Chapter 35 Exercises: Philosophical Practice

Exercise 1: The Deathbed Reflection (Thought Experiment)

Close your eyes, if you can, and place yourself in the following scene with as much detail as you can generate.

You are ninety years old. You have lived your full life. You are comfortable, not in pain, and your mind is clear. You are reflecting on how your life went — not as a formal accounting, but as a person who has been there, who has the full picture now that you are near the end. What you are about to remember is real; it actually happened; this is your actual life, and you are looking at it honestly.

Now: sit with this scene for a few minutes before proceeding to the questions.

Reflection questions:

  1. What would you be genuinely proud of, looking back? Not officially proud of — not the things you're supposed to say — but genuinely, privately proud of, in the way you might feel pride in a quiet moment alone?

  2. What would you wish you had done differently? Again, not the socially acceptable regrets, but the honest ones. Where did you choose security when you wanted meaning? Where did you avoid a conversation you needed to have? Where did you let a relationship atrophy because you were busy?

  3. What would feel like time well spent? Not necessarily the most productive years by external measures, but the time you would feel good about having lived?

  4. What would you wish you had spent less time on?

  5. Now work backward: What does this deathbed reflection reveal about what you actually value — as opposed to what you say you value, or what you think you should value? Where is the gap between what you lived for and what you would want to have lived for?

The philosophical connection: This exercise is a version of Heidegger's "being-toward-death" — the idea that authentic existence requires keeping your own finitude in view. It is also a version of the Stoic practice of negative visualization applied not to the loss of things but to the loss of time. Use the insights from this exercise as the basis for your Personal Philosophical Practice: what you care about should be reflected in how you spend the small daily actions of a life.

Written reflection: Write 300–500 words in response to these questions, using the deathbed frame to generate honest rather than aspirational answers. Notice when you are writing what you think you should say vs. what you actually feel. Aim for the latter.

Exercise 2: The Practice Audit (Thought Experiment)

You already have philosophical practices. You almost certainly don't call them that, and you may not have recognized them as such. But regular, sustained ways of attending to your life, of reflecting, of orienting toward what matters — these exist in most lives in various forms.

This exercise asks you to find them.

Part A: Inventory Your Existing Practices

Consider the following questions and make a list:

  • Do you have regular quiet time — morning coffee before anyone else is up, evening walks, a commute in which you don't listen to anything? What do you actually think about in those times?
  • Do you have rituals around transitions — the start of a new year, your birthday, the beginning of a new project? What role does reflection play in those rituals?
  • Do you keep any kind of journal or notebook, even irregularly? What do you write about?
  • Do you have conversations with certain people in your life that function as a kind of regular examination — talking through what matters, what isn't working, what you're trying to do?
  • Do you have any meditation or mindfulness practice, however informal?
  • Do you read things that make you think about how to live?

Part B: Identify the Tradition

For each practice you identified, ask: which philosophical tradition does this most resemble?

A morning walk in which you think about what you're grateful for is close to both Stoic negative visualization (reversed: appreciating what you have) and Buddhist mindfulness. A regular conversation with a trusted friend in which you examine your choices is close to Socratic dialogue. Journaling about what went wrong is close to the Stoic evening review.

Part C: The Gap Analysis

Compare your existing practices to the practices described in this chapter. Where are the significant gaps?

  • If you have no reflective practice at all, the gap is large — and the most important question is: what would be the smallest, most sustainable step you could take?
  • If you have a journaling practice but it has become ruminative (you write the same things over and over without progress), the gap is in the philosophical orientation — turning the journaling toward principle and insight rather than repetitive processing.
  • If you engage in intellectual reading but don't connect it to your own life, the gap is in application — the Montaigne move from ideas to self-examination.

Written reflection: Write a brief description of three existing practices you identified, including which tradition they resemble and one way you could deepen or sharpen each one.

Exercise 3: The Philosophical Character (Journaling)

Think of a person you admire for their philosophical character — not their beliefs or their professional accomplishments, but how they live. This might be someone you know personally, or a public figure, or a historical person you know through their writing.

