non-surfers need to be more specific, we just add a lot of extra words. Those extra words don’t cost us much because it doesn’t come up very often—maybe never. But for people involved in specialized activities, it’s worth it to be able to communicate a complex concept in a single word that laypeople would need lengthy phrases to convey. Having a nuanced, precise vocabulary is what jargon is all about. It’s why carpenters have at least a dozen names for different kinds of nails, and in the field of neuro-oncology, there are more than 120 types of brain and central nervous system tumors.

Because poker players are in a constant struggle to keep in-the-moment fluctuations in perspective, their jargon has a variety of terms for the concept that “bad outcomes can have an impact on your emotions that compromise your decision-making going forward so that you make emotionally charged, irrational decisions that are likely to result in more bad outcomes that will then negatively impact your decision-making going forward and so on.” The most common is tilt. Tilt is the poker player’s worst enemy, and the word instantly communicates to other poker players that you were emotionally unhinged in your decision-making because of the way things turned out.* If you blow some recent event out of proportion and react in a drastic way, you’re on tilt.

The concept of tilt comes from traditional pinball machines. To keep players from damaging the machines by lifting them to alter the course of the ball, the manufacturers placed sensors inside that disabled the machine if it was violently jostled. The flippers stopped working, the lights went off, and the word “tilt” flashed at numerous places on the layout. The origin of tilt in pinball is apt because what’s going on in our brain in moments of tilt is like a shaken pinball machine. When the emotional center of the brain starts pinging, the limbic system (specifically the amygdala) shuts down the prefrontal cortex. We light up . . . then we shut down our cognitive control center.

There are emotional and physiological signs of tilt. In poker, you can hear a poker player on tilt from several tables away. Every several hands, you hear a raised voice in an incredulous tone: “Seriously? Again?” or “I don’t know why I bother playing. I should just hand over all my money.” (Imagine the inflection of exasperation and a lot of swearing.) Along with these verbal cues, there are physiological signs of tilt. We can feel our cheeks flush and our heart race. Our respiration speeds up.

Tilt, of course, is not just limited to poker. Any kind of outcome has the potential for causing an emotional reaction. We can be tempted to make a reactive, emotional decision in a disagreement with a relationship partner, or because of bad service in a restaurant, or a comment in the workplace, or making a sale only to have it canceled, or having an idea dismissed. We’ve all had this experience in our personal and professional lives: blowing out of proportion a momentary event because of an in-the-moment emotional reaction.

By recognizing in advance these verbal and physiological signs that ticker watching is making us tilt, we can commit to develop certain habit routines at those moments. We can precommit to walk away from the situation when we feel the signs of tilt, whether it’s a fight with a spouse or child, aggravation in a work situation, or losing at a poker table. We can take some space till we calm down and get some perspective, recognizing that when we are on tilt we aren’t decision fit. Aphorisms like “take ten deep breaths” and “why don’t you sleep on it?” capture this desire to avoid decisions while on tilt. We can commit to asking ourselves the 10-10-10 questions or things like, “What’s happened to me in the past when I’ve felt this way?” or “Do I think it’s going to help me to be in this state while I’m making decisions?” Or we can gain perspective by asking how or whether this will have a real effect on our long-term happiness.

If you are part of a truthseeking pod, that pod can incorporate questions designed to sniff out tilt and reduce the number of decisions we execute while on tilt. We can incorporate vigilance around ticker watching when evaluating each other’s decisions, including the most obvious question: “Do you think maybe you are/were on tilt?” We can follow that with time-traveling questions like, “Do you think this will really matter in the long run?” If we make the concept of tilt and its negative impact on decision quality part of the discussion, it creates accountability around tilt to the group. Ignoring the signals of emotional decision-making raises the prospect of having to answer for it. That, in turn, will get us positive reinforcement from the group for recognizing the signs of tilt and avoiding decision-making in that state. It also trains good habits of mind so we can run these processes on our own, acting as our own decision buddy.

At the very beginning of my poker career, I heard an aphorism from some of the legends of the profession: “It’s all just one long poker game.” That aphorism is a reminder to take the long view, especially when something big happened in the last half hour, or the previous hand—or when we get a flat tire. Once we learn specific ways to recruit past and future versions of us to remind ourselves of this, we can keep the most recent upticks and downticks in their proper perspective. When we take the long view, we’re going to think in a more rational way.

Ulysses contracts: time traveling to precommit

The most famous traveler of antiquity, the Homeric hero Odysseus, was also a mental time traveler. One of the legendary trials on his journey home involved the island of the Sirens. Sailors passing the island became so entranced by the Sirens’ song that they would steer toward the shore, crashing to their deaths on the rocky shoal around the island. Aware of the fate that befell any sailor who heard the song, Odysseus told his crew to tie his hands to the mast and fill their ears with beeswax as they approached the island. They could then steer safely, unaffected by the song they could not hear, while he would get to hear the Sirens’ song without imperiling the ship.

The plan worked perfectly. This action—past-us preventing present-us from doing something stupid—has become known as a Ulysses contract. (Most translations of Homer use the hero’s ancient Greek name, Odysseus. The time-travel strategy uses the hero’s ancient Roman name, Ulysses.)

