Today’s Strategic Alignment Journal post in two sentences:
We need sufficient clarity to make informed decisions, but we cannot reasonably expect to know everything those decisions will eventually make possible. What we learn through experience can deepen our understanding, challenge our assumptions and reveal opportunities that were not visible when we first decided to act.
This morning, reading Justin Welsh’s Saturday Essay, Illegible Careers, I began to see a connection between the two.
Welsh was reflecting on how his understanding of a successful career had changed since he began working for himself in 2019. He had spent much of his professional life following a fairly predictable career path, one in which the next step was usually recognizable. Working for himself changed that. He could make a decision that seemed entirely reasonable at the time without knowing what it would eventually contribute to. Looking back seven years later, he could see connections between decisions, experiences and opportunities that would have been almost impossible to anticipate when he began.
Welsh makes an observation that I think extends well beyond careers:
Your career doesn’t need to make sense in advance to make sense in hindsight.
I think the same could be said about the future more broadly.
The future doesn’t need to make sense in advance to make sense in hindsight. We spend considerable time trying to determine how things will unfold before we commit ourselves to a course of action. We develop plans, establish goals, identify milestones and make projections based on what we believe is likely to happen.
There is good reason for doing these things. They help us organize our thinking, establish priorities and make informed decisions. The difficulty arises when we begin to expect that the future should unfold according to the picture we have constructed, or when we become reluctant to act because we cannot see how everything will eventually fit together.
What We Know Today Cannot Tell Us Everything About Tomorrow
Every decision is made with a particular level of understanding. We know some things, believe others to be true and recognize, hopefully, that there are things we do not yet know. The information available to us helps us determine what makes sense under the circumstances. But making a sound decision does not mean we can anticipate every consequence, opportunity or development that may follow. Some information only becomes available after we have acted. Some possibilities only become apparent because of the experience that follows. And some of the most consequential developments may have very little resemblance to what we originally set out to accomplish.
Welsh describes how his healthcare consulting work led him to begin writing online to attract customers. Through writing, he discovered that a significant portion of his audience was interested in learning how to build an online presence rather than purchasing healthcare consulting services. That discovery eventually led to courses, digital products and a different understanding of how he could create value. Each decision was informed by what he knew at the time, but each experience also revealed something that influenced what he did next. He did not begin with a complete picture of the business he would eventually build. The picture developed as he made decisions, observed the results and recognized opportunities that had not previously been visible.
Consider what might have happened had he remained committed to his original direction.
Had Welsh insisted on remaining faithful to his original understanding of what his business should become, he might have overlooked the information his audience was giving him. He could have continued writing exclusively about healthcare, treating interest in other subjects as a distraction from his original purpose. Instead, he recognized that what he was learning warranted reconsideration. This does not mean that every unexpected response should cause us to change direction. It means that we need to remain attentive to information that may challenge our assumptions about where the greatest opportunities lie.
Clarity Before Action, Greater Clarity Through Experience
I believe clarity needs to precede action. We need to understand what we are trying to accomplish, why it matters, what is influencing the situation and whether the action we are considering is appropriate. Without that understanding, we risk confusing activity with progress and investing resources in decisions that have not been adequately considered. But I also recognize that the clarity required to make an initial decision is not necessarily the full extent of the clarity we will eventually need. Once we act, we encounter circumstances, responses and information that allow us to develop a more complete understanding of what we are dealing with.
Both stages require us to take responsibility for the quality of our thinking and decisions.
Before acting, we have a responsibility to examine the situation carefully enough to make a considered decision. After acting, we have a responsibility to pay attention to what the experience reveals.
The first helps us determine whether we have good reason to proceed. The second helps us determine whether those reasons remain valid, whether our assumptions have been supported and whether the next decision should be different from the one we originally anticipated.
It is possible to make a reasonable decision that does not produce the expected outcome. It is also possible to achieve the expected outcome and subsequently discover that a different opportunity has emerged. Neither circumstance automatically makes the original decision right or wrong. What matters is whether we understand what has happened and use that understanding to inform what comes next. The ability to reconsider a decision in light of new information is not necessarily evidence that the original decision was poorly made. Sometimes it is evidence that we are learning what could not reasonably have been known beforehand.
When the Original Plan Becomes a Limitation
I think this is particularly relevant to how we approach planning and strategy. We invest considerable effort in developing plans that describe where we want to go and how we intend to get there. We establish performance measures, allocate resources and create expectations around particular outcomes. These are necessary disciplines. But plans are developed at a particular point in time, using the information, assumptions and circumstances available at that point. As those circumstances change, the relevance of the plan must be examined.
