Decision-Making as an Orientation Skill in Poker and Everyday Life: Annie Duke’s Thinking in Bets and the Philosophy of Orientation

Reinhard G. Mueller

Read the preface to this essay series here.

Endnotes

1 Annie Duke, Thinking in Bets: Making Smarter Decisions when You Don’t Have All the Facts (New York: Portfolio/Penguin, 2018). Quotes from this book are abbreviated as TB.

2 The abbreviation PO refers to the English translation of the primary book of the philosophy of orientation: Werner Stegmaier, What is Orientation? A Philosophical Investigation, transl. by Reinhard G. Mueller (Boston/Berlin: De Gruyter, 2019).

When you’re playing poker, you must quickly gather a multitude of information on each move: the cards on the table, the cards in your hand and those you suspect in your opponents’ hands, the stakes on the table, the other players’ skills and game strategies, the different options you have, and the bets and risks you’re willing to take. You have to make your decisions under the pressure of time and without reaching any certainty. As such playing poker displays what you do when you orient yourself: In each move, you pause to think, you weigh the alternative paths of action and decide for the one that seems most promising. When we’re unsure of how to proceed, we seek to orient ourselves by evaluating our alternatives before making a decision.

Playing poker is of course less complex than ‘real life’ because it’s a game with limited options, strict rules, clear winners and losers, and a regulated number of participants, who have all committed to follow the rules and play the game in a specific (sometimes virtual) place at a specific time. However, the decision-making skills acquired through professional poker-playing may be expanded beyond the game and applied to our everyday and professional life so that we may become better decision-makers as such – this is the claim of Annie Duke’s Thinking in Bets (2018) [Endnote 1]. Annie Duke is one of the most successful professional poker players of all time, nicknamed “the Duchess of Poker,” and in this book, she collects what she’s learned over the course of her poker career about decision-making skills as such and develops it into a philosophy of life that’s based on the orientation mode of “thinking in bets.” In this essay, I investigate, via the concepts of the philosophy of orientation, Annie Duke’s Thinking in Bets and scrutinize as to what extent one can universalize the orientation skill of decision-making with regard to our everyday and professional life.

Conceiving of decision-making in life via gambling metaphors isn’t new, but probably as old as it has been around, that is, since at least a few thousand years BC. According to ancient Greek myth, Zeus, Poseidon, and Hades threw the dice so that they could make a decision on how to split the universe among themselves; Hermes and Pan were considered the gods of gambling. In Roman times, Julius Caesar – always confident that luck and the gods were on his side – famously described the fateful crossing of the Rubicon river with his army toward Rome in the words iacta alea est, “the dice have been cast.” Gambling was common in ancient China, ancient Greece, in Roman times, the Middle Ages, and then especially since the 17th century, when it became increasingly professionalized and was studied in probability calculations by mathematicians.

One of these was Blaise Pascal, not only a mathematician, but also a physicist, theologian, inventor, writer, and philosopher. He made the notion of gambling prominent in philosophy and put one of the most pressing questions of human existence – does God exist? – into the metaphorical frame of a wager: Since, Pascal argues, God is outside the realm of human reason (“reason can decide nothing here”) and we’re nevertheless forced to choose whether we live according to the Christian faith, we’re also compelled to decide, whether we’re aware of it or not, on God’s existence. It’s an unavoidable decision because our way of living life from day to day is also already an implied decision on our faith. He compares this coercion of having to decide to that of having to place a bet: “you must wager. It is not optional,” “you are under the necessity of playing.” And if we would “estimate these two chances,” he argues, it’s clear that “there is an equal risk of gain and of loss” since human reason has no footholds regarding matters of God. However, even if the chances for God’s existence are 50/50, these two options nevertheless differ, according to Pascal, considering what you’d gain in each case: “If you gain” when betting that God exists, then “you gain all,” but “if you lose, you lose nothing.” He concludes: “Wager, then, without hesitation that He is.” Hence, if it turns out He exists and you’ve bet your life on it (by living accordingly), then you’d gain infinitely more (eternal happiness) compared to what you’d lose if you had bet against His existence, which is equal to “nothingness” – “those poisonous pleasures, glory and luxury” (Pensées, No. 233).