It’s the perfect interaction between past-you, present-you, and future-you. Ulysses recognized that his future-self (along with his crew) would become entranced by the Sirens and steer toward the rocks. So he had his crew fill their ears with wax and tie his hands to the mast, literally binding his future-self to better behavior. One of the simplest examples of this kind of contract is using a ride-sharing service when you go to a bar. A past version of you, who anticipated that you might decide irrationally about whether you are okay to drive, has bound your hands by taking the car keys out of them.

Most illustrations of Ulysses contracts, like the original, involve raising a barrier against irrationality. But these kinds of precommitment contracts can also be designed to lower barriers that interfere with rational action. For example, if we are trying to eat healthier, we might identify that an irrational decision point occurs when we go to the mall with someone, agree to meet them in a couple hours, and spend idle time in the food court. A barrier-inducing Ulysses contract could involve us not going to the mall at all or budgeting our time tightly so we have just enough time to accomplish our intended purpose. A barrier-reducing contract would be to precommit to carry healthy snacks in our bag, so we can increase the probability, if we’re doing any idle eating, that we can make a better choice since we have drastically reduced the effort it takes to grab a healthier snack.

Ulysses contracts can come in varying levels of how much your hands are bound, ranging from physically preventing acting on a decision to just committing in advance to certain actions without any barriers save the commitment itself. Regardless of the level of binding, precommitment contracts trigger a decision-interrupt. At the moment when we consider breaking the contract, when we want to cut the binding, we are much more likely to stop and think.

When you are physically prohibited from deciding, you are interrupted in the sense that you are prevented from acting on an irrational impulse; the option simply isn’t there. That’s the brute-force way to do this kind of time traveling. Past-Ulysses interrupted present-Ulysses’s decision by taking the decision, literally, out of his hands.

In most situations, you can’t make a precommitment that’s 100% tamper-proof. The hurdles aren’t necessarily high, but they nevertheless create a decision-interrupt that may prompt us to do the bit of time travel necessary to reduce emotion and encourage perspective and rationality in the decision. A lawyer attending a settlement negotiation can make a precommitment, with the client or other lawyers on their team, as to the lowest amount they would accept in a settlement (or the highest amount they would agree to pay to settle). Home buyers, understanding that in the moment they might get emotionally attached to a home, can commit in advance to their budget. Once they decide on a house they want to buy, they can decide in advance what the maximum amount they’d be willing to pay for it is so that they don’t get caught up in the moment of the bidding.

Throwing out all the junk food in our house makes it impossible for midnight-us to easily, mindlessly, down a pint of ice cream. But as long as we have a car or food delivery services, that kind of food is still available somewhere. It just takes a lot more effort to get it. The same is true if we ask the waiter not to put the bread basket on the table at the restaurant. We can still, obviously, get bread, but now we have to ask the waiter to bring it. In fact, even Ulysses had to rely on his crew to ignore him if, upon hearing the Sirens’ song, he signaled them to free him.

Ulysses contracts can help us in several ways to be more rational investors. When we set up an automatic allocation from our pay into a retirement account, that’s a Ulysses contract. We could go through the trouble of changing the allocation, but setting it up initially gives our goal-setting, System 2–self a chance to precommit to what we know is best for our long-term future. And if we want to change the allocation, we have to take some specific steps to do so, creating a decision-interrupt.

Investment advisors do this with clients, determining in advance, as they are discussing the client’s goals, the conditions under which they would buy, sell, hold, or press their positions on particular stocks. If the client later wants to make an emotional decision in the moment (involving, for example, a sudden rise or drop in the value of an investment), the advisor can remind the client of the discussion and the agreement.

In all these instances, the precommitment or predecision doesn’t completely bind our hands to the mast. An emotional, reactive, irrational decision is still physically possible (though, to various degrees, more difficult). The precommitments, however, provide a stop-and-think moment before acting, triggering the potential for deliberative thought. Will that prevent an emotional, irrational decision every time? No. Will we sometimes still decide in a reflexive or mindless way? Of course. But it will happen less often.

Decision swear jar

We all know about the concept of a swear jar: if someone swears, they put a dollar in the jar. The idea behind it is that it will make people mindful about swearing and reduce how much they do it. A “decision swear jar” is a simple kind of precommitment contract that we can apply to many of the key concepts of this book. For the decision swear jar, we identify the language and thinking patterns that signal we are veering from our goal of truthseeking. When we find ourselves using certain words or succumbing to the thinking patterns we are trying to avoid because we know they are signs of irrationality, a stop-and-think moment can be can be created. You can think about this as a way to implement accountability.

We have discussed several patterns of irrationality in the way we lodge beliefs and field outcomes. From these, we can commit to vigilance around words, phrases, and thoughts that signal that we might be not be our most rational selves. Your list of those warning signs will be specific to you (or your family, friends, or enterprise), but here is a sample of the kinds of things that might trigger a decision-interrupt.

This is by no means a complete list, but it provides a flavor of the kinds of statements and thinking that should trigger vigilance on our part.

