Case Study 1 — Chapter 23: Procrastination and Time Mastery

Jordan: The Thing That's Actually Hard

Background

Week six of the Strategic Director role. Jordan has a team of twelve. He has budget authority. He has a three-year customer experience strategy document that is his primary deliverable for Q1 and that has had eight slides and an empty Section 3 for four weeks.

He is aware of this. He opens the document every morning. He closes it every evening. In between, he attends meetings, responds to email, conducts one-on-ones, reviews analytics reports, and drafts communications for his team. He is, by any external measure, producing at the level the role requires.

Section 3 — Market Segment Prioritization — requires him to recommend which of the company's four customer segments should receive primary investment over the next three years. It is the hardest decision in the document. Every other section leads toward this one. He has been preparing to write Section 3 for four weeks.

He has not written Section 3.

The Audit

Jordan applies the chapter's framework, starting with the task aversiveness inventory.

Boredom: Low. The strategy work is genuinely interesting to him.

Performance anxiety: High. The section requires committing to a recommendation that will be visible to senior leadership, will shape resource allocation decisions, and will be right or wrong in ways that will be evaluated over a three-year horizon. Not starting means not being wrong yet.

Resentment: Low. He chose this role.

Ambiguity: Moderate. He has the data. He has the framework. He has done the analysis. What he doesn't have is certainty — and he has been treating certainty as a prerequisite for writing.

Perfectionism: High. He has been preparing for Section 3 by gathering more information — additional market data, a competitor analysis, an informal survey of the sales team — as if the right additional data point would eliminate the risk of being wrong.

He writes in his work journal: I'm not avoiding because I don't have enough information. I'm avoiding because I have to make a real recommendation and I might be wrong and senior leadership will know I was wrong. The research is cover. I've been researching Section 3 for three weeks. I know what the recommendation is. I'm just not writing it down.

This is the moment the procrastination becomes visible: the avoidance had looked like diligence. More research, more preparation, more context-gathering. All productive. All in the service of not committing.

The Self-Compassion Check

The previous version of Jordan would have, at this point, generated a fairly harsh internal response to this recognition. He had, until recently, treated his own failures and avoidance with a self-critical voice that was several degrees harsher than anything he would apply to a direct report.

He notices the pull toward that voice now. You've been wasting four weeks. A real strategic director doesn't avoid the hard section.

He pauses. He has been practicing self-compassion for six months, first theoretically (Chapter 10's self-compassion work) and now with more intentionality. He tries the alternative:

This is a hard decision. Being asked to make a three-year resource recommendation with real consequences is genuinely difficult. You've done thorough preparation. The avoidance makes sense — it's protecting you from being wrong in a visible way. The question is whether you want to keep protecting yourself or whether you want to produce the work.

The second response doesn't make Section 3 easier to write. But it does remove one obstacle: the shame charge that had been accumulating around the document. Every day he opened it with "I've been avoiding this again" had added to the aversive weight. The self-compassion response doesn't add to it.

The Implementation Intention

Jordan writes the implementation intention:

When I sit down at my desk at 8:15 AM on Tuesday — before opening email, before Slack, before anything — I will open the strategy document to Section 3 and write the recommendation sentence. Just the sentence. Not the full argument. Just: "I recommend that we prioritize [segment] as the primary investment target over the next three years." That sentence. That's all I need to produce in the first block.

He notes what the implementation intention does: it reduces the task from "write Section 3" (which implies completing a full, coherent, well-argued section) to "write one sentence" (which is undeniably achievable and is not the final version). It specifies the time, the preconditions (before email, before Slack), and the deliverable.

He also knows, from his own self-knowledge and the self-regulation research, that Tuesday morning after he's reviewed his email is not the right context for this work. He does his best thinking in the first hour of the morning, before the day's inputs have populated his head. He has been violating this consistently for six weeks, opening email first because the inbox is reliably solvable and the document is not.