Going beyond the religious context, Annie Duke’s Thinking in Bets aligns with Pascal’s insight that we’re always already placing bets when we make decisions in life simply by the way we live it, by the paths of action we choose, and thus by how we spend our time. As such, we’re always already forced to gamble – whether we’re aware of it or not. In this aspect, Werner Stegmaier connects with both Blaise Pascal and Annie Duke: “In everyday orientation, one is rather condemned to play – not ‘for fun,’ but as seriously as a gambler who must continuously place bets under persistent uncertainty” (PO 54) [Endnote 2]. There are always alternatives, both Duke and Stegmaier highlight, to the ways we orient ourselves in life, but we must choose, and each choice will lead to different outcomes. It is this coercion of perpetually having to make choices and “bet” on our paths of action that Mike Hodges, founder of the Foundation for Philosophical Orientation, referred to in the opening question of his FPO inauguration speech: “How shall we spend our time?”

“Thinking in Bets” and the Philosophy of Orientation

Annie Duke’s Thinking in Bets aligns with the basic premises of the philosophy of orientation. Orientation is, for Werner Stegmaier, the achievement of finding one’s way successfully in new situations; we always orient ourselves under the conditions of uncertainty and the pressure of time, and in each orientation, “alternatives are always possible and must be decided on” (PO 15). The things we do, the ways we live our lives and the meaning we give to them always have alternatives: “One does not find a meaning of life, but one decides for a certain meaning and thus against others.” (PO 37) For Annie Duke, making decisions in poker as well as in life likewise take place under uncertainty and the pressure of time, and you obviously try to succeed in both poker and life. And while Werner Stegmaier points out that scientific theories always fall short of grasping the complexities of our everyday orientation (PO 7), Annie Duke likewise highlights that our lives will be less successful if we navigated it like a game of chess (instead of poker): John von Neumann (1903-1957), the pioneer of game theory, already emphasized this point: chess doesn’t compare to decision-making in life because in chess all options are surveyable and can, in principle, be calculated (TB 20f.). Poker, on the other hand, involves uncertainty and luck: While in chess a complete newbie never beats a pro, this is indeed possible in poker, because luck or, philosophically speaking, “contingency” plays a much greater role. Whereas Werner Stegmaier underscores that, since we constantly face uncertainty, we’re required to act with courage – “as far as orientation is always under uncertainty, it always requires courage” (PO 34) – Annie Duke argues for a probabilistic way of dealing with decisions to detach ourselves from our emotions when making them. Since, for her, we can “never be sure of the future” (TB 231), we become better and more rational decision-makers when we make our beliefs and expectations as explicit as possible. “Thinking in bets” means that you “wrap your arms around uncertainty” (TB 36) and that we realize “we’ve been betting all along” (TB 36). Just as Werner Stegmaier stresses the aspects of orientation’s risks, alternativity, and decidability, Annie Duke foregrounds that “every decision has risks, regardless of whether we acknowledge them”; “whenever we choose an alternative,” we’re “automatically rejecting every other possible choice” and there’s always “potential opportunity cost in any choice we forgo” (TB 42). Even “not placing a bet on something is, itself, a bet” (TB 44). Conceiving of the alternativity of our lives, the fact that we could have always decided and acted differently, via the metaphor of gambling then entails, for her, realizing that we’re betting less against others but rather “against all the future versions of ourselves that we are not choosing”; and what’s at stake is not just money but anything that may have value for us, be it “money, time, happiness, health, or whatever we value” in our lives (TB 46).

While poker indeed includes an element of luck, it isn’t based on luck alone, by contrast to, let’s say, the lottery or roulette. In fact, it’s quite the contrary: every professional poker player will highlight, according to Annie Duke, that it’s a game of skill that requires many years of experience if you ever want to have a chance of competing on a professional level. It’s this part of poker, the very skill of “making smarter decisions when you don’t have all the facts,” that Annie Duke explores in Thinking in Bets and that she expands on and applies to our everyday and professional lives, and that she augments with current research in psychology and sociology. So, what can we do to become better decision-makers?

