Chapter 4 Exercises: Cognitive Biases

Part A: Identifying Biases in Action

Exercise 4.1 — The Bias Hunt (Level 1 | 15 minutes)

Review your recent decisions and experiences and identify at least one example of each of the following biases operating in your own thinking:

  1. Confirmation bias — What belief have you been gathering evidence for recently? Have you actively sought disconfirming evidence?

  2. Availability heuristic — What risk or probability have you estimated primarily based on how easily examples came to mind?

  3. Anchoring — Where has a first number or first impression influenced your subsequent evaluation?

  4. Sunk cost fallacy — Where are you continuing something primarily because of past investment rather than future expected value?

  5. Planning fallacy — What have you planned optimistically that is likely taking longer or costing more than you estimated?

Exercise 4.2 — The Confirmation Bias Audit (Level 2 | 20 minutes)

Pick one belief you hold about an important area of your life — a relationship, a work situation, yourself.

List the evidence you have that supports this belief. Now force yourself to list evidence that challenges it. If you cannot find any, that itself is interesting data.

Consider: If the disconfirming evidence were true, what would that mean? How does it feel to take it seriously?

Exercise 4.3 — The Outside View (Level 2 | 20 minutes)

Think of a project or goal you are currently pursuing. Estimate: - How long it will take to complete - The probability of achieving your target outcome

Now apply the outside view: Think of similar projects done by other people in similar circumstances. What is the typical outcome? The typical timeline? The base rate of success?

Compare your inside view estimate to the outside view estimate. Which is more generous? Why?

Part B: Applying Debiasing Strategies

Exercise 4.4 — Consider the Opposite (Level 2 | 20 minutes)

Pick a decision you are currently considering or a belief you hold firmly.

For ten minutes, seriously generate the best possible case for the opposite position. Write it out as if you were a skilled advocate for the opposing view.

After the exercise: Does your original position feel different? More or less certain? Did any of the opposing arguments reveal genuine weaknesses in your position?

Exercise 4.5 — The Pre-Mortem (Level 2 | 30 minutes)

Choose a current plan or project — something you are invested in succeeding.

Imagine it is twelve months from now and the project has failed catastrophically. Write a brief "failure report": 1. What went wrong? 2. What early warning signs did you ignore? 3. What risks did you underweight? 4. What assumptions turned out to be wrong?

Return to your current planning: Does the failure report reveal anything you have not adequately considered?

Exercise 4.6 — Loss Framing vs. Gain Framing (Level 1 | 15 minutes)

Take three important decisions or situations in your life. For each, write two versions of the situation — one framed in terms of gains, one in terms of losses.

Example: "This new job has $10,000 higher salary than my current one" vs. "I am currently leaving $10,000 on the table."

After writing both versions: Which version feels more motivating? More anxiety-producing? Does the framing change how urgently you feel you need to act?

Exercise 4.7 — The Sunk Cost Inventory (Level 3 | 45 minutes)

Make an honest list of things you are currently continuing primarily because of past investment: - A relationship or friendship - A career path or specific job - A project, habit, or commitment - A belief or identity

For each, answer: 1. If I were starting fresh today, would I choose this? 2. What is the realistic expected future value? 3. What is the actual cost of continuing? 4. What is the psychological cost of acknowledging that the prior investment cannot be recovered?

This exercise does not require action — it requires honest assessment. What do you notice?

Exercise 4.8 — Motivated Reasoning Check (Level 2 | 20 minutes)

Identify a belief you hold on a topic connected to your identity (political, religious, relational, professional).

Now read or engage with a high-quality argument for the opposing view. As you read, notice: - What is your immediate emotional response? - Do you find yourself searching for flaws in the argument before fully understanding it? - Do you apply different standards of evidence to this argument than you would to an argument that confirmed your view?

Reflection: Is your response to the opposing view evidence-responsive, or identity-protective?

Part C: Going Deeper

Exercise 4.9 — Bias Journaling (Level 2 | Ongoing)

For two weeks, keep a brief daily bias journal. Each day, record at least one instance of a cognitive bias you observed: - In yourself (most valuable) - In a conversation or news story - In a decision-making process around you

Note: which bias, what the situation was, what a debiased response might have looked like.

Reflection at end of two weeks: Which biases are most prevalent in your daily experience? In what domains are you most and least prone to biased thinking?

Exercise 4.10 — The Kahneman Read (Level 2 | Extended)

Read chapters 11–14 of Daniel Kahneman's Thinking, Fast and Slow (on anchoring, availability, and representativeness).

After reading each chapter, write a brief paragraph describing an instance from your own life where that bias has operated. Be as specific as possible — not "I have experienced anchoring" but "When negotiating my salary at my current job, I was anchored by the initial number the recruiter mentioned, and my counteroffer was less ambitious than it would have been without that anchor."

Exercise 4.11 — External Review Experiment (Level 2 | 30 minutes + conversation)

Identify one current decision or belief that matters to you.

Ask someone you trust — ideally someone who will not simply affirm your existing position — to play devil's advocate. Their job: find the weaknesses in your reasoning, the evidence you might be underweighting, the alternatives you have not fully considered.

After the conversation: 1. Was there anything in the challenge you had not already considered? 2. How did it feel to have your reasoning examined? 3. Does your position feel different after the external review?

Exercise 4.12 — Jordan's Campaign Decision (Level 2 | 20 minutes)

Reread the opening vignette of this chapter.

Identify: 1. Which specific cognitive biases are operating in Jordan's campaign research process? 2. What debiasing strategies could he have used? 3. Does the fact that Option B might actually be the right choice affect your evaluation of his process? (Should it?)

Exercise 4.13 — Prospect Theory and Your Decisions (Level 2 | 30 minutes)

Think of three significant decisions you have made in the past year involving uncertainty or risk.

For each: 1. How did you evaluate the gains and losses? 2. Did loss aversion influence the decision? (Were you more motivated to avoid a potential loss than to pursue an equivalent gain?) 3. Did you weight small probabilities too heavily? (Were you influenced by unlikely but dramatic downside scenarios?) 4. What would a more calibrated decision-making process have looked like?

Exercise 4.14 — Calibration Training (Level 2 | 30 minutes)

Test your calibration — how well your confidence matches your accuracy.

Answer the following 10 questions. For each, provide your best estimate AND your confidence level (0–100% that you are correct):

  1. In what year did the Berlin Wall fall?
  2. How many bones are in the adult human body?
  3. What is the approximate population of Canada?
  4. In what year was the first iPhone released?
  5. What is the boiling point of water at sea level in Fahrenheit?
  6. How many countries are in the United Nations?
  7. What is the capital of Australia?
  8. Approximately how long does it take light to travel from the Sun to Earth?
  9. What fraction of the Earth's surface is ocean?
  10. How many symphonies did Beethoven compose?

After checking your answers: What percentage of your "90% confident" answers were correct? "70% confident"? This is your calibration. Most people are overconfident.

(Answers: 1989, 206, 38 million, 2007, 212°F, 193, Canberra, 8 minutes, about 71%, 9)

Exercise 4.15 — Building Your Debiasing Toolkit (Level 3 | 30 minutes)

Based on everything in this chapter, design a personal debiasing protocol for the area of your life where biased thinking is most costly.

Include: 1. The most likely biases in this domain 2. Specific triggers that tend to activate them 3. Three specific debiasing strategies you will use (with implementation details) 4. How you will know the strategy worked (or didn't)

This does not need to be elaborate. It needs to be specific and realistic.