Exercises: The Unexamined Life

1. Thought Experiment: The Contradiction Test

You hold, with varying degrees of confidence, a set of values. For most people, the short list includes things like honesty, loyalty, ambition, kindness, security, freedom, and authenticity.

For this exercise, pick the three values you'd say are most important to you — the ones you'd defend first if someone challenged you. Write them down.

Now construct a scenario — ideally a realistic one, not a philosophy-class extremity — in which two of those values come into direct conflict. Not a tension you can manage by splitting the difference, but a genuine either/or: to fully honor one, you must compromise the other.

Some possibilities:

  • Honesty vs. loyalty: Your closest friend's business partner asks you, privately, what you know about your friend's reliability. You know things that, if you shared them honestly, would end the partnership — and might destroy your friend's business. What do you do?
  • Ambition vs. kindness: Pursuing the career opportunity you've worked toward for years requires directly competing against someone you care about, in circumstances where only one of you can win.
  • Security vs. authenticity: The version of yourself that your family and employer expect is not the version you recognize when you're alone. Becoming fully authentic means disrupting every safe relationship you have.

After you've constructed the scenario:

  1. What do you actually do? Don't philosophize yet — just gut-check your immediate instinct.
  2. What does that instinct reveal about which value you actually rank higher?
  3. Is that ranking one you endorse on reflection, or is it a surprise?
  4. Is there a way to understand your values differently — to define them more precisely — that removes the conflict? Or is the conflict real?

The goal is not to resolve the tension. The goal is to notice that you have a hierarchy of values you've probably never explicitly stated, and to begin making it visible.

2. Journaling: The Unexamined Choice

Write about a time when you made a significant decision based on assumptions you'd never examined. This might be a career choice, a relationship decision, a move, a major purchase, a political commitment, a religious position you adopted or abandoned.

The question is not: was it the right decision? The question is: what were you taking for granted?

Prompts to help you get there:

  • What did you assume, without deciding, about what "success" meant in that context?
  • What did you assume about what kind of person you were (or wanted to be)?
  • What did you assume about what other people would think, and how much that mattered?
  • What did you assume about the future — that it would resemble the past, that circumstances would stay stable, that you would stay the same?
  • If you had been asked, before making the decision, to defend each of those assumptions, could you have? Would you have wanted to?

After writing, add one more paragraph: Would you make the same choice today? Not because you have better information (you probably do), but because you've examined the assumptions differently.

3. Framework Resonance: Your Gut Theory of the Good Life

This exercise is different from the others: it doesn't ask you to apply any framework yet. Instead, it asks you to identify the framework you're already implicitly using.

Read the following three rough descriptions of what makes a life good. For each, notice your immediate reaction — not what you think you should believe, but what resonates:

View A: The Achievement View. A good life is one in which you accomplish things that matter — build something, contribute something, leave something behind. What makes your life go well is not whether it feels good but whether it has significance. A life of pleasant stagnation is worse than a life of difficult growth.

View B: The Relationship View. A good life is one in which you love and are loved, belong to people and communities, and experience genuine connection. What makes your life go well is not what you've built alone but what you've shared. Accomplishment without connection is hollow.

View C: The Experience View. A good life is one in which you are fully alive — curious, engaged, open to beauty and strangeness. What makes your life go well is the richness and depth of your experience. A wide, adventurous life is better than a narrow, secure one.

Now:

  1. Which view resonates most strongly? Which feels most like your view?
  2. Which feels most alien — and why?
  3. Are there ways in which you believe all three? How do you weight them?
  4. Can you construct a scenario in which following your primary view would require you to sacrifice something from the other two?

Keep these responses. You'll return to them in Part II when we examine consequentialism, virtue ethics, and existentialism in detail. The question then will be: did your gut theory survive contact with the arguments?

4. Dialogue: The Philosophy of Someone You Know

Choose someone whose life you know reasonably well — a parent, a close friend, a mentor, a partner. Without asking them directly (yet), try to reconstruct their philosophy of life.

  • What do they seem to believe makes a life go well?
  • What would they be willing to sacrifice for what?
  • What assumptions do they seem to make about the world — about whether people are basically good or bad, about whether effort leads to reward, about whether security or adventure is the right default?
  • What do they seem to believe they owe other people?

Now, if possible, have a conversation with them. Not a confrontational interrogation, but an open one: "I've been thinking about what makes a good life — I'm curious what you think." Listen carefully.

After the conversation:

  • Was your reconstruction accurate?
  • What assumptions surfaced that you hadn't noticed before?
  • Did they ask you the question back? What was your answer?

This exercise has a second purpose: practicing the principle of charity before we formally introduce it in Chapter 2. When you hear a view that's different from yours, your task is to understand it as well as its holder does before you evaluate it.

5. Dinner Party: Socrates, Your Most Pragmatic Friend, and a Seven-Year-Old

You're hosting a dinner, and your three guests are:

  • Socrates (fifth-century BCE, executed for asking too many questions, genuinely believed the examined life was the only life worth living)
  • Your most pragmatic friend (the one who always asks "but what does this accomplish?" and has zero patience for navel-gazing)
  • A seven-year-old child (who has no filter, asks "why?" to everything, and has not yet learned which questions are supposed to be embarrassing)

The topic: "What makes something worth doing?"

Imagine the conversation. Let it be specific — let Socrates push back on the pragmatist's "does it work?" standard, let the child ask the question that derails both of them, let your pragmatic friend say what any sensible person would say when cornered by an ancient Greek.

Where does the conversation go? Who changes whose mind? What does the child ask that neither adult can answer?

After you've imagined it:

  • What does this conversation reveal about the question?
  • Where do you land in the argument?
  • What would you say if you were the fourth guest?

6. Progressive Project: Your Philosophical Starting Point

This is the first entry in your Personal Philosophy document.

Write three paragraphs — honest, unpolished, exactly what you believe right now, not what you think you should believe:

Paragraph 1: What makes a good life? Not in theory. In your life — what would make your life go well? What would have to be true, ten or twenty years from now, for you to feel that it was a life well lived?

Paragraph 2: What's right and wrong? How do you decide, when you face a hard moral choice, what the right thing to do is? Is it about consequences — what outcome is best? Is it about rules — what would you do if everyone did the same? Is it about who you want to be — what a good person would do? Or something else?

Paragraph 3: What can you know for certain? Is there anything you are absolutely sure of? How do you decide when something is reliable enough to act on? When do you trust your gut, when do you trust experts, and when do you trust neither?

These three paragraphs are your starting point. Date them. Keep them exactly as written. At the end of each part of this book, you'll return to them and note: what has changed, and why.

The goal is not to get it right. The goal is to get it honest.