Live on Substack #3: Unmasking the Strategy Success Trap

Unmasking the Strategy Success Trap: Why Booms Lead to Busts!

How should your company react to amazing success? Join us for a spirited conversation diagnosing the fatal strategic missteps of companies that went through unearned booms during COVID-19.

We reveal why giants like Peloton and Fiverr abandoned their profitable, long-term business models to chase massive, temporary demand.

We explore how this pursuit of tactical success led to impulsive, nearsighted decisions—such as Peloton becoming a capital-intensive manufacturing/logistics operation—which guaranteed a crash and painful layoffs. Discover the critical difference between “structural change” (permanent) and “cyclical noise” (temporary).

Learn the essential discipline of long-term strategy. A sound strategy must act as a risk-management tool during good times, allowing companies like Amazon and Uber to leverage windfalls to build a lasting, sustainable advantage.

True success is measured not by the peak of a boom, but by the depth of a normalization the company can survive. Prepare your company for the threat of a disruption brought about by success beyond its wildest dreams.

This is a public episode. If you’d like to discuss this with other subscribers or get access to bonus episodes, visit longtermstrategy.substack.com/subscribe

Live on Substack #3: Unmasking the Strategy Success Trap

Unmasking the Strategy Success Trap: Why Booms Lead to Busts!

How should your company react to amazing success? Join us for a spirited conversation diagnosing the fatal strategic missteps of companies that went through unearned booms during COVID-19.

We reveal why giants like Peloton and Fiverr abandoned their profitable, long-term business models to chase massive, temporary demand.

We explore how this pursuit of tactical success led to impulsive, nearsighted decisions—such as Peloton becoming a capital-intensive manufacturing/logistics operation—which guaranteed a crash and painful layoffs. Discover the critical difference between “structural change” (permanent) and “cyclical noise” (temporary).

Learn the essential discipline of long-term strategy. A sound strategy must act as a risk-management tool during good times, allowing companies like Amazon and Uber to leverage windfalls to build a lasting, sustainable advantage.

True success is measured not by the peak of a boom, but by the depth of a normalization the company can survive. Prepare your company for the threat of a disruption brought about by success beyond its wildest dreams.

This is a public episode. If you’d like to discuss this with other subscribers or get access to bonus episodes, visit longtermstrategy.substack.com/subscribe

Ep 31 – Escaping the Short-Term Trap

This is a free preview of a paid episode. To hear more, visit longtermstrategy.substack.com

You have a hunger for game-changing results. As a CEO, board member, or strategic planner, you aspire to produce big results. While you know methods that work, you still find yourself drifting back into short-term thinking in these tumultuous days. Without daily activities guiding you toward a True North—a preferred long-term destination—you run the risk of being sucked into the 24-hour news cycle or latest drama.

How do you build the strategic muscles necessary to withstand even daily shocks and surprises?

The opposite of conventional strategy is true. Stop chasing short-term survival; outsiders and technology cannot save you from constant disruption. Conventional wisdom demanding “twice the results in half the time” is fundamentally flawed. Real game-changing success requires robust long-term strategic muscle.

We expose the 25 fatal obstacles infecting C-suites with short-term thinking, providing definitive ‘obstacle knowledge’ so you can become a robust, different kind of strategist who can preemptively design for disruption.

Tune in to join me in tackling this wicked problem. I’ll share the approach we took to designing the Long-Term Strategy Conference 2025 held in June.

I’m Francis Wade and welcome to the JumpLeap Long-Term Strategy Podcast.

P.S. Here’s a LLM prompt you can copy and paste into an LLM to deepen your understanding:

Act as a strategic planning consultant. I just listened to a podcast about long-term strategic planning. Here’s the core insight I learned: “Big results need years. Long time frame and big results go together. If you try to commit to big goals on short time frames, it doesn’t work.”

My current strategic planning challenge is: [DESCRIBE IN ONE SENTENCE YOUR BIGGEST STRUGGLE WITH LONG-TERM THINKING IN YOUR ORGANIZATION].

