Parrish

Clear Thinking- Shane Parrish

Preface

That night I started asking myself questions that I’d continue exploring for the next decade. How can we get better at reasoning? Why do people make bad decisions? Why do some people consistently get better results than others who have the same information? How can I be right more often, and decrease the probability of a bad outcome when lives are on the line?

While the rest of us are chasing victory, the best in the world know they must avoid losing before they can win. It turns out this is a surprisingly effective strategy.

In order to get the results we desire, we must do two things. We must first create the space to reason in our thoughts, feelings, and actions; and second, we must deliberately use that space to think clearly. Once you have mastered this skill, you will find you have an unstoppable advantage.

Decisions made through clear thinking will put you in increasingly better positions, and success will only compound from there.

Together we’ll uncover the missing link between behavioral science and real-world results and turn ordinary moments into extraordinary results.

If there is a tagline to my life, it is “Mastering the best of what other people have already figured out,” and this book is a tribute to that belief.

It’s safe to assume that anything useful in this book is someone else’s idea, and that my main contribution is to put the mosaic of what I’ve learned from others who came before me out there for the world.

Introduction: The Power of Clear Thinking in Ordinary Moments

What happens in ordinary moments determines your future.

We’re taught to focus on the big decisions, rather than the moments where we don’t even realize we’re making a choice. Yet these ordinary moments often matter more to our success than the big decisions. This can be difficult to appreciate.

Even when we get the big decisions directionally right, we’re not guaranteed to get the results we want.

We don’t think of ordinary moments as decisions. No one taps us on the shoulder as we react to a comment by a coworker to tell us that we’re about to pour gasoline or water onto this flame.

In most ordinary moments the situation thinks for us. We don’t realize it at the time because these moments seem so insignificant. However, as days turn into weeks and weeks turn into months, the accumulation of these moments makes accomplishing our goals easier or harder.

Each moment puts you in a better or worse position to handle the future. It’s that positioning that eventually makes life easier or harder. When our ego takes over and we show someone we’re the boss, we make the future harder. When we are passive-aggressive with a colleague at work, our relationship becomes worse. And while these moments don’t seem to matter much at the time, they compound into our current position. And our position determines our future.

What a lot of people miss is that ordinary moments determine your position, and your position determines your options. Clear thinking is the key to proper positioning, which is what allows you to master your circumstances rather than be mastered by them.

It doesn’t matter what position you find yourself in right now. What matters is whether you improve your position today.

Every ordinary moment is an opportunity to make the future easier or harder. It all depends on whether you’re thinking clearly.

Part 1: The Enemies of Clear Thinking

1.1. Thinking Badly— or Not Thinking at All

So our first step in improving our outcomes is to train ourselves to identify the moments when judgment is called for in the first place, and pause to creat space to think clearly. This training takes a lot of time and effort, because it involves counterbalancing our hardwired biological defaults evolved over many centuries. But mastery over the ordinary moments that make the future easier or harder is not only possible, it’s the critical ingredient to success and achieving your long-term goals.

For instance, like all animals, we are naturally prone to defend our territory. We might not be defending a piece of terrain on the African savanna, but territory isn’t just physical, it’s also psychological. Our identity is part of our territory too. When someone criticises our work, status, or how we see ourselves, we instinctively shut down or defend ourselves. When someone challenges our beliefs, we stop listening and go on the attack. No thoughts, just pure animal instinct.

We’re self preserving. Most of us would never intentionally push someone else down to get where we want to go. The key word here is “intentionally,” because intention involves thought. When we’re triggered and not thinking, our desire to protect ourselves first takes over. When layoffs loom at a company, otherwise decent people will quickly throw each other under the bus to keep a job. Sure, they wouldn’t consciously want to hurt their colleagues, but if it comes down to “them versus me,” they will ensure they come out on top. That’s biology.

Conscious processing takes both time and energy. Evolution favoured stimulus-response shortcuts because they’re advantageous for the group: they enhance group fitness, group survival, and reproduction.

Here’s how each essentially functions:

• The emotion default: we tend to respond to feelings rather than reasons and fact.

• The ego default: we tend to react to anything that threatens our sense of self-worth or our position in a group hierarchy.

• The social default: we tend to conform to the norms of our larger social group.

• The inertia default: we’re habit forming and comfort seeking. We tend to resist change, and prefer ideas, processes, and environments that are familiar.

There are no hard edges between defaults; they often bleed into one another. Each on their own is enough to cause unforced errors, but when they act together things quickly go from bad to worse.