Once we recognize that we should watch out for particular words, phrases, and thoughts, when we find ourselves saying or thinking those things, we are breaking a contract, a commitment to truthseeking. These terms are signals that we’re succumbing to bias. Because if we are cutting the binding when we catch ourselves saying or thinking these things, it can trigger a moment of reflection, interrupting us in the moment. Popping out of the moment like that can remind us of why we took the trouble to list terms that signal potential decision traps.

The swear jar is a simple example of a Ulysses contract in action: we think ahead to a hazard in our decision-making future and devise a plan of action around that, or at least commit that we will take a moment to recognize we are veering away from truthseeking. Better precommitment contracts result from better anticipation of what the future might look like, what kinds of decisions we want to avoid, and which ones we want to promote. That takes thoughtful reconnaissance.

Reconnaissance: mapping the future

Operation Overlord, the Allied forces operation to retake German-occupied France starting in Normandy, was the largest seaborne invasion in military history. It involved planning and logistics on an unprecedented scale. What if the forces were delayed at the start by bad weather? What if the airborne landing force had trouble communicating by radio due to the terrain? What if significant numbers of paratroopers were blown off course? What if currents interfered with the beach landings? What if the forces on the different beaches remained separated? Countless things could go wrong, with tens of thousands of lives at stake and, potentially, the outcome of the war.

All those things did go wrong, along with many other challenges encountered on D-Day and immediately thereafter. The Normandy landings still succeeded, though, because they prepared for as many potential scenarios as possible. Reconnaissance has been part of advance military planning for as long as horses have been used in battle. The modern military, of course, has evolved from sending scouts by horse and reporting back to the main forces to planes, drones, satellites, and other high-tech equipment gathering information about what to expect in battle.

The Navy SEAL team that caught and killed Osama bin Laden wouldn’t have entered his compound without knowing what they would find beyond the walls. What buildings were there? What was their layout and purpose? What differences might it make if they conducted the raid in different kinds of weather or different times of day? What other people would be present and what risks would they pose? What would they do if bin Laden wasn’t there? What was the team trying to commit to, given what they knew about each of those things (and, of course, numerous others)? Just as they relied on reconnaissance, we shouldn’t plan our future without doing advance work on the range of futures that could result from any given decision and the probabilities of those futures occurring.

For us to make better decisions, we need to perform reconnaissance on the future. If a decision is a bet on a particular future based on our beliefs, then before we place a bet we should consider in detail what those possible futures might look like. Any decision can result in a set of possible outcomes.

Thinking about what futures are contained in that set (which we do by putting memories together in a novel way to imagine how things might turn out) helps us figure out which decisions to make.

Figure out the possibilities, then take a stab at the probabilities. To start, we imagine the range of potential futures. This is also known as scenario planning. Nate Silver, who compiles and interprets data from the perspective of getting the best strategic use of it, frequently takes a scenario-planning approach. Instead of using data to make a particular conclusion, he sometimes takes the approach of discussing all the scenarios the data could support. In early February 2017, he described the merits of scenario planning: “When faced with highly uncertain conditions, military units and major corporations sometimes use an exercise called scenario planning. The idea is to consider a broad range of possibilities for how the future might unfold to help guide long-term planning and preparation.”

After identifying as many of the possible outcomes as we can, we want to make our best guess at the probability of each of those futures occurring. When I consult with enterprises on building decision trees and determining probabilities of different futures, people frequently resist having to make a guess at the probability of future events mainly because they feel like they can’t be certain of what the likelihood of any scenario is. But that’s the point.

The reason why we do reconnaissance is because we are uncertain. We don’t (and likely can’t) know how often things will turn out a certain way with exact precision. It’s not about approaching our future predictions from a point of perfection. It’s about acknowledging that we’re already making a prediction about the future every time we make a decision, so we’re better off if we make that explicit. If we’re worried about guessing, we’re already guessing. We are already guessing that the decision we execute will result in the highest likelihood of a good outcome given the options we have available to us. By at least trying to assign probabilities, we will naturally move away from the default of 0% or 100%, away from being sure it will turn out one way and not another. Anything that moves us off those extremes is going to be a more reasonable assessment than not trying at all. Even if our assessment results in a wide range, like the chances of a particular scenario occurring being between 20% and 80%, that is still better than not guessing at all.

This kind of reconnaissance of the future is something that experienced poker players are very familiar with. Before making a bet, poker players consider each of their opponents’ possible responses (fold, call, raise), and the likelihood and desirability of each. They also think about what they will do in response (if some or all of the opponents don’t fold). Even if you don’t know much about poker, it should make sense that a player is better off considering these things before they bet. The more expert the player, the further into the future they plan. Before making that decision to bet, the expert player is anticipating what they’ll do following each response, as well as how the action they take now affects their future decisions on the hand. The best players think beyond the current hand into subsequent hands: how do the actions of this hand affect how they and their opponents make decisions on future hands? Poker players really live in this probabilistic world of, “What are the possible futures? What are the probabilities of those possible futures?” And they get very comfortable with the fact that they don’t know exactly because they can’t see their opponent’s cards.