Based on this insight, identify three specific symptoms in my organization that indicate we’re stuck in short-term thinking. Then suggest one concrete conversation starter I can use this week to begin reframing our strategic discussions.

P.P.S. Want more? For subscribers, I have generated at least 5 more prompts, available below the paywall.

Show Notes

https://strategyconf.fwconsulting.com/conference-topics-2025/ – The full list of 25 Obstacles

The full video is available below for subscribers. So are the other LLM Prompts mentioned above.

Ep 31 – Escaping the Short-Term Trap

This is a free preview of a paid episode. To hear more, visit longtermstrategy.substack.com

You have a hunger for game-changing results. As a CEO, board member, or strategic planner, you aspire to produce big results. While you know methods that work, you still find yourself drifting back into short-term thinking in these tumultuous days. Without daily activities guiding you toward a True North—a preferred long-term destination—you run the risk of being sucked into the 24-hour news cycle or latest drama.

How do you build the strategic muscles necessary to withstand even daily shocks and surprises?

The opposite of conventional strategy is true. Stop chasing short-term survival; outsiders and technology cannot save you from constant disruption. Conventional wisdom demanding “twice the results in half the time” is fundamentally flawed. Real game-changing success requires robust long-term strategic muscle.

We expose the 25 fatal obstacles infecting C-suites with short-term thinking, providing definitive ‘obstacle knowledge’ so you can become a robust, different kind of strategist who can preemptively design for disruption.

Tune in to join me in tackling this wicked problem. I’ll share the approach we took to designing the Long-Term Strategy Conference 2025 held in June.

I’m Francis Wade and welcome to the JumpLeap Long-Term Strategy Podcast.

P.S. Here’s a LLM prompt you can copy and paste into an LLM to deepen your understanding:

Act as a strategic planning consultant. I just listened to a podcast about long-term strategic planning. Here’s the core insight I learned: “Big results need years. Long time frame and big results go together. If you try to commit to big goals on short time frames, it doesn’t work.”

My current strategic planning challenge is: [DESCRIBE IN ONE SENTENCE YOUR BIGGEST STRUGGLE WITH LONG-TERM THINKING IN YOUR ORGANIZATION].

Based on this insight, identify three specific symptoms in my organization that indicate we’re stuck in short-term thinking. Then suggest one concrete conversation starter I can use this week to begin reframing our strategic discussions.

P.P.S. Want more? For subscribers, I have generated at least 5 more prompts, available below the paywall.

Show Notes

https://strategyconf.fwconsulting.com/conference-topics-2025/ – The full list of 25 Obstacles

The full video is available below for subscribers. So are the other LLM Prompts mentioned above.

Beyond the Annual Planning Checklist: How Government Executives Reclaim Inspiring Purpose

Imagine you lead a government ministry, department, or agency. As you approach the season for submitting annual reports and corporate plans, you realize something is missing. The very reason you entered public service is being lost in paperwork.

This challenge isn’t unique to any single country—it’s a global phenomenon affecting government leaders worldwide, whether they’re working within established national development frameworks or considering creating one.

A Case Study in National Vision: Jamaica’s Experience

To understand this dynamic, consider Jamaica’s Vision 2030—one of the world’s most comprehensive national development plans. For over 16 years, more than one hundred government organizations have submitted detailed annual plans to parent ministries, creating a rigorous process that private sector executives often admire. It represents a remarkable achievement in sustained strategic execution.

Dr. Wesley Hughes, the plan’s architect, originally envisioned something transformational. In his forward to the Vision 2030 document, he wrote: “Today, our children have access to technologies that were once considered science fiction. They seek opportunities to realize their full potential. This Plan is to ensure that, as a society, we do not fail them.”

Hughes continued: “We have a duty to ourselves, to the sacrifices of past generations and to the hopes of future generations, to preserve the best of our country and to transform the worst. The outcome in 2030 is dependent on the decisions we make today.”

However, as insiders know, even the most well-intentioned national frameworks can become sources of bureaucratic dread rather than inspiration. How does this happen, and what can leaders worldwide learn from this experience?