Tuesday Morning

8:17 AM. Jordan opens the strategy document. He navigates to Section 3.

He writes: "I recommend that we prioritize the enterprise segment as the primary investment target over the next three years, based on the lifetime value differential, the competitive moat potential in this segment, and the under-utilization of our existing advantage in enterprise relationship management."

He reads it back.

Then he writes the next sentence: "This recommendation requires us to make the following hard trade-offs..."

And then the paragraph after that.

Forty minutes later he closes the document. Section 3 has 420 words. It is not complete. It is a draft. It exists.

He opens his email. The inbox has accumulated overnight. He does not feel relieved in the way he expected to feel. He feels something more like: oh. That's what that was.

He writes in his journal: The information was always there. What wasn't there was my willingness to be wrong in writing. The sentence was the hard part — the commitment that could be evaluated. Everything else was just explaining the commitment. Once I wrote the sentence, the rest followed.

I spent four weeks preparing for twenty seconds of commitment.

The Structural Change

Jordan makes three structural changes following Tuesday morning:

First: He blocks 8:00–9:30 AM as "protected" on his calendar five days per week, labeled "deep work." He calls his EA to hold this block against meeting requests. The block is not for catching up; it is for the work that most requires his thinking.

Second: He stops opening email before this block. He puts his phone in the desk drawer when he sits down in the morning. He has tried this before (Chapter 13), but this time he has learned something that makes the friction more meaningful: the inbox is not productive avoidance. It is just avoidance.

Third: He adopts the next-action discipline. Every project in his management system now has a specified physical next step — not "work on strategy" but "write the risk analysis paragraph in Section 4." When he opens the strategy document in the morning, he does not have to decide what to do with it. The decision has already been made.

The Team Observation

Week eight. Jordan conducts a one-on-one with Priya, who recently joined his team from another department and is new to the kind of work his team does.

She mentions, without being asked, that she is struggling to start a stakeholder analysis. "I keep thinking I need more information, but every time I get more information I feel like I need more."

Jordan recognizes the pattern immediately. He shares what he learned: "You already have enough information to produce a draft. The thing that looks like needing more information is actually uncertainty about whether you'll get it right. The analysis might be wrong. But a draft that's wrong is better than no draft, because a draft can be revised. You can't revise nothing."

Then: "What's the first sentence of the analysis?"

Priya looks at him. "I don't know."

"If you had to write it in the next thirty seconds — imperfectly, just to have something — what would it be?"

She writes it down. Jordan looks at it. "That's good. That's the analysis, in outline. Now the rest is filling in the argument."

Two days later she sends him the draft.

Analysis Questions

1. Jordan's procrastination on Section 3 manifested as productive-looking avoidance — additional research, competitor analysis, stakeholder conversations. What made this form of avoidance harder to detect than simple task avoidance? How does the task aversiveness audit help clarify what was actually happening?

2. Jordan's self-compassion practice is explicitly applied in this case study — he notices the harsh internal voice and tries the alternative. The chapter notes that self-criticism after procrastination increases subsequent procrastination. What specifically in Jordan's internal shift changed his relationship to the document — not just his feelings about it?

3. Jordan's implementation intention specifies a single sentence as the deliverable for Tuesday's first block. Why is this specificity — "just the sentence, not the full section" — important? What psychological function does it serve relative to a more ambitious deliverable?

4. The structural changes Jordan makes — protected morning block, no email before writing, next-action discipline — address the environmental and structural dimension of procrastination rather than the emotional dimension. The chapter argues that structural interventions are necessary but not always sufficient for chronic procrastination. Why are they sufficient here? What does the sufficiency suggest about the category of Jordan's procrastination?

5. Jordan transfers the insight directly to his interaction with Priya: "You can't revise nothing." The chapter's section on perfectionism frames this as the distinction between generative and evaluative thinking. How does Jordan's question — "What would the first sentence be?" — function as a behavioral activation intervention in Priya's procrastination pattern?