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The Two Meetings That Turn Long-Term Strategy Into Motion

Most top executives can generate urgency around a quarterly target. The mechanisms are familiar: dashboards, deadlines, compensation levers. People move.

But ask those same executives to build genuine momentum toward a grand aspiration which needs a fifteen-year horizon, and something strange happens. They show up. They nod. They wait for the pressure to pass.

This isn’t insubordination. It’s a rational response to a broken process. And if you’ve ever led a strategic planning cycle that produced a polished document nobody touched again, you already know the symptom. The question is whether you’ve correctly diagnosed the cause.

The Real Problem Is Sequence, Not Ambition

CEOs who struggle to activate major aspirations or breakthrough results typically frame it as a people problem — their teams aren’t bold enough, disciplined enough, or strategically literate enough. Frequently, they apply pressure to fix the problem and become too directive. They hope their personal energy fills the void.

Perhaps just as often, they do the opposite and become too passive. In this mode they back off, hoping organic energy fills the void. It rarely does.

Neither framing is quite right. In the end, CEO’s migrate towards short-term goals because they don’t have a reliable way to maintain both short-, mid-, and long-term momentum.

The deeper issue is that most organizations try to do too much in a single planning meeting.

Effective accomplishment of all three phases at the same time requires two distinct meetings, held weeks apart, each demanding a different posture from the leader. Getting the sequence right changes what the plan is, who owns it, and how fast it can move.

Clarifying Misconceptions About Long Horizons

Before the two meetings make sense, two widespread beliefs need to be addressed:

the first is that long-range planning is inherently vague, and therefore not worth taking seriously.

Mistake 1) This is a problem for CEOs who truly have big aspirations, because long-range planning calls for the decades needed to make breakthrough goals realistic and credible to stakeholders. Without adequate time, executives play the game mentioned before. They show up, nod, and wait for the pressure to disappear.

This view of long-range planning being vague is understandable but technically wrong.

The planning tools appropriate for year one of a strategy are genuinely different from those suited to year twenty-five — but that doesn’t mean the far end of the horizon is a guess. It just needs to be equipped in the right way.

For example, the Rolling Wave Technique leads to the use of different methods, mindsets and discussions for short- and long-term phases. It provides operational details in the short term, and higher-altitude targets and milestones in the long term.

Neither end is more rigorous than the other. They are rigorous in different ways. The confusion exists because precious few use the technique. It’s just not taught in most business schools as a component of corporate strategy.

Mistake 2) The second faulty belief is that long-term aspirations don’t matter. To explain why this is so wrong, consider a historical example.

Medieval cathedral builders routinely committed to projects spanning two to three centuries. No individual craftsman who broke ground would see the finished nave. Yet construction continued across generations, through plagues and political upheaval, because the aspiration was large enough to give the work meaning — and specific enough to give it credible direction. Floor plans existed. Proportions were specified. Progress was measurable even when the endpoint was a lifetime away.

This points to a counterintuitive truth: the grander the ambition, the more likely it is to unlock discretionary effort — the creativity and energy people typically reserve for pursuits they actually care about.

Modest, short-term goals produce compliance. In corporate life, these tend to be overwhelmingly financial.

Transformative goals, properly constructed, produce ownership. The audacity of a well-chosen endpoint is itself a management tool, one that most corporations never pick up.

With these misconceptions cleared up, here are the details of both meetings and how they are conducted.

Meeting One: The CEO Goes Quiet

The first meeting has one non-negotiable design principle: the CEO sponsors but does not lead. Or facilitate.

This is harder than it sounds. Most executives who have reached the top of an organization have done so partly through the force of their vision. They arrive at planning sessions having already formed views about where the company should go. The instinct is to share those views early — to inspire the team with a compelling picture of the future and let the session fill in the details.

Resist it. Completely.

The goals of this first meeting are for the executive team to construct the long-range aspiration themselves and define the means to accomplish it. That means choosing a target year — somewhere between fifteen and thirty years out — and then building the assumptions, scenarios, and numbers required to define what success looks like at that point.

It’s followed by the use of the Rolling Wave Technique to lay out a plan for the entire horizon, with more details in closer than later years.

Facilitators can guide the process. The CEO’s role is to hold the space while that process unfolds, tolerating the discomfort of an outcome they did not pre-select and cannot entirely predict.

What makes this worthwhile is what it produces: genuine co-ownership. Every figure the team debated, they will later defend. Every scenario they stress-tested, they trust because they built it. A strategic target and plan defined by the CEO and handed to the team is a document. A strategy the team constructed is a commitment — and the difference shows up in execution, not in the planning room.

For example, one team member assumes a technology shift in five years. Another assumes fifteen. Both assumptions are driving their instincts about investment and timing, silently, in every meeting they attend. Naming those beliefs, debating them, and converting them into dated claims is one of the most underrated outputs of a well-run long-range planning session. It also reveals where the team’s consensus is genuine and where it is merely polite.

Meeting Two: The CEO Becomes an Instigator

Several weeks after the first meeting — long enough for the plan to feel real, not so long that momentum fades — the CEO calls a second session. It has a single agenda item, framed as a question:

“Using the same logic we built together, how much faster could we realistically get there?”

The phrasing matters more than it might appear. This is not a demand for “twice the output in half the time” — the kind of arbitrary stretch target that produces creative accounting and quiet cynicism. It is an invitation to apply the team’s own reasoning to a compression problem. They set the destination and the pathway. Now they are being asked whether the chosen route is as efficient as it could be.

And because the team built the original logic, they are the only people positioned to answer the question credibly. They know which assumptions were conservative. They know where interdependencies between units create natural leverage — and where they create drag. They know which technologies on the industry’s horizon could compress a transition the plan assumed would take a decade. They know where the plan padded timelines because of organizational inertia rather than genuine constraint.

That collective intelligence almost never gets activated, because the question that unlocks it is almost never asked. Unfortunately, leaders tend to apply pressure before the team has built the logic, which means compression becomes a negotiation rather than an analysis. The two-meeting sequence reverses that order — and the difference in what the team produces is striking.

The best version of this second meeting doesn’t only produce a revised plan. It produces a set of credible acceleration options: specific conditions under which the timeline compresses, specific investments or decisions that could trigger those conditions, and an honest accounting of what would have to be true for the faster scenario to hold. The team leaves not just aligned, but strategically fluent in a way that one-off retreats almost never achieve.

Case in point: Before 2017, one of my clients in the Jamaican financial sector had never put a date to an assumption: “the average local customer is not ready for online services.”

When I challenged them to place a date on the moment when 50% of the population would reach that threshold, they predicted: 2028. They wove that date into their plan.

Three years later when the COVID-19 pandemic arrived, that plan was simply accelerated (i.e. compressed) to be implemented within months rather than a decade. They were lucky.

The Resilience Dividend

There is a benefit to this process that rarely appears in planning frameworks: the organization becomes significantly harder to surprise.

An executive team that has jointly built a long-range plan, surfaced its embedded assumptions, dated them, stress-tested scenarios, and explored acceleration options has essentially pre-thought a wide range of futures.

When the external environment forces their hand — a market disruption, a technology shift, a crisis that compresses years into months — they are not improvising. They are activating a version of something they already worked through. The decisions feel fast because they had already built the internal logic needed to respond.

This is not a theoretical benefit. Organizations routinely discover, under pressure, that their plans contained a faster path they simply hadn’t chosen to pursue yet. The companies best positioned to accelerate in a crisis are the ones that already knew, in principle, how acceleration was possible — because they had asked themselves exactly that question before one was forced on them.

The slow work of building shared logic, it turns out, is what makes rapid response possible. Resilience isn’t built in the crisis. It’s built in the room, in the meeting before the meeting, when the CEO is quiet enough to let the team think.

Why This Rarely Happens — and What to Do About It

The reason most aspirations which require long-term strategies end up stalling is that the people accountable for executing them never felt genuinely accountable for creating them. The CEO’s vision, however compelling, remains the CEO’s vision. Rollout becomes performance. Compliance replaces conviction. And when conditions change, there is no one in the room who feels responsible for updating the logic — because the logic was never theirs.

The two-meeting structure addresses this not through a motivational technique but through a structural one. Ownership is built in at the design stage. The compression question in the second meeting then activates that ownership, rather than challenging it.

The process asks something genuinely difficult of the CEO: to be quiet and patient at the moment when they most want to speak, and to ask a question — rather than issue an instruction — at the moment when they most want to apply pressure. Both moves feel counterintuitive. Both, consistently, work.

Begin with the meeting where you say less than you ever have before. What comes next will surprise you.

Use These LLM Prompts to Apply This Framework

Copy any of the following into an AI assistant to put the ideas in this article to work for your organization.

  1. Pressure-test your current strategy “Here is our current strategic plan: [paste or summarize]. Using the Rolling Wave principle from the article I just read, identify where our plan conflates short-, mid-, and long-term planning into a single approach. What assumptions are we treating as facts? Which ones should have a specific date attached to them?”
  2. Prepare for Meeting One “I am a CEO preparing to run a long-range planning session where my role is to facilitate, not lead. Our industry is [X]. Help me design a 3-hour agenda that guides my executive team to construct a 20-year aspiration themselves, without me imposing a conclusion. Include the questions I should ask — and the ones I should resist asking.”
  3. Surface your team’s hidden assumptions “Here are the key assumptions embedded in our strategy: [list them]. For each one, challenge me to convert it from an open-ended belief into a dated, falsifiable claim. Then identify which assumptions, if wrong, would most significantly change our direction or timeline.”
  4. Run the compression question “Here is a summary of our long-range plan: [paste summary]. Assume the logic is sound. Now help me identify: which parts of this plan are paced by genuine external constraints, and which are paced by internal inertia or conservative thinking? Where could the timeline realistically compress — and what would have to be true for that to happen?”
  5. Build your resilience map “Based on the strategic plan below [paste], identify the three to five external disruptions — technology shifts, market changes, regulatory moves — most likely to force an acceleration of our timeline. For each, describe what an already-prepared organization would do in the first 90 days, versus one that had never considered the scenario.”
Posted on

The Two Meetings That Turn Long-Term Strategy Into Motion

Most top executives can generate urgency around a quarterly target. The mechanisms are familiar: dashboards, deadlines, compensation levers. People move.

But ask those same executives to build genuine momentum toward a grand aspiration which needs a fifteen-year horizon, and something strange happens. They show up. They nod. They wait for the pressure to pass.

This isn’t insubordination. It’s a rational response to a broken process. And if you’ve ever led a strategic planning cycle that produced a polished document nobody touched again, you already know the symptom. The question is whether you’ve correctly diagnosed the cause.

