Planning Is Good. Those Who Plan Don't Suffer

"The right plan keeps you from carrying by hand the weight you could have sent by truck."

I was 18 years old when I joined the Army through the Officer Preparation Corps (NPOR). The first three months of basic training were grueling. In that initial phase, the rule was simple: obey. You don't debate the plan. You execute, follow orders, adapt to the terrain, and endure in silence.

In the fourth month, however, everything flips overnight. You become the leader. Now you are the one receiving the assignment, gathering the squad, assigning roles, and organizing the operation. Right on my very first mission in command, I learned the most enduring management lesson of my life.

The task was straightforward: reconnoiter a watercourse. We gathered around the map and put together what we thought was a flawless technical plan. We requisitioned every piece of equipment we might need: inflatable boat, measuring tape, plumb line, survey stakes... a complete arsenal to measure banks, depth, and current.

We only forgot to request one item: the truck.

Reality hit immediately. We had to carry the boat and all the measuring gear by hand, walking for miles on foot to the reconnaissance point. While the squad marched exhausted with the equipment on their shoulders, the sergeant drove slowly alongside us in the exact truck we had failed to request, smiling out the window and repeating:

"Planning is good... those who plan don't suffer."

I never forgot that scene.

Why do we forget "the truck" in business? The Planning Fallacy

More than fifteen years working in software engineering, data, and operations have shown me that this mistake is not exclusive to 18-year-old cadets. It happens every week in companies of every size.

Teams spend days debating the tech stack, the cloud architecture diagram, or the color-coded Gantt chart for the executive presentation, yet forget the basic operational logistics required to make the work happen. They start an integration sprint without partner sandbox credentials. They buy expensive AI tools before cleaning the source data. They demand faster delivery from developers whose test environment breaks three times a week.

In behavioral science, this bias has a well-documented name. In 1979, psychologists Daniel Kahneman and Amos Tversky formulated a concept that Kahneman later expanded in Thinking, Fast and Slow (2011): the Planning Fallacy.

When we plan an initiative, our brains naturally default to the "inside view": we focus narrowly on the technical steps of the task itself (the boat, the tape, the plumb line) and silently assume the surrounding environment will work without friction. We ignore the "outside view", which accounts for logistical dependencies, approvals, input quality, and operational transport.

What 16,000 projects reveal about rushing into execution

Skipping that logistical review to "start coding right away" carries a steep price. In How Big Things Get Done (2023), Oxford University professor Bent Flyvbjerg and journalist Dan Gardner analyzed the world's largest database of project performance: over 16,000 projects across 136 countries and 20 fields, ranging from infrastructure to enterprise IT transformations.

Their findings dismantle the myth that "moving fast and fixing it along the way" is a strategy:

• 91.5% of projects overrun budget, schedule, or both;
• Only 0.5% deliver on budget, on time, and with the promised benefits simultaneously;
• Information technology ranks among the categories with the highest fat-tailed risk: when upfront preparation fails, cost and schedule overruns don't miss by 10%, they multiply several times over.

Comparing the rare 0.5% of winners against the failures, Flyvbjerg summarized the winning discipline in four words: "Think slow, act fast."

Effective leaders don't write fifty-page bureaucratic documents nobody reads; they test critical dependencies before ordering the squad to march. They verify the truck is booked before pulling the boat out of the warehouse.

Specific goals require real execution conditions

There is a second common management trap: believing pressure can replace preparation.

In a landmark paper published in American Psychologist (2002), organizational psychologists Edwin Locke and Gary Latham synthesized 35 years of empirical research on Goal-Setting Theory across more than 40,000 participants.

They proved that specific, measurable goals consistently outperform vague exhortations to "do your best." Yet their research highlights a decisive moderator: situational constraints and resources. When leaders set ambitious goals without removing operational blockers or providing the necessary tools, specific goals stop driving productivity and start generating burnout, risky shortcuts, and frustration.

Planning is not about predicting every turn of the future. It is about aligning three things before kickoff: where we want to go, how we will measure progress, and what logistics will keep the team from hauling dead weight.

A Simplified OKR with "The Truck Check"

To apply this on Monday morning without adding corporate bureaucracy, I use a lean structure that pairs a Simplified OKR with an explicit dependency check:

• Objective: What do we want to achieve in one clear, jargon-free sentence?
• Key Result 1 (Source visibility): How will we measure our current baseline with reliable data?
• Key Result 2 (Impact metric): Which concrete efficiency, cost, or quality metric must move, and by how much?
• Key Result 3 (Operational fix): How many real process deviations or bottlenecks will we eliminate during the cycle?
• The Truck (Critical dependencies): Which credentials, data pipelines, approvals, or infrastructure must be ready on day zero so the team can execute without improvising?

Practical example in a real operation

Objective: Reduce fuel waste in internal transport operations.

1. KR1: Map 100% of refueling events at the source by the end of month one.
2. KR2: Reduce average fuel consumption per machine by 15% to 20% within 90 days.
3. KR3: Identify and fix at least 5 recurring route or logging deviations.
4. The Truck: Ensure vehicle QR Code tags, a lightweight offline-capable mobile app for operators, and daily dashboard ingestion are working before holding drivers accountable for the target.

Simple, direct, and verifiable. Nobody marches out carrying an inflatable boat on their back hoping for a miracle at the end of the quarter.

Four questions before your next delivery

Before kicking off your next sprint, approving a budget, or pushing your team for speed, pause for five minutes and ask out loud:

1. What is our real objective, and what metric will prove beyond opinion that we succeeded?
2. What is our truck here? Which access, contract, test environment, or clean dataset are we forgetting to request because it seems too obvious?
3. Who will carry this weight in daily operations after the kickoff slides are closed?
4. If something stalls halfway through, which external dependency should we have unlocked today?

Leadership isn't just assigning tasks from afar. It is preventing unnecessary suffering. It is paving the road with intelligence so your team's energy goes entirely into real outcomes rather than hauling the weight that a lack of foresight left behind.

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Verifiable references and further reading

• Kahneman, D., & Tversky, A. (1979). Intuitive prediction: Biases and corrective procedures. TIMS Studies in Management Science, 12, 313-327 / Kahneman, D. (2011). Thinking, Fast and Slow. Farrar, Straus and Giroux.
• Flyvbjerg, B., & Gardner, D. (2023). How Big Things Get Done: The Surprising Factors Behind Every Successful Project, from Home Renovations to Space Exploration. Crown Currency / Oxford Global Projects (dataset of 16,000+ projects).
• Locke, E. A., & Latham, G. P. (2002). Building a practically useful theory of goal setting and task motivation: A 35-year odyssey. American Psychologist, 57(9), 705-717.