PDF Summary:Clear Thinking, by Shane Parrish

Most people are bad at thinking clearly. Unconsciously, we let knee-jerk emotional reactions or the need to feel “smart” push us toward poor choices that harm our careers, relationships, and overall life satisfaction. However, the world’s most successful people have discovered ways to overcome their innate irrational tendencies and consistently make decisions that align with their goals. In Clear Thinking, former intelligence agent Shane Parrish explains that by cultivating certain mental habits and acting more systematically, you too can maximize your potential for success.

In this guide, you’ll learn four mental habits that’ll help you think clearly when it matters most. That said, it’s impossible to always think perfectly, so you’ll also learn how to compensate for the times when your thinking inevitably falls short. We’ll supplement Parrish’s guidance with ideas from other books about effective decision-making, such as Decisive and Thinking in Bets. We’ll also dive deeper into the psychology behind Parrish’s theory by exploring ideas from books such as A Mind for Numbers and Thinking, Fast and Slow.

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Habit #4: Inspire Yourself With Lofty Ambitions

If you want to accomplish great things, another habit to adopt is setting a high bar for your own work, says Parrish. If you don’t make this commitment, you’ll get mediocre results. Human beings are motivated to fit in with those around them, and mediocre work is the norm. If you want to accomplish something greater, you must be ready to stand out as “different” and be negatively judged for it.

(Shortform note: According to Grant Cardone in The 10X Rule, the reason people default to mediocre work is that they want to avoid the risk of trying and failing to achieve grand, ambitious goals. However, setting low standards only guarantees disappointment, since achieving something mediocre is rarely satisfying. Instead, if you set goals that are 10 times as ambitious as those you’d normally set, the prospect of achieving this wild success will make you excited to act. Setting goals that excite you will also motivate you to persevere in the face of negative judgment.)

To inspire yourself, identify people who embody the high standards that you want to adopt, and intentionally commit to fitting in with them. Parrish explains that this doesn’t necessarily mean cutting “average” people out of your life. Just spend as much time with your role models as possible (either directly or through media such as books and podcasts). This will inspire you to act like them.

(Shortform note: In Wanting, Luke Burgis also recommends spending time with role models who can inspire you to do great things. However, he adds that sometimes, it’s also necessary to do the opposite: Cut off contact with all your role models and engage in deep, solitary introspection. Doing so can help you distinguish your meaningful aspirations from the misleading ones you may have picked up from flawed role models.)

Follow a Decision-Making System

A second way to improve your ability to think rationally is by following a decision-making system. Parrish contends that much of our daily behavior runs on autopilot, based on habits or emotional reactions. Typically, this kind of automatic decision-making is helpful and efficient, but it also increases your chances of making a mistake. Thus, when you need to make a decision with important consequences, the author recommends deliberating using a step-by-step process. This maximizes your chance of reaching the best possible outcome.

The Psychology of Unconscious Decision-Making

In Thinking, Fast and Slow, Daniel Kahneman offers a more detailed explanation of the way we make unconscious choices “on autopilot.” He asserts that the human mind can think using two different systems: System 1, which is fast and intuitive, and System 2, which is slow and deliberate. Most of the time, we rely solely on System 1 to unconsciously guide our everyday tasks.

The main reason System 1 leads us to make mistakes is that it relies on various heuristics, or rules of thumb, that work well in most situations but fail in certain circumstances. For instance, if you use System 1 to quickly guess how often something occurs, you’ll base your answer on how easily you can recall examples of it happening. For this reason, people overestimate how likely they are to die in a plane crash while underestimating their risk of heart disease.

Parrish’s recommendation to use a decision-making framework for important decisions may work because it prompts you to shift into System 2 thinking, which helps you avoid automatically following these biased heuristics.

In the following sections, we’ll describe three steps you can follow to procedurally make effective decisions in high-stakes situations:

• Step #1: Clarify What You Want to Accomplish
• Step #2: Brainstorm Potential Solutions
• Step #3: Assess Which Solution Is Best

Step #1: Clarify What You Want to Accomplish

When making a decision, your first step should be clarifying the problem your decision is intended to solve, Parrish says. Reflect on what you’re trying to accomplish and what’s standing in your way.