How We’re Our Own Enemy: Biases and Blind-Spots

Before delving into the ways of how we can improve our decision-making, Annie Duke expounds how we’re naturally inclined to become bad decision-makers through our own fraudulent thinking patterns – that is, through our biases, fallacies, psychological tendencies, and emotions, all of which create blind-spots in our orientation. The four psychological tendencies impeding our decision-making skills she addresses are: (1.) “resulting,” which is connected with (2.) “hindsight bias”; (3.) “motivated reasoning” that goes hand in hand with (4.) “self-serving bias.”

(1.) “Resulting” refers to our mind’s erroneous tendency of “drawing an overly tight relationship between results and our decision quality” (TB 8): when winning at poker, especially when you’re on a winning spree, you may think it’s because of your skill, your decisions, and your superior insights into the game. However, poker has taught Annie Duke that success at gambling isn’t necessarily the result of one’s superiority because of the element of chance. And the same is true in our everyday life, where, she argues, we tend to see any outcome success as unquestioned proof of the succeeder’s decision-making skills: “Resulting is a routine thinking pattern that bedevils all of us” (TB 8). The simple fact that we’re successful and happy in a new position, career step, relationship, etc., doesn’t necessarily mean, she argues, that we’ve made great decisions. The first task for anyone who wants to improve his or her decision-making skills is therefore to distinguish as best as possible between skill and luck in the process. She calls this “fielding outcomes” – fielding them into the skill or luck “basket”: Through a close analysis of how lucky we were and where exactly we failed or succeeded, we will gain footholds for a more successful future orientation by keeping track of what worked well and what didn’t under the specific circumstances, instead of relying on luck alone. As the situation for making decisions in poker is limited and the rules are clear, it is indeed easier – though not always fully ascertainable – to delineate between skill and luck. In life, however, situations are in principle unlimited and the criteria for success are always a matter of perspective; and it’s therefore a lot more difficult to distinguish between luck and skill ‘in real life.’ Here, more so than in poker, “outcomes are rarely all skill or all luck” (TB 88). Annie Duke therefore suggests that we consider making this call – whether something was luck or skill – likewise as a “bet” and that we try to be as truthfulness as possible when fielding the outcomes. In this regard, the orientation mode of “thinking in bets” means that we become self-referential and critical judges of the relationship we draw between our own actions and the outcomes we encounter.

Connected with resulting is (2.) “hindsight bias,” which is “the tendency, after an outcome is known, to see the outcome as having been inevitable” (TB 10). Our narrative mind, psychology studies show, always tells its own stories beginning with the outcomes. In poker, as well as in life, we’re psychologically inclined to think that outcomes were predetermined once they happen, as if there were a linear time line that has always already been decided on and we’re simply confronted with such pre-determined happenings. The ancient Greeks connected this notion with the Moirai, the three “Fates” who weave human destinies on their tapestries, which is out of human control. The future, however, Annie Duke argues (agreeing with the premises of the philosophy of orientation), is always unknown and its uncertainty ineradicable. Fully relying on the Fates, the gods, God, or a pre-determined harmony of the universe, would mean that we hold on to unconditional footholds, as if they were certainties, and do away with life’s inevitable uncertainty. Since nobody can know the future, we become better decision-makers, Annie Duke argues, if we start thinking in probabilities, based on uncertainties, and make them as explicit as possible when we’re deciding on alternatives. Confronting “hindsight bias” thus entails critical awareness of the fact that things could have always turned out differently.

