In boardrooms, schools, and homes alike, we are obsessed with plans. Five-year visions. Ten-year goals. Detailed roadmaps with milestones and targets. It looks impressive, all that structure, all that certainty. But let’s be honest: life has never followed our spreadsheets.

The truth is, we have confused planning with progress.

Every year, leaders, teachers, even parents sit down to plan the perfect path. “By next term, my students will…” “By next quarter, our school will…” And yet, the world refuses to behave. The economy shifts. Technology changes. Children evolve. What looked clear on paper begins to blur in reality.

Dwight D. Eisenhower, who planned the largest military operation in history, once said, “Plans are useless, but planning is indispensable.” He understood something we have forgotten, that the act of planning helps us think, but clinging to the plan blinds us.

We create detailed roadmaps not because they work, but because they comfort us. They make uncertainty feel less terrifying. But certainty is a dangerous illusion. The leaders most confident in their long-term plans are often the least prepared when reality shifts.

In education, we see this too. Schools cling to rigid syllabi, yearly targets, and fixed curriculums that assume learning moves in straight lines. But learning, like life, is rarely linear. Some children leap ahead; others spiral, pause, return, and grow in unpredictable bursts. The best educators are not the ones who control every lesson, they are the ones who adapt when the class takes an unexpected turn.

John Lennon captured it perfectly: “Life is what happens when you are busy making other plans.”

Why Rigidity Fails

Rigid plans create brittle systems, in organizations, in classrooms, and in people. When leaders fear deviation, they start rewarding compliance instead of creativity. When teachers stick to scripts, they stop noticing what’s really happening in front of them.

A perfect plan is like a glass sculpture, beautiful but fragile. The slightest shock, and it shatters.

Adaptive leaders, on the other hand, are fluid. They watch, listen, and shift. They ask, “What’s true now?” not “What did we predict then?” They don’t measure success by whether the plan was followed, but by whether progress was made.

Charles Darwin never said “survival of the fittest” in the way we use it. What he actually observed was that “It is not the strongest of the species that survives, nor the most intelligent, but the one most adaptable to change.” That’s as true in schools and boardrooms as it is in nature.

The best strategists today are not prophets; they are learners. They plan for flexibility, not permanence. They hold their goals lightly and their curiosity tightly.

A CEO I met recently told me, “We stopped planning in quarters. We plan in questions.” That is the right instinct. What if schools did the same? Instead of “How do we cover all chapters by March?”, we ask, “What are children most curious about right now, and how can we build on that?”

In the classroom, adaptive teaching looks like this: a teacher senses confusion, pauses mid-lesson, and lets students explain concepts to each other. The plan dissolves, but real learning begins. That is leadership in action, staying responsive, not rigid.

Steve Jobs once said, “You can’t connect the dots looking forward; you can only connect them looking backward.” Meaning: clarity comes in hindsight. The only thing we can truly control is our willingness to stay awake and adapt.

The best founders, principals, and teachers I know operate on short horizons. Not because they lack vision, but because they understand movement creates momentum. They take one deliberate step, watch what happens, and adjust.

They don’t chase perfection, they chase learning. They don’t say, “We know the path.” They say, “We will discover it.”

In truth, adaptability is a higher form of strategy. It’s strategy that breathes.

The pandemic proved it brutally: every plan can collapse overnight. The leaders who thrived were not the ones with polished binders; they were the ones who responded, who listened, pivoted, improvised. The same applies in education reform.

We don’t need more rigid curricula or pre-set blueprints. We need dynamic classrooms where students and teachers co-create the journey, respond to feedback, and adjust course, just as the best organizations do.

So, perhaps it’s time to stop obsessing over the perfect five-year plan and start mastering the five-day pivot.

Because the future is not waiting for your approval. It’s unfolding, right now, and it belongs to those who can dance with it.

As philosopher Alan Watts wrote, “The only way to make sense out of change is to plunge into it, move with it, and join the dance.”

And in education, as in life, that may be the only plan that still works.