This is true of most strategic thinking. Whether it involves sales strategies, business strategies, or courtroom strategies, the best strategists are considering a fuller range of possible scenarios, anticipating and considering the strategic responses to each, and so on deep into the decision tree.

This kind of scenario planning is a form of mental time travel we can do on our own. It works even better when we do it as part of a scenario-planning group, particularly one that is open-minded to dissent and diverse points of view. Diverse viewpoints allow for the identification of a wider variety of scenarios deeper into the tree, and for better estimates of their probability. In fact, if two people in the group are really far off on an estimate of the likelihood of an outcome, that is a great time to have them switch sides and argue the other’s position. Generally, the answer is somewhere in the middle and both people will end up moderating their positions. But sometimes one person has thought of a key influencing factor the other hasn’t and that is revealed only because the dissent was tolerated.

In addition to increasing decision quality, scouting various futures has numerous additional benefits. First, scenario planning reminds us that the future is inherently uncertain. By making that explicit in our decision-making process, we have a more realistic view of the world. Second, we are better prepared for how we are going to respond to different outcomes that might result from our initial decision. We can anticipate positive or negative developments and plan our strategy, rather than being reactive. Being able to respond to the changing future is a good thing; being surprised by the changing future is not. Scenario planning makes us nimbler because we’ve considered and are prepared for a wider variety of possible futures. And if our reconnaissance has identified situations where we are susceptible to irrationality, we can try to bind our hands with a Ulysses contract. Third, anticipating the range of outcomes also keeps us from unproductive regret (or undeserved euphoria) when a particular future happens. Finally, by mapping out the potential futures and probabilities, we are less likely to fall prey to resulting or hindsight bias, in which we gloss over the futures that did not occur and behave as if the one that did occur must have been inevitable, because we have memorialized all the possible futures that could have happened.

Scenario planning in practice

A few years ago, I consulted with a national nonprofit organization, After-School All-Stars (ASAS), to work with them on incorporating scenario planning into their budgeting.* ASAS, founded in 1992 by Arnold Schwarzenegger, provides three hours of structured after-school programming for over 70,000 underserved youth in eighteen cities across the United States. They depend heavily on grants for funding and were struggling with budget planning, given the uncertainty in the grant award process. To help them with planning, I asked for a list of all their grant applications and how much each grant was worth. They provided me with a list of all their outstanding grant applications and the award amounts applied for. I told them that I didn’t see how much each grant was worth in the information they provided. They pointed to the column of the award amounts sought. At that point, I realized we were working from different ideas about how to determine worth. The misunderstanding came from the disconnect between the expected value of each grant and the amount they would be awarded if they got the grant.*

Coming up with the expected value of each grant involves a simple form of scenario planning: imagining the two possible futures that could result from the application (awarded or declined) and the likelihood of each future. For example, if they applied for a $100,000 grant that they would win 25% of the time, that grant would have an expected value of $25,000 ($100,000 × .25). If they expected to get the grant a quarter of the time, then it wasn’t worth $100,000; it was worth a quarter of $100,000. A $200,000 application with a 10% chance of success would have an expected value of $20,000. A $50,000 grant with a 70% chance of success would be worth $35,000. Without thinking probabilistically in this way, determining a grant’s worth isn’t possible—it leads to the mistaken belief that the $200,000 grant is worth the most when, in fact, the $50,000 grant is. ASAS recognized that uncertainty was causing them problems (to the point where they felt enslaved by it in their budgeting), but they hadn’t wrapped uncertainty into their planning or resource-allocation process. They were flying by the seat of their pants.

After I worked with the national office, ASAS made estimating the likelihood of getting each grant part of their planning. The benefits they got from scenario planning were immediate and substantial:

Grant prospecting is similar to sales prospecting, and this process can be implemented for any sales team. Assign probabilities for closing or not closing sales, and the company can do better at establishing sales priorities, planning budgets and allocating resources, evaluating and fine-tuning the accuracy of its predictions, and protecting itself against resulting and hindsight bias.

A more complex version of scenario planning occurs when the number of possible futures multiplies and/or we go deeper into the tree, considering what we will do next in response to how things turn out and what the set of outcomes of that next decision is and so on.

Consider the scenario planning involved in Seahawks coach Pete Carroll’s much-criticized Super Bowl decision, trailing by four, twenty seconds remaining, one time-out, second-and-goal at the Patriots’ one-yard line. Carroll has two general choices, run or pass, and they in turn lead to multiple scenarios.

If Carroll calls for a run, these are the possible futures: (a) touchdown (immediate win); (b) turnover-fumble (immediate loss); (c) tackle short of the goal line; (d) offensive penalty; and (e) defensive penalty. Futures (c)–(e) branch into additional scenarios. The most likely failure scenario, by far, is that the runner is tackled before reaching the end zone. Seattle could stop the clock with its final time-out, but if they run the ball again and do not score, time will expire.

