Clear Thinking

By: Shane Parrish

Clear thinking book cover

I am a fan of Shane Parrish’s blog ( I was excited to learn he was writing a book on decision making and mental models.

Overall, I felt the book was solid with some actionable models that can be used to evaluate decisions and avoid common mistakes that lead to poor decisions or a lack of clarity on why a decision failed.

Below I will summarize some of the insights I gained.

One of the central themes of the book is the concept of positioning yourself for success by mastering the art of clear thinking. Parrish argues that the best in the world understand the significance of avoiding losses before pursuing victories. By consistently making well-positioned decisions, individuals can gain an advantage over others, regardless of their level of intelligence.

“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.”

pg. 112

Parrish highlights the role of ordinary moments in shaping our positions and, consequently, our options in life. He stresses that clear thinking is crucial for proper positioning, allowing individuals to master their circumstances rather than being controlled by them.

“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.”

pg 122

Throughout the book, Parrish identifies several cognitive defaults that hinder clear thinking.

The defaults are

  1. Emotion default – doing what makes us feel good
  2. Ego default – doing what preserves or boosts our ego
  3. Social default – doing what is commonly accepted by society
  4. Inertia default – continuing to do what has been done

He emphasizes the importance of recognizing and overcoming these defaults to make rational decisions.

Strength is the power to press pause on your defaults and exercise good judgment. It doesn’t matter what’s going on in the world, or how unfair things may seem. It doesn’t matter that you feel embarrassed, threatened, or angry. The person who can take a step back for a second, center themselves, and get out of the moment will outperform the person who can’t.

Self-awareness and self-control emerge as essential elements in the quest for clear thinking. Parrish discusses the significance of holding oneself accountable, understanding personal strengths and weaknesses, and mastering emotions and desires to achieve long-term goals.

Furthermore, the book explores the concept of confidence and its role in decision-making. Parrish distinguishes between genuine confidence, rooted in competence and self-trust, and shallow confidence, based on external validation. He emphasizes the importance of confidence in navigating social pressure and embracing individuality.

Not all confidence is created equally. Sometimes, it comes from a track record of applying deep knowledge successfully, and other times it comes from the shallowness of reading an article. It’s amazing how often the ego turns unearned knowledge into reckless confidence.

pg 368

Parrish also discusses the value of learning from mistakes and accepting responsibility for one’s decisions. He advocates for a process-oriented approach to decision-making, focusing on the quality of the decision-making process rather than solely on outcomes.

The book concludes with insights on wisdom, discipline, and the pursuit of a fulfilling life. Parrish encourages readers to reflect on their daily choices and prioritize personal growth and happiness over external achievements.

My collection of clipped quotes

I enjoy reading books on my Kindle so I can easily highlight quotes. Below you will find all the insights I highlighted. I am publishing them for my own benefit so I can quickly recall things that stuck with me as I read Clear Thinking.