The Real Problem Is Sequence, Not Ambition

CEOs who struggle to activate major aspirations or breakthrough results typically frame it as a people problem — their teams aren’t bold enough, disciplined enough, or strategically literate enough. Frequently, they apply pressure to fix the problem and become too directive. They hope their personal energy fills the void.

Perhaps just as often, they do the opposite and become too passive. In this mode they back off, hoping organic energy fills the void. It rarely does.

Neither framing is quite right. In the end, CEO’s migrate towards short-term goals because they don’t have a reliable way to maintain both short-, mid-, and long-term momentum.

The deeper issue is that most organizations try to do too much in a single planning meeting.

Effective accomplishment of all three phases at the same time requires two distinct meetings, held weeks apart, each demanding a different posture from the leader. Getting the sequence right changes what the plan is, who owns it, and how fast it can move.

Clarifying Misconceptions About Long Horizons

Before the two meetings make sense, two widespread beliefs need to be addressed:

the first is that long-range planning is inherently vague, and therefore not worth taking seriously.

Mistake 1) This is a problem for CEOs who truly have big aspirations, because long-range planning calls for the decades needed to make breakthrough goals realistic and credible to stakeholders. Without adequate time, executives play the game mentioned before. They show up, nod, and wait for the pressure to disappear.

This view of long-range planning being vague is understandable but technically wrong.

The planning tools appropriate for year one of a strategy are genuinely different from those suited to year twenty-five — but that doesn’t mean the far end of the horizon is a guess. It just needs to be equipped in the right way.

For example, the Rolling Wave Technique leads to the use of different methods, mindsets and discussions for short- and long-term phases. It provides operational details in the short term, and higher-altitude targets and milestones in the long term.

Neither end is more rigorous than the other. They are rigorous in different ways. The confusion exists because precious few use the technique. It’s just not taught in most business schools as a component of corporate strategy.

Mistake 2) The second faulty belief is that long-term aspirations don’t matter. To explain why this is so wrong, consider a historical example.

Medieval cathedral builders routinely committed to projects spanning two to three centuries. No individual craftsman who broke ground would see the finished nave. Yet construction continued across generations, through plagues and political upheaval, because the aspiration was large enough to give the work meaning — and specific enough to give it credible direction. Floor plans existed. Proportions were specified. Progress was measurable even when the endpoint was a lifetime away.

This points to a counterintuitive truth: the grander the ambition, the more likely it is to unlock discretionary effort — the creativity and energy people typically reserve for pursuits they actually care about.

Modest, short-term goals produce compliance. In corporate life, these tend to be overwhelmingly financial.

Transformative goals, properly constructed, produce ownership. The audacity of a well-chosen endpoint is itself a management tool, one that most corporations never pick up.

With these misconceptions cleared up, here are the details of both meetings and how they are conducted.

Meeting One: The CEO Goes Quiet

The first meeting has one non-negotiable design principle: the CEO sponsors but does not lead. Or facilitate.

This is harder than it sounds. Most executives who have reached the top of an organization have done so partly through the force of their vision. They arrive at planning sessions having already formed views about where the company should go. The instinct is to share those views early — to inspire the team with a compelling picture of the future and let the session fill in the details.

Resist it. Completely.

The goals of this first meeting are for the executive team to construct the long-range aspiration themselves and define the means to accomplish it. That means choosing a target year — somewhere between fifteen and thirty years out — and then building the assumptions, scenarios, and numbers required to define what success looks like at that point.

It’s followed by the use of the Rolling Wave Technique to lay out a plan for the entire horizon, with more details in closer than later years.

Facilitators can guide the process. The CEO’s role is to hold the space while that process unfolds, tolerating the discomfort of an outcome they did not pre-select and cannot entirely predict.

What makes this worthwhile is what it produces: genuine co-ownership. Every figure the team debated, they will later defend. Every scenario they stress-tested, they trust because they built it. A strategic target and plan defined by the CEO and handed to the team is a document. A strategy the team constructed is a commitment — and the difference shows up in execution, not in the planning room.

For example, one team member assumes a technology shift in five years. Another assumes fifteen. Both assumptions are driving their instincts about investment and timing, silently, in every meeting they attend. Naming those beliefs, debating them, and converting them into dated claims is one of the most underrated outputs of a well-run long-range planning session. It also reveals where the team’s consensus is genuine and where it is merely polite.

Meeting Two: The CEO Becomes an Instigator

Several weeks after the first meeting — long enough for the plan to feel real, not so long that momentum fades — the CEO calls a second session. It has a single agenda item, framed as a question:

“Using the same logic we built together, how much faster could we realistically get there?”

The phrasing matters more than it might appear. This is not a demand for “twice the output in half the time” — the kind of arbitrary stretch target that produces creative accounting and quiet cynicism. It is an invitation to apply the team’s own reasoning to a compression problem. They set the destination and the pathway. Now they are being asked whether the chosen route is as efficient as it could be.

And because the team built the original logic, they are the only people positioned to answer the question credibly. They know which assumptions were conservative. They know where interdependencies between units create natural leverage — and where they create drag. They know which technologies on the industry’s horizon could compress a transition the plan assumed would take a decade. They know where the plan padded timelines because of organizational inertia rather than genuine constraint.

That collective intelligence almost never gets activated, because the question that unlocks it is almost never asked. Unfortunately, leaders tend to apply pressure before the team has built the logic, which means compression becomes a negotiation rather than an analysis. The two-meeting sequence reverses that order — and the difference in what the team produces is striking.

The best version of this second meeting doesn’t only produce a revised plan. It produces a set of credible acceleration options: specific conditions under which the timeline compresses, specific investments or decisions that could trigger those conditions, and an honest accounting of what would have to be true for the faster scenario to hold. The team leaves not just aligned, but strategically fluent in a way that one-off retreats almost never achieve.

Case in point: Before 2017, one of my clients in the Jamaican financial sector had never put a date to an assumption: “the average local customer is not ready for online services.”

When I challenged them to place a date on the moment when 50% of the population would reach that threshold, they predicted: 2028. They wove that date into their plan.

Three years later when the COVID-19 pandemic arrived, that plan was simply accelerated (i.e. compressed) to be implemented within months rather than a decade. They were lucky.

The Resilience Dividend

There is a benefit to this process that rarely appears in planning frameworks: the organization becomes significantly harder to surprise.

An executive team that has jointly built a long-range plan, surfaced its embedded assumptions, dated them, stress-tested scenarios, and explored acceleration options has essentially pre-thought a wide range of futures.

When the external environment forces their hand — a market disruption, a technology shift, a crisis that compresses years into months — they are not improvising. They are activating a version of something they already worked through. The decisions feel fast because they had already built the internal logic needed to respond.

This is not a theoretical benefit. Organizations routinely discover, under pressure, that their plans contained a faster path they simply hadn’t chosen to pursue yet. The companies best positioned to accelerate in a crisis are the ones that already knew, in principle, how acceleration was possible — because they had asked themselves exactly that question before one was forced on them.

The slow work of building shared logic, it turns out, is what makes rapid response possible. Resilience isn’t built in the crisis. It’s built in the room, in the meeting before the meeting, when the CEO is quiet enough to let the team think.

Why This Rarely Happens — and What to Do About It

The reason most aspirations which require long-term strategies end up stalling is that the people accountable for executing them never felt genuinely accountable for creating them. The CEO’s vision, however compelling, remains the CEO’s vision. Rollout becomes performance. Compliance replaces conviction. And when conditions change, there is no one in the room who feels responsible for updating the logic — because the logic was never theirs.

The two-meeting structure addresses this not through a motivational technique but through a structural one. Ownership is built in at the design stage. The compression question in the second meeting then activates that ownership, rather than challenging it.

The process asks something genuinely difficult of the CEO: to be quiet and patient at the moment when they most want to speak, and to ask a question — rather than issue an instruction — at the moment when they most want to apply pressure. Both moves feel counterintuitive. Both, consistently, work.

Begin with the meeting where you say less than you ever have before. What comes next will surprise you.

Use These LLM Prompts to Apply This Framework

Copy any of the following into an AI assistant to put the ideas in this article to work for your organization.

  1. Pressure-test your current strategy “Here is our current strategic plan: [paste or summarize]. Using the Rolling Wave principle from the article I just read, identify where our plan conflates short-, mid-, and long-term planning into a single approach. What assumptions are we treating as facts? Which ones should have a specific date attached to them?”
  2. Prepare for Meeting One “I am a CEO preparing to run a long-range planning session where my role is to facilitate, not lead. Our industry is [X]. Help me design a 3-hour agenda that guides my executive team to construct a 20-year aspiration themselves, without me imposing a conclusion. Include the questions I should ask — and the ones I should resist asking.”
  3. Surface your team’s hidden assumptions “Here are the key assumptions embedded in our strategy: [list them]. For each one, challenge me to convert it from an open-ended belief into a dated, falsifiable claim. Then identify which assumptions, if wrong, would most significantly change our direction or timeline.”
  4. Run the compression question “Here is a summary of our long-range plan: [paste summary]. Assume the logic is sound. Now help me identify: which parts of this plan are paced by genuine external constraints, and which are paced by internal inertia or conservative thinking? Where could the timeline realistically compress — and what would have to be true for that to happen?”
  5. Build your resilience map “Based on the strategic plan below [paste], identify the three to five external disruptions — technology shifts, market changes, regulatory moves — most likely to force an acceleration of our timeline. For each, describe what an already-prepared organization would do in the first 90 days, versus one that had never considered the scenario.”
Posted on

The Two Meetings That Turn Long-Term Strategy Into Motion

Most top executives can generate urgency around a quarterly target. The mechanisms are familiar: dashboards, deadlines, compensation levers. People move.

But ask those same executives to build genuine momentum toward a grand aspiration which needs a fifteen-year horizon, and something strange happens. They show up. They nod. They wait for the pressure to pass.

This isn’t insubordination. It’s a rational response to a broken process. And if you’ve ever led a strategic planning cycle that produced a polished document nobody touched again, you already know the symptom. The question is whether you’ve correctly diagnosed the cause.

The Real Problem Is Sequence, Not Ambition

CEOs who struggle to activate major aspirations or breakthrough results typically frame it as a people problem — their teams aren’t bold enough, disciplined enough, or strategically literate enough. Frequently, they apply pressure to fix the problem and become too directive. They hope their personal energy fills the void.

Perhaps just as often, they do the opposite and become too passive. In this mode they back off, hoping organic energy fills the void. It rarely does.

Neither framing is quite right. In the end, CEO’s migrate towards short-term goals because they don’t have a reliable way to maintain both short-, mid-, and long-term momentum.

The deeper issue is that most organizations try to do too much in a single planning meeting.

Effective accomplishment of all three phases at the same time requires two distinct meetings, held weeks apart, each demanding a different posture from the leader. Getting the sequence right changes what the plan is, who owns it, and how fast it can move.