If Carroll calls for a pass, the possible futures are (a) touchdown (immediate success); (b) turnover-interception (immediate failure); (c) incomplete pass; (d) sack; (e) offensive penalty; and (f) defensive penalty. Again, the first two futures essentially end the game and the others branch off into additional play calling and additional outcomes.

The main difference between passing and running is that calling a pass likely gives Seattle a total of three plays to score, instead of two if Carroll calls a running play. An unsuccessful run would require that Seattle use their final time-out to stop the clock so they could run a second play. An incomplete pass would stop the clock and leave Seattle with a time-out and the chance to call those same two running plays. An interception, which negates the possibility of a second or third offensive play, is only a 2%–3% probability, a small price to pay for three chances to score rather than two. (A turnover caused by a fumble on a running play is 1%–2%.)*

Notice that the option of the extra play doesn’t reveal itself without this kind of scouting of the future. Even after the fact, with lots of time to analyze the decision, very few commentators saw this advantage.

The important thing is that we do better when we scout all these futures and make decisions based on the probabilities and desirability of the different futures. ASAS couldn’t guarantee it would get awarded every grant it applied for, but it could, through good process, make better decisions about which grants to prioritize and how much revenue to expect from the basket of grant proposals they submitted. Despite the outcry, I’d like to think that Pete Carroll didn’t lose much sleep over his decision to call for Wilson to pass.

Reconnaissance of the future dramatically improves decision quality and reduces reactivity to outcomes. So far, we have talked about thinking ahead to what the future might look like. But it turns out that better decision trees, more effective scenario planning, results from working backward rather than forward.

Backcasting: working backward from a positive future

All methods of imagining the future are not created equal. You know that Chinese proverb, “A journey of a thousand miles starts with a single step”? Turns out, if we were contemplating a thousand-mile walk, we’d be better off imagining ourselves looking back from the destination and figuring how we got there. When it comes to advance thinking, standing at the end and looking backward is much more effective than looking forward from the beginning.

The distorted view we get when we look into the future from the present is similar to the stereotypical view of the world by Manhattan residents, poked fun at by the famous New Yorker cover. The cover was a drawing of a map from the perspective of a person from New York. In that view, half the map covers a few blocks of the city. While you can see all the buildings on Ninth Avenue and even vehicles and people, the Hudson River and New Jersey are just horizontal strips. The entire United States occupies the same amount of space as the distances between Ninth and Tenth avenues. Beyond a strip of the Pacific Ocean are three tiny lumps, labeled “China,” “Japan,” and “Russia.”

When we forecast the future, we run the risk of a similar distortion. From where we stand, the present and the immediate future loom large. Anything beyond that loses focus.

Imagining the future recruits the same brain pathways as remembering the past. And it turns out that remembering the future is a better way to plan for it. From the vantage point of the present, it’s hard to see past the next step. We end up over-planning for addressing problems we have right now. Implicit in that approach is the assumption that conditions will remain the same, facts won’t change, and the paradigm will remain stable. The world changes too fast to assume that approach is generally valid. Samuel Arbesman’s The Half-Life of Facts makes a book-length case for the hazards of assuming the future is going to be like the present.

Just as great poker players and chess players (and experts in any field) excel by planning further into the future than others, our decision-making improves when we can more vividly imagine the future, free of the distortions of the present. By working backward from the goal, we plan our decision tree in more depth, because we start at the end.

When we identify the goal and work backward from there to “remember” how we got there, the research shows that we do better. In a Harvard Business Review article, decision scientist Gary Klein summarized the results of a 1989 experiment by Deborah Mitchell, J. Edward Russo, and Nancy Pennington. They “found that prospective hindsight—imagining that an event has already occurred—increases the ability to correctly identify reasons for future outcomes by 30%.”

A huge urban planning project requires enormous amounts of money, materials, commitment—and the vision to work backward from a distant future goal. When Frederick Law Olmsted designed Central Park, for example, he recognized that a lot of the charm of the park, and a lot of enjoyment that people would get from it, would take decades, as the landscape changed and matured. People walking through Central Park when it opened to the public in 1858 would have seen a lot of barren land. Even in 1873, when construction was substantially completed, there was a lot of undergrown foliage. The trees, shrubs, and plants were clearly recent transplants. None of those visitors would recognize Central Park today. But Olmstead would because he was starting from what it would develop into.

The most common form of working backward from our goal to map out the future is known as backcasting. In backcasting, we imagine we’ve already achieved a positive outcome, holding up a newspaper with the headline “We Achieved Our Goal!” Then we think about how we got there.

Let’s say an enterprise wants to develop a three-year strategic plan to double market share, from 5% to 10%. Each person engaged in the planning imagines holding up a newspaper whose headline reads “Company X Has Doubled Its Market Share over the Past Three Years.” The team leader now asks them to identify the reasons they got there, what events occurred, what decisions were made, what went their way to get the enterprise to capture that market share. This enables the company to better identify strategies, tactics, and actions that need to be implemented to get to the goal. It also allows it to identify when the goal needs to be tweaked. Backcasting makes it possible to identify when there are low-probability events that must occur to reach the goal. That could lead to developing strategies to increase the chances those events occur or to recognizing the goal is too ambitious. The company can also make precommitments to a plan developed through backcasting, including responses to developments that can interfere with reaching the goal and identifying inflection points for re-evaluating the plan as the future unfolds.

