Why Your 2050 Strategy Must Start Today: Lessons from a 15-Year Failure

Will your organization survive the next 25 years? More importantly, are the decisions you’re making today planting the seeds of future irrelevance?

The US Coast Guard wrestled with these questions and discovered something counterintuitive: to truly understand today’s challenges, you need to view them from 25 years in the future. Their Project Evergreen initiative proved this—but only after failing spectacularly for 15 years first.

The Expensive Lesson: Brilliant Strategy, Zero Implementation

Imagine pouring 15 years into strategic planning. Your organization assembles the best minds, conducts sophisticated scenario workshops, and produces detailed roadmaps. The forecasts are prescient. The analysis is sharp. The strategies are comprehensive.

Then everything hits reality and dies on impact.

This was Project Evergreen’s painful trajectory. Every strategic plan they delivered landed, in their words, “like most additional work at an office with an already full plate: dead on arrival.” Inbox after inbox received these plans. Nearly all went unimplemented.

The Coast Guard had built “isolated, independent cogs” that required “considerable effort to forcefully engage into the many turning mechanisms” of actual organizational planning. Picture trying to force a rigid gear into machinery that’s already running—that’s what executing these strategies felt like for frontline teams.

Why did meticulously crafted strategies produce such dismal results?

The Question That Poisoned 15 Years of Planning

For a decade and a half, Project Evergreen asked what seemed like a perfectly reasonable question: “What should the Coast Guard do?”

If you’ve sat through strategic planning sessions, this probably sounds familiar. It’s typically the first question on the agenda. What should we do about artificial intelligence? How should we respond to digital transformation? What’s our climate change strategy?

The problem isn’t obvious at first glance. This question appears logical, even necessary. But it creates a fatal dynamic.

When you ask “What should we do?” you’re asking workshop participants—typically senior strategists and consultants—to prescribe solutions. These prescriptions then get handed down to implementers who weren’t in the room and didn’t shape the solutions. As the Coast Guard discovered, “the ideal people to do the job might not be in the room.”

This creates what I call supply-side strategy: strategists manufacture solutions and push them onto implementers. Those solutions arrive as rigid directives disconnected from operational reality.

The fundamental flaw isn’t that strategists are separated from implementers—there are simply too many implementers to fit in a retreat. The flaw is the question itself.

Present-Forward Thinking: Perfect for Tactics, Fatal for Transformation

That innocent-sounding question—”What should we do?”—invisibly locks your thinking into a present-forward orientation.

Present-forward thinking starts with today. It analyzes current problems, extrapolates existing trends, and prescribes solutions based on incremental projections. This approach works brilliantly for everyday management. It’s ideal for hitting quarterly targets, solving operational problems, and managing predictable challenges.

But for 25-year transformation? It’s disastrous.

Why? Because present-forward thinking generates tactical responses to current conditions. It can’t account for fundamental shifts in your organization’s operating environment. It can’t help you prepare for demands that don’t yet exist. It treats the future as a slightly modified version of today.

Case in point: In 2001, Kodak had abundant, recent evidence that digital photography was no threat to traditional business. The present-forward mindset dominated the thinking of executives and blocked the possibilities.

Managers use present-forward thinking each day because it’s the default mode for problem-solving. But that’s exactly why it fails for long-range strategy. This familiar mode becomes invisible, and organizations apply it to challenges it was never designed to address.

The Cognitive Shift That Changed Everything

After 15 years of failure, the Coast Guard discovered the fundamental shift required: from present-forward to future-back thinking.

This framework, developed by strategy theorists Mark Johnson and Josh Suskewicz, represents a complete cognitive reorientation. Instead of starting with today’s problems and projecting forward, you start with 2050’s probable demands and work backward.

The new question becomes: “What demands will the organization face?”

This isn’t semantic trickery. It’s a fundamentally different way of thinking about strategy.