The second pair of psychological tendencies that interferes with our decision-making ability is that of (3.) “motivated reasoning” and (4.) “self-serving bias.” They relate to something that Friedrich Nietzsche once pointed out in an aphorism:

“‘I have done that’ says my memory. I could not have done that – says my pride and remains implacable. Finally – my memory gives up.” (Beyond Good and Evil, No. 68)

If our memory and our pride are in conflict with each other, then it’ll be our pride, Nietzsche holds, that wins and distorts our memory: we naturally tend to blur our perception of reality so that it better aligns with our beliefs and self-perception. Annie Duke shows, though without referring to this quote, that Nietzsche’s intuition has indeed been confirmed by empirical research: What she calls “motivated reasoning,” for an “irrational circular information processing pattern” (TB 59), refers to the fact that we naturally seek that which confirms our beliefs and tend to filter out disagreeing information because we don’t want to be wrong (TB 61). And curiously, research demonstrates that higher intelligence in fact makes this “blind-spot bias” stronger: “being smart makes it worse” (TB 62). Motivated reasoning goes hand in hand with “self-serving bias,” according to which we’re prone to connecting successful outcomes with our allegedly great orientation skills and unsuccessful ones with unfavorable circumstances: we tend to “take credit for the good stuff and blame the bad stuff on luck” (TB 89). And since we’re naturally competitive and want to think of ourselves as superior to others (at least in some regard), we also tend to reverse this perception when observing other people: “we use the same black-and-white thinking as with our own outcomes, but now we flip the script” and ascribe others’ success to their luck and their bad outcome to their bad decision-making skills (TB 97).

So, if we now know about these fraudulent thinking patterns that we fall victim to, what can we do about them? Annie Duke suggests we need to reorient ourselves, reshape our habits, and revalue our values. This reorientation involves, she argues: being more self-critical of our success, more generous when giving credit to others, and considering mistakes as learning opportunities, as everyone will make mistakes given the uncertainty of the future. Reshaping our habits thus entails a revaluation of values: “feeling good about ourselves from being a good credit-giver, a good mistake-admitter, a good finder-of-mistakes-in-good-outcomes, a good learner, and (as a result) a good decision-maker” (TB 108). Reshaping one’s routines is usually a slow process that takes place step by step, by changing one routine at a time; according to the philosophy of orientation, changing routines “has the structure of transposed continuities” (PO 87). The overarching value or attitude Annie Duke proposes in the orientation mode of “thinking in bets” is the ideal of “accurate self-critique,” of “accuracy and truthseeking” (ibid.). And in this regard, she suggests, we should make use of our own competitive nature and seek to become better credit-givers than our peers, more willing than others to admit mistakes, and more willing to explore possible reasons for an outcome with an open mind (ibid.). Before describing below how we can cooperate with others in order to reach these goals, I address another major obstacle that Annie Duke highlights and that frequently interferes with our decision-making ability: our own emotions.

Distancing Ourselves from Our Own Emotions

Emotions, positive or negative, may strongly influence our decision-making ability by narrowing the horizons of our orientation and exaggerating the immediate situation at the costs of the bigger picture and our long-term orientations. In poker, the state of emotional distress, frustration, or anger that is mentally disorienting and that impedes one’s decision-making skills is called “tilt” or “steam.” Annie Duke describes the physiological signs of tilt thus: “We feel our cheeks flush and our heart race. Our respiration speeds up” (TB 198). When this happens and you’re “on tilt,” it’s best to realize that you’re not “decision fit” (TB 199) and you better walk away from the table, gain some distance, calm down. In life, too, we tend to make emotional decisions when rational distance might have opened up wider horizons. When we’re emotional, we ‘zoom in’ on the nearest things and the most recent experiences, or as Annie Duke puts this: “we’re ticker watchers of our own lives” (TB 193).

