7 Serendipity Strategies

A substantial amount of recent published research related to serendipity comes from the field of information science. Often, this research is focused on ways that digital environments might be designed to support serendipitous information discovery.

Whether the environment is virtual or physical, there are a lot of similarities between information-seeking behavior and opportunity-seeking behavior. Therefore, many of the strategies that can help digital information seekers experience serendipity more often can be employed by opportunity seekers as well.

In one study, a group of British researchers interviewed 14 creative professionals to try and identify specific strategies that the professionals perceived as increasing the likelihood of serendipity. The participants in the study all reported that they frequently experienced serendipity, and they all claimed to adopt strategies that increase its likelihood.

The goal of the study was to identify strategies that could be used to drive the design of digital information environments to better support serendipity. However, the participants were from various creative fields, so their reported strategies for stimulating serendipity were not specific to information-seeking behavior.

The strategies that the participants said they commonly used to support the serendipity process included:

  • varying their routines
  • being observant
  • making mental space
  • relaxing their boundaries
  • drawing on previous experiences
  • looking for patterns
  • seizing opportunities

The study authors also make the point that these strategies are all “tightly linked to related behaviors and character traits.”[1] This is an important point, since our goal is to develop a body of properties, principles, and practices that stimulate serendipity.

Properties are essentially character traits, and behaviors can be correlated to specific practices. So, these strategies should be easily integrated into a framework that stimulates opportunity-oriented serendipity.

In this post, I would like to discuss and expand upon each of these strategies and map them to distinct properties that should be cultivated by anyone looking to stimulate serendipity in their life.


Variability is the capability or liability to vary or change; to break away from fixed patterns.

Study participants suggested that breaking out of predictable routines exposed them to different people, places, and information. This, in turn, provided new opportunities for making valuable connections.[2]

Routines can be good. They can help us efficiently complete mundane tasks, they can eliminate the need to re-think each step in a simple process, and they can help prevent us from getting sidetracked by endless distractions. But routines can also put us into a mindless “autopilot” mode, stifling our creativity by inhibiting our natural inclination to notice and discover.

There are lots of small ways to shake up our personal daily routine. We can take a different route to work, or choose a different walking, running, or cycling route. We can try a new coffee shop, restaurant, or bar. We can engage in a new hobby or activity. Or we can simply strike up a conversation with a stranger.

But when it comes to expanding opportunity as it relates to our goals, we probably want to focus on new people, places, and information that might be relevant to our purpose.

To that end, we can attend meetups, conferences, lectures, or classes. We can learn a new skill or master a new tool. We can read new or different websites, blogs, trade publications, or peer-reviewed journals. We must push ourselves to do different things, and to do things differently.

If we constantly move in the same restricted space, and operate within the same self-imposed constraints, we are needlessly limiting our opportunities.

If we want to use the property of variability to expand our opportunities, we must establish relationships with new people, explore new places, and consume new information.


In the Makri et al. study, being observant is suggested as a serendipity strategy. But the study authors and participants use a variety of other terms to describe this strategy, including being aware, attentive, perceptive, assiduous, alert, curious, and inquisitive.

They also discuss the importance of going beyond merely noticing environmental changes, but of recognizing and being receptive to connections, seeing things that others might not, getting the best out of what’s available to you, and even of elevating our senses to a higher level of performance.[3]

Since we’re really talking about a heightened sense of awareness and attentiveness here, I’m going to map the authors’ strategy of being observant to the more inclusive property of mindfulness.

Most simply, mindfulness is the state or quality of being conscious or aware of something.

Mindfulness is sometimes variously interpreted as a state, a trait, or a set of skills and techniques. There are lots of fuzzy concepts of mindfulness that invoke spiritual states and emotional experiences, or that link mindfulness to meditation or other therapeutic practices. And many of these practices are indeed beneficial.

But as a starting point, we’re interested in mindfulness as a property (trait). And we’re looking for a simple concept of mindfulness that relates primarily to attention, focus, and awareness.

A straightforward explanation from recent psychological literature defines mindfulness as a receptive attention to and awareness of present events and experience.[4]

Mindfulness gives us the perceptual flexibility we need to simultaneously see both the broader perspective and the critical situational details. This in turn gives us the insight we need to recognize and evaluate opportunities that might otherwise escape our attention.

As mentioned, there are many practices that can help us cultivate mindfulness, including meditation, tai chi, qigong, and yoga. We will explore these and others in future posts.