1.3. The Ego Default

Our ego tempts us into thinking we’re more than we are. Left unchecked, it can turn confidence into overconfidence or even arrogance. We get a bit of knowledge on the internet and suddenly we are full of hubris. Everything seems easy. As a result, we take risks that we may not understand we’re taking. We must resist this kind of unearned confidence, though, if we are to get the results we desire.

One example I’ve seen too many times in a workplace is when you stop putting in 100 percent of what you are capable of because you feel underappreciated. The ego grabs your unconscious, throws your long-term goals out the window, and sets you sailing on a path toward destruction.

Our desire to feel right overpowers our desire to be right.

The ego default urges us to feel right at the expense of being right. Few things feel better than being right— so much so that we will unconsciously rearrange our world into arbitrary hierarchies to maintain our beliefs and feels better about ourselves.

1.4. The Social Default

Doing something different means you might underperform, but it also means you might change the game entirely. If you do what everyone else does, you’ll get the same result that everyone else gets. Best practices aren’t always the best. By definition they’re average.

If you don’t know enough about what you’re doing to make your own decisions, you probably should do what everyone is doing. If you want better-than-average results, though, you’ll have to think clearly and thinking clearly is thinking independently. Sometimes you have to break free of the social default and do something differently from those around you. Fair warning: it’s going to get uncomfortable.

It’s easy to take comfort in the fact that other people agree with us. As legendary investor Warren Buffett pointed out, though, “The fact that other people agree or disagree with you makes you neither right nor wrong. You will be right if your facts and reasoning are correct.”

The people executing established practices say they want new ideas, but they don’t want the bad ones. And because they so want to avoid the bad ones, they never deviate enough to find good ones.

Warren Buffett similarly highlighted the effects of the social default in his 1984 letter to Berkshire Hathaways’s shareholders:

Most managers have very little incentive to make the intelligent-but-with-some-chance-of-looking-like-an-idiot decision. Their personal gain/loss ratio is all too obvious: if an unconventional decision works out well, they get a pat on the back and, if it works out poorly, they get a pink slip. (Failing conventionally is the route to go; as a group, lemmings may have a rotten image, but no individual lemming has ever received bad press.)

Lemmings might make small changes, sure, but not the changes they need in order to make an outsize impact.

1.5. The Inertia Default

The inertia default pushes us to maintain the status quo. Starting something is hard but so too is stopping something. We resist change even when change is for the best.

The Latin word inertia means literally “inertness”: that is, laziness or idleness. In physics, “inertia” refers to an object resisting change in its state of motion. Hence, a popular way of stating Newton’s first law of motion— the law of inertia— is this: “A body in motion tends to stay in motion, and a body at rest tends to stay at rest.

The physicist Leonard Mlodinow sums it up this way: “Once our minds are set in a direction, they tend to continue in that direction unless acted upon by some outside force.” This cognitive inertia is why changing our minds is hard.

Inertia keeps us doing things that don’t get us what we want. It operates in our subconscious largely undetected until its effects are too hard to counter.

1.6. Default to Clarity

Many of the algorithms you’re running have been programmed into you by evolution, culture, ritual, your parents, and your community. Some of these algorithms help move you closer to what you want; others move you further away.

You unconsciously adopt the habits of the people you spend time with, and those people make it easier or harder for you to achieve progress toward what you want to achieve. The more time you spend with people, the more likely you start to think and act as they do.

The people with the best defaults are typically the ones with the best environment. Sometimes it’s part of a deliberate strategy, and sometimes it’s just plain luck. Either way, it’s easier to align yourself with the right behaviour when everyone just is already doing it.

The way to improve your defaults isn’t by willpower but by creating an intentional environment where your desired behaviour becomes the default behaviour.

Part 2: Building Strength

Criticizing others is easier than coming to know yourself.

—Bruce Lee

Here are four key strengths you’ll need:

Self-accountability: holding yourself accountable for developing your abilities, managing your inabilities, and using reason to govern your actions

Self-knowledge: knowing your own strengths and weaknesses— what you’re capable of doing and what you’re not

Self-control: mastering your fears, desires, and emotions.

Self-confidence: trusting in your abilities and your value to others.

2.1. Self-accountability

People who lack self-accountability tend to run on autopilot. This is the exact opposite of commanding your own life. These people constantly succumb to external pressure: seeking rewards, avoiding punishments, and measuring themselves against other people’s scoreboards. They’re followers, not leaders. They don’t take responsibility for their mistakes. Instead, they always try to blame other people, circumstances, or bad luck— nothing’s ever their fault.

Well, I have news for you. It’s all your fault.

There is always something you can do in the moment today to better your position tomorrow. You might not be able to solve the problem, but your next action will make the situation better or worse. There us always an action you can control, however tiny, that helps you achieve progress.