The qualities you are looking for are not intellectual brilliance (though that may be present). They are the practical qualities of the examined life: equanimity in difficult circumstances, intellectual honesty about what they don't know, genuine courage in speaking truth when it's uncomfortable, care for others that is expressed in practice rather than in statement, the capacity to be present and non-reactive when others are panicking.

Write 400–600 words addressing the following:

  1. Who is this person? Describe them concretely — not in summary but in specific scenes or moments in which their philosophical character was visible.

  2. What specific qualities do you most admire in them? Name at least three. Try to be precise: not just "equanimity" but "the way they respond to bad news without catastrophizing while still taking it seriously."

  3. Speculate: what practices might have formed this character? The Stoic tradition holds that character is formed by practice, not by intention. If this person has genuine equanimity, they probably practiced it — through some form of regular reflection, deliberate cultivation of perspective, sustained engagement with adversity. What might those practices look like?

  4. Which of their qualities would you most want to cultivate in yourself? What specific practice from this chapter would be most likely to help you cultivate it?

A note on the exercise: The point is not to imitate the person. You are your own person with your own temperament and circumstances. The point is to use their character as a mirror — to make concrete and vivid what philosophical character can look like in actual human form, and to ask what you can learn from that concreteness.

Exercise 4: Which Framework Resonates? (Comparative Reflection)

This chapter described three primary approaches to daily philosophical practice:

The Stoic Approach: Systematic, structured, textually grounded. Daily practices with defined content — morning meditation, evening review, specific exercises like negative visualization. The practice proceeds by applying Stoic principles to your life with regularity and discipline. It has a clear schedule, clear questions, clear goals.

The Buddhist Approach: Less structured, more experiential, rooted in present-moment attention. The formal practice (meditation) develops a capacity (mindfulness) that then operates informally throughout the day. The emphasis is on quality of attention rather than on applying a set of principles. Goals are articulated differently: not "apply principle X to your evening" but "see clearly without automatic reactivity."

The Socratic Approach: Dialogical, relational, questioning-centered. The practice happens primarily through conversation and rigorous self-questioning rather than through solitary ritual. It requires another person, or at minimum an internal dialogue that genuinely challenges your assumptions rather than confirming them. The emphasis is on honest inquiry rather than on equanimity or attention.

Reflection questions:

  1. Which of these three approaches most resonates with your temperament? Why? What does this say about how you learn and grow?

  2. Which seems most foreign or difficult? Is that foreignness a reason to avoid it, or a reason to explore it?

  3. Are these approaches mutually exclusive? Can you see how a person might draw on all three? How would they fit together in a single practice?

  4. Is there something important about philosophical practice that all three of these approaches seem to share, despite their differences?

Written reflection: 250–400 words identifying your primary approach and your rationale.

Exercise 5: Philosophical Dialogue (Discussion/Writing)

The Morning Routine Debate

Consider two philosophical traditions asked about how to begin the day philosophically:

The Stoic position: Begin the day with deliberate preparation. Before engaging with the world, remind yourself of what you can and cannot control. Anticipate difficulty and prepare for it philosophically. Set a clear intention for the kind of person you want to be today. Review a principle or a passage from a Stoic text. Then proceed to your day with your philosophical bearings established.

The Zen Buddhist position: Begin the day with open, non-grasping awareness. Sit in silence, or practice morning meditation, without agenda. Don't approach the day armed with a framework you're going to apply — approach it with beginner's mind, ready to see what is actually there rather than what you expect. Equanimity is not prepared for in advance; it arises from the quality of attention you bring to each moment as it comes.

Discussion questions:

  1. What is the most fundamental disagreement between these two positions? Is it about what equanimity is, or about how to cultivate it, or about something else?

  2. Which morning routine do you think would be more effective in practice? What evidence or reasoning supports your view?