In planning a trial strategy after taking a new case, a trial lawyer can imagine the headline of winning at trial. What favorable rulings did the lawyer get along the way? How did the most favorable testimony play out? What kind of evidence did the judge allow or throw out? What points did the jury respond to?

If our goal is to lose twenty pounds in six months, we can plan how to achieve that by imagining it’s six months from now and we’ve lost the weight. What are the things we did to lose the weight? How did we avoid junk food? How did we increase the amount of exercise we were doing? How did we stick to the regimen?

Imagining a successful future and backcasting from there is a useful time-travel exercise for identifying necessary steps for reaching our goals. Working backward helps even more when we give ourselves the freedom to imagine an unfavorable future.

Premortems: working backward from a negative future

If you know medical terms or watch forensic-crime dramas on TV, you are familiar with a postmortem: that’s where a medical examiner determines the cause of death. A premortem is an investigation into something awful, but before it happens. We all like to bask in an optimistic view of the future. We generally are biased to overestimate the probability of good things happening. Looking at the world through rose-colored glasses is natural and feels good, but a little naysaying goes a long way. A premortem is where we check our positive attitude at the door and imagine not achieving our goals.

Backcasting and premortems complement each other. Backcasting imagines a positive future; a premortem imagines a negative future. We can’t create a complete picture without representing both the positive space and the negative space. Backcasting reveals the positive space. Premortems reveal the negative space. Backcasting is the cheerleader; a premortem is the heckler in the audience.

Imagining a headline that reads “We Failed to Reach Our Goal” challenges us to think about ways in which things could go wrong that we otherwise wouldn’t if left to our own (optimistic, team-player) devices. For the company with the three-year plan to double market share, the premortem headline is “Company Fails to Reach Market Share Goal; Growth Again Stalls.” Members of the planning team now imagine delays in new products, loss of key executives or sales or marketing or technical personnel, new products by competitors, adverse economic developments, paradigm shifts that could lead customers to do without the product or rely on alternatives not on the market or in use, etc.

A lawyer trying a case now considers favorable evidence being disallowed, undiscovered evidence undermining the case, drawing an unsympathetic judge, and the jury disliking or distrusting the main witnesses.

When we set a weight-loss goal and put a plan to reach that goal in place, a premortem will reveal how we felt obligated to eat cake when it was somebody’s birthday, how hard it was to resist the bagels and cookies in the conference room, and how hard it was to find time for the gym or how easy it was to find excuses to procrastinate going. There has been a massive amount written about visualizing success as a way to achieve our goals. Because that’s such a common element in self-help strategies, conducting a premortem (with its negative visualization) may seem like a counterproductive way to succeed.

Despite the popular wisdom that we achieve success through positive visualization, it turns out that incorporating negative visualization makes us more likely to achieve our goals. Gabriele Oettingen, professor of psychology at NYU and author of Rethinking Positive Thinking: Inside the New Science of Motivation, has conducted over twenty years of research, consistently finding that people who imagine obstacles in the way of reaching their goals are more likely to achieve success, a process she has called “mental contrasting.” Her first study, of women enrolled in a weight-loss program, found that subjects “who had strong positive fantasies about slimming down . . . lost twenty-four pounds less than those who pictured themselves more negatively. Dreaming about achieving a goal apparently didn’t help that goal come to fruition. It impeded it from happening. The starry-eyed dreamers in the study were less energized to behave in ways that helped them lose weight.”

She repeated these results in different contexts. She recruited college students who claimed to have an unrequited crush. She then prompted one group to imagine positive scenarios of initiating a relationship, and another group to imagine negative scenarios of how that would play out. The results were similar to those in the weight-loss study: five months later, the subjects indulging in the positive scenario planning were less likely to initiate the relationship. She found the same results when studying job seekers, students before a midterm exam, and patients undergoing hip replacement surgery.

Oettingen recognized that we need to have positive goals, but we are more likely to execute on those goals if we think about the negative futures. We start a premortem by imagining why we failed to reach our goal: our company hasn’t increased its market share; we didn’t lose weight; the jury verdict came back for the other side; we didn’t hit our sales target. Then we imagine why. All those reasons why we didn’t achieve our goal help us anticipate potential obstacles and improve our likelihood of succeeding.

A premortem is an implementation of the Mertonian norm of organized skepticism, changing the rules of the game to give permission for dissent. Being a team player in a premortem isn’t about being the most enthusiastic cheerleader; it’s about being the most productive heckler. “Winning” isn’t about the group feeling good because everyone confirms their (and the organization’s) narrative that things are going to turn out great. The premortem starts with working backward from an unfavorable future, or failure to achieve a goal, so competing for favor, or feeling good about contributing to the process, is about coming up with the most creative, relevant, and actionable reasons for why things didn’t work out.

The key to a successful premortem is that everyone feels free to look for those reasons, and they are motivated to scour everything—personal experience, company experience, historical precedent, episodes of The Hills, sports analogies, etc.—to come up with ways a decision or plan can go bad, so the team can anticipate and account for them.

