Exercises — Chapter 23: Procrastination and Time Mastery

These exercises require honesty about avoidance — which is itself something people often put off. Notice any resistance to completing them.

Part 1: Diagnosing Your Procrastination

Exercise 23.1 — The Procrastination Profile

Identify your top three most-avoided tasks or projects — things you consistently intend to do but consistently delay.

For each:

(a) Category: Is the primary driver of avoidance boredom, performance anxiety, resentment, ambiguity, perfectionism, or something else? Be specific.

(b) Pattern: How does the avoidance manifest? Do you avoid through other work, through distraction, through research and preparation, through scheduling more conversations? Name the specific form your avoidance takes.

(c) Duration: How long have you been avoiding this? What is the actual consequence of the continued delay?

(d) Emotion: Sit with the thought of starting this task right now. What is the specific feeling that arises? Name it precisely — not "resistance" or "I don't want to," but the specific emotional texture.

Exercise 23.2 — Situational vs. Chronic

(a) Is your procrastination primarily situational (specific tasks, specific domains) or does it show up consistently across most effortful pursuits?

(b) If situational: what do the avoided tasks have in common? What specific characteristic makes them most aversive?

(c) If chronic: when did the pattern begin? Are there domains where it does not appear? What is different about those domains?

(d) The chapter notes that chronic procrastination is associated with self-criticism and lower self-compassion. Is this pattern present for you? What does your internal voice say when you've been avoiding something important?

Exercise 23.3 — The Task Aversiveness Inventory

Choose one task you are currently procrastinating on. Rate each source of aversiveness (1 = not a factor; 10 = primary driver):

(a) Which factor scored highest? How does knowing the primary driver change what the most useful intervention would be?

(b) If ambiguity scored high: write down the single most specific first step you could take. Not "work on it" — the actual physical first action.

(c) If perfectionism scored high: what would "good enough for now" look like? What specifically would have to be true for the first draft to be adequate to exist (not to be final)?

Part 2: The Emotion Regulation Problem

Exercise 23.4 — The Relief Pattern

The chapter notes that avoidance produces short-term relief and longer-term cost.

(a) Identify the specific relief you get when you avoid a particular task. What are you doing instead? What does that alternative provide — stimulation, a sense of completion, social connection, distraction?

(b) How long does the relief last? What happens after it fades?

(c) Map the wellbeing arc: relief at avoidance → (what comes next, and when) → (cost, if any).

(d) Does knowing the arc change anything about the felt appeal of avoidance in the moment? If not, why not? What would have to be different about your relationship to the pattern for the knowledge to translate to behavior?

Exercise 23.5 — Self-Compassion for Procrastination

The research shows that self-criticism after procrastination increases subsequent procrastination. Self-compassion reduces it.

(a) Write down what you typically say to yourself when you discover you've been avoiding an important task. Be honest.

(b) Now write what you would say to a close friend who told you they'd been struggling to start an important project for three weeks. (Most people find this significantly kinder.)

(c) Notice the gap between the two. What would it take to apply the second response to yourself?

(d) The next time you notice you've been procrastinating, try this sequence: 1. Acknowledge the delay without judgment: "I've been avoiding this." 2. Recognize common humanity: "This is hard for a lot of people; I'm not uniquely broken." 3. Identify the specific emotional obstacle: "What specifically was I avoiding?" 4. Identify the next specific step: "What would I do next if I were to start now?"

Apply this sequence to a current avoidance pattern. Notice what happens.

Part 3: Getting Started

Exercise 23.6 — The Two-Minute Start

Choose one task you've been avoiding.

Your only commitment: spend two minutes on it. Not working on it toward completion — just starting. Open the document, write one sentence, sketch one element, make one list, take one note. Two minutes.

(a) Set a timer for two minutes and do this now (or at a specified time within 24 hours).

(b) After the two minutes: Did you continue past the timer? If so, what happened to the aversive feeling once you were in the work?

(c) If the aversive feeling remained even after starting: what was its texture? Is this information about the specific obstacle?

(d) Apply this exercise to three different avoided tasks over the next week. Notice whether any pattern emerges about what changes once started vs. what remains aversive.

Exercise 23.7 — Implementation Intentions for Procrastination

Choose one task you've been avoiding for more than a week.

Write three implementation intentions that address initiation:

1. Primary initiation intention: When [specific time/situation/cue], I will [specific first step] in [specific location].

2. Recovery intention (for when the primary fails): If I miss [the primary cue] because [likely obstacle], then I will [alternative initiation].

3. Self-compassion intention (for after a gap): When I notice I've avoided the task again, I will [self-compassion response] and then [specific re-entry step].

After one week: (a) Were the intentions used? If not, was the trigger wrong, the task too vague, or the initiation too ambitious? (b) What would you revise?

Exercise 23.8 — Behavioral Activation Experiment

The chapter describes the finding that motivation tends to follow behavior rather than precede it.

Design an experiment: choose a task you have been waiting to feel motivated to start. Start it anyway — right now, or at a specified time — and observe what happens to motivation and engagement as you work.

Instructions: - Set a timer for 15 minutes - Begin the task (using your implementation intention from Exercise 23.7 if applicable) - At 10-minute mark, briefly note your current mood and engagement level (not stopping the work — just a quick internal check) - At 15 minutes, stop and evaluate

(a) Did engagement increase after starting? If so, when — immediately, gradually, or not until some threshold was crossed?