Complaining is not a strategy. You have to work with the world as you find it, not as you would have it be.

—Jeff Bezos

Too often, the people we ask for feedback are kind but not nice. Kind people will tell you things a nice person will not. A kind person will tell you that you have spinach on your teeth. A nice person wont because it’s uncomfortable. A kind person will tell us what holds us back even when it’s uncomfortable. A nice person avoids giving us critical feedback because they’re worried about hurting our feelings. No wonder we end up thinking people will be interested in our excuses.

One of the most common mistakes people make is bargaining with how the world should work instead of accepting how it does work. Anytime you find yourself or your colleague complaining “that’s not right,” or “that’s not fair,” or “it shouldn’t be that way,” you are bargaining, not accepting. You want the world to work in a way that it doesn’t.

Failing to accept how the world really works puts your time and energy toward proving how right you are. When the desired results don’t materialize, it’s easy to blame circumstances or others. I call this the wrong side of right. You’re focused on your ego not the outcome.

Solutions appear when you stop bargaining and start accepting the reality of the situation. That’s because focusing on the next move, rather than how you got here in the first place, opens you up to a lot of possibilities. When you put outcome over ego, you get better results.

You can’t control everything, but you can control your response, which makes circumstances better or worse. Each response has an impact on the future, taking you either a step closer to or a step further from the outcomes you want and the person you want to be.

One effective question to ask yourself before you act is, “Will this action make the future easier or harder?” This surprisingly simply question helps change your perspective on the situation and avoid making things worse.

Facing reality is hard. It’s much easier to blame things we have no control over than look for our own contributions.

Too often we fight against the feedback the world gives us, to protect our beliefs. Rather than changing ourselves, we want the world to change. And if we don’t have the power to change it, we do the only thing we feel we can do: complain.

Complaining isn’t productive. It only misleads you into thinking that the world should function in a way that it doesn’t. Distancing yourself from reality makes it harder to solve the problems you face. There is always something you can do today to make the future easier, though, and the moment you stop complaining is the moment you start finding it.

There are points in the process of becoming a chronic victim when people realize they’re lying to themselves. They realize the story they’re telling themselves isn’t quite true. They know they’re responsible. But facing reality and taking responsibility is hard. It’s uncomfortable. It’s so much easier to hide and to blame other people, circumstances, or luck.

The lesson was an important one: the things you choose not to do often matter as much as the things you choose to do. The real test of a person is the degree to which they are willing to nonconform to do the right thing.

If you pay attention to chronic victims, you’ll notice how fragile they are— how dependent their attitudes and feelings are on things they don’t control. When things go their way, they’re happy; when things don’t, they’re defensive, passive-aggressive, and occasionally aggressive-aggressive. If their spouse is in a bad mood, they’re in a bad mood too. If they hit traffic on the way to work, they bring their anger and frustration to work with them. If a project they’re leading isn’t on track, they blame someone on their team.

2.4. Self-Confidence

It’s only human to have doubts about whether you are up to a given task. Even the most capable people have doubts about this from time to time. But those who have self-confidence never give in to feelings of despair or worthlessness. That’s just another ego trap. Instead, confident people stay focused on completing the task at hand, even if it involves relying on the help of others to do so. Every successful task only further serves to deepen your trust in yourself, and that’s how confidence is earned.

Confidence also Comes from How You Talk to Yourself

The first thing we did was to focus on our breathing. Your breath is a powerful tool that helps you calm your mind.

The most important voice to listen to is the one that reminds you of all that you’ve accomplished in the past. And while you might not have done this particular thing before, you can figure it out.

I asked, “If you could pick one trait that would predict how someone would turn out, what would it be?”

“That’s easy,” he said. “How willing they are to change their mind about what they think they know.”

The most valuable people, he continued, weren’t the ones with the best initial ideas, but the ones with the ability to quickly change their minds. They were focused on outcome over ego. By contrast, he said, the people most likely to fail were those obsessed with minute details that supported their point of view.

When everything is on your shoulders and the cost of being wrong is high, I told her, you tend to focus on what’s right instead of who’s right. The more I’d given up wanting to be right, the better the outcomes I had. I didn’t care about getting the credit; I cared about getting the results.

Self-confidence is the strength to focus on what’s right instead of who’s right. It’s the strength to face reality. It’s the strength to admit mistakes, and the strength to change your mind. Self-confidence is what it takes to be on the right side of right.

Outcome over ego.

2.6. Setting the Standards

It is inevitable if you enter into relations with people on a regular basis. . . that you will grow to be like them. . . . Place is an extinguished piece of coal nest to a live one, and either it will cause the other one to die out, or the live one will make the other reignite. . . . Remember that if you consort with someone covered in dirt you can hardly avoid getting a little grimy yourself.