Werner Stegmaier addresses this issue in the context long-term decision-making in life and the distortions we encounter in states of anxiety or despair: “even though anxiety and despair may urge your need for orientation, they usually do not help you in finding a good orientation; instead, they limit this even more. Decisions on new directions of your life, if made under their influence, become questionable again when the situation has calmed down” (PO 37). For him, it’s not only emotions, but also moods that may limit an orientation’s view: “A mood (Stimmung)” brings, “like the tuning (stimmen) of an instrument,” “all tones to a different pitch,” and in different moods, “situations are experienced in different ways” (PO 30). Orientation usually oscillates between the basic moods of ‘unsettlement’ and ‘reassuring calmness’; other moods relevant for orientation are anxiety, despair, and depression, all of which are modes of disorientation. While all moods shape our orientation’s views in distinct ways, emotions such as the anger, sadness or fear about losing, or the happiness and excitement about winning strongly narrow the horizons of our orientation so that we focus only on the immediate cause of the emotion. The decision-making strategies Annie Duke proposes in this regard are therefore directed at distancing oneself from the immediate situation and widening the horizons of orientation through what she calls “mental time travel.”

1. She refers to Suzy Welch’s “10-10-10” strategy, according to which you put the immediate, emotionally charged, situation into a broader perspective by asking yourself: “What are the consequences of each of my options in ten minutes? In ten months? In ten years?” (TB 188) Such distancing and rationalizing helps toning down one’s emotions involved in the moment, by putting any loss or gain into the bigger picture and the context of one’s long-term goals. We shift from an emotional to a more rational orientation mode.

2. Another strategy she recommends is making a “Ulysses contract” with yourself or others, according to which you – just as Odysseus did (or by his Roman name: Ulysses) when he had to face the Sirens – make a decision or set up a rule that you stick to in a challenging situation, such as determining a maximum amount of money you’re willing to lose at the table. A contract helps “raising a barrier against irrationality” (TB 201). This orientation strategy relates to what Werner Stegmaier calls “resoluteness”: the “attitude of no longer changing a decision (Entscheidung) in one ‘point’ and thus no longer taking further footholds into account even if the situation suggests it” (PO 61). You then make a decision about your future decision-making.

3. Just as military strategists prepare a “reconnaissance” before battle in order to anticipate any surprising scenarios, Annie Duke suggests – and consults companies in this way – that one engage in explicit scenario planning for different possible futures, including precise amounts of expected outcome probabilities. Such kind of planning permits preparing for potentially overwhelming challenges and avoiding any “tilt” or “steam” situations (TB 208-212). This strategy relates to and puts into practice what Werner Stegmaier calls “gaining an overview” of the situation: first, you “overlook everything that is relevant in this situation,” second, you are “focusing and defocusing” on individual aspects (here: the different scenarios), and third, you combine these two steps by putting the individual footholds into the wider horizon of overview, here: estimating the probabilities (PO 38-40).

4. Another orientation strategy that helps broadening the view of the situation is what Annie Duke refers to with “backcasting” and “premortems”: Backcasting means to “identify a goal and work backward from there to ‘remember’ how we got there,” i.e. we clearly and in detail envision a future state where we want to be and then expound the details of how we got there. “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” (TB 220). In psychology, this is often referred to as ‘visualizing success.’ Research shows that this way of thinking strengthens our “ability to correctly identify reasons for future outcomes” (TN 219). And one can further improve this orientation strategy by complementing it with what she calls “premortems”: “a premortem is the investigation into something awful, but before it happens” (TB 221). A premortem (Lat. ‘before death’) is the opposite of backcasting and means that you imagine a failed future state and cast back the steps that have led you to it from the viewpoint of the imagined future. Psychological research found, according to Annie Duke, that backcasting helps visualizing and thus orienting oneself more clearly toward a goal; and premortems increase one’s motivation to act upon it: “we have to have positive goals, but we are more likely to execute on those goals if we think about the negative futures” (TB 224). By means of backcasting and premortems, our thinking oscillates between a successful and an unsuccessful future outcome, and this perspectizing permits not only a more comprehensive picture of possible futures by illuminating blind-spots, but it also pushes us to act.

All these orientation strategies are possible by virtue of the achievement we gain from what Werner Stegmaier calls the orientation “skill” of “thinking”: thinking, which we experience in manifold modes, permits one’s “distancing from the given situation,” here: our own emotions. And regarding different future outcomes, “thinking provides an orientation with projections of orientations, which can, in different situations, be applied in different ways” (PO 97-99). As such, the achievement of thinking permits an orientation not only to widen the horizons of an emotional charged situation but also to consider alternative ways of framing it and its future.