One of the risks is that we become so invested in the original plan that we interpret new information primarily in terms of whether it supports what we have already decided. We may dismiss an emerging opportunity because it was not part of the strategy. We may continue pursuing an initiative because resources have already been committed to it. Or we may interpret an unexpected outcome as failure without considering what it tells us about the assumptions on which the original decision was based. In each case, our commitment to the plan can interfere with our ability to recognize what is actually happening.
There is also a difference between having a clear direction and insisting on a predetermined route.
Direction helps us establish what matters and provides a basis for evaluating choices. The route represents our current understanding of how we might get there. When we confuse the two, changing the route can feel like abandoning the destination. Yet there may be circumstances in which remaining committed to the original route is precisely what prevents us from making meaningful progress. The challenge is to know what should remain constant, what needs to be reconsidered and what new information is sufficiently important to warrant a change.
Not Everything That Makes Sense in Hindsight Was Inevitable
There is another aspect of Welsh’s observation that I think deserves attention. When we look back over our experiences, we can often identify connections that were not apparent while events were unfolding. A conversation led to an introduction. An unsuccessful proposal helped us recognize a problem with our positioning. A project revealed a capability we had not previously considered valuable. A decision to pursue one opportunity introduced us to another. Looking backward, these experiences can appear to form a logical progression.
But we should be careful not to confuse the ability to construct a coherent story with evidence that everything happened as it needed to happen. Hindsight gives us access to information that was unavailable when the original decisions were made. It also allows us to connect events selectively, sometimes giving greater significance to experiences because we now know what followed. Not every decision contributed positively to the eventual outcome. Not every detour was necessary. And not every unsuccessful effort becomes valuable simply because we can identify something we learned from it.
The more useful exercise is to consider what actually changed as a result of those experiences. What did we come to understand that we had not understood before? Which assumptions were challenged? What did we discover about our capabilities, our customers, our circumstances or the opportunities available to us? And perhaps most importantly, did that understanding influence the decisions we subsequently made? Experience alone does not guarantee better judgment. Its value depends partly on our willingness to examine it and allow what we discover to influence how we think and act.
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What Becomes Possible Beyond the Original Problem
Returning to yesterday’s Matchbox article, I find myself considering how much of what eventually became possible could reasonably have been anticipated when the original problem was being addressed. The immediate challenge was clear enough. The solution was practical and specific. But the commercial possibilities that emerged extended far beyond the circumstances that prompted the initial idea. What began as a response to a restriction became something with an entirely different scale of opportunity.
Welsh’s experience illustrates a similar process over a much longer period. His decisions were not all directed toward an outcome he had identified seven years earlier. Some created opportunities, some challenged his assumptions and others helped him recognize what was not working. The business he eventually developed was influenced by what he learned along the way.
In both stories, the eventual outcome was not fully visible at the beginning, but that did not prevent the people involved from making decisions that made sense in their immediate circumstances.
I think we sometimes place an unreasonable burden on our decisions by expecting them to explain too much of the future.
We want assurance that the direction we choose will lead to the outcome we imagine. We want to know that the time, effort and resources we commit will produce the return we anticipate. These are legitimate considerations, particularly when the consequences of a decision are significant. But there is a point beyond which the demand for certainty becomes an obstacle rather than a safeguard. We cannot reasonably expect today’s information to answer every question that tomorrow’s experience may raise.
The future will be influenced by decisions we have not yet made, information we have not yet encountered and circumstances we cannot fully anticipate.
That does not make planning futile or careful decision-making unnecessary. It makes both more important, provided we understand their limitations. We need sufficient clarity to make the next appropriate decision, the discipline to follow through and the willingness to reconsider our direction when what we learn gives us reason to do so.
Perhaps what makes the future intelligible in hindsight is not that everything was connected by a plan we failed to recognize at the time. It may be that each experience contributed to an understanding that made subsequent decisions possible. We can look back and see how one thing led to another, even though we could not have predicted the sequence in advance.
And perhaps this is enough. We do not have to know how every decision will eventually fit into the story of our lives, careers or organizations. We do need to understand why we are making the decisions before us, remain attentive to what follows and recognize when what we have learned calls for a different response.
Strategic Reflection Prompt
Are you expecting your current plans and decisions to account for more of the future than they reasonably can? What have your recent experiences revealed that you could not have known beforehand, and how is that new understanding influencing what you decide to do next?
About Giselle
Most costly decisions begin with a wrong read of the situation.
I’m Giselle Hudson — The Pre-Fixer. I help leaders see the real problem before they act, in my writing and in my work. I don’t fix; I pre-fix. Most advisers jump to solutions before they’ve found the real problem. I find it first — the part that isn’t fully visible yet. Once we see that clearly, everything else falls into place, and confident, right action can follow.
Through my daily Strategic Alignment Journal, I explore leadership, decision-making, and the patterns that shape organizations — helping leaders make sense of complexity before they commit significant time and money to the wrong thing.
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