Clear Thinking is one of those books that comes at the subject from a different angle than you might expect: instead of a deep dive into decision making and tools for making smart decisions, the first part of the book is about how to avoid getting into a position where you have to make a bad decision. The second half then focuses on how to make the decision itself. Nice short book full of insight.

Clear Thinking by Shane Parrish

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.

they rarely find themselves forced into a decision by circumstances.

A little knowledge can be a dangerous thing

Confidence doesn’t make bad outcomes any less likely or good outcomes more likely, it only blinds us to risk.

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

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

The inertia default pushes us to maintain the status quo. Starting something is hard but so too is stopping something.

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

To stop our defaults from impeding good judgment, we need to harness equally powerful biological forces. We need to take the same forces that the defaults would use to ruin us and turn them to our advantage.

Establishing rituals is the key to creating positive inertia.

You 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.

One of the most common mistakes people make is bargaining with how the world should work instead of accepting how it does work.

One effective question to ask yourself before you act is, “Will this action make the future easier or harder?”

the things you choose not to do often matter as much as the things you choose to

Understanding what you do and don’t know is the key to playing games you can win.

The quicker you accept reality, though, the quicker you can deal with the implications,

it’s only after we accept reality that we can attempt to change it.

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.

Outcome over ego.

Be self confident enough to be able to support your rivals idea

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.”

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.

Choose the right exemplars—ones that raise your standards. Exemplars can be people you work with, people you admire, or even people who lived long ago. It doesn’t matter. What matters is they make you better in a certain area, like a skill, trait, or value. (b) Practice imitating them in certain ways. Create space in the moment to reflect on what they’d do in your position, and then act accordingly.

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.”3 Don’t throw away the apple because of a bruise on the skin.

never allow myself to have an opinion on anything unless I know the other side’s argument better than they do.”

If you imagine your exemplars watching you, you’d tend to do all the things you know they’d want you to do and avoid the things you know would get in the way. It’s important to engage in this thoughtful exercise often. You have to keep doing it until you acquire a new pattern of thinking, feeling, and acting. Keep practicing until the pattern becomes second nature: an element of who you are, rather than just who you want to be.

The formula for failure is a few small errors consistently repeated.

There 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.

There’s nothing more important for a leader than getting the most out of your crew. Often that comes down to removing obstacles that limit potential.

There is a gap in our thinking that comes from believing that the way we see the world is the way the world really works. It’s only when we change our perspective—when we look at the situation through the eyes of other people—that we realize what we’re missing. We begin to appreciate our own blind spots and see what we’ve been missing.

Alcoholics Anonymous has a helpful safeguard for its members. They call it HALT—an acronym that stands for Hungry, Angry, Lonely, and Tired. When you feel like having a drink, they say, ask yourself whether any of these conditions apply. If so, deal with the real problem—hunger, anger, loneliness, or fatigue—instead of reaching for a drink.

In my conversation with Nobel laureate Daniel Kahneman, the godfather of cognitive biases and thinking errors, he revealed an unexpected way we can improve our judgment: replacing decisions with rules.2

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

Another safeguarding strategy is to increase the amount of effort it takes to do things that are contrary to your goals.

“What am I trying to achieve?” and “Is this moving me closer to that or further away?” These seem like basic questions, but they’re often forgotten in the heat of the moment.

Note: There are several strategies we can use to avoid the defaults - add friction - make rules for yourself - shift your perspective - add guardrails

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.

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.

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.

SAFEGUARD: Build a problem-solution firewall. Separate the problem-defining phase of the decision-making process from the problem-solving phase.

“To understand is to know what to do.”

SAFEGUARD: 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.

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.

The best decision-makers know this, and see binary thinking as a sign that we don’t fully understand a problem—that we’re trying to reduce the problem’s dimensions before fully understanding them.

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.

THE OPPORTUNITY-COST PRINCIPLE: Consider what opportunities you’re forgoing when you choose one option over another.

THE 3-LENS PRINCIPLE: View opportunity costs through these three lenses: (1) Compared with what? (2) And then what? (3) At the expense of what?fn4

THE TARGETING PRINCIPLE: Know what you’re looking for before you start sorting through the data.

THE HIFI PRINCIPLE: Get high-fidelity (HiFi) information— information that’s close to the source and unfiltered by other people’s biases and interests.

SAFEGUARD: Run an experiment. Try something out to see what kinds of results it yields.

SAFEGUARD: Evaluate the motivations and incentives of your sources. Remember that everyone sees things from a limited perspective.

THE 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.

When the cost of a mistake is low, move fast.

THE ALAP PRINCIPLE: If the cost to undo a decision is high, make it as late as possible.

You need to be so careful when there is one simple diagnosis that instantly pops into your mind that beautifully explains everything all at once. That’s when you need to stop and check your thinking.

THE 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.

A margin of safety is a buffer between what you expect to happen and what could happen. It’s designed to save you when surprises are expensive.

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.

make major decisions and then sleep on them before telling anyone.fn1 However, 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.

FAIL-SAFE: Set up trip wires to determine in advance what you’ll do when you hit a specific quantifiable time, amount, or circumstance.

SAFEGUARD: 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.

“There is no effectiveness without discipline, and there is no discipline without character.