Thinking in Bets in Interindividual Orientations

While “thinking in bets” is initially a self-referential and critical discourse we’re engaged in with ourselves, we can and should, Annie Duke suggests, also recruit other people in our decision-making processes, ideally through what she calls a “buddy system” (TB 119). She proposes that you can improve your decision-making skills by establishing a group discourse for making decisions based on her guiding value of “accurate self-critique” (TB 108). Such a group, she expounds, ideally takes the form of a stable “truthseeking group,” with at least three members, that avoids “confirmatory thought” in favor of “exploratory thought” and that’s oriented to “truthseeking, objectivity,” “open-mindedness,” “accountability” and “diversity of ideas” (TB 129f.). Not only can this group implement and put into practice the “reshaping of habits” mentioned above – its members compete to become “the best credit-giver, the best mistake-admitter, and the best finder-of-mistakes-in-good-outcomes” (TB 133) – but these routines of orientation are then also internalized or, as Nietzsche would call it, “incorporated” into our being, becoming an unquestioned part of our decision-making routines and thinking. As Annie Duke puts it: “We internalize the group’s approval, and, as a matter of habit, we begin to do the kind of things that would earn it when we are away from the group (which is, after all, most of the time)” (TB 134). The group thus facilitates the internalization of the orientation mode of “thinking in bets”: “being in an environment where the challenge of a bet is always looming works to reduce motivated reasoning” (TB 136). You will be more cautious and careful, she argues, before making any ‘black and white’ statements and try to discover your own biases and blind-spots.

Not only is the value of ‘open-mindedness,’ in the philosophy of orientation, a crucial “virtue of ethical orientation” as far as it permits viewing the situation from others’ perspectives: “someone capable of open-mindedness is, more than others, open for moral behaviors and moral utterances that are foreign to him or herself” (PO 243). But these decision-making groups also rely on important interindividual orientation virtues. On the one hand, they are those essential for “interactions and communications with others” (PO 241) – in this case, the “trust” in the “reliability” of all group members that they follow the values of accuracy, exploratory thought, and truthful dissent, which furthermore require the orientation virtues of “resoluteness” and “adherence to principles” (ibid.). On the other hand, these groups implement the virtues that are, for Werner Stegmaier, involved in “communication of information and knowledge,” and these are, “fact-orientation and truthfulness,” which permeate the entire critical discourse of the group (PO 242).

Deliberately arranging truthful dissent between different opinions and parties has of course become the organizing principle in, for instance, parliamentary or corporate oppositions, in academic discourses such as a thesis defense or in debating clubs, but also in CIA “red teams” and the State Department’s “Dissent Channel” (TB 139f.) However, when organizing such groups, we’re likewise prone to impeding our own decision-making capacities, namely because we naturally tend to navigate toward people who are similar to ourselves, thereby reducing the richness of dissenting perspectives in a group. Annie Duke therefore advocates for the conscious inclusion of as many different viewpoints as possible in our group permitting the greatest possible diversity of thought.

“Thinking in Bets” and the Philosophical Tradition

As far as the basic values that guide Annie Duke’s orientation mode of “Thinking in Bets” are those of “accurate self-critique,” “truthseeking,” and, in interindividual regard, multiperspectivity, her approach follows, philosophically speaking, the core ideas of the Enlightenment. Her concepts closely align with, for instance, Gottfried Wilhelm Leibniz (1646-1716), who conceived of Enlightenment as a critical discourse of individually different and limited viewpoints for the sake of truthseeking, in which all souls (he calls them “monads”) will gain a richer and more objective image of the world so that they recognize more of the truth and of God’s pre-determined harmonic universe (Monadology). Though Annie Duke doesn’t refer to God or a predetermined harmony, she indeed continues the Enlightenment tradition of multiperspectival and critical truthseeking, not with regard to final truths, but to better decision-making.