The third serendipity strategy that the study authors discuss is that of making mental space. This is said to be necessary because a crowded conscience leaves less cognitive space available for picking up on new things, and because stress and mood can leave us closed off to serendipity.

The authors dive a little deeper, though, and explain that by replacing conscious thoughts with unconscious ones, we can encourage the association of unrelated ideas and enable mental connections to be revealed. They further suggest that when we can escape our typical task-based focus, we can achieve a more associative state.[5]

Their discussion goes a bit beyond the idea of simply clearing one’s head, so I am going to map the strategy of making mental space to the property of equanimity.

Equanimity is mental calmness, stability, and composure; a state of equilibrium. It is an important virtue in many religions and is one of the four sublime attitudes in Buddhism.

Equanimity enables us to accept things the way they are, and to accept wherever we happen to be. It allows us to achieve a cognitive balance, to free ourselves from attachment to outcome, and to react to environmental changes without undue emotion. Equanimity creates the mental space we need to suppress excessive sensory noise and distraction.

Equanimity also allows us a path toward making optimal choices by facilitating cognitive flexibility when we encounter the unfamiliar, unplanned, or unexpected.[6]

As with mindfulness, there are a variety of contemplative and meditative methods that can be used to help cultivate equanimity.


The participants in the Makri et al. study emphasized the importance of being able to relax intellectual and physical boundaries in order to make connections.

Relaxing boundaries between disciplines can establish valuable interdisciplinary connections, and transferring knowledge between domains can lead to significant breakthroughs. Relaxed boundaries enable us to make unexpected and insightful connections by absorbing environmental input without judgment.[7]

The willingness to relax boundaries in this way is somewhat analogous to the trait of openness to experience described by the five-factor model of human personality.

Open people tend to be intellectually curious, willing to try new things, and demonstrate a higher level of creativity and awareness than closed people. Open people’s thinking tends to be broad and deep, whereas closed people’s thinking tends to be narrow and shallow.

The property of receptivity is the general willingness to relax rigid boundaries and remain open and responsive to new ideas and experiences.

Receptivity allows us to actively embrace what life presents. Receptivity allows us to consider new ideas and new ways of thinking, and leaves us open to novelty. Receptivity allows us to recognize and exploit opportunity rather than letting opportunity pass us by.

Receptivity is critical for stimulating serendipity, because it keeps us ever open to possibility.


Serendipity often involves the ability to connect dissimilar things in some meaningful way. To do this, we must often compare new experiences to our previous ones. This is particularly important when attempting to project some future value or benefit.[8]

The property of experientiality is the tendency to derive from experience or observation.

We rely heavily on our memories of past events when we try to visualize and plan for the future. We also rely on our past experiences when we encounter a situation that requires us to make a decision with incomplete information.

In fact, the process of learning from past experience can reroute our brain circuitry so that we can rapidly categorize new input and respond appropriately.[9]

The ability to draw on past experiences to envision possible future outcomes is essential to serendipity. And as it turns out, researchers are beginning to realize that many of the same cognitive processes we use to retrieve past events from memory are the same ones we use to simulate future events.[10]

In order to mentally project the future, we may require a constructive cognitive system that flexibly extracts and then recombines various elements from our previous experiences.[11]

Research into how our brains use similar processes to recall past events and imagine future ones is ongoing. But in order to stimulate serendipity, all we need to know is that we must find ways to efficiently and creatively map new information to old information in order to see new opportunities and visualize their potential value.


The Makri et al. study participants related the ability to find patterns in their environments; to see alignments. These patterns and alignments might not always be meaningful in themselves, but people who are prone to serendipity are able to construct or extract something meaningful from them.[12]

The ability to see patterns or alignments in environmental input and construct meaning correlates to the property of associativity, which is the ability to readily associate disparate ideas or things.

Steve Jobs once said, “Creativity is just connecting things. When you ask creative people how they did something, they feel a little guilty because they didn’t really do it, they just saw something.”

Associativity and analogical thinking are essential to human creativity. In the general sense, associativity allows us to draw purposeful connections between seemingly dissimilar elements or phenomena. But it is analogy, specifically, that is often the wellspring of novel concepts and breakthrough innovation.

The cognitive process of analogy enables us to mentally map attributes and relations from a source domain of knowledge to a target domain. This facilitates knowledge transfer and allows us to think across categories and conceptual boundaries.[13]

Analogical thinking also relates to experientiality. Often, we will receive environmental cues that remind us of a past experience, and we will apply past patterns to our present problem or perceived opportunity.

There are some fallacies and biases that can derail analogical reasoning, though. But fortunately, we can engage in exercises that will help us sharpen our analogical thinking and associativity skills and avoid common pitfalls.