Clarifying Misconceptions About Long Horizons

Before the two meetings make sense, two widespread beliefs need to be addressed:

the first is that long-range planning is inherently vague, and therefore not worth taking seriously.

Mistake 1) This is a problem for CEOs who truly have big aspirations, because long-range planning calls for the decades needed to make breakthrough goals realistic and credible to stakeholders. Without adequate time, executives play the game mentioned before. They show up, nod, and wait for the pressure to disappear.

This view of long-range planning being vague is understandable but technically wrong.

The planning tools appropriate for year one of a strategy are genuinely different from those suited to year twenty-five — but that doesn’t mean the far end of the horizon is a guess. It just needs to be equipped in the right way.

For example, the Rolling Wave Technique leads to the use of different methods, mindsets and discussions for short- and long-term phases. It provides operational details in the short term, and higher-altitude targets and milestones in the long term.

Neither end is more rigorous than the other. They are rigorous in different ways. The confusion exists because precious few use the technique. It’s just not taught in most business schools as a component of corporate strategy.

Mistake 2) The second faulty belief is that long-term aspirations don’t matter. To explain why this is so wrong, consider a historical example.

Medieval cathedral builders routinely committed to projects spanning two to three centuries. No individual craftsman who broke ground would see the finished nave. Yet construction continued across generations, through plagues and political upheaval, because the aspiration was large enough to give the work meaning — and specific enough to give it credible direction. Floor plans existed. Proportions were specified. Progress was measurable even when the endpoint was a lifetime away.

This points to a counterintuitive truth: the grander the ambition, the more likely it is to unlock discretionary effort — the creativity and energy people typically reserve for pursuits they actually care about.

Modest, short-term goals produce compliance. In corporate life, these tend to be overwhelmingly financial.

Transformative goals, properly constructed, produce ownership. The audacity of a well-chosen endpoint is itself a management tool, one that most corporations never pick up.

With these misconceptions cleared up, here are the details of both meetings and how they are conducted.

Meeting One: The CEO Goes Quiet

The first meeting has one non-negotiable design principle: the CEO sponsors but does not lead. Or facilitate.

This is harder than it sounds. Most executives who have reached the top of an organization have done so partly through the force of their vision. They arrive at planning sessions having already formed views about where the company should go. The instinct is to share those views early — to inspire the team with a compelling picture of the future and let the session fill in the details.

Resist it. Completely.

The goals of this first meeting are for the executive team to construct the long-range aspiration themselves and define the means to accomplish it. That means choosing a target year — somewhere between fifteen and thirty years out — and then building the assumptions, scenarios, and numbers required to define what success looks like at that point.

It’s followed by the use of the Rolling Wave Technique to lay out a plan for the entire horizon, with more details in closer than later years.

Facilitators can guide the process. The CEO’s role is to hold the space while that process unfolds, tolerating the discomfort of an outcome they did not pre-select and cannot entirely predict.

What makes this worthwhile is what it produces: genuine co-ownership. Every figure the team debated, they will later defend. Every scenario they stress-tested, they trust because they built it. A strategic target and plan defined by the CEO and handed to the team is a document. A strategy the team constructed is a commitment — and the difference shows up in execution, not in the planning room.

For example, one team member assumes a technology shift in five years. Another assumes fifteen. Both assumptions are driving their instincts about investment and timing, silently, in every meeting they attend. Naming those beliefs, debating them, and converting them into dated claims is one of the most underrated outputs of a well-run long-range planning session. It also reveals where the team’s consensus is genuine and where it is merely polite.

Meeting Two: The CEO Becomes an Instigator

Several weeks after the first meeting — long enough for the plan to feel real, not so long that momentum fades — the CEO calls a second session. It has a single agenda item, framed as a question:

“Using the same logic we built together, how much faster could we realistically get there?”

The phrasing matters more than it might appear. This is not a demand for “twice the output in half the time” — the kind of arbitrary stretch target that produces creative accounting and quiet cynicism. It is an invitation to apply the team’s own reasoning to a compression problem. They set the destination and the pathway. Now they are being asked whether the chosen route is as efficient as it could be.

And because the team built the original logic, they are the only people positioned to answer the question credibly. They know which assumptions were conservative. They know where interdependencies between units create natural leverage — and where they create drag. They know which technologies on the industry’s horizon could compress a transition the plan assumed would take a decade. They know where the plan padded timelines because of organizational inertia rather than genuine constraint.

That collective intelligence almost never gets activated, because the question that unlocks it is almost never asked. Unfortunately, leaders tend to apply pressure before the team has built the logic, which means compression becomes a negotiation rather than an analysis. The two-meeting sequence reverses that order — and the difference in what the team produces is striking.

The best version of this second meeting doesn’t only produce a revised plan. It produces a set of credible acceleration options: specific conditions under which the timeline compresses, specific investments or decisions that could trigger those conditions, and an honest accounting of what would have to be true for the faster scenario to hold. The team leaves not just aligned, but strategically fluent in a way that one-off retreats almost never achieve.

Case in point: Before 2017, one of my clients in the Jamaican financial sector had never put a date to an assumption: “the average local customer is not ready for online services.”

When I challenged them to place a date on the moment when 50% of the population would reach that threshold, they predicted: 2028. They wove that date into their plan.

Three years later when the COVID-19 pandemic arrived, that plan was simply accelerated (i.e. compressed) to be implemented within months rather than a decade. They were lucky.

The Resilience Dividend

There is a benefit to this process that rarely appears in planning frameworks: the organization becomes significantly harder to surprise.

An executive team that has jointly built a long-range plan, surfaced its embedded assumptions, dated them, stress-tested scenarios, and explored acceleration options has essentially pre-thought a wide range of futures.

When the external environment forces their hand — a market disruption, a technology shift, a crisis that compresses years into months — they are not improvising. They are activating a version of something they already worked through. The decisions feel fast because they had already built the internal logic needed to respond.

This is not a theoretical benefit. Organizations routinely discover, under pressure, that their plans contained a faster path they simply hadn’t chosen to pursue yet. The companies best positioned to accelerate in a crisis are the ones that already knew, in principle, how acceleration was possible — because they had asked themselves exactly that question before one was forced on them.

The slow work of building shared logic, it turns out, is what makes rapid response possible. Resilience isn’t built in the crisis. It’s built in the room, in the meeting before the meeting, when the CEO is quiet enough to let the team think.

Why This Rarely Happens — and What to Do About It

The reason most aspirations which require long-term strategies end up stalling is that the people accountable for executing them never felt genuinely accountable for creating them. The CEO’s vision, however compelling, remains the CEO’s vision. Rollout becomes performance. Compliance replaces conviction. And when conditions change, there is no one in the room who feels responsible for updating the logic — because the logic was never theirs.

The two-meeting structure addresses this not through a motivational technique but through a structural one. Ownership is built in at the design stage. The compression question in the second meeting then activates that ownership, rather than challenging it.

The process asks something genuinely difficult of the CEO: to be quiet and patient at the moment when they most want to speak, and to ask a question — rather than issue an instruction — at the moment when they most want to apply pressure. Both moves feel counterintuitive. Both, consistently, work.

Begin with the meeting where you say less than you ever have before. What comes next will surprise you.

Use These LLM Prompts to Apply This Framework

Copy any of the following into an AI assistant to put the ideas in this article to work for your organization.

  1. Pressure-test your current strategy “Here is our current strategic plan: [paste or summarize]. Using the Rolling Wave principle from the article I just read, identify where our plan conflates short-, mid-, and long-term planning into a single approach. What assumptions are we treating as facts? Which ones should have a specific date attached to them?”
  2. Prepare for Meeting One “I am a CEO preparing to run a long-range planning session where my role is to facilitate, not lead. Our industry is [X]. Help me design a 3-hour agenda that guides my executive team to construct a 20-year aspiration themselves, without me imposing a conclusion. Include the questions I should ask — and the ones I should resist asking.”
  3. Surface your team’s hidden assumptions “Here are the key assumptions embedded in our strategy: [list them]. For each one, challenge me to convert it from an open-ended belief into a dated, falsifiable claim. Then identify which assumptions, if wrong, would most significantly change our direction or timeline.”
  4. Run the compression question “Here is a summary of our long-range plan: [paste summary]. Assume the logic is sound. Now help me identify: which parts of this plan are paced by genuine external constraints, and which are paced by internal inertia or conservative thinking? Where could the timeline realistically compress — and what would have to be true for that to happen?”
  5. Build your resilience map “Based on the strategic plan below [paste], identify the three to five external disruptions — technology shifts, market changes, regulatory moves — most likely to force an acceleration of our timeline. For each, describe what an already-prepared organization would do in the first 90 days, versus one that had never considered the scenario.”
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The AI Assistant: Automating Administrative Friction and “Shadow Work”

