Beyond Luck: How to Harness Uncertainty for Innovation and Opportunity

Coincidence and serendipity are closely related concepts, linked by their shared reliance on unexpected events. Both describe moments when life takes an unplanned turn, yet they differ in important ways. Coincidence can be agnostic to outcome—sometimes positive, sometimes negative—while serendipity is, by definition, a fortunate discovery that opens new doors to value, growth, or innovation.

Exploring these concepts side by side sharpens our language and deepens our understanding of how chance intersects with choice. More importantly, it highlights a uniquely human advantage: while AI dominates the world of the known, humans excel at cultivating serendipity in the unknown. Entrepreneurship embodies this strength—transforming uncertainty into new products, services, and opportunities. By cultivating the conditions for serendipity, we increase the likelihood that hidden possibilities become pathways to innovation and progress.

About the author: Jeff Hulett leads Personal Finance Reimagined, a decision-making and financial education platform. He teaches personal finance at James Madison University and provides personal finance seminars. Check out his book -- Making Choices, Making Money: Your Guide to Making Confident Financial Decisions.

Jeff is a career banker, data scientist, behavioral economist, and choice architect. Jeff has held banking and consulting leadership roles at Wells Fargo, Citibank, KPMG, and IBM.

How coincidence and serendipity happen

Coincidence and serendipity may feel like pure chance, but they follow recognizable patterns. Both emerge when the threads of our lives intersect in ways that can be described and understood. Four key characteristics shape these moments:

1. Life Path: Time and Situation,

2. Convergence,

3. Valence, and

4. Expectations.

Together, these elements explain not only how coincidences occur, but also what makes certain ones transform into the positive discoveries we call serendipity.

Life Path: Time and Situation

Our lives can be understood as paths forged by situations unfolding through time. Each morning, we wake, follow routines, and step into new contexts—whether exercising, logging into work, or meeting a client. Every activity stands for a situation, a moment in which we occupy time and space. Even when contexts feel familiar, like going to the same gym or office, no two situations are ever truly identical—different people, weather, or moods make each moment distinct. This is why situations are both similar to the past and yet new in subtle but important ways. Some more so than others.

When we link individual situations together, we create a life path. Looking backward, that path feels fixed and almost deterministic—we can trace the steps we took yesterday, last year, or even a decade ago. Looking forward, however, the path is uncertain. The present becomes a unique crossroads, the point where the fixed past meets multiple possible futures. Every choice in the moment holds the power to alter direction. At work, for instance, you might answer an urgent email, step into a meeting, or take a short break. Each decision branches into a different segment of the path.

Our decision environment is shaped not only by external circumstances but also by the deep imprint of our neurobiology and upbringing. Much of this influence operates subconsciously—we are often unaware of how strongly it guides our choices. Dopamine, often described as the brain’s anticipatory reward and learning neurotransmitter, plays a central role by signaling expected rewards and surprises, motivating us toward certain futures over others. While these embedded patterns shape our life path automatically, it is possible to rewire aspects of the decision environment through discipline and the use of structured decision tools.

Coincidences and serendipities both occur along these paths. They are not planned or forced; rather, they emerge as unexpected crossings between two or more life paths at a particular point in time. While there is always a random element, the likelihood of convergence is not entirely accidental. Our neurobiology—especially the ways dopamine and other systems shape motivation, attention, and timing—creates natural alignments that bring people into shared situations. In this sense, coincidence and serendipity carry both the surprise of chance and the subtle influence of our human wiring, which increases the probability of such encounters.

Convergence

The second characteristic is convergence, the degree to which life paths intersect. Full convergence happens when two people—or two separate life paths—share the same situation at the same time.

Full convergence is direct: you and a former colleague end up in the same restaurant while traveling in a city far from home. A low degree of convergence might be parallel: two people never meet but are dealing with strikingly similar circumstances, such as launching startups in different countries at the same time.

Both coincidence and serendipity are rooted in convergence. They rely on the intersection of paths that were not deliberately coordinated. Without convergence, there can be no shared situation, and thus no spark of coincidence or serendipity. As we will discuss later, there are ways to increase lower convergence to achieve full convergence.

Valence

Valence is the degree to which a shared situation feels positive or negative. It is here that coincidence and serendipity diverge most clearly.

Coincidence is agnostic with respect to valence. A coincidence might be positive (running into an old friend, discovering two people share the same birthday), negative (two cars colliding at the same intersection, a bad outcome of unexpected timing), or neutral.  Coincidences can surprise us in ways that feel delightful, disastrous, or indifferent.

Serendipity, by definition, carries a positive valence. It is the “happy accident,” the discovery of something good or valuable when you were not seeking it.