Specifically, try to identify the problem’s underlying cause before taking action. Often, people waste time and effort pursuing solutions that feel productive but end up creating the conditions for the problem to return. For example, a company might repeatedly hire last-minute contractors to hit important deadlines (at significant expense) instead of realizing that training a new full-time team would make it consistently easier to meet deadlines.

(Shortform note: A useful thought exercise to uncover root causes is the “Five Whys.” In The Lean Startup, Eric Ries recommends that startup founders ask themselves “Why did this problem occur?” five times in a row, tracing the origin of a problem backward through a chain of causes, before deciding which problem to solve. For example, imagine your weekly team meetings are too long. Using the Five Whys, you might reason that meetings run long because there’s no set agenda, there’s no agenda because your team has no process for compiling them, and so on. By the fifth “why,” you realize that the real problem to address is the fact that your company’s culture discourages process improvements.)

Additionally, Parrish notes that if you separate the act of clarifying the problem you’re trying to solve from the act of solving it, you’re less likely to jump to misguided solutions. Think deeply about what you’re really trying to accomplish, then step away for some time before considering courses of action.

(Shortform note: Stepping away after clarifying the problem doesn’t just help you avoid misguided solutions—it can also help you come up with better ones. In A Mind for Numbers, Barbara Oakley explains that when you stop focusing on the task of problem-solving, you shift into the diffuse mode of thinking: a relaxed, big-picture mode that allows your mind to make intuitive connections between diverse concepts. When you return, you may be able to spot solutions you wouldn’t have otherwise considered.)

Step #2: Brainstorm Potential Solutions

After you’ve clarified what you want to accomplish, it’s time to brainstorm potential solutions. Parrish contends that to do this well, you must think beyond your first couple of ideas. People often get stuck in false dichotomies, believing they must choose between Option A and Option B when the best solution is actually a hidden Option C. To avoid this, ensure that you’re always considering at least three options when making important decisions.

(Shortform note: Be careful not to consider too many options, either. In Decisive, Chip and Dan Heath argue that considering three or four options is ideal—any more than this can feel overwhelming. Three or four options are all you need: This range keeps you from falling into the trap of binary thinking and ensures that you have backup options in mind in case your first choice falls through.)

Additionally, try to come up with solutions combining the benefits of multiple options—a strategy called integrative thinking. According to Parrish, it takes effort to challenge your initial rigid understanding of your options and discover their hidden nuances, but it’s almost always worth it. For example, imagine a marketing professional who’s trying to decide between a high-production campaign that’s prestigious but expensive, or a social media-based campaign that’s affordable but amateurish. After consideration, they realize they could produce a single polished video to establish prestige, then focus on social media clips to keep the overall budget low.

(Shortform note: Parrish credits the concept of integrative thinking to the business researcher Roger Martin, who explores the approach more comprehensively in The Opposable Mind. According to Martin, integrative thinking is difficult because it involves more than just combining the benefits of multiple options. Rather, it’s about understanding the distinct, often conflicting perspectives behind each option and integrating insights from these perspectives to come up with truly innovative solutions. For example, when designing the iPhone, Steve Jobs integrated his team’s focus on feature-rich functionality with his view that technology should be intuitive to use, resulting in a device that felt revolutionary.)

Step #3: Assess Which Solution Is Best

Next, assess which potential solution is best. Parrish describes two things you need to do this well: appropriate decision criteria and effective information sourcing.

Decision criteria are the measures you use to judge whether a decision advances your long-term goals. Come up with a list of criteria and rank each one in terms of its impact on your goals. For instance, if you’re deciding what kind of business to start, you might prioritize skill development opportunities first, then profit potential, and finally networking opportunities. Clearly articulating your criteria will make it easier to accurately assess the quality of your options.