In this episode, we’re discussing how to use AI to automate "shadow work", the boring, repetitive tasks like data entry and invoicing that drain our energy. By viewing AI as a "million interns" that need clear instructions and human supervision, the hosts share how to streamline everything from professional billing to personal life choices like cooking and movies. While AI can sometimes make mistakes or "hallucinate," the episode explains that investing time in training your AI assistant can remove administrative friction and help you focus on the work that actually matters. (If you’re reading this in a podcast directory/app, please visit https://productivitycast.net/147 for clickable links and the full show notes and transcript of this cast.) Enjoy! Give us feedback! And, thanks for listening! If you'd like to continue discussing The AI Assistant: Automating Administrative Friction and "Shadow Work" from this episode, please click here to leave a comment down below (this jumps you to the bottom of the post). In this Cast | The AI Assistant: Automating Administrative Friction and "Shadow Work" Ray Sidney-Smith Augusto Pinaud Art Gelwicks Francis Wade Show Notes | The AI Assistant: Automating Administrative Friction and "Shadow Work" Resources we mention, including links to them, will be provided here. Please listen to the episode for context. "Deep Work" and "Shallow Work" by Cal Newport Flow Theory by Dr. Mihaly Csikszentmihalyi Personal Productivity Club Raw Text Transcript Raw, unedited and machine-produced text transcript so there may be substantial errors, but you can search for specific points in the episode to jump to, or to reference back to at a later date and time, by keywords or key phrases. The time coding is mm:ss (e.g., 0:04 starts at 4 seconds into the cast’s audio). Read More Voiceover Artist | 00:00 Are you ready to manage your work and personal world better to live a more fulfilling, productive life? Then you've come to the right place. Welcome to ProductivityCast, the weekly show about all things personal productivity. Here are your hosts, Ray Sidney Smith and Augusto Pinault with Frances Wade and Art Gelwix. Raymond Sidney-Smith | 00:18 Welcome everybody to productivity cast the weekly show about all things personal productivity. I'm Ray Sidney Smith. Francis Wade | 00:25 And I'm Francis Wade. Raymond Sidney-Smith | 00:28 Welcome, gentlemen, and welcome, everyone. To ProductivityCast this week. We're diving into the world of artificial intelligence and its growing role in our personal productivity. This is going to be a part of an ongoing series we're calling the AI-powered professional. And in today's episode, we'll be exploring how AI tools are moving beyond simple task management to tackle tedious shadow work, things like administrative friction, small repetitive tasks, and context switching overhead that drains our time and energy. And so we're going to talk about how to approach shadow work with AI, how to overcome the problem, and we can talk about some of the solutions that we have utilized throughout the So let's get into this. Raymond Sidney-Smith | 01:13 Episode. Raymond Sidney-Smith | 01:16 And first, let's spend a little bit of time talking about what exactly is administrative friction and shadow work. Does anybody want to kind how they... Raymond Sidney-Smith | 01:26 Of tackle. Raymond Sidney-Smith | 01:28 Perceive what shadow work or administrative friction is. Francis Wade | 01:32 Sure, it's the stuff that I have to do to Execute the day. So it tends to be repetitive stuff. I don't have a choice. I must do it. No one else can do it. Typically, or I could train someone to do some of it, but most of it It's not worth training someone else to do it because there's probably some nuance that only I know. I see these things as a bit of a tax in the sense that In order to achieve your overall objectives, you have to do them. And yes, if you can get them automated, "Polite you, but point is that they're mandatory, they're required, and you don't have a choice.  So I know how I feel when I'm doing them because my heart sinks and my energy drops and I go through a whole metamorphosis into someone who wishes he were doing something else. So that's an emotional Sugar for me. Or a Marco. Augusto Pinaud | 02:34 You know, for me, the shadow work is all that work that is required to do to really be able to focus on being productive. And I'm dead. And the reason is, as Francis was saying, it's normally it's not the fun work. Okay. But it's the fun, it's the work that you need to do. To be able to get to that fun work to get to that. Work in which you can really focus and you can shine. And Us bored. As tedious That's it is. It's critical to be able to get a good session of productivity. Raymond Sidney-Smith | 03:13 Yeah. Cal Newport defines his concept of Shallow work. As I think what we think of as what we call shadow work. And so there's this concept of often performed while you're doing other things and doesn't create a lot of value. And I've always had a problem with the concept of shallow work and deep work. I think that those definitions, deep work being high value, items that you're highly focused on just really sounds like flow work to me. And so, but I define flow work, of course, the way that Dr. Mihaly Csikszentmihalyi talks about it. And The goal here is to really look at this from a lens of if we're doing all of this administrative work, I think that there is some great value to some of it. As I typically use the example that you could have a five minute phone call and have a client say, let's sign the million dollar contract. Right. Was the five minute phone call worth it? Absolutely. And some people would consider that an administrative issue. Burden, right? That would be administrative friction having to take and have that five minute phone call.  So we have to kind of parse apart those things that are high value and don't take a lot of time. Those things that are low value and take little bits of time or lots of time, each of which are kind of problematic in their own way.  And then being able to overcome those through various mechanisms. Artificial intelligence is just one of them.  So we have to be mindful that what we're talking about here today is just one of the ways in which you can overcome this. But I don't think that AI ultimately becomes the panacea. It is just one option that you have among many for being able to overcome these kinds of issues. Couple things that I wanted to kind of talk about here is that I think that Data entry generally is administrative friction and is a classic type of shadow work that you can think of. And Honestly, data entry is what computers were built for.  You know, the whole concept of being able to take data and run calculations or structure it in a way I think is the archetypal form of shallow, shadow work. Francis Wade | 05:50 The data entry I have an intern that works with me or an associate who works with me and She was doing an entry job And I thought about it for a minute, because she was not enjoying it. And I said, It's one of those, again, it's one of those taxes that at some point you've got to pay because We all have to enter data at some point. And we'll try all our best to not have to do it. But again, it's one of those sinking feelings that after you thought of everything and you realize that at the end of all your thinking, you still have to enter the data. There's no shortcut available. You got to do it. And I entered I remember. , entering data early in There's a way to it. Into data and I was trying to share this with her That's more skillful. Because you're paying attention to what you're doing. You're not checking out to the point where you're making mistakes. And at the same time, you're taking care of your well-being.  So you're not engaging in conversations that are dragging you downhill and getting you depressed. That there's a way you have to manage your mind. And manage your attention. To do good data entry so that you don't do nonsense.  So it's actually, I tried to paint this picture for her. It's actually a skill. That Once you have it, you can always Do it. Use it. But it's not a skill to... Resist in the sense that you wish it weren't there. It actually has so much, sometimes the data has so much value, that you need to bring your best skills to your data entry.  So that you don't end up resisting it. You don't end up resenting it. And you don't end up making mistakes so it's a skill in and of itself. And funnily enough, after I gave her this, very inspirational explanation. I ended up spending It must have been at least six hours entering data. There was no way. I was yeah. And I actually did some automation. I did a little lab coding to kind of speed it up. But that could only get me so far. But not go any further. And I thought, I'm eating my own dog food, taking my own medicine. But I agree. Raymond Sidney-Smith | 08:19 Yeah, I'll say this. There are so many ways to ease the burden of data entry. Again, it's about the ways in which input and output in computer communication in human-computer interaction that we just don't think about.  So, you know, Our input options for a device are typically in an input perspective. There's audio, right? You can put audio through a microphone into it, which is what we're doing right now, recording the podcast.  And then there's video, having the device take in video. Or images and then of course mouse and keyboard and if you have a touch screen or a touchpad like a Wacom board, you're capable of putting in some kind of handwriting or hand drawing some kind of, you know, stylus type input or touch inputs into the device....
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What Does Perspective Mean in GTD?

In this episode, we're discussing the concept of perspective as a contrast to the GTD concept of control. We explore the "Horizons of Focus" and the different altitudes of self-management, ranging from the "runway" of daily actions to the "50,000-foot" level of life purpose. We debate whether perspective is a tactical relationship or a pseudonym for context while contrasting top-down visioning with bottom-up execution. From discussing the "elasticity" needed in planning to identifying incongruencies between our values and our careers, we explore how these various layers of focus can transform mundane tasks into meaningful progress toward a fulfilling life. (If you’re reading this in a podcast directory/app, please visit https://productivitycast.net/146 for clickable links and the full show notes and transcript of this cast.) Enjoy! Give us feedback! And, thanks for listening! If you'd like to continue discussing what perspective means in the context of GTD from this episode, please click here to leave a comment down below (this jumps you to the bottom of the post). In this Cast | What Does Perspective Mean in GTD? Ray Sidney-Smith Augusto Pinaud Art Gelwicks Francis Wade Show Notes | What Does Perspective Mean in GTD? Resources we mention, including links to them, will be provided here. Please listen to the episode for context. Getting Things Done by David Allen The 8th Habit by Dr. Stephen Covey Unlimited Power by Tony Robbins Tony Robbins Audio Programs GTD "Horizons of Focus" Model Personal Productivity Club Raw Text Transcript | What Does Perspective Mean in GTD? Raw, unedited and machine-produced text transcript so there may be substantial errors, but you can search for specific points in the episode to jump to, or to reference back to at a later date and time, by keywords or key phrases. The time coding is mm:ss (e.g., 0:04 starts at 4 seconds into the cast’s audio). Read More Voiceover Artist | 00:00 Are you ready to manage your work and personal world better to live a more fulfilling, productive life? Then you've come to the right place. Welcome to ProductivityCast, the weekly show about all things personal productivity. Here are your hosts, Ray Sidney Smith and Augusto Pinot with Francis Wade and Art Gelwix. Raymond Sidney-Smith | 00:18 Welcome back, everybody, to Productivity Cast, the weekly show about all things personal productivity. I'm Ray Sidney Smith. Augusto Pinaud | 00:24 And I'm Augusto Pinaud. Francis Wade | 00:26 I'm Francis Wade. Art Gelwicks | 00:28 And I'm Art Gelwicks. Raymond Sidney-Smith | 00:29 Welcome, gentlemen, and welcome to our listeners to this week's episode. Today, we are going to be talking about perspectives as a contrast to last week's episode on the GTD concept of control.  So in order to start off the conversation, I want to lay the groundwork with perspectives. The Getting Things Done March 2015 edition appendixes. Glossary of terms definition given for perspective. And it says, one of the two key elements of self and organizational management, along with control, and it refers to point of view, focus, altitude of horizon. We have this concept of horizons of focus in getting things done. And what I'm hearing from the definition is that David Allen is saying that each one of those horizons of focus is a perspective. That's what the terminology is talking about. And so with that in mind, I wanted to ask, Is. Perspective the right term? And what does perspective mean to you in your own. Francis Wade | 01:33 My mind perspective is a pseudonym for context. And as someone smart said, context is decisive. The background story from which you take your actions is all important. And it's malleable. And most of us just wake up into the context that human beings wake up into every day, which is something close to survival. Survival, desperation, fear, you know, how can I make it through the day kind of, point of view. I think that's the default.  And then to Create a new context, tics. Or any perspective takes. Conscious act for the most part conscious action it takes deliberate effort. I think this is all important. I think the book GT is really about that. And perspectives is one way of seeing it. I think this idea that... The context of your life is decisive is an idea that's been around probably since the Greeks. And that's something worth paying attention to.  So yes, it's vitally important. Art Gelwicks | 02:41 What I think is interesting about this looking at perspective and how it breaks down is that often perspective is not related to ourselves. If you look at the GTD structure you've got, and I'll work from the bottom up, Actions, Projects, Goals, Vision, Life The first four of those categories are often... Stolen for lack of a better term by corporate and work environments. To set the messaging. For everything that you're supposed to be doing and that becomes the context, for lack of a better term, that those get applied in. It's difficult for us to translate goals, vision and life into actual real life things, because every time we think about it, we think about, you know, the next five year plan at work.  So... If we think about it from the perspective of how they relate to each other, perspectives in my book, are pretty much whatever you're dealing with and the thing above and the thing below it.  So projects is a good example. If you're working on projects, The projects need to align to the strategic goals that you have. If it's business, obviously you have business strategic goals. If it's personal goals, The things that you're doing should align to those. You have to determine what those are, but they should be tied to it. And below that, the actions necessary to execute those projects.  So the perspective is less... What the term would lend me to believe, which is a view on things and more of a relationship. Raymond Sidney-Smith | 04:27 I certainly see perspectives for me. As a vertical planning tool. And so each of the additional perspectives above the actions level or the ground level in at least GTD lingo, you are seeing a different and therefore you were planning at a different time. "layer of time" So it's for me, I always think of time horizons is that, you know, projects are within our time bound within about a year and then you keep stepping up to further and further distances of time. Accepting the horizon too, which is areas of focus and accountability, which ends up being something that is it's a maintenance level.  So, While each of the time horizons keep going up in that sense, Horizon 2 is the exception there because it's maintenance. It's ongoing maintenance. And if you're like me and you've created other horizons, other perspectives, then you may have other time horizons in that sense as well. They're not going away. And so that has an infinite horizon in essence.  So I'm looking at it on a regular basis purely because it's perennial. It's always going to be there. The interesting thing about perspectives for me is that I think that there is a clear... I don't know if I want to say contrast or argument between other systems, other methodologies, other thought processes on this and perspectives. I'll give you one example, which is Dr. Stephen Covey's The Eighth Habit, where he talks about the concept of the four intelligences. And if... Control and perspective are really the only two vectors of a productivity system, then Where does something like the four intelligences fit. And I would say that Dr. Covey would say that this is perhaps a completely different dimension.  You know, the four intelligences being mental intelligence or IQ, physical intelligence, PQ, emotional intelligence, EQ, and spiritual intelligence, SQ. And so he has this perspective on the four intelligences and how they map to all of the rest of how you would develop in his language, you know, finding your voice and helping others find theirs. And so I'm always... I don't know if I'm conflicted because I have myself learned to deal with where these things fit in my own system. But I can see that there can be a difficulty for folks to think about how Picking. IQ, PQ, EQ, SQ, and turning that into vision, discipline, passion, and conscience in the eighth habit world, and then seeing the somewhat limited I wouldn't say limited, but more simplistic view of the perspective concept. And I'm curious from all of you, Do you see a conflict or do you see... Perspective is just basically holding other I. Art Gelwicks | 07:38 Think perspectives are a more tactical term. Approach. They're more tangible. We associate them with things and activities that we have going on. Stephen Covey's concepts are more to understand people. I want to say spheres of influence. I don't know that they necessarily relate directly to each other. There is no dotted line. It is difficult at best. To translate. For example, projects into mental intelligence, you're not going to be able to make that connection easily without it stopping. Significant amount of work. Raymond Sidney-Smith | 08:18 Yeah, but to interject right there, like, so if we step up a few horizons and we get to vision and purpose and principles, then we're really starting to connect. The concepts of what he's talking about there at the very top levels of the system.  So it's not really closer to the tactical level, but more when he starts talking about, you know, creating vision, right, which he defines kind of as applied imagination. And then he we keep stepping down to these other, not stepping down, but going around the four quadrants, right? To figure out passion and discipline and conscious and otherwise.  So it's, At those upper horizons, it starts to bleed over one another. I.
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What Does in Control Mean in GTD?

