The Road Not Traveled



What might have been?


For some, the question invites poignant reflection on missed opportunities, as in the famous line from John Greenleaf Whittier’s poem “Maud Muller”: “For of all sad words of tongue or pen/The saddest are these: ‘It might have been.’”


For others, the same question prompts rapt speculation about chains of events set in motion by a single choice or occurrence, and how different circumstances might have yielded different outcomes. This theme is particularly common in the “alternative history” genre of popular literature and media: Philip K. Dick’s The Man in the High Castle (what if the Axis had won the Second World War?), Philip Roth’s The Plot Against America (what if Charles Lindbergh had succeeded in his bid for the U.S. presidency?), and the Apple TV + show For All Mankind (what if the Soviets had been the first to put a man on the moon?).


Yet asking “what might have been?” doesn’t need to mean wallowing in regret or getting wrapped up in elaborate counterfactuals, as entertaining as those can be. In fact, contemplating the path not taken is a powerful mode of analysis and learning. For organizations, it can reveal how they arrived at where they are now, and what that suggests about where they should go next.


To grasp how the path not taken illuminates decisive events and choices, consider two related concepts: contingency and overdetermination. Both help us to examine the causes of change over time.


Contingency refers to the individual actions—often seemingly minor at the time—on which major events and turning points can hinge. For instance, during the U.S. Civil War, a Union Army corporal stumbled upon a copy of Confederate battle plans lying in the grass at a recently-vacated camp site. This “lost dispatch” helped the Union emerge victorious at the battle of Antietam, which in turn emboldened President Abraham Lincoln to sign the Emancipation Proclamation declaring an end to slavery in the states that had seceded. Here, considering the path not taken—the starkly different timeline that might have unfolded had a single document not turned up when it did—underscores the contingency of those events.


The opposite of contingency is overdetermination: when several factors all pointed toward the same outcome. Some analysts argue, for instance, that the collapse of the Soviet Union was overdetermined. Instead of emphasizing contingency and individual agency—such as the role of Mikhail Gorbachev and the choices he made—they cite long-term forces like economic decline, ethnic nationalism, and demographic changes. All of those factors, they argue, made the USSR’s fall virtually inevitable. Thus, most of the paths-not-taken would likely have produced the same outcome.


What does this kind of analysis look like for organizations?


Take one major foundation that stood by a struggling grantee just as it was getting off the ground. The foundation’s support, as inconsequential as it may have seemed at the time, allowed the grantee’s pioneering work to continue. This paved the way for the foundation’s decisive backing for that sector as it grew—and for the grantee’s central, influential role in that growth. It also cemented the foundation’s own values, including its willingness to stand up for its core causes in the face of adversity. Examining the path not taken—what would have happened if the foundation had instead abandoned its grantee—underscores the importance of its choice both for the foundation’s identity and for the sector as a whole.


Consider, by contrast, a tech firm that was acquired by a larger company years after its founding. The firm has always looked back on this acquisition as a turning point, and some employees still wonder—sometimes wistfully—what might have happened had it been acquired by a different buyer. But a thoughtful analysis of the path not taken suggests that the firm’s destiny was overdetermined: deep industry trends, market demand, and the firm’s own innovations would likely have taken it in the same direction, even with a different acquirer. Such an analysis helps put the what-ifs to rest and shifts the focus to the firm’s true defining moments and enduring qualities, including its capacity for innovation and leadership’s instinct for where the market was going.


What kinds of insights should organizations look for in their analysis of paths not taken? It helps to focus on a few general applications:


1. Understand identity and values. Understanding who we are, whether as an individual or as an organization, means understanding who we chose to be—and not to be. By examining the path not taken, organizations can pinpoint the choices that shaped who they became, what role the rejected alternatives played in that story, and what all of this says about their core identity and values. In other words, they can better understand what they stand for by examining what they stood for—and what they didn’t.


2. Recognize the importance of individual choices, past and present. Examining the path not taken often reveals contingency: how present-day outcomes were not inevitable. This helps organizations better recognize, even celebrate, the impact of those choices and the individuals who made them. More importantly, understanding how an organization’s past leaders confronted a future that was uncertain and in flux, just as ours is today, can help organizations communicate the urgency of the present—the gravity and meaning of the choices they make today.


3. Let go of the “what-ifs”. It’s impossible to prove a counterfactual. Nevertheless, a thoughtful, evidence-based examination of what might have been can help organizations get beyond the what-ifs and focus on what really mattered, and still matters: the moments that shaped who they are today.


4. Revisit old ideas. Sometimes, examining the path not taken does reveal missed opportunities—a long-forgotten idea that could not be pursued at the time but makes sense to revisit today, in different or more favorable circumstances. By studying what might have been but wasn’t and why, organizations can avoid reinventing the wheel—or, more accurately, revisit an idea for a wheel that could not be built then but might be built now.


Ultimately, the path not taken—like Robert Frost’s road less traveled—is overgrown, shrouded in mystery. We can never be entirely certain where it would have led us. But we can make well-informed guesses based on our knowledge of the larger terrain—guesses that help us understand where we are and where we’re going, or even invite us to pursue similar paths today. And that can make all the difference.


Arielle Gorin, a Saybrook Senior Consultant, is currently engaged on a multigenerational family history for a private client, as well as a study of a global beauty company.