(Shortform note: When setting decision criteria, it’s important to recognize that you won’t be able to satisfy them all. In The Paradox of Choice, Barry Schwartz explains that many people regularly make themselves unhappy by striving to find the best option available, every time. They waste time looking for an option that will fulfill everything they want, then feel regret any time they find out that a better option was available. Instead, plan to accept an option as “good enough” if it fulfills just one or two of your top-ranked criteria. This will help you make strong decisions while avoiding the inevitable dissatisfaction that comes from chasing perfection.)

Information sourcing is the process of gaining enough context to understand which option best fulfills your criteria. Effective information sourcing involves learning from people with extensive experience making the kinds of decisions you want to make. Parrish recommends communicating with these experts directly, if possible. Anyone who summarizes an expert’s advice filters it through their own assumptions about what matters, which might not match yours. To return to our example: As part of deciding what kind of business to start, you might interview an entrepreneur about their experience starting multiple companies.

(Shortform note: Like Parrish, Roger Martin (The Opposable Mind) acknowledges that people who pass on advice inevitably filter it through their biases. However, he takes this idea further: Even when you’re getting information directly from an expert, their frame of reference can bias the advice in a way that makes it less applicable in your situation. This frame of reference may include anything from their resources to their personality. With this in mind, Martin recommends synthesizing information from multiple sources, especially when trying to solve complex problems. This way, you can counterbalance individual biases and arrive at a more objective understanding.)

How to Compensate for Irrational Thinking

Even if you build the right mental habits and stick to an optimal decision-making framework, you can’t completely escape irrationality, Parrish says. As we’ve discussed, human beings are subject to powerful biological impulses, and it’s unrealistic to assume you can permanently conquer them. However, if you acknowledge this fact, you can compensate for inevitable moments of irrationality and reduce the likelihood they’ll lead to bad decisions.

(Shortform note: In Nudge, Richard Thaler and Cass Sunstein propose an ethic of governance based on this same logic. They contend that policymakers should compensate for inevitable human irrationality by designing environments that subtly influence people to pick the options that they’d choose if thinking clearly. For example, a city council might discourage smoking by requiring stores to keep tobacco products out of sight in opaque cases, so buying them feels like less of an obvious choice.)

In this section, we’ll explore three tips for protecting yourself from the consequences of irrational thinking:

• Tip #1: Make Bad Decisions More Effortful
• Tip #2: Limit Your Risks
• Tip #3: Learn From Every Mistake

Tip #1: Make Bad Decisions More Effortful

Plan for moments of irrational thinking by increasing the effort it takes for you to make bad decisions, recommends Parrish. First, identify your bad habits, then create circumstances in which it’s more difficult to indulge them. You’ll find yourself naturally doing the right thing just because it’s your easiest option.

For example, imagine you frequently work late into the night, ruining your sleep. You decide to tell your significant other that they have permission to walk in and shut your computer off at 7 p.m., no matter what. Since convincing them to let you continue working would be difficult and unpleasant, you naturally plan for this 7 p.m. cutoff instead.

Another way to make bad decisions more effortful is by setting yourself rules that forbid these decisions completely. Parrish explains that rules help you avoid the emotional struggles required to make good decisions on a case-by-case basis, helping you act wisely with less willpower. For example, you might improve your sleep by setting the rule that you’ll never bring electronic devices into your bedroom.

Religious Barriers to Bad Decisions

According to Roy F. Baumeister and John Tierney (Willpower), religious or spiritual practices often improve people’s lives by making bad decisions more effortful. These practices offer clear rules of behavior, often framed as divine mandates, that help adherents conserve mental effort they’d otherwise spend wrestling with everyday decisions—just like the self-imposed rules that Parrish suggests.

Furthermore, religious and spiritual practices create circumstances in which the unpleasant experience of judgment makes it more effortful to choose bad decisions. When adherents feel as if they’re being observed—by their spiritual community and by a higher power—it raises the perceived cost of bad decisions. By Parrish’s logic, this makes these bad decisions easier to resist.