  3. Is there anything the Stoic and the Zen practitioner could agree on about the philosophical morning?

  4. How does each tradition's morning practice connect to its broader understanding of what a good human life looks like?

Written option: Write a dialogue (800–1,000 words) in which a Stoic and a Zen Buddhist discuss their morning practices with each other. Neither should "win" — the goal is genuine mutual inquiry.

Exercise 6: The Dinner Party

You are hosting a dinner party and you can invite any three people from history or from the philosophical traditions covered in this book. Your assignment for this chapter: Pierre Hadot, Marcus Aurelius, and Thich Nhat Hanh.

Before writing, think about who these people are and what they represent:

  • Pierre Hadot (1922–2010): The French scholar who recovered philosophy as a way of life from the academic tradition. He is not himself an ancient Stoic — he is a modern scholar deeply influenced by them, someone who both understands the practices theoretically and has clearly been shaped by them personally.
  • Marcus Aurelius (121–180 CE): The Roman Emperor who was also a practicing Stoic philosopher. The Meditations are his philosophical notebook — his actual practice of philosophy as a way of life. He has seen what it means to try to practice philosophy under enormous pressure and temptation, with enormous power and responsibility.
  • Thich Nhat Hanh (1926–2022): Vietnamese Buddhist monk, poet, peace activist. A practitioner of "engaged Buddhism" — the application of Buddhist practice to social and political life. He has integrated philosophy and practice so thoroughly that the distinction seems to dissolve.

Questions to drive the dinner conversation:

  1. What would Marcus Aurelius make of Hadot's thesis — that what he was doing in writing the Meditations was performing spiritual exercises? Would he recognize that description?

  2. Thich Nhat Hanh argues that mindfulness must be engaged — it must be applied to one's relationship to the suffering of the world, not just to one's inner life. How would the Stoics respond? Is there a tension between Stoic equanimity and Buddhist engaged compassion?

  3. All three figures have practiced philosophy under extreme circumstances — Marcus as emperor, Thich Nhat Hanh during the Vietnam War, Hadot as a scholar in occupied France. What have they learned from that about what philosophical practice actually consists of?

  4. What is the single most important practice that each would recommend to someone who wanted to begin living philosophically today?

Written exercise: Write the dinner conversation (600–900 words). Let it be a genuine dialogue, not a summary of positions.

Progressive Project Checkpoint: Design Your Personal Philosophical Practice

This is the central application exercise of Chapter 35, and it connects directly to the Personal Philosophy you have been developing throughout this book.

The Task:

Design a Personal Philosophical Practice — a realistic, sustainable daily and weekly routine of philosophical reflection. This is not an aspiration document. It is a commitment document, which means it should describe practices you will actually do, not practices that represent your highest ambitions for the kind of person you would like to be.

Guidelines for the design:

Be specific and realistic. "I will journal more" is not a practice. "I will spend 10 minutes before bed answering three questions (what went well? what could I do better? what principle applies?) in a dedicated journal" is a practice. The more specific, the more likely you are to actually do it.

Smaller is better. Three practices you maintain for six months are more valuable philosophically than fifteen practices you abandon after a week. Start with two or three that you are genuinely committed to. You can add more over time.

Name your tradition. For each practice, identify which philosophical tradition it draws on and what it is designed to develop. This helps you understand why you're doing it and what to expect from it.

Design for your temperament. If you are not a writer, don't build a practice around daily journaling. If you hate sitting still, don't design a practice centered on formal sitting meditation. Philosophical practice must fit the practitioner.

Your document should include:

  1. Daily practice(s) — what you will do every day, how long it will take, and what tradition(s) it draws on

  2. Weekly practice(s) — what you will do weekly (a longer journaling session, a philosophical conversation, careful reading of a text)

  3. Monthly practice(s) — the larger reviews and revisions

  4. Connection to your Personal Philosophy — how does this practice connect to what you have said you value and believe throughout this book? What qualities are you trying to cultivate?

  5. Starting today — what is the first thing you will do when you close this book?

Length: 400–600 words. This is a commitment you are making to yourself; write it accordingly.