In this episode we’re discussing the concept at the core of personal management: control. Specifically, we’ll be philosophizing about what control truly means within the context of the Getting Things Done (GTD) methodology. We’ll start with David Allen’s definition, which ties control to the workflow stages of capturing, clarifying, organizing, reflecting, and engaging. But does that definition fully capture the complex, often psychological, reality of feeling “in control”? Then, we explore how to build tangible systems and “guardrails” that move us from simply feeling overwhelmed to being confidently in command of our work and personal lives.

(If you’re reading this in a podcast directory/app, please visit https://productivitycast.net/145 for clickable links and the full show notes and transcript of this cast.)

Enjoy! Give us feedback! And, thanks for listening!

If you’d like to continue discussing what control means in the context of GTD from this episode, please click here to leave a comment down below (this jumps you to the bottom of the post).

In this Cast | What Does Control Mean in GTD?

Ray Sidney-Smith

Augusto Pinaud

Art Gelwicks

Francis Wade

Show Notes | What Does Control Mean in GTD?

Resources we mention, including links to them, will be provided here. Please listen to the episode for context.

Getting Things Done (GTD) by David Allen

How to Get Control of Your Time in Your Life by Alan Lakein

Freedom.to (A Focus application used to block digital distractions)

Fitbit watch (Used to track sleep)

Byron Katie’s process (A methodology for managing unwanted thoughts or feelings)

Raw Text Transcript

Raw, unedited and machine-produced text transcript so there may be substantial errors, but you can search for specific points in the episode to jump to, or to reference back to at a later date and time, by keywords or key phrases. The time coding is mm:ss (e.g., 0:04 starts at 4 seconds into the cast’s audio).

Read More

Voiceover Artist | 00:00

Are you ready to manage your work and personal world better to live a more fulfilling, productive life? Then you’ve come to the right place. Welcome to ProductivityCast, the weekly show about all things personal productivity. Here are your hosts, Ray Sidney-Smith and Augusto Pinaud with Francis Wade and Art Gelwicks.

Raymond Sidney-Smith | 00:19

Welcome back, everybody, to ProductivityCast, the weekly show about all things personal productivity. I’m Ray Sidney-Smith.

Augusto Pinaud | 00:25

And I’m Augusto Pinaud.

Francis Wade | 00:26

I’m Francis Wade.

Art Gelwicks | 00:28

And I’m Art Gelwicks.

Raymond Sidney-Smith | 00:29

Welcome, gentlemen, and welcome to our listeners to this episode. Today, we are going to do some philosophizing, I suppose, and hopefully bringing ourselves from that level down to the practical. We’re going to be talking about control. And what I wanted to do was to preface this with The concept of control and perspective in the Getting Things Done or GTD methodology perspective, which is that that’s where came up to me in the first place. And over the years, it has changed. And so I want to talk about what does control mean to each of us and how do we actually make the concept of control practical even tangible in our own worlds. I’m going to define what David Allen says of control in Getting Things Done in the March 2015 edition, in the appendix, in the glossary of Getting Things Done terms, he actually gives a definition for control And then we’re going to talk a little bit about what, the concept of GTD control is so that we can then define what We think of it as in contrasting terms. 

So he says of control, one of the two key elements of self and organizational management along with perspective. And so that’s what he calls control in the most basic terms. And if we think about it from the concept of control and perspective, control are the steps of the or stages of the workflow going from capturing to clarifying to organizing, reflecting and engaging on the action level of the horizons of focus. That is what he considers control. 

And then as we go up the horizons on the y-axis, we then have projects and so on and so forth going up the horizons. And that’s what he considers perspective. 

So control are the actions that we take on the lowest level of the horizons of focus and everything above that becomes perspective. So kind of thinking of it as looking down at the actionability of the thing above itself. 

So when you’re at the highest level, Horizon 5 purpose and principle You are looking down at the other’s vision, goals, areas of focus and accountability, projects, and actions. So that is the GTD definition. And… We have all probably thought of it as being insufficient in some way, shape or form in our own worlds. And now what I’d like to do is to ask you all, gentlemen. How do you define control? And what is… If I think Art gave a really great example before we started recording, if someone came to you and said, I’m feeling out of control, how do you help them get in control or under control in their life?

Francis Wade | 03:10

So I think David Allen’s definition is basically a process definition. So he’s saying, here are the steps. Or managing tasks. And the ones that really start with capturing and so forth are basically the steps for managing tasks. And I suppose that I’m guessing that what he means by control is that the… Process of managing tasks is in control. Now, that has a very specific meaning in my world. I was trained in part as an industrial engineer. And we love For those of you who know the Leningrad-Stewart charts and control charts, we love the idea of measuring processes so that they stay in control. That’s not practical for most people to be able to use these kind of diagnostic tools. But the way I would advise to answer your question, Reem, someone who tells me that they’re out of control… Is to ask them What do you mean? Because the word control is a psychological object The definition has changed and it varies and there’s no uniform. Understanding of what it means. 

So you have to go to the next step and say, When you say control, the question I would ask is when you say control, What specifically? Symptoms are the ones that you notice and I would imply in real life. Not just in your emotional life, but in The Hard Tensible Life where are those symptoms occurring? Such that you’re led to conclude that you’re feeling out of control. 

So I would immediately go to and I would focus and start to break down their response. Between I’ve mentioned psychological objects like I’m feeling stressed, I’m feeling unhappy, I’m feeling unworthy, I’m feeling lazy. As opposed to I arrive at half of my appointments at least ten minutes late. Okay, there we go. That’s one. That’s a tangible object. We can work with that. What else do you have? Well… I wake up in the middle of the night three times out of the week. With something that I forgot to do. That’s two. All right, that’s another tangible activity. 

So I would look for the tangible symptoms. The things that you can put your finger on, you can touch, you can see. 

And then accumulate those so that we move the conversation from and feeling out of control. Towards And again, in the lingo of industrial engineers is defects. We’re looking for defects. And we’re looking to put them together so that we can say, okay, with these five defects, the root cause of them are Because the truth is, control is a lag indicator. Peely Walter Control is a lag indicator. Comes a lot after. The things that you Did or didn’t do. 

So we’re trying to go all the way back so that When we start to… Figure out what they should do, We’re actually looking at things that they did do or need to do or didn’t do. In tangible reality. 

So that’s how I would tackle it. Said that to me.

Art Gelwicks | 06:21

Control to me is a very… Unlike the industrial… Definition of it. I look at it from the almost the psychological side of it. Control is a perceived state of comfort It’s a lack of stress. It’s a… Point of awareness. Of activity And I think when someone says they are out of control, my first reaction is to ask the question, When do you feel things went out of control. Because I need to know contextually Is this something that is a recurring feeling, which means that it is probably systemic. To a process failure Or is it something that has recently happened, which may be triggered by an environmental response or some external factor that has pushed things off the rails? But control itself like a, can be an extremely negative impact. On work and process and quality of work. Having a sense of control. I don’t know is necessarily an extremely positive thing. It’s basically neutral. You feel like, okay, if I’m in control, I can do… What I need to do. If I’m out of control, I can’t do what I need to do. But at no point are we saying that if I’m in control, I can do better things. I’m just saying that I can do things. 

So to me, I always look at it from the mental aspect of it more than the process one, because The process one I can chase. I mean, I can look at the measures. I can look at the metrics involved and say, OK, this is working. This isn’t this. But that doesn’t necessarily, again, translate to a lack of control. And we’ve all seen it. We’ve had people who have processes that work somewhat. But they feel like they are in control, but we know looking at it, it’s like, no, you’re not. As much as you think you are, you’re careening wildly down the highway. 

So… The subjectivity of that term and the amorphousness of that term makes it difficult to have that initial conversation.