• Epictetus

Few things are more important in life than avoiding the wrong people. It’s tempting to think that we are strong enough to avoid adopting the worst of others, but that’s not how it typically works.

We unconsciously become what we’re near. If you work for a jerk, sooner or later you’ll become one yourself. If your colleagues are selfish, sooner or later you’ll become selfish. If you hang around someone who’s unkind, you’ll slowly become unkind. Little by little, you adopt the thoughts and feelings, the attitudes and standards of the people around you.

This was inspired by this Bill Walsh quote: “Champions behave like champions before they’re champions. They have a winning standard of performance before they are winners.

I remembered a story I’d read about Henry Kissinger. A staffer had drafted a memo and left it on Kissinger’s desk for him to read. A while later Kissinger approached him and asked if it was his best work. The staffer said no and rewrote the entire memo. The next day the staffer ran into Kissinger again and asked what he thought. Kissinger asked him again if this was the best he could do. The staffer took the memo and rewrote it yet again. The next morning the same scenario played out, only this time the poor staffer stated that yes indeed it was his best work. Kissinger replied, “Okay, now I’ll read it,

Working with a master firsthand is the best education; it’s the surest way of raising the bar. Their excellence demands your excellence. But most of aren’t lucky enough to have that opportunity. Still, not all is lost. If you don’t have the chance to work with a master directly, you can still surround yourself with people who have higher standards by reading about them and their work.

2.7. Exemplars + Practice

When you choose the right exemplars— people with standards higher than yours— you can transcend the standards you’ve inherited from parents, friends, and acquaintances.

One of the biggest mistakes that I see people make is they don’t want to learn from someone who has a character blemish or a worldview that doesn’t align with theirs. Seneca captured the right approach when he said in On the Tranquility of the Mind, “I shall never be ashamed of citing a bad author if the line is good.” Or, as Cato the Elder put it, “Be careful not to rashly refuse to learn from others.” Don’t throw away the apple because of a bruise on the skin.

As Seneca said, “Happy is he who can improve others not just when he is in their presence, but even when he is in their thoughts!

Strengths of character result from habit. . . . We acquire them just as we acquire skills. . . We become builders, for instance, by building, and we become harpists by playing the harp. So too we become just by doing just actions, temperate by doing temperate actions, brave by doing brave actions.

—Aristotle.

There’s no substitute for practicing with the real thing, yet sandboxes can remove the downside of the mistakes you inevitably make when practicing. At the intelligence agency, we’d always practice and rehearse before an operation in an environment in which it was safe to fail. We treated the practice as if it were the operation itself; we’d do all the things we planned on doing during the operation and tried to predict and respond to all the things that could conceivably happen. If something didn’t go as planned, we would adapt. And sometimes we’d fail. Failing in that sandbox, though, provided a learning opportunity with few real-world consequences, whereas failing in a real operation could cost people their lives.

Part 3: Managing Weaknesses

3.1. Knowing Your Weaknesses

The formula for failure is a few small errors consistently repeated. Just because the results aren’t immediately felt doesn’t mean consequences aren’t coming. You are smart enough to know the potential results; you just don’t necessarily realize when they’re coming. While good choices repeated make time your friend, bad ones make it your enemy.

Whatever our weaknesses and whatever their origins, the defaults will handily take command of our lives if we don’t manage them. Moreover, we’re often unaware when they do.

The story of the USS Benfold provides an important example of how to recognize and overcome blind spots.

The Benfold was one of the worst-performing warships in the entire US Navy. Commissioned in 1996 for duty in the Pacific Fleet, it housed one of the Navy’s most advanced arsenals of missiles and technology at the time. Its radar system was so advanced that it could track a bird from fifty miles. But it was falling short.

What’s incredible is how he didn’t do it. He didn’t fire or demote anyone. He didn’t change the hierarchy. He didn’t change any technology. The only real change was within himself. He started to identify his potential blind spots, and to look at the world from the crew’s perspective.

Abrashoff observed one of the ship’s usual Sunday afternoon cookouts shortly after assuming command, and noticed a long line of sailors waiting to get their lunch while officers cut to the head of the line to get their food. Not only that, but after getting their food, the officers went to a private deck to eat apart from the sailors.

A supply officer approached him and said, “You don’t understand. You go to the head of the line.” Abrashoff shrugged this off, saying it didn’t seem right to him. He waited in line, got his food, and then sat down with the sailors. The next weekend everyone waited in line and ate together. No command was ever issued.