Location 112While 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.
Location 122In 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.
Location 169Each moment puts you in a better or worse position to handle the future. It’s that positioning that eventually makes life easier or harder.
Location 172A good position allows you to think clearly rather than be forced by circumstances into a decision. One reason the best in the world make consistently good decisions is they rarely find themselves forced into a decision by circumstances. You don’t need to be smarter than others to outperform them if you can out-position them. Anyone looks like a genius when they’re in a good position, and even the smartest person looks like an idiot when they’re in a bad one.
Location 183What 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.
Location 186Every ordinary moment is an opportunity to make the future easier or harder. It all depends on whether you’re thinking clearly.
Location 223Rationality is wasted if you don’t know when to use it.
Location 230In the space between stimulus and response, one of two things can happen. You can consciously pause and apply reason to the situation. Or you can cede control and execute a default behavior.
Location 238So 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 create 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.
Location 300The emotion default: we tend to respond to feelings rather than reasons and facts. 2. The ego default: we tend to react to anything that threatens our sense of self-worth or our position in a group hierarchy. 3. The social default: we tend to conform to the norms of our larger social group. 4. The inertia default: we’re habit forming and comfort seeking. We tend to resist change, and to prefer ideas, processes, and environments that are familiar.
Location 368Not all confidence is created equally. Sometimes, it comes from a track record of applying deep knowledge successfully, and other times it comes from the shallowness of reading an article. It’s amazing how often the ego turns unearned knowledge into reckless confidence.
Location 486Doing 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 results that everyone else gets.[*] Best practices aren’t always the best. By definition, they’re average.
Location 493Our desire to fit in often overpowers our desire for a better outcome. Instead of trying something new, we tell ourselves something new.
Location 539The inertia default pushes us to maintain the status quo.
Location 547“Once our minds are set in a direction, they tend to continue in that direction unless acted upon by some outside force.”[2] This cognitive inertia is why changing our minds is hard.
Location 579Inertia also prevents us from doing hard things. The longer we avoid the hard thing we know we should do, the harder it becomes to do. Avoiding conflict is comfortable and easy. The longer we avoid the conflict, however, the more necessary it becomes to continue avoiding it.
Location 583Groups create inertia of their own. They tend to value consistency over effectiveness, and reward people for maintaining the status quo. Inertia makes deviating from group norms difficult. The threat of standing out in a negative way too often keeps people in line. As a result, group dynamics end up favoring people who don’t deviate from the defaults.
Location 612You 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.
Location 655Strength is the power to press pause on your defaults and exercise good judgment. It doesn’t matter what’s going on in the world, or how unfair things may seem. It doesn’t matter that you feel embarrassed, threatened, or angry. The person who can take a step back for a second, center themselves, and get out of the moment will outperform the person who can’t.
Location 666Self-accountability: holding yourself accountable for developing your abilities, managing your inabilities, and using reason to govern your actions
Location 668Self-knowledge: knowing your own strengths and weaknesses—what you’re capable of doing and what you’re not
Location 670Self-control: mastering your fears, desires, and emotions
Location 671Self-confidence: trusting in your abilities and your value to others
Location 764You can put energy into things you control or things you don’t control. All the energy you put toward things you don’t control comes out of the energy you can put toward the things you can.
Location 766While no one chooses difficult circumstances, adversity provides opportunity.
Location 783You 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.
Location 904Self-control is about creating space for reason instead of just blindly following instincts.
Location 913Emotional intensity is far less important in the long run than disciplined consistency. Inspiration and excitement might get you going, but persistence and routine are what keep you going until you reach your goals.
Location 919Self-confidence is about trusting in your abilities and your value to others.
Location 920You need self-confidence to think independently and to stand firm in the face of social pressure, ego, inertia, or emotion.
Location 961People who are confident aren’t afraid of facing reality because they know they can handle it. Confident people don’t care what other people think about them, aren’t afraid of standing out, and are willing to risk looking like an idiot while they try something new.
Location 964Crucially, they also know that to outperform the crowd, you have to do things differently sometimes, and that hecklers and naysayers inevitably tend to follow. They take their feedback from reality, not popular opinion.
Location 968Self-confidence is also the strength to accept hard truths. We all have to deal with the world as it is, not as we want it to be. The quicker you stop denying inconvenient truths and start responding to difficult realities, the better.
Location 1000Admitting you’re wrong isn’t a sign of weakness, it’s a sign of strength. Admitting that someone has a better explanation than you shows that you’re adaptable. Facing reality takes courage. It takes courage to revise your ideas, or rethink something you thought you knew. It takes courage to tell yourself something is not working. It takes courage to accept feedback that bruises your self-image.
Location 1087Champions don’t create the standards of excellence. The standards of excellence create champions.[*]
Location 1099The difference between average and exceptional results for a leader often comes down to whether they’re consistently getting more out of smart but otherwise lazy people.
Location 1128Masters of their craft don’t merely want to check off a box and move on. They’re dedicated to what they do, and they keep at it. Master-level work requires near fanatical standards, so masters show us what our standards should be. A master communicator wouldn’t accept a ponderous, rambling email. A master programmer wouldn’t accept ugly code. Neither of them would accept unclear explanations as understanding.