The National Vision Compliance Trap

The primary problem—whether in Jamaica or any country with strategic planning processes—is that organizations typically complete their internal plans before “aligning” them with the national vision. Compliance checking becomes the final step rather than the foundational starting point.

This approach is fundamentally backwards, like deciding to travel somewhere before determining why the journey matters.

Consequently, civil servants feel constrained rather than inspired by their national development framework. For countries without established national plans, this offers a crucial lesson: the implementation process matters as much as the vision itself.

Universal Principles for Government Leaders

Whether you’re operating within an existing national framework or considering developing one, the solution involves reclaiming strategic voice through fundamental questions:

“What does our country need from this organization to accomplish our national vision?”

“What game-changing outcomes aren’t explicitly captured in current planning but have become critical?”

“What goals should influence the next (or first) iteration of national planning?”

Reconnect with Original Purpose

Study Dr. Hughes’ approach as a model. He didn’t create Vision 2030 as bureaucratic compliance exercise—he crafted it as a covenant with future generations. Government leaders worldwide can apply this principle by:

  • Returning staff to the original purpose behind strategic frameworks
  • Connecting teams with the deeper reasons they joined public service
  • Making inspirational founding documents part of organizational culture
  • Recognizing that most public servants want to accomplish more than mere survival

From Following to Leading: The Jamaica Model and Beyond

Jamaica’s experience offers both cautionary tale and opportunity. The country now stands at a unique inflection point—with remaining years in the Vision 2030 timeline that could become its finest contribution to national development.

This mirrors a broader truth: research shows humans overestimate short-term potential while underestimating long-term possibilities. Strategic initiatives often build momentum gradually, achieving exponential impact toward their timeline’s end.

For countries without national development plans, Jamaica’s experience suggests several critical design principles:

  • Start with inspirational purpose, not compliance requirements, and convert these into frequent practices.
  • Build implementation processes that energize rather than drain participants.
  • Create feedback loops that celebrate progress toward transformational goals.
  • Design planning cycles that connect daily work to generational impact.

The Global Leadership Choice

Whether you’re working within Jamaica’s Vision 2030, another country’s national framework, or considering developing strategic planning processes, the fundamental choice remains the same.

The question isn’t whether you have authority to lead transformational change—you do. The question is whether you have courage to use it.

Right now, government leaders across the globe face this choice. Will you spend your tenure perfecting compliance reports? Or will you use strategic planning as foundation for breakthrough leadership?

Dr. Hughes designed Vision 2030 to prevent society from failing its children. His vision applies universally: every government leader has opportunity to ensure their work serves future generations rather than mere bureaucratic efficiency.

Lessons for Countries Without National Plans

Jamaica’s experience offers valuable insights for nations considering comprehensive strategic planning:

  1. Start with inspirational architecture like Hughes created—connect planning to generational responsibility.
  2. Design implementation processes that inspire rather than constrain participants.
  3. Build momentum systems that recognize long-term strategic initiatives often achieve greatest impact at timeline’s end.
  4. Create cultural integration that makes strategic thinking part of daily organizational life.

History won’t remember executives who filed the most thorough paperwork. It will remember those who transformed their area of responsibility when game-changing leadership mattered most.

The choice, and the legacy, are yours—whether you’re building on Jamaica’s model or creating your own path toward national transformation.

When Good News Becomes a Business Risk: How Falling Crime Can Disrupt Your Strategy

A Shift Few Leaders Expect

Falling crime rates are usually celebrated as a sign of progress. Safer communities, stronger economies, and a brighter future—what’s not to like? Yet for business leaders, this kind of change can also be profoundly disruptive. If your company has been operating for decades in an environment shaped by insecurity, what happens when that reality suddenly shifts?

Jamaica offers a striking example. For years, high levels of violence defined everyday life and business practices. Many firms adapted, building their operations on an assumption of danger. Now, crime is falling. If this trend proves durable, the very foundations of corporate strategy in the country could be shaken.