The final serendipity strategy described by participants in the Makri et al. study was the tendency to seize opportunities, even when there might be significant time or risk involved.[14]

Exploiting opportunity when it is presented and recognized is at the very core of serendipity, and this ability maps quite neatly to the property of enterprise.

Enterprise is variously defined as the readiness to engage in difficult action, or the willingness to do something new that takes a lot of effort, despite apparent risks. Enterprising people are not afraid to embark on bold new ventures or undertake difficult projects.

Sometimes enterprise is used synonymously with initiative. But enterprise is more than just initiative, really, since it combines initiative and effort with the willingness to take risks and face obstacles.

As a personal quality or property, enterprise is often a result of what many people would call the “entrepreneurial mindset.” This mindset has been defined as “the ability to rapidly sense, act, and mobilize, even under uncertain conditions,” and understanding how people recognize and act on entrepreneurial opportunities is a recurring theme in entrepreneurship research.[15]

Successful entrepreneurs can balance their own thoughts and motivations within the context of dynamic and uncertain environments and still choose an effective course of action. Research suggests that a better understanding of our own thought processes (metacognition) can help us deploy cognitive strategies that allow us to think and act more adaptively.[16]

Fortunately, we don’t have to be “born entrepreneurs” to develop the property of enterprise. Metacognition, it turns out, is a learned process that can be enhanced through training.[17] We can all use metacognitive strategies to train ourselves to think and act more adaptively and appropriately when we encounter perceived opportunity.


Drawing from research in the field of information science, we identified seven strategies that can increase serendipitous results for information seekers.

Since there are similarities between information seekers and opportunity seekers, we mapped those strategies to seven properties that can be fostered to stimulate serendipity in both digital and physical environments.

The properties of variability, mindfulness, equanimity, receptivity, experientiality, associativity, and enterprise are a solid core set of properties that we can cultivate to encourage serendipity.

We will identify more properties, as well. But for now, we can begin to explore specific principles and practices that we can use to cultivate these seven essential properties in our minds and in our lives.

My next post, however, will discuss a model for serendipity that will give us a sound framework for the strategic application of these foundational properties.


1. Stephann Makri et al., “’Making my own luck’: Serendipity Strategies and How to Support Them in Digital Information Environments,” Journal of the Association for Information Science and Technology 65, no. 11 (2014): 2186. https://doi.org/10.1002/asi.23200

2. Ibid., 2187.

3. Ibid., 2187-2188.

4. Kirk Warren Brown, Richard M. Ryan, and J. David Creswell, “Mindfulness: Theoretical Foundations and Evidence for its Salutary Effects,” Psychological Inquiry 18, no. 4 (2007): 212. https://doi.org/10.1080/10478400701598298

5. Makri et al., “’Making my own luck’,” 2189.

6. Gaelle Desbordes et al., “Moving beyond Mindfulness: Defining Equanimity as an Outcome Measure in Meditation and Contemplative Research,” Mindfulness (N Y) 6, no. 2 (April 2015): 13. https://doi.org/10.1007/s12671-013-0269-8

7. Makri et al., “’Making my own luck’,” 2189-2190.

8. Ibid., 2190-2191.

9. Biotechnology and Biological Sciences Research Council, “Past Experience Is Invaluable For Complex Decision Making, Brain Research Shows,” ScienceDaily, May 15, 2009, https://www.sciencedaily.com/releases/2009/05/090513130930.htm

10. Daniel L. Schacter and Donna Rose Addis, “The Cognitive Neuroscience of Constructive Memory: Remembering the Past and Imagining the Future,” Philosophical Transactions of the Royal Society B: Biological Sciences, 362, no. 1481 (May 2007), 780. https://doi.org/10.1098/rstb.2007.2087

11. Ibid, 774.

12. Makri et al., “’Making my own luck’,” 2191.

13. Joel Chan and Christian Schunn, “The Impact of Analogies on Creative Concept Generation: Lessons from an In Vivo Study in Engineering Design,” Cognitive Science, 39, no. 1 (January 2015), 2. https://doi.org/10.1111/cogs.12127

14. Makri et al., “’Making my own luck’,” 2191-2192.

15. J. Michael Haynie et al., “A Situated Metacognitive Model of the Entrepreneurial Mindset,” Journal of Business Venturing 25, no. 2 (2010): 217. https://doi.org/10.1016/j.jbusvent.2008.10.001

16. Ibid, 219.

17. Ibid, 218.

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