When the Coast Guard made this shift, they began identifying what they call “robust strategic needs”—outcomes required by specific long-term futures, each demanding particular strategic responses.

Here’s the critical difference: prescriptive solutions constrain implementers. Strategic needs empower them.

Prescriptions say “do this.” Strategic needs say “accomplish this outcome”—and then trust implementers to craft solutions suited to their specific contexts and the evolving reality they’re navigating.

How Future-Back Thinking Works in Practice

Project Evergreen now runs workshops that map multiple plausible 2050 scenarios. They explore various futures the Coast Guard might face—different geopolitical landscapes, climate conditions, technological capabilities, maritime threats.

Then something critical happens. As the project team explained: “The solution space had to be left to the people who were actually going to implement the solution.”

Instead of receiving detailed instructions, implementers receive strategic needs. They’re asked to “deconstruct and then reconstruct” these needs for their specific operational contexts.

This approach works because objectives spanning 25 years can’t be prescribed with any accuracy. The future will unfold in unexpected ways. Game-changing strategies require flexible frameworks that can adapt as conditions evolve. Strategic needs provide that framework. Rigid tactical plans don’t.

The result: Project Evergreen became what they call a “backdoor strategic contributor”—guiding organizational direction without constraining operational flexibility.

The 2025 Payoff from 2050 Thinking

Here’s where this approach delivers immediate value.

Future-back thinking reveals which of today’s “urgent” priorities are actually superfluous. When you clearly understand the demands your organization will face in 25 years, some current problems simply fade in importance. The larger perspective exposes which fires are worth fighting and which will burn out on their own.

This prevents wasting resources on solutions that won’t address actual long-term demands.

It also transforms implementer motivation. Instead of following someone else’s prescriptions, teams gain the autonomy to design solutions matched to their reality. That autonomy—the flexibility to meet strategic needs in contextually appropriate ways—creates genuine engagement and inspiration.

Applying This to Your Organization

Consider your organization’s long-range planning through this lens.

The present-forward approach asks: “What should we do about immediate challenges?” This generates aspirational goals—”become industry leader,” “achieve digital transformation,” “reach carbon neutrality”—often disconnected from implementation reality. These sound impressive in board presentations but provide little practical guidance for teams expected to deliver them.

The future-back approach asks: “What demands will our organization face in 2050?” This identifies strategic needs that divisions must customize for their contexts.

For example, rather than prescribing “implement AI across all functions, ”you might identify a strategic need for “decision-making capabilities that scale with data complexity.” Different departments can then develop solutions suited to their unique challenges—customer service might deploy conversational AI, logistics might focus on predictive routing, finance might build automated risk assessment.

A flexible framework instead of a rigid mandate.

The Counterintuitive Truth

The Coast Guard’s expensive lesson offers a counterintuitive truth: you need tomorrow’s perspective to understand today’s priorities.

Organizations that begin with present-forward thinking remain trapped in tactical responses to current conditions. They mistake busy-work for strategy. They confuse detailed plans with transformation.

Organizations that embrace future-back thinking gain something more valuable: clarity about which current actions actually matter for long-term survival.

That 25-year horizon isn’t about predicting the future perfectly. It’s about developing the perspective to distinguish signal from noise in the present.

The question isn’t whether your organization will face existential demands by 2050. It will. The question is whether you’re building the strategic foundation today to meet those demands—or whether you’re sowing the seeds of irrelevance while obsessing over quarterly results.

The answer starts with asking a different question.


Source: Project Evergreen’s Long-Range Strategic Planning, United States Naval Institute


The YouTube Strategy School: Why Your MBA Didn’t Teach You Strategic Thinking

Annie’s hands trembled as she reread the email from her CEO. “Let’s talk about developing your strategic capabilities.”

She’d just earned her MBA with honors, landed a promotion to Chief Marketing Officer, and crushed her Strategic Planning course with an A-. Now, three weeks before Christmas, her boss wanted to discuss her lack of strategic thinking.

The meeting went poorly.