Raymond Sidney-Smith | 08:49

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Procrastination Versus Conscious Deferral, Part 2

In this episode of ProductivityCast, we continue our deep dive into the psychological and tactical differences between stalling out and stepping back. While Part 1 focused on defining the core constructs of procrastination and conscious deferral, Part 2 moves into the "why" and the "how." (If you’re reading this in a podcast directory/app, please visit https://productivitycast.net/144 for clickable links and the full show notes and transcript of this cast.) Enjoy! Give us feedback! And, thanks for listening! If you'd like to continue discussing the concepts of procrastination, conscious deferral and/or unconscious deferral from this episode, please click here to leave a comment down below (this jumps you to the bottom of the post). In this Cast | Procrastination vs Conscious Deferral Ray Sidney-Smith Augusto Pinaud Art Gelwicks Francis Wade Show Notes | Procrastination vs Conscious Deferral Resources we mention, including links to them, will be provided here. Please listen to the episode for context. Key Takeaways Practice Persistent Starting: Don’t focus on the final outcome; focus on the act of beginning. Success is the aggregate of many small "starts." Diagnose the "Anchor Weight": If you are avoiding a task, it is likely due to a "lack of definition." Take five minutes to clarify the very next physical step to lower the barrier to entry. Distinguish Deferral from Procrastination: Conscious deferral is a strategic choice based on missing resources; procrastination is choosing a lower-value activity (like escapist media) over a high-priority intent. Utilize Retrospective Planning: After completing a difficult project, perform a "post-mortem" to document the steps you took. This creates a historical record that reduces anxiety for similar future tasks. Stop the "Shoulding": Avoid labeling yourself a "procrastinator." Using the term often induces shame and a "fear-based response" that further erodes the confidence needed to begin. Timestamps [01:51] The Anchor Weight: Why lack of definition causes stalling. [07:50] Unconscious Deferral vs. Procrastination: The role of the unconscious mind. [12:32] The Danger of Identity Labeling: Why calling yourself a "procrastinator" is harmful. [20:12] Moving Past Anxiety: Tactics for getting the ball rolling on new projects. [27:29] Persistent Starting: Using Dr. Neil Fiore’s technique to overcome blocks. [36:38] The Hunter-Gatherer Brain: Why our biology fights against long-term goals. [44:31] The Benefits of Procrastination: Using it as a filter for the unnecessary. Resources Mentioned Books: The Now Habit by Dr. Neil Fiore Atomic Habits by James Clear Concepts/Methods: Getting Things Done (GTD) The Byron Katie method for questioning thoughts. Retrospective (Backwards) Planning. People: Gretchen Rubin (The Four Tendencies/Upholders). Raw Text Transcript Raw, unedited and machine-produced text transcript so there may be substantial errors, but you can search for specific points in the episode to jump to, or to reference back to at a later date and time, by keywords or key phrases. The time coding is mm:ss (e.g., 0:04 starts at 4 seconds into the cast’s audio). Read More Voiceover Artist 0:00 Are you ready to manage your work and personal world better to live a fulfilling productive life, then you've come to the right place productivity cast, the weekly show about all things productivity. Here, your host Ray Sidney-Smith and Augusto Pinaud with Francis Wade and Art Gelwicks. Raymond Sidney-Smith 0:17 And Welcome back, everybody to productivity cast, the weekly show about all things personal productivity, I'm Ray Sidney Smith. Augusto Pinaud 0:24 I am Augusto Pinaud. Francis Wade 0:26I'm Francis Wade. Art Gelwicks 0:27 And I'm Art Gelwicks. Raymond Sidney-Smith | 00:29Welcome, gentlemen, and welcome to our listeners to this episode of ProductivityCast. Today, we are going to continue our conversation around procrastination and conscious deferral. And the conversation last time really covered mostly us discussing the defining nature of or just defining the nature of these two constructs, both procrastination and conscious deferral. And so what I'd like us to do is So if you have not listened to that episode, I would highly recommend that you hop back to the part one of this particular two episodes, and then we will now continue today in terms of really discussing the What we're going to do today is then start discussing why we procrastinate in the first place? What are some of the understandings of why we procrastinate and what are reasons for conscious deferral?And then we will… Discuss probably in and amongst that ways in which you can overcome procrastination and when it's probably appropriate to do conscious deferral. When it actually may not be, and it then bleeds back into procrastination. And there's a fine line there, of course.So let's talk about what are the major reasons why You all procrastinate. What are the reasons you've determined that procrastination ekes its way into your everyday life?Art Gelwicks | 01:51I'll throw myself under the bus first. One of the most common reasons that I'll put something off is lack of definition. If I haven't taken time to truly define out all the steps necessary to execute something, it winds up with this anchor weight attached to it to say, "Well, you don't know what you don't know, and you don't know quite what you're supposed to do, so maybe you should go do something else." Whether true or not, That's kind of where things wind up getting pushed to.So that, I'd say that's my primary one is lack of definition around what I'm supposed to be executing.Augusto Pinaud | 02:28Yeah, I need to agree with you 100%. For me… I can tell. By Monday morning. How good or bad my weekly review was on Friday. And I wish to tell that all of them are incredibly good. And I get out of there with a clear mind. And sometimes it doesn't happen. Even sometimes I do some kind of weekly review on Friday. I need to compliment that over the weekend because that is Lack of clarity, that lack of have that clear list of projects and actions, all that it produce is emergencies, fires and procrastination in my world.Francis Wade | 03:12I have a question though then, because the kind of the procrastination that Art was talking about sounds to me more like conscious deferral. That he's not unconsciously Putting off. The lack of definition. He's consciously doing it.Well, I should ask him. Are you unconsciously doing it because you haven't defined the action or are you consciously doing.Art Gelwicks | 03:33It? No, it's… I would agree it would look like conscious deferral that I'm making that action that, I don't have enough detail, therefore I can't get started. I'm not going to give it that level of credit. It's really a, it's a two-step problem. And the more I think about it, the first step in the problem is recognizing that I now need to allocate time to gather that information to know what I need to do for that thing.So for example, let's say I'm planning out an online ad. And I have some of the information I need, but I don't have all of it. And I know it needs to go out at a certain time.Well, I could just say it needs to be done. Or… What happens is I recognize that I need to spend some time filling in those gaps of the process necessary for that item, which means I'm going to have to chase down information to fill those gaps.So to execute that Task? There's a bunch of extra work that I need to front load. And that makes that task feel bigger, creating a bigger anchor, creating a bigger roadblock, therefore, subconsciously encouraging me to push that back to do things that I know I can accomplish and move forward on, which unfortunately winds up in that thing getting pushed back to a point where it becomes problematic.So. There may be times where that's a conscious thing where I say, look, I just don't know what I need to know. Therefore, I'm not going to do that thing. But to me, that's not procrastination. You're absolutely right. That's a choice. That's somebody hasn't provided me an update or something like that. That's a waiting on or a follow up. It's when I myself have not defined things clearly enough. To say Should or should I not proceed with this? That's when the procrastination part will kick in and say, you know what, why don't you hold off on that? You can go do something that you feel better about. And it's, I think it's the feel part more than anything. Because there isn't a rational reason to delay that work. It has to be done. There's nothing about it that says that you shouldn't be doing it. But there's a subconscious feeling there that's saying there's an almost an anxiety that's attached to it. Saying, you're going to find something that is going to be a real problem. Maybe you should put that off. I don't know if that helps any of us.Augusto Pinaud | 06:00No. And you bring a great point that it's that anxiety. It's the procrastination. It starts happening because I start getting all that anxiety of, is this really up to date? Is this really possible? The valuable task that I need to move forward? Is this really what need to happen? Or not. And that or not is the killing part of that.Francis Wade | 06:25I have a different, not different, but I have a… As I'm thinking about this, I wrote a an article on procrastination. It was a long time, like a decade ago. But I basically said that Something along the lines that procrastination was not well defined. And it seemed more like a The feeling. Than a fact. But what's happened over the years is that If someone were to ask me if I procrastinate, I would say no. I don't have that. Kind of self-talk. I don't use that term.
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Procrastination Versus Conscious Deferral, Part 2