The same dynamic applies globally. Whether it’s crime, inflation, regulation, or even cultural norms, long-standing conditions shape business models. When those conditions change, the leaders who cling to old assumptions often suffer the most.

Beyond Skepticism: Could the Change Be Real?

History encourages caution. In Jamaica, crime dipped after the 2010 “Dudus crackdown,” when nearly a hundred criminals were eliminated or fled. The effect was temporary; crime rebounded. Understandably, leaders today hesitate to celebrate.

But current indicators suggest something different. The Citizens Security Plan (CSP), launched in 2020, has applied coordinated interventions across policing, communities, and schools. These are not random shifts but measurable, systemic efforts. According to Dianne McIntosh of the Citizens Security Secretariat (CSS), the downward trend was predicted and intentional, not accidental.

If this approach is sustainable, Jamaica may be entering a new era. For business leaders, that requires more than casual observation—it demands strategic reconsideration.

When Old Assumptions Become Dangerous

Executives often claim to have “a long-term plan.” Sometimes it exists only in their heads; other times it’s reduced to lofty mission statements. But when tested, many leadership teams struggle to articulate a coherent strategy. That’s manageable when conditions remain stable. It’s perilous when they change.

Falling crime isn’t just a social good—it’s an economic shock. Studies suggest that Jamaica’s high crime rate has shaved 2–4% off annual GDP growth. If that burden is lifted, the economy could expand in ways that reward some sectors while destabilizing others.

Consider Colombia. Between 2002 and 2010, murders and kidnappings plummeted. While the country as a whole benefited, one sector suffered: private security. With half a million armed guards—more than the army and police combined—the industry had thrived on fear. When violence declined, demand collapsed. Firms that assumed the old reality would last indefinitely faced sudden disruption.

The same could happen anywhere. Companies built on entrenched conditions may discover that their core business model no longer fits.

Lessons from a Pandemic Surprise

This pattern isn’t limited to crime. In 2017, a financial services client dismissed the idea that their country was ready for online banking. They imagined digital adoption as a distant event.

In discussions, I encouraged them to carve out an actual timeline: a 10-year goal. Then the COVID-19 pandemic hit. Overnight, physical branches closed, and the digital future arrived.

Fortunately, the company had at least sketched out a plan. They accelerated it, shifting in months what they thought would take a decade. Those without foresight were left scrambling.

The lesson is clear: change rarely arrives on schedule. Leaders who prepare for disruption—whether it comes from crime rates, technology, or global crises—are positioned to adapt. Those who rely on yesterday’s success become their own worst enemy.

Why Foresight Matters Now

Harvard professor Clay Christensen once observed that organizations grow addicted to what made them successful. They defend the familiar rather than exploring the new. This is comforting but risky.

If crime falls sustainably, a country like Jamaica will experience profound change. Real estate values could climb. Tourism could expand. Consumer confidence could rise. Yet industries tied to fear—private security, certain insurance products, or defensive real estate designs—may shrink.

Globally, the principle is the same: whenever a long-standing challenge begins to ease, leaders must ask, what happens to us if the world really does change?

Turning Good News into Strategic Advantage

Falling crime is an undeniable win for society. But for business leaders, it’s also a challenge. The question is not whether to celebrate, but whether to adapt.

Here are three steps to consider:

  1. Validate the Data
    Don’t rely on rumors or short-term headlines. Understand the leading indicators, the policies behind them, and whether the change is likely to last.
  2. Stress-Test Your Model
    Ask how your operations, costs, and markets would shift if the old assumptions disappeared. If your business relies on high levels of fear, inflation, or any entrenched condition, prepare alternatives.
  3. Rebuild Before You’re Forced To
    Waiting until the change is undeniable often means it’s too late. Instead, use foresight to redesign your company around the future that could emerge.

The Bottom Line

A safer society is a gift. But it is also a test of leadership. True foresight requires seeing risks where others see only triumph.

The companies that thrive will be those willing to let go of outdated assumptions and embrace a new normal—even when the news is good.


This article is based on a column I wrote for the Jamaica Gleaner published on Sep 14, 2025.