For example, penicillin was a serendipitous discovery. Alexander Fleming was not searching for antibiotics, but mold accidentally contaminated a petri dish and revealed bacteria-killing properties. That event was not just a coincidence—it carried enormous positive valence, turning chance into transformative medical progress.

Thus, serendipity is best understood as a subset of coincidence—a coincidence with an intrinsically positive outcome.

Expectations

The final characteristic is expectation. Both coincidence and serendipity share an element of surprise. They arise outside of deliberate planning, catching us off guard in ways that defy normal prediction.

Expectations highlight a psychological dimension: we are wired to notice and remember unexpected patterns. Cognitive science tells us that surprise enhances memory formation and sparks dopamine release, giving coincidental or serendipitous events an outsized impact on how we interpret our lives.

Yet there is a difference:- A coincidence is simply unexpected convergence, regardless of whether it benefits us.- Serendipity goes further: it is unexpected convergence that exceeds our expectations in a positive way, adding value to our lives that we did not anticipate.

Expanded Definitions

Bringing these characteristics together allows for sharper definitions:

Coincidence is the unexpected convergence of life paths in time and situation, carrying positive, negative, or neutral valence. It is marked by surprise and does not require intentionality. Coincidences remind us of life’s unpredictability—they can delight us, harm us, or simply leave us amused at improbable overlaps.

Serendipity is a coincidence with positive valence. It is the convergence of life paths that unexpectedly yields something beneficial or delightful, often greater than what we might have imagined or sought. Serendipity requires the same ingredients as coincidence—life paths, convergence, surprise—but it is distinguished by its constructive, value-adding outcome.

Similarities and Differences include:

1. Life path: Coincidence emerges from unexpected crossings of situations through time. Serendipity is the same.

2. Convergence: Coincidence is the intersection of two or more paths in shared situations. Serendipity is the same.

3. Valence: Coincidence can be positive, negative, or neutral. Serendipity is always positive.

4. Expectations: Coincidence involves surprise but is not necessarily beneficial. Serendipity involves surprise that exceeds expectations in a beneficial way.

Operationalizing Serendipity: From Coincidence to Innovation

“Life can only be understood backwards; but it must be lived forwards.”

― Søren Kierkegaard

Earlier, we considered how our past is fixed and how our future is deeply influenced by upbringing and neurobiology. At first glance, this might suggest that the future is deterministic. It is true that straying from the “default decision environment” shaped by our parents and biology is difficult. Yet with the right decision supports, we can reframe that environment, minimize bias, and make choices that optimize our path forward.

Understanding serendipity conceptually is useful, but the real question is: how can we apply it in daily life? Unlike coincidence, which may simply amuse or inconvenience us, serendipity provides a practical pathway for navigating uncertainty and uncovering new opportunities.

Seneca’s timeless phrase, “Luck is what happens when preparation meets opportunity,” reminds us that the luck of serendipity is not dumb luck—it can be cultivated. Coincidence may create the chance encounter, but serendipity transforms it into a positive outcome when readiness, adaptability, and action come together.

As noted earlier with Alexander Fleming’s discovery of penicillin, his situation demonstrates this principle. The mold contamination was a coincidence, but his years of scientific preparation allowed him to see its value. Fleming’s experience shows that what looks like “luck” is in fact more probabilistic—the prepared mind is far more likely to convert an unexpected event into breakthrough serendipity.

Psychologist Carol Dweck offers a modern complement to this insight: “Becoming is better than being.” Preparation is not a one-time achievement but an ongoing process of growth. The growth mindset ensures that when opportunities arise—whether expected or accidental—we are open, adaptable, and able to capture their value.

The real challenge for us is the same: to cultivate the conditions that raise the probability of turning chance collisions into meaningful outcomes, transforming uncertainty into discovery and innovation.

Serendipity as a Tool for the Unknown

Our biggest blind spot lies in the unknown unknowns—the challenges and opportunities that exist but are invisible to us. By focusing only on what we know, or what we can imagine, we risk ignoring the full range of choices open to us. Thomas Schelling put it well: we often confuse the unfamiliar with the improbable. In other words, just because you cannot imagine it, does not mean it cannot happen. Schelling illustrated this with the attack on Pearl Harbor, which inflicted heavy American casualties and temporarily placed the United States at a severe strategic disadvantage in World War II. American policymakers struggled to imagine Japan launching a direct attack across the Pacific, and because they failed to envision the unfamiliar, they failed to prepare. What seemed improbable turned out to be the tactic of the Japanese, showing how dangerous it can be to dismiss what lies outside our more familiar imagination.

The way to uncover the unknown is to actively engage with serendipity. Rather than treating it as random luck, we can cultivate it as a practice.