Conducting a premortem creates a path to act as our own red team. Once we frame the exercise as “Okay, we failed. Why did we fail?” that frees everyone to identify potential points of failure they otherwise might not see or might not bring up for fear of being viewed as a naysayer. People can express their reservations without it sounding like they’re saying the planned course of action is wrong. Because of that, a planning process that includes a premortem creates a much healthier organization because it means that the people who do have dissenting opinions are represented in the planning. They don’t feel like they’re shut out or not being heard. Everyone’s voice now has more value. The organization is less likely to discourage dissent and thereby lose the value of diverse opinions. Those who have reservations are less likely to have resentment or regret build if things don’t work out; their voices were represented in the strategic plan.

Incorporating this type of imagining of the negative space into a truthseeking group reinforces a new habit routine of visualizing and anticipating future obstacles. As always, when a group we are part of reinforces this kind of thinking, we are more likely in our own thinking to consider the downside of our decisions.

Imagining both positive and negative futures helps us build a more realistic vision of the future, allowing us to plan and prepare for a wider variety of challenges, than backcasting alone. Once we recognize the things that can go wrong, we can protect against the bad outcomes, prepare plans of action, enable nimble responses to a wider range of future developments, and assimilate a negative reaction in advance so we aren’t so surprised by it or reactive to it. In doing so, we are more likely to achieve our goals.

Of course, when we backcast and imagine the things that went right, we reveal the problems if those things didn’t go right. Backcasting doesn’t, therefore, ignore the negative space so much as it overrepresents the positive space. It’s in our optimistic nature (and natural in backcasting) to imagine a successful future. Without a premortem, we don’t see as many paths to the future in which we don’t reach our goals. A premortem forces us to build out that side of the tree where things don’t work out. In the process, we are likely to realize that’s a pretty robust part of the tree.

Remember, the likelihood of positive and negative futures must add up to 100%. The positive space of backcasting and the negative space of a premortem still have to fit in a finite amount of space. When we see how much negative space there really is, we shrink down the positive space to a size that more accurately reflects reality and less reflects our naturally optimistic nature.

We make better decisions, and we feel better about those decisions, once we get our past-, present-, and future-selves to hang out together. This not only allows us to adjust how optimistic we are, it allows us to adjust our goals accordingly and to actively put plans in place to reduce the likelihood of bad outcomes and increase the likelihood of good ones. We are less likely to be surprised by a bad outcome and can better prepare contingency plans.

It may not feel so good during the planning process to include this focus on the negative space. Over the long run, however, seeing the world more objectively and making better decisions will feel better than turning a blind eye to negative scenarios. In a way, backcasting without premortems is a form of temporal discounting: if we imagine a positive future, we feel better now, but we’ll more than compensate for giving up that immediate gratification through the benefits of seeing the world more accurately, making better initial decisions, and being nimbler about what the world throws our way.

Once we make a decision and one of those possible futures actually happens, we can’t discard all that work, even—or especially—if it included work on futures that did not occur. Forgetting about an unrealized future can be dangerous to good decision-making.

Dendrology and hindsight bias (or, Give the chainsaw a rest)

One of the goals of mental time travel is keeping events in perspective. To understand an overriding risk to that perspective, think about time as a tree. The tree has a trunk, branches at the top, and the place where the trunk meets the branches. The trunk is the past. A tree has only one, growing trunk, just as we have only one, accumulating past. The branches are the potential futures. Thicker branches are the equivalent of more probable futures, thinner branches are less probable ones. The place where the top of the trunk meets the branches is the present. There are many futures, many branches of the tree, but only one past, one trunk.

As the future becomes the past, what happens to all those branches? The ever-advancing present acts like a chainsaw. When one of those many branches happens to be the way things turn out, when that branch transitions into the past, present-us cuts off all those other branches that didn’t materialize and obliterates them. When we look into the past and see only the thing that happened, it seems to have been inevitable. Why wouldn’t it seem inevitable from that vantage point? Even the smallest of twigs, the most improbable of futures—like the 2%–3% chance Russell Wilson would throw that interception—expands when it becomes part of the mighty trunk. That 2%–3%, in hindsight, becomes 100%, and all the other branches, no matter how thick they were, disappear from view.

That’s hindsight bias, an enemy of probabilistic thinking.

Judge Frank Easterbrook, a leading jurist and member of the U.S. Court of Appeals for the Seventh Circuit, warned about the danger in the legal system of assessing probabilities after one of the potential futures has occurred. Jentz v. ConAgra Foods involved a “hot” grain bin owned by ConAgra and the company it hired (named West Side) to investigate and deal with the cause of the burning smell, smoke, and raised temperatures from the bin. After failing to solve the problem, West Side’s foreman told ConAgra to call the fire department. He then told some of his employees to remove tools from a tunnel to the bin that could impair firefighters’ access.