“You’re just not being strategic enough,” he said, arms crossed.

“Can you give me specific examples?” Annie asked, pulling out her notebook.

He waved his hand vaguely. “It’s hard to explain. I just know it when I see it.”

She pressed for details. He offered hollow phrases about “seeing the big picture” and “thinking long-term.” Nothing concrete. Nothing actionable. By the time she left his office, both were frustrated.

Now it’s January. Annie sits at her desk, surrounded by expensive textbooks and highlighted case studies, completely lost. She can recite Porter’s Five Forces backward. She built financial models that made her professors weep with joy. Yet somehow, she’s failing at the very thing her degree promised to teach.

The brutal irony? Her CEO can’t articulate what strategic thinking actually is because he developed the skill unconsciously, through years of pattern recognition. Annie can’t demonstrate it because her MBA systematically removed the very experiences that build strategic intuition.

They’re both trapped. And neither understands why.

The MBA’s Fatal Flaw

Annie isn’t alone in this predicament. Across boardrooms worldwide, formally trained managers struggle to translate their academic frameworks into real strategic insight. They possess intellectual tools but lack the deeper capability that separates strategic thinkers from strategic memorizers.

Here’s what business schools won’t tell you: becoming genuinely strategic isn’t about learning more frameworks. It’s about understanding that strategy professionals operate in three distinct seasons—and most never experience the first two.

Season 3: Creation and Mobilization
This is the visible season. Senior leaders gather to craft corporate strategy over one to three months. PowerPoint decks multiply. The C-Suite debates market positioning. Consultants bill impressive hours. This is what most people imagine when they picture “strategic work.”

Season 2: Focused Skill Building
Between major strategic initiatives, professionals identify capability gaps and target specific learning. They read journals, attend workshops, and study new frameworks. MBA programs excel at teaching a few basic Season 2 skills.

Season 1: Curiosity-Driven Exploration
This is the secret season. The forgotten season. The season where strategic intuition actually develops.

And it’s completely absent from formal business education.

Warren Buffett’s Secret Curriculum

To understand why Season 1 matters so profoundly, consider how Warren Buffett transformed Katherine Graham from overwhelmed newspaper heiress into one of America’s most respected CEOs.

In 1963, 46-year old Graham suddenly inherited control of The Washington Post after her husband’s death. She’d been a housewife with zero business experience. Now she faced a company, competitors, and boardroom dynamics she didn’t understand. Terrified but determined, she reached out to Buffett for guidance.

What happened next reveals everything about how strategic thinking actually develops.

Buffett didn’t send her to business school. He didn’t recommend management textbooks. He didn’t even explain financial statements, despite being one of the world’s greatest investors.

Instead, according to researcher Cedric Chin, Buffett quietly assembled a curated collection of annual reports from diverse companies across multiple industries. Then he sat with Graham and walked her through them, one by one.

But here’s the crucial detail: they didn’t analyze balance sheets or scrutinize financial ratios. They discussed stories. Why did this CEO make that decision? What pattern do you notice across these three retail failures? How did this manufacturer navigate technological disruption?

Over months of discussing hundreds of these narratives, Graham developed something more valuable than financial expertise. She built a mental library of business patterns—a sixth sense for recognizing strategic situations before they fully materialized.

The result? A powerful 28-year tenure that transformed The Washington Post into a media powerhouse.

Any MBA professor would dismiss Buffett’s approach as unscientific, inefficient, and impossible to grade. Yet it produced extraordinary results. Why?

The Ill-Structured Domain Problem

Corporate strategy isn’t like chess. Chess has clearly defined rules, limited possible moves, and objective evaluation of positions. Master chess by studying enough positions and you’ll reliably improve.

Strategy operates differently. It’s what cognitive scientists call an “ill-structured domain”—a field where:

  • The rules constantly change
  • Problems arrive with incomplete information
  • Multiple valid solutions often exist
  • Varying contexts determine which frameworks apply
  • Pattern recognition trumps analytical rigor

In ill-structured domains, you don’t become expert by memorizing frameworks. You develop expertise through massive exposure to varied cases, gradually building intuition about what patterns matter and which don’t.