Baumeister and Tierney state that if you’re not religious or spiritual, you can still gain these benefits by joining secular organizations that offer guiding rules and peer accountability, such as gyms and martial arts schools.

Tip #2: Limit Your Risks

A second way you can compensate for your irrational thinking is by limiting what you have to lose. Parrish argues that since no one can make perfect decisions all the time, it’s rational to assume things will go wrong. Make choices that protect you in worst-case scenarios, even if they seem overly cautious. The author recommends picturing the worst possible outcome, then preparing for something twice as severe. This strategy keeps you safe even if shocking, unprecedented disasters occur.

(Shortform note: In The Black Swan, Nassim Nicholas Taleb provides further justification for Parrish’s extremely cautious advice. Taleb asserts that human beings consistently underestimate how surprising the future can be: We develop oversimplified models of reality and assume they’re far more accurate than they really are. Thus, in a fundamentally unpredictable world, we should give up on trying to predict what might go wrong and instead make plans for withstanding extreme disasters.)

According to Parrish, it’s particularly important to limit your risks when you’re first learning how to do something. Instead of jumping into high-risk, high-reward environments as soon as you can, seek low-stakes environments where you can experiment freely and gain expertise through trial and error. This way, when the time comes for you to make high-stakes decisions, your most costly mistakes will already be behind you. For example, if you’ve been tasked with delivering an important keynote address for your company at a huge conference, you might practice giving your presentation to other teams in your organization who can give you feedback.

(Shortform note: Low-stakes practice environments give you the freedom to learn from your mistakes, but how do you ensure you’re actually learning? In So Good They Can’t Ignore You, Cal Newport asserts that optimal learning experiences meet two conditions. First, they must be appropriately challenging: You learn the most when a task requires you to stretch your skills slightly beyond your comfort level. Second, they must give precise, immediate feedback showing what you’re doing right and wrong. For instance, a tennis coach might call out that you’re dropping your elbow when swinging, or a code analysis tool could highlight when you make a coding mistake.)

Tip #3: Learn From Every Mistake

A third way to compensate for your irrational thinking is by treating every mistake as a learning opportunity. Parrish asserts that this is a major way high achievers set themselves apart: Instead of pretending they don’t act irrationally or make mistakes, they take responsibility and work to avoid repeating their mistakes.

To do this, you must learn to accurately identify when you’ve made a mistake. Most people judge their decisions purely by their results, making it impossible to tell whether they made those decisions wisely or just got lucky. Instead of focusing on results, look for mistakes in how you made your decision: Was your logic flawed? Did you let your emotions impair your thinking? Your goal should be to formulate a consistent, well-informed, rational decision-making process, even if it doesn’t succeed every time.

The best way to identify flaws in your decision-making process is to keep a tangible record of your thoughts while making a decision, rather than relying on your memory. This keeps your ego from convincing you that you were smarter or more rational than you actually were at the time.

The Right Way to Learn From Results

In Thinking in Bets, Annie Duke provides a more comprehensive explanation of the ways that high performers improve their decision-making processes. She clarifies that it’s not impossible to learn from the results of your decisions. Rather, the key skill is determining which results you can learn from, and which you can’t.

Whenever you evaluate the outcome of one of your decisions, you tell yourself a narrative: You either believe that the result occurred primarily due to your choices and actions, or due to luck. The reason many people fail to improve their rational decision-making process is that they mistake one kind of result for the other.

For example, imagine the CEO of an online clothing retailer adds a new line of retro goth clothing to their inventory, then reports record-setting profits due to an unrelated era of growth in the online fashion industry. If they attribute the profits to their sharp decision to start appealing to goth nostalgia (instead of luck), they’ll never realize that they have a distorted idea of what customers want.

Parrish’s advice to reference a record of your thoughts is one way to accurately assess the degree to which your actions (or luck) influenced the outcome. Duke recommends another way to do so: Observe and learn from the results of other people’s decisions. This is difficult to do well because your ego pushes you to attribute others’ successes to luck and their failures to bad decisions. Strive to counteract this bias by consciously taking it into consideration.