In this episode of ProductivityCast, we continue our deep dive into the psychological and tactical differences between stalling out and stepping back. While Part 1 focused on defining the core constructs of procrastination and conscious deferral, Part 2 moves into the "why" and the "how." (If you’re reading this in a podcast directory/app, please visit https://productivitycast.net/144 for clickable links and the full show notes and transcript of this cast.) Enjoy! Give us feedback! And, thanks for listening! If you'd like to continue discussing the concepts of procrastination, conscious deferral and/or unconscious deferral from this episode, please click here to leave a comment down below (this jumps you to the bottom of the post). In this Cast | Procrastination vs Conscious Deferral Ray Sidney-Smith Augusto Pinaud Art Gelwicks Francis Wade Show Notes | Procrastination vs Conscious Deferral Resources we mention, including links to them, will be provided here. Please listen to the episode for context. Key Takeaways Practice Persistent Starting: Don’t focus on the final outcome; focus on the act of beginning. Success is the aggregate of many small "starts." Diagnose the "Anchor Weight": If you are avoiding a task, it is likely due to a "lack of definition." Take five minutes to clarify the very next physical step to lower the barrier to entry. Distinguish Deferral from Procrastination: Conscious deferral is a strategic choice based on missing resources; procrastination is choosing a lower-value activity (like escapist media) over a high-priority intent. Utilize Retrospective Planning: After completing a difficult project, perform a "post-mortem" to document the steps you took. This creates a historical record that reduces anxiety for similar future tasks. Stop the "Shoulding": Avoid labeling yourself a "procrastinator." Using the term often induces shame and a "fear-based response" that further erodes the confidence needed to begin. Timestamps [01:51] The Anchor Weight: Why lack of definition causes stalling. [07:50] Unconscious Deferral vs. Procrastination: The role of the unconscious mind. [12:32] The Danger of Identity Labeling: Why calling yourself a "procrastinator" is harmful. [20:12] Moving Past Anxiety: Tactics for getting the ball rolling on new projects. [27:29] Persistent Starting: Using Dr. Neil Fiore’s technique to overcome blocks. [36:38] The Hunter-Gatherer Brain: Why our biology fights against long-term goals. [44:31] The Benefits of Procrastination: Using it as a filter for the unnecessary. Resources Mentioned Books: The Now Habit by Dr. Neil Fiore Atomic Habits by James Clear Concepts/Methods: Getting Things Done (GTD) The Byron Katie method for questioning thoughts. Retrospective (Backwards) Planning. People: Gretchen Rubin (The Four Tendencies/Upholders). Raw Text Transcript Raw, unedited and machine-produced text transcript so there may be substantial errors, but you can search for specific points in the episode to jump to, or to reference back to at a later date and time, by keywords or key phrases. The time coding is mm:ss (e.g., 0:04 starts at 4 seconds into the cast’s audio). Read More Voiceover Artist 0:00 Are you ready to manage your work and personal world better to live a fulfilling productive life, then you've come to the right place productivity cast, the weekly show about all things productivity. Here, your host Ray Sidney-Smith and Augusto Pinaud with Francis Wade and Art Gelwicks. Raymond Sidney-Smith 0:17 And Welcome back, everybody to productivity cast, the weekly show about all things personal productivity, I'm Ray Sidney Smith. Augusto Pinaud 0:24 I am Augusto Pinaud. Francis Wade 0:26I'm Francis Wade. Art Gelwicks 0:27 And I'm Art Gelwicks. Raymond Sidney-Smith | 00:29Welcome, gentlemen, and welcome to our listeners to this episode of ProductivityCast. Today, we are going to continue our conversation around procrastination and conscious deferral. And the conversation last time really covered mostly us discussing the defining nature of or just defining the nature of these two constructs, both procrastination and conscious deferral. And so what I'd like us to do is So if you have not listened to that episode, I would highly recommend that you hop back to the part one of this particular two episodes, and then we will now continue today in terms of really discussing the What we're going to do today is then start discussing why we procrastinate in the first place? What are some of the understandings of why we procrastinate and what are reasons for conscious deferral?And then we will… Discuss probably in and amongst that ways in which you can overcome procrastination and when it's probably appropriate to do conscious deferral. When it actually may not be, and it then bleeds back into procrastination. And there's a fine line there, of course.So let's talk about what are the major reasons why You all procrastinate. What are the reasons you've determined that procrastination ekes its way into your everyday life?Art Gelwicks | 01:51I'll throw myself under the bus first. One of the most common reasons that I'll put something off is lack of definition. If I haven't taken time to truly define out all the steps necessary to execute something, it winds up with this anchor weight attached to it to say, "Well, you don't know what you don't know, and you don't know quite what you're supposed to do, so maybe you should go do something else." Whether true or not, That's kind of where things wind up getting pushed to.So that, I'd say that's my primary one is lack of definition around what I'm supposed to be executing.Augusto Pinaud | 02:28Yeah, I need to agree with you 100%. For me… I can tell. By Monday morning. How good or bad my weekly review was on Friday. And I wish to tell that all of them are incredibly good. And I get out of there with a clear mind. And sometimes it doesn't happen. Even sometimes I do some kind of weekly review on Friday. I need to compliment that over the weekend because that is Lack of clarity, that lack of have that clear list of projects and actions, all that it produce is emergencies, fires and procrastination in my world.Francis Wade | 03:12I have a question though then, because the kind of the procrastination that Art was talking about sounds to me more like conscious deferral. That he's not unconsciously Putting off. The lack of definition. He's consciously doing it.Well, I should ask him. Are you unconsciously doing it because you haven't defined the action or are you consciously doing.Art Gelwicks | 03:33It? No, it's… I would agree it would look like conscious deferral that I'm making that action that, I don't have enough detail, therefore I can't get started. I'm not going to give it that level of credit. It's really a, it's a two-step problem. And the more I think about it, the first step in the problem is recognizing that I now need to allocate time to gather that information to know what I need to do for that thing.So for example, let's say I'm planning out an online ad. And I have some of the information I need, but I don't have all of it. And I know it needs to go out at a certain time.Well, I could just say it needs to be done. Or… What happens is I recognize that I need to spend some time filling in those gaps of the process necessary for that item, which means I'm going to have to chase down information to fill those gaps.So to execute that Task? There's a bunch of extra work that I need to front load. And that makes that task feel bigger, creating a bigger anchor, creating a bigger roadblock, therefore, subconsciously encouraging me to push that back to do things that I know I can accomplish and move forward on, which unfortunately winds up in that thing getting pushed back to a point where it becomes problematic.So. There may be times where that's a conscious thing where I say, look, I just don't know what I need to know. Therefore, I'm not going to do that thing. But to me, that's not procrastination. You're absolutely right. That's a choice. That's somebody hasn't provided me an update or something like that. That's a waiting on or a follow up. It's when I myself have not defined things clearly enough. To say Should or should I not proceed with this? That's when the procrastination part will kick in and say, you know what, why don't you hold off on that? You can go do something that you feel better about. And it's, I think it's the feel part more than anything. Because there isn't a rational reason to delay that work. It has to be done. There's nothing about it that says that you shouldn't be doing it. But there's a subconscious feeling there that's saying there's an almost an anxiety that's attached to it. Saying, you're going to find something that is going to be a real problem. Maybe you should put that off. I don't know if that helps any of us.Augusto Pinaud | 06:00No. And you bring a great point that it's that anxiety. It's the procrastination. It starts happening because I start getting all that anxiety of, is this really up to date? Is this really possible? The valuable task that I need to move forward? Is this really what need to happen? Or not. And that or not is the killing part of that.Francis Wade | 06:25I have a different, not different, but I have a… As I'm thinking about this, I wrote a an article on procrastination. It was a long time, like a decade ago. But I basically said that Something along the lines that procrastination was not well defined. And it seemed more like a The feeling. Than a fact. But what's happened over the years is that If someone were to ask me if I procrastinate, I would say no. I don't have that. Kind of self-talk. I don't use that term.
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Procrastination Versus Conscious Deferral, Part 1

What if procrastination is not always procrastination? In this episode of ProductivityCast, we begin exploring the difference between true procrastination and conscious deferral, and why that distinction matters more than most people realize. This conversation challenges the labels we use, the judgment we attach to delay, and the hidden reasons we avoid certain tasks, making this a thought-provoking starting point for anyone who has ever wondered whether they are putting something off or making a more intentional choice. (If you’re reading this in a podcast directory/app, please visit https://productivitycast.net/144 for clickable links and the full show notes and transcript of this cast.) Enjoy! Give us feedback! And, thanks for listening! If you'd like to continue discussing procrastination versus conscious deferral from this episode, please click here to leave a comment down below (this jumps you to the bottom of the post). In this Cast | Procrastination Versus Conscious Deferral Ray Sidney-Smith Augusto Pinaud Art Gelwicks Francis Wade Show Notes | Procrastination Versus Conscious Deferral Resources we mention, including links to them, will be provided here. Please listen to the episode for context. In this first part of a two-part discussion, the ProductivityCast team examines the meaning of procrastination and questions whether the term has become too broad, judgmental, and unhelpful. The conversation begins by comparing common definitions of procrastination and quickly moves into a deeper exploration of whether all delay should be treated the same. The hosts distinguish between unconscious delay, conscious prioritization, and what Ray describes as conscious deferral, which is the intentional decision to postpone something for a clear reason. They also explore how the label of procrastination can create shame, obscure the real causes of delay, and distort how we interpret other people’s behavior in work and life. The episode ultimately reframes procrastination as a more complex mix of perception, prioritization, emotional regulation, and context, setting up a follow-up discussion on how to handle procrastination at both the project and task levels. Key Takeaways: Not every delay is procrastination; some delays are intentional, rational, and better understood as conscious deferral. Labeling yourself or others as a procrastinator can add shame without revealing the real cause of the delay. A better question than “Why am I procrastinating?” may be “What is preventing this from feeling clear, doable, or important right now?” In leadership and collaboration, replacing blame with curiosity helps uncover obstacles, competing priorities, or missing information. Much of what looks like procrastination may actually be displaced activity, where you are still doing something, just not the thing you believe you should be doing. Timestamps: [00:00] Introducing the problem of procrastination vs. conscious deferral [00:02] Why common definitions of procrastination may be too simplistic [00:05] Internal judgment, external judgment, and who gets to define procrastination [00:09] The emotional weight of procrastination and the case for conscious deferral [00:13] Unconscious choices, intuition, and the hidden reasons behind delay [00:19] How to think about procrastination in teams, leadership, and collaboration [00:33] Procrastination as displaced activity and preview of Part 2 Resources Mentioned: Wikipedia definition of procrastination Dr. Gary Klein on intuition Conversations for Action Raw Text Transcript Raw, unedited and machine-produced text transcript so there may be substantial errors, but you can search for specific points in the episode to jump to, or to reference back to at a later date and time, by keywords or key phrases. The time coding is mm:ss (e.g., 0:04 starts at 4 seconds into the cast’s audio). Read More Voiceover Artist 0:00 Are you ready to manage your work and personal world better to live a fulfilling productive life, then you've come to the right place productivity cast, the weekly show about all things productivity. Here, your host Ray Sidney-Smith and Augusto Pinaud with Francis Wade and Art Gelwicks. Raymond Sidney-Smith 0:17 And Welcome back, everybody to productivity cast, the weekly show about all things personal productivity, I'm Ray Sidney Smith. Augusto Pinaud 0:24 I am Augusto Pinaud. Francis Wade 0:26I'm Francis Wade. Art Gelwicks 0:27 And I'm Art Gelwicks. Raymond Sidney-Smith 0:28Welcome gentlemen, and welcome to our listeners to this episode of ProductivityCast. Today we're gonna be talking about procrastination versus or and conscious deferral. And what we're gonna do is we're gonna define procrastination. I think everybody procrastinates a little bit and sometimes a lot in their lives, and we wanna talk about why we procrastinate and what are some of the things we. Do when we consciously defer projects, goals, and tasks from what we are [00:01:00] presently and actively working on, and then we can close out with discussion on maybe if you are struggling with procrastination, what are some things that. If it's hindering your productivity, what can you do to get over that hump? And we can give some quick tips for folks to get started with conquering procrastination at the end. So let's start off at the top, which is, let's all get on perhaps the same page relating to procrastination. How do you define procrastination? I am gonna pause here for a moment. Francis, if you could just stay if everybody just stays off mute, I wanna see, I can void out your audio, so don't worry about muting yourself. Only because when I'm wondering if that has something to do with why it gets into the drift mode. 'cause when you are muted Oh. I'll start us off and you all can perhaps add on to the definition. And I went to a bunch of different places, but I think Wikipedia actually ended up having a, an interesting [00:02:00] definition that I don't necessarily agree with. And I think this is helpful for us to start the conversation, which is Wikipedia defines procrastination as an action of unnecessarily and. Voluntarily delaying or postponing something despite knowing that there will be negative consequences for doing so. So I immediately feel like this is not true in some perspective here because it says unnecessarily and voluntarily, and we know that not everybody is aware of the. Negative consequences and sometimes there are not negative consequences for procrastinating. And so I'm curious about just that base level definition from Wikipedia. Do you agree or disagree? That only works if you're taking involuntary delay and giving it a different name because [00:03:00] procrastination is a blanket term that any sort of a delay on something. It's either do it or don't do it. And if you do it, you're in action. If you're not, you're procrastinating. It's not about the how, so I don't know that I necessarily agree with their definition of procrastination. But I also don't think the term necessarily needs to include the cause. It is a delay of action. When an action should be taken. Maybe phrase it that way or it would be. Beneficial for an action to be taken, what the trigger of that could be, any number of things. And I don't think they, they are remotely related to the term procrastination. So this is where I have some difficulty because the most tasks, of course, are delayed until later. If not every task that you plan to do in the future is based on a delay and. There's a cost for delaying any [00:04:00] task. In other words it's, there's a risk that it might not get done. So the only way to remove the risk of doing a task and not doing a task in the future is to do it. No. So by that definition, procrastination covers every single task. That is, in other words, every time demand, every one that you're gonna do in the future, at that point, the verb procrastinate loses its value because all it's saying is, whatever you're not doing, whatever task you're not doing. No. At that point, I don't think it has much value. So I don't like the, I don't like the idea that procrastination is putting off a task. I don't think it, it adds a lot of value. I think there's a, what if we were to re rephrase the definition? 'cause we were all about definitions to procrastination. Being inaction when action should be taken. Because theoretically, if you're not doing something and you're [00:05:00] supposed to be doing that thing, you're either unintentionally putting it off. You're intentionally putting it off. It's an either or situation. There is a, there's a decision point for the conscious part, but the unconscious part, no, it can just happen. One of the things when we talk about what is procrastination, we never start to look at it from the standpoint of saying, okay, this, take something simple. Taking out the trash. I choose not to take out the trash. Or I'm going to do something else. I may have chosen to do something else. And what ha what happens is taking out the trash gets put off. But if that context isn't provided in the definition, the perception is then, oh, you procrastinated on taking out the trash. No, I did make a conscious decision to do something else I prioritized over. So when we go back to [00:06:00] procrastination. I still think it comes back to that inaction when action is warranted. How you get to that point could be any number of factors, but I think that's as simple in my mind. That's as simple as it gets. A piece that comes into mind for me though, is that your wife might say that you were procrastinating,
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Blue Ocean Strategy Had a Flaw No-One Talks About