This is why Annie’s MBA, for all its rigor, failed her. Business schools teach Season 2 skills in Season 2 format: structured, analytical, framework-driven. But strategic intuition develops in Season 1, through unstructured, curiosity-driven exploration of countless business stories.

Her professors taught her to dissect strategies. Buffett’s method taught Graham to recognize them in the wild.

Annie’s Accidental Discovery

Over the Christmas holidays, Annie found herself doing something she normally avoided: falling down a YouTube rabbit hole.

It started innocently. She’d always wondered why Apple’s iPhone crushed Blackberry, Nokia, and Ericsson—giants that seemed untouchable until they weren’t. A Google search led her to a documentary video. That led to another. And another.

Four hours later, having watched 21 videos spanning mobile phone history, product launches, and CEO interviews, she emerged with a strange new capability. She could now answer a question she’d never consciously considered: “What would I have done differently as CMO at Nokia?”

But immediately, guilt set in. Had she just wasted an evening on the digital equivalent of binge-watching reality TV or TikTok? Shouldn’t she be reading the Harvard Business Review journal articles sitting in her queue?

What Annie didn’t realize: she’d accidentally stumbled into Season 1 learning.

That “wasted” evening accomplished something her expensive Strategic Planning course never could. By immersing herself in multiple failure narratives, she began building the pattern recognition library that expert strategists draw from automatically.

One case study teaches frameworks. Twenty-one interconnected stories start building intuition.

Building Your Own Season 1 Practice

The transformation Annie needs won’t come from reading one more business book or taking another certification course. She needs to deliberately create her Season 1 practice.

Here’s what that looks like:

Consume voraciously, but with purpose.
Watch YouTube documentaries about business failures. Read long-form narratives about company transformations. Follow industry evolution stories across decades. The key isn’t passive consumption—it’s exposing yourself to enough varied cases that patterns start emerging naturally.

Ask the practitioner’s question.
Don’t just absorb stories. Constantly ask: “What would I have done as CMO/CEO/strategist/consultant in this situation?” This active engagement transforms entertainment into training.

Seek variety over depth initially.
Early in Season 1, breadth matters more than depth. Sample retail failures, tech disruptions, manufacturing transformations, and service industry evolution. Cross-industry patterns are often more valuable than industry-specific expertise.

Let curiosity lead.
Unlike Season 2’s targeted learning, Season 1 works best when you follow genuine interest. That four-hour YouTube session worked for Annie because she authentically wanted to understand mobile phone competition.

Connect consumption to creation.
Eventually, Season 1 exposure fuels Season 2 learning, which prepares you for Season 3 execution. But the sequence matters. Don’t rush to application before you’ve built sufficient pattern recognition.

The Real Competitive Advantage

When Annie returns to her next major strategic initiative—her next Season 3 moment—she’ll show up differently. Not because she learned new frameworks, but because she’s developed strategic peripheral vision.

She’ll recognize patterns her CEO can’t articulate but knows when he sees. She’ll spot familiar dynamics in unfamiliar situations. She’ll propose approaches that feel intuitively right, even if she can’t immediately explain why.

This is what her boss meant by “strategic thinking.” Not framework mastery. Pattern fluency.

And her company becomes the ultimate beneficiary. Now they have a CMO who brings genuine strategic intuition to every discussion—the kind of thinking that can’t be faked, purchased, or crammed before a meeting.

It just has to be grown, season by season, story by story.

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P.S. You are invited to share in my compilation of strategy-related YouTube videos at StratCinema.org

P.P.S. This article is based on a column I wrote for the Jamaica Gleaner.

P.P.P.S. Here are some LLM prompts you can use for further learning.

