We are very good at explaining the past.

After something has unfolded, successfully or otherwise, our minds instinctively weave a story in reverse. We explain outcomes through decisive leadership, good strategy, clear intent, or, when things don’t go to plan, through poor execution or flawed decisions. These stories feel convincing because they are coherent. They offer a sense of order and meaning after the fact.

What they often miss, however, is the role of the unexpected: timing, luck, relationships, circumstance, and the contributions of many others that don’t sit neatly inside a narrative of individual agency. We tend to overemphasise our skill and capacity, and underestimate how much emerged through conditions we did not control or even see.

This matters because the stories we tell about how things worked strongly shape how we plan for the future.

Why strategic planning so often falls short

Strategic planning is not inherently flawed. The challenge lies in the assumptions that often sit beneath it.

Much strategic planning implicitly treats the future as an extension of the past. It assumes that most variables will remain relatively stable, that cause and effect can be mapped in advance, and that change will come from ordering the pieces correctly and getting them to do what we think needs to be done.

There is a useful reminder here from philosopher Alfred Korzybski, who famously observed that “the map is not the territory.” Any plan, model, or strategy is a representation of reality, not reality itself. Maps can be incredibly useful, they help us orient, coordinate, and make sense of complexity, but only if we remember their limits.

In increasingly complex and dynamic systems, the gap between the map and the territory can widen quickly. Assumptions that once held, can no longer. Feedback loops shift and new actors and constraints appear. Yet our strategies often remain fixed to the map we created, even as the territory itself changes beneath our feet. When this happens, the problem is not that we lack better maps, but that we forget they are maps at all.

But most of the systems we are working in today, organisations, communities, economies, ecological and social systems, are not stable. They are dynamic, interconnected, and constantly evolving. Small changes can have disproportionate effects. New constraints appear. Old assumptions quietly stop holding.

As a result, plans are frequently derailed by things we hadn’t accounted for. Priorities shift. Urgent demands crowd out the work we intended to focus on. Energy gets pulled into responding rather than reflecting. And often, there is little space built in to pause, sense what is changing, and adapt how we are operating.

In many cases, disruption is treated as failure, rather than as information.

Why we keep returning to this way of planning

Given these limitations, it’s worth asking why we hold so tightly to traditional approaches to strategy and action. Part of the answer is deeply human.

Our nervous systems crave certainty. From an evolutionary perspective, predictability equals safety. Planning gives us a sense of control and coherence in an uncertain world. It reassures us that we are moving forward, being purposeful, delivering outcomes.

There is also an identity dimension. We like to believe that our actions are what produce exceptional results. That belief supports narratives of competence, merit, and control, and can quietly obscure the roles of privilege, context, and collective effort.

And then there is measurement. Targets, milestones, and performance indicators make work visible and defensible. They signal seriousness. They help us account for progress in ways that institutions recognise and reward. This attachment to certainty and control is not just personal or psychological, it is systemic.

At both individual and organisational levels, we are strongly incentivised to operate within these parameters, even when we sense they no longer serve our best interests or the realities we are working within. Career progression, funding decisions, commercial contracts, client confidence, and organisational legitimacy are often tied to demonstrations of control, predictability, and measurable outcomes.

In many contexts, opting out is not a neutral choice. Questioning certainty, slowing down, or flagging such complexity can be read as a lack of rigour or ambition. Over time, people and organisations learn, often implicitly, that to “get ahead” they must perform control, even when the ground beneath that control is visibly shifting.

At the same time, many of us are sensing something else. For all the strategies, plans, frameworks, and performance measures we have put in place, we have not meaningfully “solved” many of the issues that matter most. Homelessness persists. Inequality deepens. Loneliness grows. Systems designed to support ageing populations are under strain. Climate and biodiversity loss accelerate despite decades of targets and commitments.

This is not for lack of effort, intelligence, or goodwill. It is increasingly difficult to avoid the feeling that doing more of the same, more plans, more metrics, more control, is not resolving the underlying conditions that give rise to these challenges.

What many people are noticing is not simply that individual strategies fail, but that the dominant way we approach change itself may be part of the problem. When complex, living systems are treated as predictable machines to be optimised, the results can look impressive on paper while the deeper dynamics continue to deteriorate.

If this is the case, then the question is not why people keep getting strategy wrong, but whether the way we have been taught to think about planning, action, and change is adequate to the realities we now face.

A different orientation: direction without rigidity

None of this means that direction, intention, or discipline are unimportant. The alternative is not drifting or abandoning responsibility. What may be needed is a shift in how we hold direction.

Rather than treating strategy as a fixed destination, we can approach it as a set of intentions, a desired direction of travel, held lightly enough to adapt as conditions change. This means recognising that we are not external designers standing outside the system, but participants embedded within living systems that respond to how we show up. Here, the emphasis shifts, from outcome to process.

There is often understandable pushback against “process for process’s sake,” but I think this is more about recognising that how we work, the relational conditions we cultivate, the quality of attention we bring, the ways we listen, respond, and learn together, all fundamentally shapes what is able to emerge.

A useful metaphor here is that of a sculptor working with stone. A sculptor may begin with an intention, even a rough vision. But it is only through the process of carving, through contact with the stone, responding to its grain, its resistance, its fractures, that the final form reveals itself. The sculpture is not imposed fully formed from the outset, it is discovered through the process itself. If the sculptor tried to control every outcome in advance, ignoring what the stone is offering, the work would likely fail.

Working in complex systems is similar. The future is not something we can fully design upfront. It is something we participate in shaping through ongoing interaction, responsiveness, and care.

Process over outcome in living systems

When we prioritise process over outcome, we are not abandoning results. We are acknowledging that in complex systems, outcomes are emergent. They arise from the quality of relationships, feedback loops, and conditions we create over time.

This orientation invites different questions:

• How are we showing up to this work?
• What kinds of relationships are we building or eroding?
• Are we creating space for reflection, learning, and adjustment?
• How do we respond when the unexpected appears?

Plans, in this frame, become hypotheses rather than promises. Disruption becomes information rather than failure. And progress is measured not only by what is delivered, but by whether we are strengthening the system’s capacity to adapt, learn, and regenerate towards the outcomes we hope to see in the world.

Accounting for what we cannot control

Perhaps the most difficult part of this shift is accepting that we cannot fully control outcomes.

This does not diminish responsibility as such, rather deepens it. Asking us to take responsibility not for guaranteeing results, but for tending the conditions under which more life-affirming, resilient possibilities can emerge. Working in living systems requires staying in relationship with the territory itself, rather than clinging too tightly to the maps we have drawn.

In a world characterised by uncertainty and change, the question may no longer be “How do we execute the plan?” but rather:

• How do we stay in relationship with what is unfolding?
• How do we remain responsive without becoming reactive?
• How do we hold direction while staying open to being surprised?

Accounting for the unexpected is not a failure of strategy. It is an acknowledgement of reality.

And perhaps it is here, between intention and emergence, between direction and discovery, that more honest, resilient ways of working can begin to take shape.

This work matters not because it guarantees better outcomes, but because the challenges we are facing, socially, organisationally, and ecologically, are not yielding to control-based approaches, and pretending otherwise only deepens the gap between what we plan for and what actually unfolds.

Much of my work is about supporting people and organisations to develop these capacities in practice: learning to notice patterns rather than chase certainty, building relational conditions that can hold disagreement and ambiguity, and strengthening the ability to stay present and responsive when outcomes cannot be fully known in advance.

If this way of working resonates, particularly if you are feeling the limits of traditional planning and control, I’m always open to conversations about what it might look like to experiment with different approaches together.