Location 1193“I shall never be ashamed of citing a bad author if the line is good.”
Location 1279Life gets easier when you don’t blame other people and focus on what you can control.
Location 1304The 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.
Location 1323There are two ways to manage your weaknesses. The first is to build your strengths, which will help you overcome the weaknesses you’ve acquired. The second is to implement safeguards, which will help you manage any weaknesses you’re having trouble overcoming with strength alone. In addition, safeguards help us manage weaknesses that are impossible to overcome—for example, the ones we owe to our biological limitations.
Location 1327How to Manage Inbuilt Weaknesses Safeguards How to Manage Acquired Weaknesses Strength + safeguards
Location 1330We saw in Part 2 how strength can overcome weaknesses that we’ve acquired. For example, developing self-control empowers you to overcome emotion-driven behavior and avoid the regrets it produces. Developing self-confidence empowers you to overcome inertia and execute difficult decisions. It empowers you to overcome social pressure so that you have the strength to go against the crowd. It also empowers you to overcome your ego, acknowledge your deficiencies, and start on the path to doing and being better.
Location 1353“The first principle is that you must not fool yourself—and you are the easiest person to fool.”[1]
Location 1440and effort. Choosing goals is necessary but not sufficient for accomplishing them. You also need to pursue those goals consistently. That means continuing every day to make choices in pursuit of your goals. Every day, you have to choose to work out or to skip dessert. As these choices add up, it becomes harder, not easier, to consistently make choices that move you toward your goals and not away from them.
Location 1464your personal rules. They just accept them as features of who you are. People question decisions, but they respect rules.
Location 1564When things don’t work out the way we’d like, most of us default to blaming the world rather than ourselves. This is a form of what psychologists call self-serving bias: a tendency to evaluate things in ways that protect or enhance our self-image, which I mentioned earlier when discussing self-accountability.
Location 1577default at work. If you want to see whether your thinking is wrong, you need to make it visible. Making what was previously invisible visible gives us the best chance of seeing what we knew and what we thought at the time we made a decision. Relying on memory won’t work because the ego distorts information to make us look better than we actually were.
Location 1601squander them. The four steps to handling mistakes more effectively are as follows: (1) accept responsibility, (2) learn from the mistake, (3) commit to doing better, and (4) repair the damage as best you can.
Location 1632Mistakes turn into anchors if you don’t accept them.
Location 1632Part 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.
Location 1650The 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.
Location 1659Or 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.
Location 1669When the stakes are low, inaction hurts you more than speed. Sometimes it’s better just to make a quick choice and not spend time deliberating. Why waste time evaluating if an action is inconsequential and its effects are easily reversed? For example, if there are two identical squat racks in the gym and both are momentarily open, it makes no difference which one you take. If you wait and decide, they’ll both be taken by someone else. Just choose either one.
Location 1695Defining the problem starts with identifying two things: (1) what you want to achieve, and (2) what obstacles stand in the way of getting it.
Location 1714in order to prove we’re adding value. Just solve a problem—any problem!
Location 1714The result: organizations and individuals waste a lot of time solving the wrong problems. It’s so much easier to treat the symptoms than find the underlying disease, to put out fires rather than prevent them, or to simply punt things into the future.
Location 1730the definition principle: Take responsibility for defining the problem. Don’t let someone define it for you. Do the work to understand it. Don’t use jargon to describe or explain it. the root cause principle: Identify the root cause of the problem. Don’t be content with simply treating its symptoms.
Location 1741“What would have to be true for this problem not to exist in the first place?”
Location 1764safeguard: Build a problem-solution firewall. Separate the problem-defining phase of the decision-making process from the problem-solving phase.
Location 1790tip: 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.
Location 1795safeguard: Use the test of time. Test whether you’re addressing the root cause of a problem, rather than merely treating a symptom, by asking yourself whether it will stand the test of time. Will this solution fix the problem permanently, or will the problem return in the future? If it seems like the latter, then chances are you’re only treating a symptom.
Location 1843“Life can only be understood backwards, but it must be lived forwards.”
Location 1843Luckily, there’s a way to convert the hindsight of tomorrow into the foresight of today. It’s a thought experiment that psychologists call premortem. The concept isn’t new, it originates in Stoic philosophy. Seneca used premeditatio malorum (“the premeditation of evils”) to prepare for the inevitable ups and downs of life. The point isn’t to worry about problems; it’s to fortify and prepare for them.
Location 1855Imagining what could go wrong doesn’t make you pessimistic. It makes you prepared. If you haven’t thought about the things that could go wrong, you will be at the mercy of circumstances. Fear, anger, panic—when emotion consumes you, reason leaves you. You just react. The antidote is this principle:
Location 1858the 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.
Location 1871the second-level thinking principle: Ask yourself, “And then what?”
Location 1888just whether it meets your short-term objectives but whether it meets your long-term objectives as well. A failure to think of second-order consequences leads us unknowingly to make bad decisions. You can’t ensure the future is easier if you only think about solving the current problem and don’t give due consideration to the problems created in the process. This idea is evident when looking back at the US war in Afghanistan.
Location 1986Remember: Limiting ourselves to binary thinking before fully understanding a problem is a dangerous simplification that creates blind spots. False dualities prevent you from seeing alternative paths and other information that might change your mind. On the other hand, taking away one of two clear options forces you to reframe the problem and get unstuck.