Flaneuring and Other Paths to Serendipity

Nassim Nicholas Taleb popularized flaneuring—wandering without rigid purpose—as a way of exposing oneself to the “convex benefits” of serendipity. By strolling through unfamiliar environments, he opens the door to encounters and insights that cannot be planned in advance. This is a powerful metaphor for embracing the unknown, but it is not the only way. Other thinkers and innovators have developed practices to actively create serendipity.

• Weak Ties and Network Diversity: Sociologist Mark Granovetter showed that opportunity often comes not from close friends but from acquaintances—our “weak ties.” These looser connections expose us to different worlds and unexpected information. Seeking out diverse relationships, or attending events outside one’s normal circles, expands the surface area for serendipity.

• The Medici Effect: Frans Johansson describes how Renaissance Florence flourished when artists, scientists, and philosophers collided in shared spaces. Serendipity thrives at intersections. Today, innovators recreate this effect by intentionally blending disciplines—whether in cross-functional teams, maker labs, or global conferences—where unexpected combinations spark new ideas.

• Serendipity Structures: Some organizations design environments that maximize chance encounters. Google famously engineered its campus so employees from unrelated departments would bump into each other, believing these “collisions” would generate innovation. At a personal level, this can mean rotating workspaces, joining cross-industry forums, or even arranging digital platforms to surface surprising content.

• Curiosity and Play: Playfulness lowers our guard and encourages nonlinear exploration. Companies like 3M and Google institutionalized this through “20% time” for personal projects, which produced serendipitous breakthroughs like the Post-it Note and Gmail. Individually, pursuing hobbies, tinkering with tools, or following a hunch into a new subject invites positive accidents.

• Growth Mindset: Psychologist Carol Dweck shows that people with a growth mindset see setbacks and surprises as opportunities to learn, while those with a fixed mindset often dismiss them. For example, in her research with students, she found that those encouraged to embrace challenges and “learn from mistakes” were more likely to persist and improve after failure. In the context of serendipity, this mindset is crucial: when an unexpected event occurs, a growth-oriented perspective increases the odds of converting coincidence into discovery.

Each of these practices underscores a larger point: serendipity does not have to be left entirely to chance. Philosophers often describe three traditional kinds of luck: resultant luck (when outcomes are shaped by factors outside our control), circumstantial luck (the situations we happen to face or avoid), and constitutive luck (the traits and tendencies we are born with). These all describe luck that happens to us.

But serendipity suggests something more—a fourth kind of luck: cultivated luck. This is luck we actively encourage by preparing ourselves, widening our networks, experimenting across disciplines, and adopting a growth mindset. Cultivated luck changes our relationship with chance. Rather than being at the mercy of “dumb luck,” we can apply intelligence and preparation to tilt the odds in our favor, raising the probability that unexpected encounters transform into meaningful opportunities. In this way, serendipity becomes not just a happy accident, but a strategy for innovation and discovery.

Symbiotic Exchange

Flaneuring and other practices are not solitary. When we share ideas, we lend pieces of our known paths to others, while they lend theirs to us. This is symbiotic serendipity: my known path may illuminate your unknowns, while your perspective may help me discover my own.

The Faith to Explore

Engaging in serendipity requires a kind of faith. By definition, the return is not immediate or easily measurable. The temptation—especially in an efficiency-obsessed world—is to spend nearly all of our energy optimizing what is already known or managing risks we can quantify. Yet it is precisely the uncharted and uncertain that contain the seeds of transformation.

This is where humans retain a profound comparative advantage over artificial intelligence. AI is accelerating rapidly, but its strength lies in the known and the predictable. It processes vast datasets, identifies patterns, and forecasts outcomes with remarkable precision. But AI is limited by its training material—it can only draw from what already exists.

Humans, by contrast, excel in the realm of the unknown. Where AI refines what already exists, we imagine what could be—asking “what if” questions, experimenting, and generating entirely new data. This creative capacity drives entrepreneurship: the ability to develop products, services, and relationships that no dataset has yet captured. Each trial, error, and breakthrough extends the frontier of knowledge. As AI colonizes the knowns, the human advantage shifts toward innovation and discovery, suggesting a renaissance for small businesses and entrepreneurs who are uniquely positioned to turn uncertainty into opportunity.

That ability—to envision, to hypothesize, and to create new data through curiosity and experimentation—is uniquely human. It is why serendipity is not just a happy accident, but a discipline of innovation. Where AI refines the known, humans expand the possible.

A powerful example comes from entrepreneurship, where every new venture begins with uncertainty. At Personal Finance Reimagined, we support early-stage founders by acting as a fractional CFO and helping them raise capital. These entrepreneurs are, by definition, stepping into the unknown—seeking to fill gaps with products and services that improve lives, though the exact form of that improvement is not always clear at the outset. Each pitch meeting, investor introduction, or product iteration is a potential collision point where preparation and opportunity converge. Just as serendipity requires faith, so does entrepreneurship: founders cannot know in advance which conversation will spark funding or which idea will gain traction, but they do know that immersing themselves in these collisions increases the probability of finding the breakthrough that defines their path.