Show me an organisation in which employees take ownership, and I will show you one that beats its competitors,” says Abrashoff. “Captains need to see the ship from the crew’s perspective. They need to make it easy and rewarding for crew members to express themselves and their ideas.

3.2. Protecting Yourself with Safeguards

Safeguards are tools for protecting ourselves from ourselves— from weaknesses that we don’t have the strength to overcome.

There are lots of safeguard strategies, though. My favourites include prevention, creating rules for yourself, making checklists, shifting your frame of reference, and making the invisible visible.

Safeguard Strategy 1: Prevention

You can use the principles behind HALT as a safeguard for decision-making in general. If you have an important decision to make, ask yourself: “Am I hungry? Am I angry or otherwise emotional? Am I lonely or otherwise stressed by my circumstances, such as being in an unfamiliar environment or pressed for time? Am I tired, sleep-deprived, or physically fatigued?” If the answer is yes to any of these questions, avoid making the decision if you can. Wait for a more opportune time. Otherwise, your defaults will take over.

Safeguard Strategy 2: Automatic Rules for Success

Why not bypass individual choices altogether and creat an automatic behaviour— a rule— that requires no decision-making in the moment and that gets no pushback from others?

Having a rule means not having to decide at every meal. The executions path is short, and less error prone.

In a quirk of psychology, people typically don’t argue with your personal rules. They just accept them as features of who you are. People question decisions, but they respect rules.

Kahneman told me his favourite rule was never to say yes to a request on the phone. He knows that he wants people to like him, so he wants to say yes in the moment, but after filling up his schedule with things that didn’t make him happy, he decided to be more vigilant about what he agrees to and why.

The way I did this was to imagine a film crew following me around documenting how successful I was. Regardless of whether I was a success or not, how would I act to show someone I deserved my success? What would I want them to see? What am I doing that I would want them not to see because I’m embarrassed or ashamed?

Another effective rule I’ve seen is that if you wouldn’t move something out of your schedule in the next two days for it, just say no.

Safeguard Strategy 3: Creating Friction

If there were a recipe for accumulated disaster, it would be giving the best of ourselves to the least important things things and the worst of ourselves to the most important things.

It’s easy to underestimate the role ease plays in decision-making. Since behaviour follows the path of least resistance, a surprisingly successful approach is to add friction where you find yourself doing things you don’t want to do.

Safeguard Strategy 4: Putting in Guardrails

Safeguard Strategy 5: Shifting Your Perspective

Changing your perspective changes what you see.

I once had a coworker who was also a friend. One day he walked into my office with some news. “I figured out what I’m doing wrong,” he said. "I’m so busy trying to prove to everyone I’m right that I can’t see the world from their point of view.

From that point on, whenever he discussed something with anyone at work, he would start by offering his impressions of how the other person saw things. Then he would ask, “What did I miss?

When the other person is done answering that first question, my friend still doesn’t offer his own thoughts right away. He first asks a follow up: “What else did I miss?”

This approach to interpersonal communication is an example of a reference-shifting safeguard. Asking the two questions, and listening to the answers people gave him, forces him to see things through other people’s eyes. Taking the time to do that protects him against a tendency that he identified as a weakness.

3.3. How to Handle Mistakes

Mistakes are an unavoidable part of life. Even the most skilled people make mistakes, because there are so many factors beyond our knowledge and control that impact our success. This is true especially when we’re pushing the boundaries of knowledge or potential. On the frontier of what we can know or do, there are no wagon tracks to follow, no familiar landmarks, no mile markers, no road maps to guide us. We’re moving forward without the benefit of anyone else’s hindsight. Mistakes will happen. Part of taking command of our lives is managing those missteps when they do happen.

Everyone makes mistakes because everyone has limitations. Even you. Trying to avoid responsibility for your decisions, your actions, or their outcomes, though, is tantamount to pretending you don’t have limitations. One thing that sets exceptional people apart from the crowd is how they handle mistakes and whether they learn from them and do better as a result.

Mistakes present a choice: whether to update your ideas, or ignore the failures they’ve produced and keep believing what you’ve always believed. More than a few of us choose the latter.

The biggest mistake people make typically isn’t their initial mistake. It’s the mistake of trying to cover up and avoid responsibility for it. The first mistake is expensive; the second costs a fortune.

The four steps to handling mistakes more effectively are as follows: (1) accept responsibility, (2) learn from the mistake, (3) commit to doing better, (4) repair the damage as best you can.

Mistakes turn into anchors if you don’t accept them. Part of accepting them is learning from them and then letting them go. We can’t change the past, but we can work to undo the effects it’s had on the future.

The most powerful story in the world is the one you tell yourself. That inner voice has the power to move you forward or anchor you to the past. Choose wisely.