(b) If engagement did not increase: what specifically was different about this task? Was the aversive feeling about the starting or about the work itself?

(c) The chapter notes that the anticipatory feeling is usually worse than the feeling of actual engagement. Was this true in your experience?

Part 4: Time Mastery Systems

Exercise 23.9 — The Eisenhower Matrix Audit

Over the next two days, log how you spend your time. At the end of day 2, categorize each activity:

(a) What percentage of your time is Q2? (Research suggests most people spend under 15% here; high-performers target 30–40%.)

(b) What is your most important Q2 activity that is currently receiving the least time?

(c) Design one structural change to protect 30 additional minutes of Q2 time per day. Be specific about when, where, and what you will protect it against.

Exercise 23.10 — Timeboxing Practice

Choose one task that you have been approaching as open-ended ("work on it until it's done") and convert it to a timeboxed format.

(a) Define: what will you work on, for how long, and what is the deliverable at the end of the timebox? (Not completion — what specifically will be produced in this specific time window?)

(b) Set a timer. Work on nothing but the specified task. When the timer ends, stop.

After the timebox: (c) How much progress did you make compared to a similar open-ended session? (d) Did having a defined endpoint affect your experience of the work — either the aversiveness of starting or the quality of engagement during? (e) How many timeboxes would be required to complete this task? Schedule them.

Exercise 23.11 — The Weekly Review Practice

The Getting Things Done weekly review practice:

1. Collect: Gather everything out of your head — every open commitment, every someday/maybe, every project with an unclear status — into one list.

2. Process: For each item: Is it actionable? If not, delete it or put it in a reference file. If yes: identify the very next physical action required.

3. Organize: Place each next action in the correct context (calendar, next-action list, waiting-for list).

4. Review: Review your calendar for the coming week and your next-action lists. Are there conflicts? Missing commitments? Unrealistic timelines?

5. Do: You're now ready to actually work.

Conduct your first weekly review. Schedule 45 minutes for it.

(a) How many open commitments did you discover that had no next action identified? (b) After the review: did the sense of mental load decrease? This is the Zeigarnik effect in reverse — trusted external system → released internal monitoring. (c) Schedule a recurring weekly review for the next four weeks. Assess whether the practice reduces procrastination on any specific tasks.

Part 5: Perfectionism and the Draft

Exercise 23.12 — The Imperfect Draft

If perfectionism is a driver of your procrastination, this exercise addresses it directly.

Choose a piece of work you have been avoiding because you're not sure you can do it well enough.

Set a timer for 20 minutes. Write, design, plan, or produce the worst acceptable version of this work — the version that gets the ideas down without caring about quality. Speed is the point. Legibility is sufficient.

After 20 minutes: (a) Read what you produced. Is it as bad as you feared? (b) What would you do next to improve it? (Note: this is the editorial mode — distinct from the generative mode you just used.) (c) The chapter notes that generative and evaluative thinking need to be separated. Did you notice the difference between the two modes? (d) What would a "good enough to share" version require from here?

Part 6: Time Perspective and Temporal Intelligence

Exercise 23.13 — Your Time Perspective Profile

Reflect on your habitual orientation toward time:

(a) Past orientation: Do you tend to ruminate on past mistakes and regrets (past-negative)? Or do you draw on positive memories for comfort and identity (past-positive)? Which is more characteristic?

(b) Present orientation: Are you primarily present-hedonistic (oriented toward current pleasure and sensation)? Or present-fatalistic (sensing that effort doesn't matter because outcomes are predetermined)? Or genuinely present-focused (able to be absorbed in current experience)?

(c) Future orientation: Are you primarily future-positive (planning, setting goals, deferring gratification toward chosen ends)? Or future-negative (preoccupied with future threat and anxiety)?

(d) Zimbardo's balanced time perspective: past-positive + present-hedonistic + future-positive. Which element is most underdeveloped for you? What would strengthening it look like?

Exercise 23.14 — Planning Fallacy Correction

The planning fallacy is the consistent tendency to underestimate how long tasks take.

(a) Choose a current project with a deadline. What is your intuitive estimate for how long it will take to complete?

(b) Now use the outside view: what do projects of this type and complexity typically take? (If you've done similar projects, recall how long they actually took.)

(c) Adjust your estimate by 30–50% (the typical gap between inside-view and outside-view estimates). Does this revised estimate change how you would approach scheduling?

(d) Over the next four weeks, record your time estimates and actual time for three significant tasks. What is your personal planning fallacy ratio? Use this ratio to adjust future estimates.

Part 7: Integration

Exercise 23.15 — The System Design

Based on what you've learned in this chapter, design a time mastery system for yourself:

(a) Morning routine: What specific first task will you protect each morning before opening email or other communications? How long will that protected window be?

(b) Q2 protection: When specifically will you do your most important non-urgent work? What day/time? What duration?

(c) Implementation intentions: For your top three most-avoided current tasks, write one implementation intention each.

(d) Environmental design: Name one specific friction-reduction for your most important task and one specific friction-increase for your most common avoidance behavior.

(e) Self-compassion protocol: Write a three-sentence self-compassion response you will use the next time you notice you've been procrastinating.

(f) Weekly review: When will you conduct your weekly review? (Day, time, location.)

Your system doesn't need to be perfect. It needs to exist and be specific enough to use tomorrow.