Belief Updating: Turning Serendipity into Progress

William Blake observed: “What is now proved was once only imagined.” Serendipity works by feeding our imagination and encouraging us to revise our mental models.

Albert Einstein added: “Whether or not you can observe a thing depends upon the theory you use.” In other words, what we see depends on how we choose to see it. By updating our beliefs, we expand the range of what becomes observable.

The process is simple but powerful:

1. Expose yourself to new people, places, and ideas.

2. Capture insights through self-debriefing.

3. Update beliefs, treating them as provisional way stations rather than fixed truths.

This cycle ensures that today’s coincidences can become tomorrow’s serendipities—and, eventually, tomorrow’s innovations.

Closing Thought

Coincidence and serendipity both arise from the convergence of life paths, shaped by time, situation, and surprise. The distinction lies in valence: coincidence can be mixed or indifferent, while serendipity is inherently positive, turning chance into meaningful discovery.

This article has shown that serendipity is not random luck but cultivated luck—an outcome we can influence through preparation, openness, adaptability, and belief updating. By designing environments that encourage collisions, embracing curiosity, and applying structured decision tools, we increase the probability that hidden opportunities emerge.

Entrepreneurship is the clearest expression of this uniquely human advantage. While AI colonizes the world of the known, entrepreneurs venture into the unknown—imagining new products, services, and relationships that no dataset has yet captured. In short:

• All serendipities are coincidences.

• Not all coincidences are serendipities.

• And when cultivated deliberately, serendipity becomes one of humanity’s most powerful tools for innovation, opportunity, and entrepreneurial progress.

Resources For The Curious

• Hulett, Jeff. Seeking Less, Living More: Rethinking How We Seek Success. The Curiosity Vine, 2024. Explains how evolutionary drives and decision science shape our pursuit of success, offering context for understanding why unexpected, serendipitous events can redirect life paths.

• Hulett, Jeff. The Hidden Wealth of Time: Turning Challenges into Opportunity. The Curiosity Vine, 2025. Argues that growth mindset and intentional preparation allow individuals to leverage chance encounters and turn uncertainty into opportunity.

• Johansson, Frans. The Medici Effect: Breakthrough Insights at the Intersection of Ideas, Concepts, and Cultures. Harvard Business School Press, 2004. Introduces the concept that innovation flourishes where disciplines and cultures collide—an environment ripe for serendipity.

• Granovetter, Mark. “The Strength of Weak Ties.” American Journal of Sociology, 78(6), 1973, pp. 1360–1380. Seminal work showing how weak ties expand networks and increase exposure to unexpected opportunities.

• Roberts, Russ. Wild Problems: A Guide to the Decisions That Define Us. Portfolio, 2022. Explores uncertainty and “unknown unknowns,” framing the conditions where serendipity becomes essential to decision-making.

• Schultz, Wolfram. “Behavioral Theories and the Neurophysiology of Reward.” Annual Review of Psychology, 57, 2006, pp. 87–115. Demonstrates how dopamine signals reward prediction error, offering the neurological foundation for anticipating and responding to life path opportunities.

• Taleb, Nassim Nicholas. Antifragile: Things That Gain from Disorder. Random House, 2012. Develops the concept of benefiting from randomness and convexity, grounding practices like flânerie in cultivating serendipity.

• Pasteur, Louis. Quoted in Vallery-Radot, René. The Life of Pasteur. Doubleday, 1920. Famous maxim, “Chance favors the prepared mind,” encapsulating the disciplined readiness required to turn coincidence into serendipity.

• Seneca. Epistulae Morales ad Lucilium [Moral Letters to Lucilius]. ca. 65 CE. Includes the aphorism often paraphrased as: “Luck is what happens when preparation meets opportunity.” In the original Latin: “Fortuna est quod fit, cum praeparatio occurrit occasioni.” Seneca's concept of luck represents the idea of cultivated luck.

• Nagel, Thomas. “Moral Luck.” Proceedings of the Aristotelian Society, Supplementary Vol. 50, 1976, pp. 137–151. Introduces the distinctions between resultant luck, circumstantial luck, and constitutive luck, framing the philosophical problem of how much control individuals really have over outcomes.

• Dweck, Carol S. Mindset: The New Psychology of Success. Random House, 2006. Introduces the concept of fixed versus growth mindsets and includes the insight, “Becoming is better than being,” emphasizing the importance of continuous growth and adaptability.

• Schelling, Thomas C. Strategy and Arms Control. Twentieth Century Fund, 1961. Introduces the idea that policymakers often mistake the unfamiliar for the improbable, a concept Schelling connected to strategic surprise events like Pearl Harbor.