Part 4: Clear Thinking in Action

Often what seems like poor judgement in hindsight doesn’t even register as a decision in the moment. When the defaults conspire, we react without thinking. And that reaction doesn’t even count as a decision. Once we register the opportunity to make a conscious choice, the question becomes: How can we make the best decision possible?

The decision itself should represent the outcome of the decision-making process. That process is about weighing your options with the aim of selecting the best one, and it’s composed of four stages: defining the problem, exploring possible solutions, evaluating the options, and finally making the judgment and executing the best option. We will discuss each of these components in detail throughout this chapter.

Sometimes adults do too. Perhaps it’s because we have to make a choice so quickly that we don’t have time to evaluate the options. Or maybe it’s because we let habit choose for us, the inertia of past choices carrying us through the present moment without exploring our options. Or maybe it’s just that we let our emotions make choices without even realizing it— momentary anger, fear, or desire preempting evaluation and pushing us to act without thinking or reason.

Not every bad decision is rushed, nor is every good one made slowly. It’s not that simple.

People mistake choosing for decisiveness and the decision-making process for waffling. Part of what makes slowing down and reasoning through a problem difficult is that, to the outside observer, it might look like inaction. But that inaction is a choice.

Knowing how to use these tools depends on keeping your defaults in check so you can reason. If you can’t, you’ll just react with one of your defaults. While you might get the outcomes you desire for a while, it's only a matter of time before lack of thinking catches up to you. It’s only after you’ve mastered the defaults that the tools I describe become useful.

If you can’t keep those in check— if you’re easily swayed by emotion, if you can’t adapt to change, if you value being right more than doing what’s best— then all the tools in the world aren’t going to help you. The defaults will overwhelm you, rout your decision making-making process, and seize control of your life.

4.1. Define the Problem

Defining the problem starts with identifying two things: (1) what you want to achieve, and (2) what obstacles stand in the way of getting it.

The best decision-makers know that the way we define a problem shapes everyone’s perspective about it and determines the solutions. The most critical step in any decision-making process is to get the problem right. This part of the process offers invaluable insight. Since you can’t solve a problem you don’t understand, defining the problem is a chance to take in lots of relevant information.

A handy tool for identifying the root cause of a problem is to ask yourself, “What would have to be true for this problem not to exist in the first place?

A mentor of mine once taught me that the best way to avoid finding the perfect solution to the wrong problem at work, when time allows is to hold two separate meetings: one to define the problem, and one to come up with the solution.

One way to keep meetings short and avoid the signalling that comes from repeating information that everyone knows is simply asking everyone, “What do you know about this problem that other people in the room don’t know?

Tip: Remember that writing out the problem makes the invisible visible. Write down what you think the problem is, and then look at it the next day. If you find yourself using jargon in your description, it’s a sign that you don’t fully understand the problem. And if you don’t understand it, you shouldn’t be making a decision about it.

4.2. Explore Possible Solutions

The future is not like the weather. It doesn’t just happen to us. We shape our future with the choices we make in the present, just as our present situation was shaped by choices we made in the past.

The Bad Outcome Principle: Don’t just imagine the ideal future outcome. Imagine the things that could go wrong and how you’ll overcome them if they do.

And because they’re ready, their confidence doesn’t crack. The venture capitalist Josh Wolfe likes to say, “Failure comes from a failure to imagine failure.”

The bottom line: people who think about what is likely to go wrong and determine the actions they can take are more likely to succeed when things don’t go according to plan.

A smart way to assess your options is by using the following principle.

The Second-Level Thinking Principle: Ask yourself, “And then what?

The 3+ Principle: Force yourself to explore at least three possible solutions to a problem. If you find yourself considering only two options, force yourself to find at least one more.

There are two safeguards against binary thinking. The first is this:

Safeguard: Imagine that one of the options is off the table. Take each of the options you’re considering, and one at a time, ask yourself, “What would I do if that were not possible?”

Suppose you’re considering what to do about a job where you don’t get along with a coworker. Binary thinking tells you to stay or leave. Imagining one option is off the table forces you to see the problem differently. Imagine that, for some reason, there is absolutely no way to quit your job: You must stay. Now you are forced to see things through a new lens. What could you do to make going to work every day more enjoyable, despite the problem with your coworker? What could you do to remain at your job and still move closer to your goals? What could you do to give yourself more options in the future so you’re not stuck feeling powerless? Maybe staying means having a hard conversation with your boss and your coworker that you haven’t had yet. Maybe it means putting in for a transfer to another department. Maybe it means asking your boss if you can work remotely.