Here are instructions and 5 prompts for readers developing strategic fluency:


Before Using These Prompts

Copy and paste this context into your LLM to get better responses:

“I’m developing strategic intuition by studying business cases, company failures, and industry transformations—an approach called Season 1 learning. Unlike traditional MBA education that focuses on frameworks, I’m building pattern recognition by exposing myself to many varied business stories. I’ll be sharing cases I’ve consumed (YouTube videos, articles, books, documentaries) and asking you to help me extract strategic insights and patterns. Your role is to help me think like a practitioner who must make decisions under uncertainty, not like an academic analyzing what already happened. Push me to identify what I would have done differently and what patterns I’m noticing across multiple cases.”


Prompt 1: The Practitioner’s Debrief

“I just watched/read [title/description of case]. Here’s what happened: [2-3 sentence summary].

Now help me process this as a strategist-in-training:

  • What was the critical decision point where things could have gone differently?
  • If I were [specific role: CMO/CEO/Head of Product] at that moment, what information would I have lacked that seems obvious in hindsight?
  • What would I have needed to believe or notice to make a better choice?
  • What’s one pattern here that might appear in completely different industries?”

Prompt 2: Cross-Case Pattern Recognition

“I’ve now consumed [number] cases about [general theme: tech disruption/retail transformation/product failures/etc.]. Here are brief descriptions of 3-5 of them: [list cases with 1-sentence descriptions].

Help me identify:

  • What strategic pattern appears in at least 3 of these cases?
  • What does this pattern look like in its early stages, before the outcome is obvious?
  • When this pattern appears, what are the hard-to-see warning signs?
  • What would ‘seeing this pattern early’ have enabled in each case?
  • In what completely different context might I encounter this same pattern?”

Prompt 3: The Mental Library Builder

“I want to add this case to my ‘mental library’ of strategic patterns: [describe case].

Help me catalog it effectively:

  • What’s the one-sentence ‘pattern name’ I should remember this case by?
  • What are the 2-3 specific details that make this pattern recognizable in real-time?
  • Which other cases in my library does this connect to or contradict?
  • If I’m in a strategy meeting and this pattern is emerging, what question should I ask to test if it’s really present?
  • What’s the ‘inverse’ of this pattern—what does success look like when someone navigates this well?”

Prompt 4: The Scenario Transfer

“I just studied how [Company X] failed at [situation]. Now help me practice transferring this insight:

Imagine I’m [specific role] at a company in a completely different industry—say [name specific industry]—and I’m seeing these three signals: [describe 3 current business signals].

  • Could the pattern from [Company X]’s failure be emerging here?
  • What would I need to investigate to confirm or rule out this pattern?
  • If it IS the same pattern, what would I do in the next 30/90/180 days?
  • What would cause me to be wrong about this pattern applying?
  • What other patterns from my library might explain these signals better?”

Prompt 5: The Strategic Intuition Audit

“I’ve been doing Season 1 learning for [time period]. I’ve consumed approximately [number] cases covering [list topic areas].

Help me audit what strategic intuition I’m actually building:

  • Based on what I’ve described, what are the 3-4 patterns I seem to be recognizing most readily?
  • What types of strategic situations am I probably still blind to?
  • Where are the gaps in my mental library? (What industries, failure modes, or strategic contexts am I under-exposed to?)
  • Given my role as [your actual role], which 5 specific case types should I prioritize consuming next to build practical pattern recognition?
  • How would I know if I’m moving from ‘consuming cases’ to ‘recognizing patterns in real-time’?”

How to Use These Prompts

Start with Prompt 1 after every case you consume. Use Prompt 2 weekly after you’ve accumulated several cases. Deploy Prompt 3 when a case feels particularly instructive. Use Prompt 4 monthly to practice transferring insights to your actual work context. Run Prompt 5 quarterly to ensure your Season 1 practice is building genuine strategic intuition, not just entertainment consumption.


Note – this article is based on a column written for the Jamaica Gleaner.