While the workers were in the tunnel, the bin exploded, severely injuring the West Side employees. Those injured sued ConAgra and West Side. The jury awarded $180 million in compensatory and punitive damages. In addressing the punitive damages against West Side, Judge Easterbrook, writing for the court, pointed out that Illinois law required a “gross deviation” from the standard of care to award punitive damages. Finding no evidence in the record of any foreseeable likelihood of explosion at the time the foreman ordered the workers to remove tools from the tunnel, he concluded, “The verdict appears to be a consequence of hindsight bias—the human tendency to believe that whatever happened was bound to happen, and that everyone must have known it. If [the foreman] believed that an explosion was imminent, then he is a monster; but of that there is no evidence. Hindsight bias is not enough to support a verdict.”

Once we know there was an explosion, it’s difficult to imagine the actions of the parties when the explosion was only one of several possible futures. The members of the jury had a conflict of interest. When they heard the story of the men entering the tunnel to retrieve the tools, they knew the outcome. The jury lopped off the other branches of the tree, all the other ways things could have turned out given the situation in the grain-storage bin and, in hindsight, all they could see was a confluence of circumstances with an inevitable tragedy at the end.

Imagine how things would be different for the protagonists throughout this book if more of us acted like Judge Easterbrook.

Steve Bartman could have used a stadium full of Cubs fans with Judge Easterbrook’s perspective. They would have recognized that the Cubs losing the game was only one of many ways it could have turned out. At the moment Bartman and others around him reached for the foul ball, the branch of the future where Steve Bartman touches the ball was a small one, and the chance of the Cubs losing after that was the tiniest of twigs, requiring a number of unlikely on-field developments (like the pitching ace giving up hit after hit, and the great-fielding shortstop committing a rare error on an inning-ending double play). Just as the foreman ordering workers into the tunnel didn’t cause the explosion, Bartman touching the ball didn’t cause the loss. He just got an unlucky result, based on all the things that happened over which he had no control after the foul ball touched his hands.

Pete Carroll and the world of Monday Morning Quarterbacks could have used the judge’s reminder that we tend to assume that, once something happens, it was bound to happen. If we don’t try to hold all the potential futures in mind before one of them happens, it becomes almost impossible to realistically evaluate decisions or probabilities after.

This turned out to be a big part of the problem for the CEO in the wake of firing his president. Although he had initially characterized the decision as one of his worst, when we reconstructed the tree, essentially picking the branches up off the ground and reattaching them, it was clear that he and his company had made a series of careful, deliberative decisions. Because they led to a negative result, however, the CEO had been consumed with regret. When he looked back at his decisions, he couldn’t see all those branches and their likelihoods. He could only see the trunk. All he saw was a bad result.

The CEO removed all those other branches with a chainsaw and ran them through a wood-chipper. They disappeared and he acted as if they never existed. That’s what hindsight bias is, and we’re all running amok through the forest with a chainsaw once we get an outcome. Once something occurs, we no longer think of it as probabilistic—or as ever having been probabilistic. This is how we get into the frame of mind where we say, “I should have known” or “I told you so.” This is where unproductive regret comes from.

By keeping an accurate representation of what could have happened (and not a version edited by hindsight), memorializing the scenario plans and decision trees we create through good planning process, we can be better calibrators going forward. We can also be happier by recognizing and getting comfortable with the uncertainty of the world. Instead of living at extremes, we can find contentment with doing our best under uncertain circumstances, and being committed to improving from our experience.

Reaction to the 2016 election provides another strong demonstration of what happens when we lop branches off the tree. Hillary Clinton had been favored going into the election, and her probability of winning, based on an accumulation of the polls, was somewhere between 60% and 70%, according to FiveThirtyEight.com. When Donald Trump won, pollsters got the Pete Carroll treatment, maybe no one more than Nate Silver, founder of FiveThirtyEight.com and a thoughtful analyzer of polling data. (“Nate Silver was wrong.” “The pollsters missed it.” “Just like Brexit, the bookies blew it.” Etc.) The press spun this as a certain win for Clinton, despite the Trump branch of the tree being no mere twig at 30%–40%. By the day after the election, the Clinton branch had been severed, only the Trump branch remained, and how could pollsters and the polling process have been so blind?

One of the things poker teaches is that we have to take satisfaction in assessing the probabilities of different outcomes given the decisions under consideration and in executing the bet we think is best. With the constant stream of decisions and outcomes under uncertain conditions, you get used to losing a lot. To some degree, we’re all outcome junkies, but the more we wean ourselves from that addiction, the happier we’ll be. None of us is guaranteed a favorable outcome, and we’re all going to experience plenty of unfavorable ones. We can always, however, make a good bet. And even when we make a bad bet, we usually get a second chance because we can learn from the experience and make a better bet the next time.

Life, like poker, is one long game, and there are going to be a lot of losses, even after making the best possible bets. We are going to do better, and be happier, if we start by recognizing that we’ll never be sure of the future. That changes our task from trying to be right every time, an impossible job, to navigating our way through the uncertainty by calibrating our beliefs to move toward, little by little, a more accurate and objective representation of the world. With strategic foresight and perspective, that’s manageable work. If we keep learning and calibrating, we might even get good at it.