The $171 Million Illusion: Why We Write Plans We Know Will Fail

The $171 Million Illusion: Why We Write Plans We Know Will Fail

The Strategic Planning Ceremony-a meticulous, expensive design of a yacht for waters riddled with icebergs.

The Ritual of Self-Deception

I was staring at Slide 81-the one titled “Synergistic Velocity Trajectories: 2025-2029”-when the Director of Perpetual Motion, a man named Gary who sweated expensive cologne, paused for dramatic effect. He didn’t notice half the room subtly adjusting their laptop cameras down so they could doomscroll Twitter. I checked my own reflection. I looked committed. I looked like I believed that these 81 slides, painstakingly crafted over 11 weeks by 21 highly paid analysts, would somehow withstand the relentless, disrespectful hammer of next Tuesday.

We spend an entire fiscal quarter performing the Strategic Planning Ceremony. We commission the $4,501 consulting report. We hold the three-day, off-site, vision-boarding retreat in the cabin that smells faintly of pine and desperation. And for what? So we can nail down the Core Operating Principles for the year 2028. We are meticulously designing a yacht for a body of water we haven’t checked for icebergs or sudden seismic shifts. It’s an act of profound, organizational self-deception.

That’s where the cynicism settles in, deep and cold, like the mud you didn’t realize you tracked in until you see the stain on the expensive rug. I almost sent an email this morning, one of those furious, highly-detailed emails outlining exactly why this entire exercise was an economic and emotional drain on the organization. I typed out the first 171 words before hitting delete. Not because I didn’t believe the critique, but because Gary (and people like him) don’t speak the language of effectiveness; they speak the language of mandated process. They need the document more than they need the result.

Planning Is Performative

We operate under the delusion that planning is about prediction. We genuinely believe that if we just triangulate enough market data points-if we just make the Excel sheets complex enough, with 11 different pivot tables on Tab 1-we can somehow lock the future down. The brutal, necessary truth, which we refuse to acknowledge in the fluorescence of the boardroom, is that planning isn’t predictive. It’s performative. It’s a corporate rite of passage, a collective incantation designed to ward off the chaos of genuine uncertainty.

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The Sunroom Font Choice

Beautiful structure, debates on font choice.

VS

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Tempered Glass

Tangible; withstands market shifts.

The whole operation is designed to create the illusion of alignment and control. If you’ve ever seen truly robust, purpose-built outdoor architecture, like what Sola Spaces designs, you realize how much cognitive dissonance it takes to shift back to a discussion about “leveraging synergies.”

The Necessity of Immediate Action

I talked to someone recently who understands reality better than any executive I know. Luna B. She removes graffiti for the city. Not just painting over it-she uses specialized chemical blends and pressure washers to restore the surface entirely. Her work is immediate, messy, and undeniable. If she misses a spot, it’s still there. If her chemical ratio is off, she damages the surface. She doesn’t write 5-year plans for removing tagging. Her plan is: Look at wall, remove stain, repeat.

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“They want a 3-page risk assessment for buying a bucket of specialized solvent,” she said. “I write it, because I need the solvent, but the person who reads it has never seen actual aerosol spray paint, only PowerPoint, and they certainly haven’t had to clean up the mess at 4 AM.”

The Cost of Process (Time Allocation Analogy)

Action (Cleaning)

85%

Paperwork (Justification)

15%

Criticize the Ritual, Yet Perform the Dance

And here’s the corporate contradiction we all live: We ridicule the planning cycle, we joke about the uselessness of the 51 Strategic Imperatives, and then, come November 1, we put our head down and start writing the next one. We criticize the process, but we participate fully. We know the destination is irrelevance, but we drive the bus anyway. Why? Because the ritual itself is protective. It ensures the flow of capital and validates the positions of the people currently in power.

The real cost is the psychological damage. We teach our smartest people that their most visible, most time-consuming work-the Strategic Plan-is fundamentally disconnected from reality. We train them to compartmentalize: there’s the ‘Real Work,’ which happens in sprints and panic between 11 PM and 1 AM, and there’s the ‘Fake Work,’ which is the 9-to-5 corporate theatre of generating metrics for metrics’ sake.

I remember drafting the ‘Q3 Revenue Optimization Strategy’ a few years ago. I spent 61 hours modeling a scenario that required our primary competitor to cease all operations simultaneously. I knew it was fantasy, pure wish-casting packaged as foresight. But it fit the template. It satisfied the ‘Aggressive Growth Projection’ quota. I didn’t announce this ridiculous assumption, naturally. I just buried it deep in an appendix on page 231…

231

Fantasy Appendices Pages

From Prediction to Alignment

Maybe we need to stop asking if the plan is *accurate* and start asking if the plan is *necessary*.

I acknowledge my own failures in this space. I’ve written three separate five-year plans that failed spectacularly inside of 11 months. My biggest mistake? Believing my value lay in predicting the future, when the company only needed me to validate the current mood. I thought precision was the goal. It wasn’t. The goal was confidence, packaged neatly enough to present to the board.

The Synchronized Start

If you approach the planning process not as a predictive model but as an organizational alignment tool-a shared, temporary fiction that gets 91 departments moving in roughly the same direction-it takes on a different, slightly less frustrating utility. It becomes less about the map and more about the synchronized starting gun.

Luna, with her graffiti removal, isn’t waiting for a 1-year strategy review to tackle the damage on the municipal bridge. She acts now. The planning ritual, for all its bureaucratic bloat, is the mechanism that allows the budget to be approved and the people to be hired, even if those people end up doing something completely different 41 weeks later. It’s the permission slip, disguised as a strategy document.

The Uncomfortable Truth

So, Gary finally finished Slide 81, and we clapped-11 polite, measured seconds of applause. The plan is filed, the budget is released, and the team will now proceed to ignore the plan while executing the actual work needed to keep the doors open, iterating wildly and reacting to the market in real-time.

Employee Time Allocation (Planning vs. Execution)

Planning (3.8%)

Budgeting (4.2%)

Execution (92%)

We traded reality for a ceremony, but sometimes, ceremony is all that keeps the gears from seizing up entirely. The paradox remains: We waste immense time planning for failure, yet that act of shared planning might be the only thing ensuring future success, even if that success looks nothing like the deck on Slide 81.

Reflecting on the necessity of ritual over prediction.