Her guiding principles furthermore closely align with Immanuel Kant (1724-1804) and his three maxims of the Enlightenment: 1. Think for yourself (independent of dogmas or others’ opinions); 2. Put yourself into others’ perspectives (through critical communication with them); 3. Always think consistently with yourself. The third maxim combines maxims 1 and 2 and is, in a sense, a never-ending task as far as one continues one’s truthseeking discourse with ever-new people in ever-new situations, and one’s own thinking continually changes as well. These maxims are a crucial driving element of Annie Duke’s ‘decision-making groups’ that engage in productive interindividual dissent via critical truthseeking so that the participants can better detect each other’s blind spots and gain a more comprehensive overview of the situation they’re in.

Kant grounded his maxims and his notion of Enlightenment in his concept of reason (which we were provided for by nature – or perhaps by God) and his categorical imperative, through which we can hear the voice of reason speaking to us: “Act as if the maxims of your action were to become through your will a universal law of nature.” This means, in any situation you should ask yourself: ‘Can the principle that my decision and action are based on become a universal law?’ Annie Duke’s orientation mode of “thinking in bets” is likewise an ‘imperative,’ the imperative that tells you, ‘think in bets!’ or if spelled out: ‘decide and act as if every decision and every interpretation were a bet and as if you always have something at stake.’ However, different from Kant’s imperative, it is not categorical, i.e. universal, but rather hypothetical or conditional, referring to the condition: if you want to become a better decision-maker, then follow the imperative of thinking in bets.

Furthermore, the notion of ‘having something at stake’ in every decision, action, and orientation in life philosophically presupposes the concept of mortality: since our lives are limited and our time will run out, everything we do comes with certain stakes and risks. The time you didn’t ‘use well,’ will never return. This thought was famously put into words by the Roman poet Horace (65 BC – 8 BC): ‘memento mori’ (remember that you die) and ‘carpe diem’ (broadly: seize the day), which reappeared in various forms throughout history and, most recently, in the acronym YOLO: you only live once. In philosophy, this notion of mortality was most prominently addressed by Martin Heidegger’s (1889-1976) concept of an authentic existence in Being and Time: Only when we realize, he argues, that we’re mortal and when we put ourselves in relation to our own – always individual and singular – death, which we can never fully grasp (what Heidegger calls “Being-towards-Death”), then we have the chance of living what he calls a more “authentic” existence by making decisions on the routines of our lives, instead of simply following everyone else’s routines (he calls this ‘the they,’ das Man). Annie Duke doesn’t mention the aspect of mortality, but it is only this implied limitedness of anything in life, the scarcity of everything we value, that creates meaning, risk, and the stakes of the decisions we make. Only time, mortality, and the irreversibility of actions make our decisions into bets.

Decision-Making as an Orientation-Skill in Poker and Life

If we call decision-making an ‘orientation skill’ that one can learn in poker, then this is also due to the fact that this game requires from great players competencies in what the philosophy of orientation calls basic “orientation virtues,” which are also significant for successful orientations in everyday life. Applied to poker, these are: “overview,” regarding the entirety of the game and your distancing from the situation by means of widening the horizons; “circumspection” regarding the relevant cards in the game, the stakes, and the players; “foresight” concerning the opponents’ bets and the bets you’re willing or able to make; “insight” into your own weaknesses and fraudulent thinking patterns and those of your opponents; “precaution” regarding your potentially imprudent decisions when struck by emotions; and “confidence” and “courage” for raising the stakes when you have a good hand. In addition, playing poker successfully requires one to continually reorient oneself to different opponents and surprising game situations and, above all, to one’s virtue or skill to “use a situation’s uncertainties and decidabilities, as well as the leeways provided by the clues, footholds and signs, … to creatively master the situation” (PO 241).