Location 1991Come 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.
Location 1993Roger Martin, former dean of the Rotman School of Management in Toronto, refers to this technique as integrative thinking.[5] Rather than grappling with seemingly opposed binary options, combine them. Simplistic Either-Or options become integrative Both-And options. You can keep costs down and invest in a better customer experience. You can stay at your job and start a side hustle. You can deliver for your shareholders and protect the environment.
Location 2051the opportunity-cost principle: Consider what opportunities you’re forgoing when you choose one option over another.
Location 2054the 3-lens principle: View opportunity costs through these three lenses: (1) Compared with what? (2) And then what? (3) At the expense of what?[*]
Location 2098Clarity: The criteria should be simple, clear, and free of any jargon. Ideally, you should be able to explain them to a twelve-year-old.
Location 2100Goal promotion: The criteria must favor only those options that achieve the desired goal.
Location 2101Decisiveness: The criteria must favor exactly one option; they can’t result in a tie among several.
Location 2127The inertia default can also inspire us to adopt criteria that aren’t goal promoting. For example, upper management might fail to see that market conditions have changed. Rather than taking the time to understand the new conditions and adjust their
Location 2128criteria accordingly, they continue using the criteria they’ve used in the past even though those criteria aren’t goal promoting in the present. Criteria can also fail to be decisive. If they don’t help you narrow the options, they’re not useful. Indecisive criteria are another sign that you don’t fully understand the problem and are operating out of fear that you’ll be wrong. The social default preys on people who don’t want to take responsibility for outcomes or who don’t have clear ideas of what they want.
Location 2332safeguard: Evaluate the motivations and incentives of your sources. Remember that everyone sees things from a limited perspective.
Location 2351When you get information from other people, ask questions that yield detailed answers. Don’t ask people what they think; instead, ask them how they think.
Location 2375the hiex principle: Get high-expertise (HiEx) information, which comes both from people with a lot of knowledge and/or experience in a specific area, and from people with knowledge and experience in many areas.
Location 2415So let’s talk about how to approach an expert in a way that will set your request apart and get people excited to help you. Here are five tips:
Location 2506the asap principle: If the cost to undo the decision is low, make it as soon as possible.
Location 2512the alap principle: If the cost to undo a decision is high, make it as late as possible.
Location 2557the stop, flop, know principle: Stop gathering more information and execute your decision when either you Stop gathering useful information, you First Lose an OPportunity (FLOP), or you come to Know something that makes it evident what option you should choose.
Location 2733However, it turned out that sleeping on decisions by itself wasn’t enough. I added another element to the rule: before going to bed, I would write a note to myself explaining why I’d made the decision. Doing so allowed me to make the invisible visible.
Location 2737Living with a decision before announcing it allows you to look at it from a new perspective and verify your assumptions.
Location 2779fail-safe: Set up trip wires to determine in advance what you’ll do when you hit a specific quantifiable time, amount, or circumstance.
Location 2800Giving a team enough structure to carry out a mission but enough flexibility to respond to changing circumstances is called commander’s intent—a military term first applied to the Germans who were trying to defeat Napoleon.
Location 2837If you’re a knowledge worker, you produce decisions.[1] That’s your job. The quality of your decisions eventually determines how far you go and how fast you get there. If you learn to make great decisions consistently, you’ll quickly move past the people whose decisions are merely good.
Location 2850The story illustrates a psychological phenomenon we’ve discussed before: self-serving bias, the tendency to evaluate things in ways that enhance our self-image.
Location 2859the process principle: When you evaluate a decision, focus on the process you used to make the decision and not the outcome.
Location 2894Our tendency to equate the quality of our decision with the outcome is called resulting. Results are the most visible part of a decision. Because of that, we tend to use them as an indicator of the decision’s quality.
Location 2934the transparency principle: Make your decision-making process as visible and open to scrutiny as possible.
Location 2941Many 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.
Location 2948safeguard: Keep a record of your thoughts at the time you make the decision. Don’t rely on your memory after the fact. Trying to recall what you knew and thought at the time you made the decision is a fool’s game.
Location 2957“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?”
Location 3000Take responsibility for where you are and where you are headed.
Location 3002“There is no effectiveness without discipline, and there is no discipline without character.”[1]
Location 3067The ancient Greeks had a word for this ingredient: phronesis—the wisdom of knowing how to order your life to achieve the best results.
Location 3147Jobs had a daily ritual. Every morning 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?”[3] Whenever the answer was no too many days in a row, he said, he knew he needed to change something.
Location 3150We all have bad days, but when the answer to Job’s question is no day after day, week after week, it’s time to make a change.
Location 3182In the end, everyday moments matter more than big prizes. Tiny delights over big bright lights.
Location 3197As Aristotle says, “Knowledge of the best good carries great weight for knowing the best way to live: if we know it, then like archers who have a target to aim at, we are more likely to hit the right mark.”[1]
Location 3221Wisdom is turning your future hindsight into your current foresight.
Location 3258Improving your judgment, it turns out, is less about accumulating tools to enhance your rationality and more about implementing safeguards that make the desired path the path of least resistance. It’s about designing systems when you’re at your best that work for you when you’re at your worst. Those systems don’t eliminate the defaults, but they do help you recognize when they are running the show.

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