There is a book on the shelf of almost every serious executive in the world. It has sold over four million copies, been translated into 46 languages, and spawned an entire consulting industry. Its central idea is so compelling that once you hear it, you cannot unhear it.

The book is Blue Ocean Strategy (BOS), published in 2004 by W. Chan Kim and Renée Mauborgne. The central idea: stop fighting competitors for the same shrinking pool of customers. Create new market space where competition is irrelevant. Stop swimming in a Red Ocean of blood and churn. Find your Blue Ocean.

Every executive who has heard this wants it. The aspiration is sound. The problem is that the book quietly fails to deliver what its title promises – and that failure has cost organizations time in over two decades of strategy retreats.

The Word That Did the Damage

The most consequential editorial decision in modern management publishing happened when the authors agreed to put the word “Strategy” in the title.

That single word changed how executives read the book. Strategy implies a plan. A method. A set of steps you can follow to get from where you are to where you want to be. Executives arrived at the book expecting operational guidance. What they received instead was one of the most elegant collections of business case studies ever assembled — and no instructions for replication.

Consider the cases. Cirque du Soleil, the book’s showcase story, reinvented the circus by eliminating animals and creating a sophisticated adult entertainment category. Yellow Tail wine made wine approachable for beer drinkers by stripping out complexity and jargon. NVIDIA opened its graphics processors to general computing and created an entirely new category of accelerated processing. Taylor Swift reinvented the artist’s relationship to fans, catalog ownership, and brand extension.

Each case is vivid. Each pattern is compelling. But each story was crafted long after the journey was complete.

That is the problem. Every case in the book is retrospective. The authors identified companies that had already succeeded, mapped their moves, and presented the pattern. What they did not — and perhaps could not — provide is a repeatable method for how your company executes a similar move from scratch, in your industry, with your constraints, before the outcome is known.

This is not a minor gap. It is the structural flaw that separates the book’s promise from its delivery. And it helps explain why boardrooms around the world have produced beautiful strategy canvases (as the book instructs) and returned to fighting the same competitive battles the following Monday morning.

The Tool That Starts in the Wrong Place

There is a deeper problem, and it lives inside the book’s primary diagnostic instrument — the Eliminate, Reduce, Raise, Create grid, known as the ERRC.

To use the ERRC grid, you map what your industry currently does across every competitive factor, then decide what to eliminate, reduce, raise, and create. Every factor you analyze is defined in relation to what competitors already do. The entire diagnostic starts with your rivals.

Here is the irony: a framework designed to help you escape competition requires you to think about competition first. If your strategic imagination is anchored to what already exists, you have not left the Red Ocean. You have only rearranged your position within it. The book’s primary tool quietly undermines its central promise.

The Pattern the Book Ignores

Set aside the tool problem for a moment. Assume your team finds its Blue Ocean. You create uncontested market space, grow rapidly, and establish genuine differentiation. What happens next?

Blue Ocean Strategy is largely silent on this question. And the answer, drawn from its own case studies, is uncomfortable.

Cirque du Soleil created its blue ocean in the 1980s and spent nearly four decades defending it. New competitors entered experiential entertainment. Costs rose. The company took on debt to fund global expansion. In June 2020, it filed for bankruptcy protection.

Netflix invented streaming video and watched Disney, Amazon, Apple, and dozens of others flood the same space within a decade. Uber redefined urban transportation and has spent most of its existence losing money as imitators replicated its model in every major market.

These are not execution failures. They are the inevitable result of treating a blue ocean as a destination rather than a phase.

Every competitive advantage has an expiry date. The timeline varies — years, sometimes decades — but the sequence never changes. You create uncontested space. Competitors notice. Imitators arrive. Margins compress. The blue ocean turns red. This is not misfortune. It is the entirely predictable lifecycle of any strategic advantage, and it has been predictable for a long time.

That is the core of what Blue Ocean Strategy leaves out: a theory of time.

The book is written as though the strategic challenge is finding the right space. It is not. The deeper challenge is understanding that every space you find is already aging from the moment you enter it — and that long-term survival depends on building the next blue ocean while the current one is still profitable enough to fund it.

A framework called the Three Horizons Framework, developed by Hodgson, Curry and others, addresses precisely this gap. It argues that organizations must simultaneously protect today’s advantage, develop tomorrow’s opportunity, and explore the possibilities that will matter in five to ten years. Not sequentially. Simultaneously. Because by the time your current advantage is visibly declining, it is already too late to begin building its replacement.

Blue Ocean Strategy asks: where should we compete? The Three Horizons Framework asks: for how long, and what comes next? The first question without the second is not a strategy. It is a plan with no second act — which is exactly what Cirque du Soleil, Netflix, and Uber each discovered in turn.

The Company That Proved Both Points

Wawa is a food retailer based in the northeastern United States. It operates convenience stores, fuel stations, and quick-service restaurants — three of the lowest-margin, highest-failure-rate business categories in existence. It is also, by most available measures, one of the most successful blue ocean practitioners in American business history.

In 2009, facing a world where supermarkets, fast casual chains, and fuel retailers were all converging on its territory, Wawa’s leadership formally applied the Blue Ocean tools. The strategy canvas and ERRC grid structured their analysis and were genuinely useful. They identified that their weakest offering — food service — was also their highest-potential opportunity for differentiation.

What followed was systematic reinvention. Wawa repositioned from a convenience store that also sold food into a quality quick-service restaurant that also sold fuel and convenience items. Fresh bread baked on premises. Customizable meals made to order. High-quality coffee at accessible prices. Touchscreen ordering kiosks. A store layout redesigned with food at the center.

The results are measurable. An average 7-Eleven generates roughly US$30,000 to $35,000 in weekly revenue per store. Wawa averages US$116,000. That gap — more than three times the category standard — is what genuine blue ocean execution produces in real dollars.

Perhaps more telling is what the broader industry makes of Wawa’s performance. QSR 50, the standard industry ranking of quick-service restaurants, does not include Wawa in its listings. The reason given is that Wawa sells fuel and packaged goods, which technically classifies it as a convenience store rather than a restaurant. If Wawa were included, it would rank first in per-store sales — ahead of McDonald’s, Chick-fil-A, and Panera Bread. The most effective blue ocean practitioner in American retail is invisible to the industry supposed to be tracking it. That is what genuine category creation actually looks like.

But here is the detail that the book’s framework cannot account for, delivered in the words of Wawa’s own former CEO Howard Stoeckel: “We’re paranoid when it comes to success and we’re always reinventing ourselves.”

Not proud. Not secure. Paranoid.

Wawa has reinvented itself across more than two centuries — from dairy farming to grocery retail to convenience stores to fuel to quick-service restaurants. Each reinvention happened before the previous model was exhausted. In 2012, Stoeckel announced that Wawa was no longer a convenience store. It was, he declared, “a leading quick-service restaurant and leader in the fast-casual-to-go space that also sells gas and convenience items.” No such category existed at scale at the time. Competitors scoffed. Customers gradually came to see it exactly that way.

That move — naming a new space and teaching the market to recognize it before rivals could claim it — is not in the Blue Ocean book. It belongs to a separate body of thinking about category design, developed by writers including Christopher Lochhead, Eddie Yoon, and Nicolas Cole. Their argument is direct: whoever names the new category can dominate it for decades to come. Language is key. The market does not automatically recognize new value — someone has to hand it the vocabulary.

What Executives Should Actually Do

Blue Ocean Strategy offers the right aspiration. The ambition to escape a competitive space rather than simply fight better within it is correct, and the book makes that case more compellingly than almost anything else in the management canon.

But aspiration without method produces what most organizations have experienced: a retreat, a strategy canvas, a renewed sense of possibility, and no change the following quarter.

The complete system looks something like this. Use BOS to identify where genuine value innovation is possible — where you can create new demand rather than compete for existing demand. Apply a long-horizon lens from the moment you make your move, treating your new blue ocean as inherently temporary and building the next opportunity while the current one is still strong. Invest as much in naming and framing your new category as you do in designing it — because a blue ocean no one can describe is a blue ocean no one will defend.

The book is not wrong. It is incomplete. Read it for the vision it provides so clearly. Then build the method around it that it never supplies.

PS — Going Deeper: Five Prompts for Your AI Assistant

The arguments in this article can be taken further using any AI tool. Here are five prompts to continue the thinking:

  1. “Map my company’s current strategy against the Three Horizons Framework by Hodgson and Curry. Ask me questions about our current business, emerging threats, and what’s already replacing us in the market.”
  2. “Using Blue Ocean Strategy’s ERRC grid as a starting point, help me identify where my industry’s assumptions are so deeply embedded that we have stopped questioning them.”
  3. “Give me five examples of companies that created a genuine blue ocean, then failed to build the next one before their advantage decayed. What was the warning signal they missed in each case?”
  4. “Help me write a category definition statement for my business — not what we do, but what new space we are creating and why we should own it.”
  5. “Based on Wawa’s reinvention story, design a set of questions I can bring to my next strategy retreat to test whether we are building our next blue ocean or simply defending the current one.”