However, despite the complexity of the game, the number of relevant footholds one must take into account are, compared to everyday life, more easily discernable because the goals, priorities, and outcomes are clear. In ‘real life,’ distinguishing, for instance, between the skill and the luck ‘basket’ becomes much more difficult (is the success in your orientations that comes from your genes, your upbringing, and your education – skill or luck?). And different from poker, where you want to win as much money as possible, the ‘currencies’ in everyday life aren’t always clear, and you rather try to navigate as best as possible your different orientation worlds (family, job, hobbies, friends, etc.), trying to be successful in each of them. But it remains difficult to weigh these outcomes against each other – what’s more important: a successful career, being a great mother, a great friend?

An important element emphasized in the philosophy of orientation that Thinking in Bets doesn’t address is that of courage. Courage is needed, according to Werner Stegmaier, when anxiety and fear arise, which may happen for instance when we realize that the future is persistently uncertain and that we could have always decided differently. It’s especially demanded in ‘existential’ decisions that will shape your entire life and possibly that of many others. The reason courage is missing from Annie Duke’s conception may be that framing your life via the metaphor of ‘thinking in bets’ already alleviates anxiety and abates fears because you now consider all your decisions as mere ‘bets’ and life as a ‘game.’ Crucial life decisions then become less ‘existential’ altogether because you’re less attached to them and you no longer identify with them or their outcome. To ‘think in bets’ may as such give you courage and confidence in the face of uncertainties and challenges. In orientation, “confidence is the expectation that good orientations will continue in an unforeseen future” (PO 42). And ‘thinking in bets’ may do so especially if you believe, as for instance Caesar did, that luck is always on your side and that you’ll be the more successful, the higher the bets are you’re willing to take. However, your confidence may always turn out to be overconfidence and your belief in winning constantly may always be disappointed – when you lose your bets, as Caesar did when he was assassinated. Deciding to ‘think in bets‘ is likewise a bet.

But let’s come back to our initial question: To what extent can we universalize the orientation skills of decision-making? Since every situation of orientation is somewhat new and different, every decision is ultimately singular and its principles can, strictly speaking, not be universalized. However, we factually develop routines of decision-making, especially if situations recur in similar patterns. And it is precisely these recurring patterns at the poker table that permit players to improve through practice: you then learn how to ‘read the game,’ to better ascertain the probabilities and ‘get a feeling’ for the other players’ strategies. As far as situations of orientation also recur in similar patterns in certain fields of action, we likewise develop routines of decision-making in these areas, and this is the very aspect of what we value in experienced professionals. Successful politicians, lawyers, physicians, investors, businesspeople, artists, and athletes have learned the very nuances of their respective games, something we may call a ‘sixth sense,’ to know exactly when it’s the right time for a certain action. The ancient Greeks called the wisdom of knowing what to do at the right time Kairos (Enrico Mueller and Carlin Romano have explored this topic in our competitive essay sequence Agonistic Orientations). Kairos is likewise difficult to fully grasp or universalize in philosophical terms, and there will always remain something ungraspable and fascinating especially about those who are exceptionally skilled at mastering the most challenging situations and acting in the best way at the right time – sometimes we connect such skills with ‘genius.’

However, what we can say about the structures of decision-making as such is that we may become gradually better decision-makers when applying the orientation strategies Annie Duke proposes. They don’t tell us how we ought to decide, but rather how we can improve the conditions for making better decisions. We may still make bad decisions, but her point is that we increase the probability of making better decisions by developing habits based on her orientation strategies. These are: (1.) In order to avoid “resulting” and learn from our experiences, we need to distinguish as clearly and accurately as possible between the outcome and the decision-making process, as well as between luck and skill. (2.) We critically question our own “self-serving biases” and “motivated reasoning” as well as the implicit beliefs our orientations are based on, and we (3.) critically distance ourselves from our own emotions by widening the horizons of the situation we’re in through “mental time travel” techniques. And (4) we recruit others in our decision-making process in “decision-making groups,” which are ideally driven by the basic values that permeate the entire orientation mode of “thinking in bets,” that is: accurate self-critique, truthseeking, and multiperspectivity. Though she hardly uses the term of ‘orientation’ herself, she indeed concludes her book with metaphors of orientation: If we think in bets, she claims, we get better at “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” (TB 231).