Here’s the second safeguard against binary thinking:

Safeguard: Come up with Both-And options. Try to find ways of combining the binary. Think not in terms of choosing either X or Y, but rather having both X and Y.

Roger Martin, former dean of the Rotman School of Management in Toronto, refers to this technique as integrative thinking. Rather than grappling with seemingly opposed binary options, combine them.

As Einstein is thought to have said, “Not everything that can be counted counts, and not everything that counts can be counted.

4.3. Evaluate the Options

To speed things up, I came up with a system for them to sort decisions into three boxes:

• Decisions they could make without any input from me,

• Decisions they could make after sharing their reasoning with me so I could double-check their judgement their judgment, and

• Decisions I wanted to make myself.

But the problem persisted,

After a few months, I consulted my mentor. “Do they know what decisions they should make and what decisions you want to make?” he asked. “Are the boxes clear?”

“Yes,” I replied, “but due to the operational nature of our job, if I’m not around, they have to make decisions in the third box without me. That’s where we’re running into the biggest problems. They seem incapable of doing that.”

“Do they know the one thing that’s most important?” he probed.

“I’m not sure what you mean,” I said. “What’s the most important differs for each decision.” I listed off a few different types of decisions and how the variables were different.

“That’s not what I mean,” he replied. “Do they know what you value most?” I hesitated. He looked me square in the eye. “Shane, do you know what you value most?” I stared at him blankly. He sighed. “The problem isn’t your team. It’s you. You don’t know what’s most important. Until you do, your team will never make decisions without you. It’s too risky for them to figure out the most important thing. Communicate that to your team, and they’ll be able to make decisions on their own.”

“What if they make the wrong decision?”

“As long as they make a decision based on the most important thing, they won't be wrong.” He paused, then said slowly, “A lot of people reach their ceiling in this job because they can't figure out this one thing.”

I learned three important lessons that day. First, I couldn’t expect my team to make decisions on their own unless I told them how I wanted them to make those decisions. That meant focusing on the single most important thing and not inundating them with hundreds of variables to consider. Second, if they made the decision with the most important thing in mind, and it turned out wrong, I couldn’t I get upset with them. If I did that, they’d never make decisions without me. The third lesson was perhaps the most revealing: I myself didn’t know what the most important thing was. That’s why I couldn’t tell them.

The quality of your decisions is directly related to the quality of your thoughts. The quality of your thoughts is directly related to the quality if your information.

Many people treat all sources of information as if they’re equally valid. They’re not. While you might value getting everyone’s opinion, that doesn’t mean each opinion should be equally weighted or considered.

A lot of the information we consume is in the form of highlights, summaries, or distillations. It’s the illusion of knowledge. We learnt the answer but can't show our work.

It’s natural to think these abstractions will save us time and improve our decision-making, but in many cases they don’t. Reading a summary might be faster than reading a full document, but it misses a lot of details— details that weren’t relevant to the person summarizing the information, but that might be relevant to you. You end up saving time at the cost of missing important information. Skimming inadvertently creates blind spots.

Information is food for the mind. What you put in today shapes your solutions tomorrow. And just as you are responsible for the food that goes into your mouth, you are responsible for the information that goes into your mind. You can't be healthy if you feed yourself junk food every day, and you can't make good decisions if you’re consuming low-quality information. Higher quality inputs lead to higher quality outputs.

The person closest to the problem often has the most accurate information about it. What they tend to lack is a broader perspective. The person working on the line at McDonald’s knows how to fix a recurring problem at their restaurant better than a person merely analyzing some data. What they don’t know is how it fits into the bigger picture. They don’t know whether the problem exists everywhere, or whether the solution wold cause more harm than good if implemented globally, or how to roll the idea out to everyone.

An experiment is a low-risk way of gathering important information.

4.4. Do it!

Remember to factor the cost of analysis into your decisions. This is something many people fail to do. Most decisions require an art that balances speed and accuracy. When you move too slowly on mall decisions, you waste time and energy, no matter how accurate you may be. When you go too fast, you miss crucial information, make assumptions, overlook the basics, rush to judgment, and often solve the wrong problem. When things are hectic, however— even when speed matters— you need to slow down, just a little.

When the stakes are high, and there are no take-backs, you want to decide at the last moment possible, and keep as many options on the table as you can while continuing to gather information.

4.5. Margin of Safety

Tip: The margin of safety is often sufficient when it can absorb double the worst-case scenario. So the baseline for a margin of safety is one that could withstand twice the amount of problems that would cause a crisis or maintain twice the amount of resources needed to rebuild after a crisis.

If you’ve ever been on the inside of a business where employees can't take action until everything is approved by their boss, you’re seeing what happens without commander’s intent. There’s a single point of failure. If something happens to the boss, the business and mission fail.

Commander’s intent empowers each person on a team to initiate and improvise as they’re executing the plan. It stops you from being the bottleneck, and it enables the team to keep each other accountable to the goal without your presence.

Commander’s intent has four components: formulate, communicate, interpret, and implement. The first two components— formulate and communicate— are the responsibility of the senior commander. You must communicate the strategy, rationale, and the operational limits to them team. Tell them not just what to do but why to do it, how you arrived at your decision, so they understand the context, as well as the boundaries for effective action— what is completely off the table.

• Who needs to know my goals and the outcomes I’m working toward?

• Do they know what the most important objective is?

• Do they know the positive and negative signs to look for and what trip wire are attached to them?

One sign you’ve failed to empower your team is that you can't be away from the office for a week without things falling apart.

4.6. Learn from Your Decisions

Many people assume that good decisions get good outcomes and bad ones don’t. But that’s not true. The quality of a single decision isn’t determined by the quality of the outcome. Here’s a thought experiment that will help illuminate this concept.

Imagine you engage in a very thoughtful and intentional decision-making process concerning your career.

Making a good decision is about the process, not the outcome. One bad outcome doesn’t make you a poor decision maker any more than one good outcome makes you a genius.

Many of us have a hard time learning from our decisions. One reason is that our thinking and decision-making process is often invisible to us. We inadvertently conceal from ourselves the steps we took to reach our final decision. Once that decision gets made, we don’t stop to reflect, but just move forward. And when we look back at our decision later, our ego manipulates our memories. We confuse what we know now with what we knew at the time we made the decision. And we see the outcomes and read them back into our intentions: “Oh, I meant to do that.”

If you don’t check your thinking at the time you made the decision— what you knew, what you thought was important, and how you reasoned about it— you’ll never know whether you made a good decision or just got lucky. If you want to learn from decisions, you need to make the invisible thought process as visible and open to scrutiny as possible. The following safeguard can help:

Safeguard: Keep a record of your thoughts at the time you make the decision.

Writing down your thoughts offers several benefits. One benefit is that a written record provides information about your thought process at the time you made the decision. It makes the invisible visible. Later, when you reflect on your decision, having that record is helpful for counteracting the distorting effects of the ego default. You can truthfully answer questions like, “What did I know at the time I made the decision?” And, “Did the things I anticipated happening come about for the reasons I thought they would?”

A second benefit of recording your thoughts is that in the process if writing something, you often realize you don’t really understand it as well as you thought you did.

A third benefit to writing down your thoughts is that it allows other people to see your thinking, which is mostly invisible. And if they can see it, they can check it for errors and offer a different perspective that you might otherwise be blind to. If you can't simply explain your thinking to other people (or yourself), it’s a sign that you don’t fully understand things and need to dig deeper and gather more information.

A final benefit to writing down your thoughts is that it gives other people an opportunity to learn from your perspective. Many organizations would benefit from having a database that recorded how every person in the organization went about making decisions. Imagine the value of a searchable catalog of decisions in your organization. A system like this would allow people in different parts of the organization to check each other’s thinking.

PART 5: Wanting What Matters

5.2. The Happiness Experts

Time is the ultimate currency of life. The implications of managing the short time we have on earth are like those of managing any scarce resource: you have to use it wisely— in a way that prioritizes what’s most important.

5.3. Memento Mori

Jobs had a daily ritual. Every Corinna he would look in the mirror and ask himself, “If today were the last day of my life, would I want to do what I am about to do today?” Whenever the answer was no too many days in a row, he said he knew he needed to change something.

5.4. Life Lessons from Death

It is not that we have a short time to live, but that we waste a lot of it.

—Seneca,

On the Shortness of Life, Chapter 1

Conclusion

The Value of Clear Thinking

Good judgment is expensive, but poor judgment will cost you a fortune.

The overarching message of this book is that there are invisible instincts that conspire against good judgement. Your defaults encourage you to react without reasoning— to live unconsciously rather than deliberately.

When you revert to defaults, you engage in a game you can't win. When you live a life run on autopilot, you get bad results. You make things worse. You say things that can't be unsaid and do things that can't be undone. You might accomplish your immediate goal, but you fail to realize that you’ve made it harder to achieve your ultimate goals. All of this happens without consciously being aware you are exercising judgment in the first place.

The key to getting what you want out of life is to identify how the world works and to align yourself with it. Often people think the world should work differently than it does, and when they don’t get the outcomes they want, they try to wiggle out of responsibility by blaming other people or their circumstances. Avoiding responsibility is a recipe for misery, and the opposite of what it takes to cultivate good judgment.