When the problem is bigger than the plan

Serendipity is often portrayed as “smart luck”; a random conversation, a surprising encounter, or a fortunate accident that sparks an unexpected idea or innovation. For entrepreneurs, serendipity becomes crucial for unexpected discoveries that one stumbles upon when experiencing surprising “Aha” moments.

But there is a missing piece in this story.

When entrepreneurs try to find solutions to complex problems, they face a lot of complexity and uncertainty: Especially in the sustainability context, the problem itself is often ill-defined, and pathways to solutions remain ambiguous. Here, serendipity can be increasingly helpful, but it is not enough to just be alerted to unexpected moments; what you feel matters more than what your brain is recognizing.

My recent study, Navigating Complex Problem Spaces: How Emotion and Energy Shape Entrepreneurial Agency in Serendipitous Encounters, explores how entrepreneurs experience emotions and led them guide themselves through serendipity. 

Serendipity as an emotional experience

Traditional views of serendipity emphasize surprise, agency, and valuable outcomes, mostly through a cognitive understanding of when someone is alerted to recognize value in the unexpected. 

Yet when I observed nine early-stage entrepreneurs working on sustainability-related venture ideas, they told me something else: Whenever they experienced serendipity, they described a feeling that something had “clicked”, they spoke of “the right energy flowing”, and a sense of “something feels right.”

Interestingly, some mentioned their emotions told them when “something felt off,” when they were “in the wrong mood,” and when they lacked the energy to follow through.

It turned out that such emotions importantly shaped how they made sense of serendipity. I found two pathways:

Emotional alignment

When entrepreneurs experienced emotional alignment with an unexpected encounter, a positive feeling with the encounter resonated with their evolving understanding of the complex problem. They felt an energy that activated commitment to follow up and make something valuable out of such encounters.

Emotional misalignment

Conversely, other unexpected moments triggered emotions of discomfort and a lack of energy. Here, entrepreneurs started to rethink the problem they were trying to solve. Interestingly, later on, these became important moments of recalibration and pivoting of venture ideas.

Serendipity, in this case, was not followed through, but the emotional misalignment was unexpectedly helpful for entrepreneurs to rethink their assumptions and adjust their path.

This tells us that serendipity is about paying attention to emotions that help to decide whether to move forward or change direction.

Why complexity and uncertainty make emotion central for serendipity 

Since the entrepreneurs in this study were working on sustainability problems that happened to be highly complex, messy, and hard to define, there was no clear roadmap, and different people wanted different things. In that kind of situation, unexpected encounters were not easy to judge through logic alone. My research found that feelings became useful guides for interpretation.

When an encounter feels energizing and exciting, it can suggest that it fits the solution the entrepreneur is moving toward. When it feels uncomfortable, frustrating, or draining, that can be a sign that something does not fit or that the problem needs to be rethought.

By framing serendipity as an emotional felt experience, this work expands our understanding of the unexpected beyond the cognitive lens toward a more affective perspective.

What this means for serendipity studies

This work contributes to serendipity research in three ways. First, it positions emotion as a crucial factor, claiming that serendipity can not only be understood cognitively but must be interpreted affectively. Second, it highlights the concept of “missed serendipity” with such moments that were not pursued but yield valuable refinement or pivoting of the problem. Third, it shows the value of affective serendipity for highly complex and uncertain problems in sustainability contexts.

For researchers, this study suggests that understanding serendipity requires the attention to lived and felt experiences. For practitioners, it highlights emotions as important an important compass to navigate decision-making under uncertainty.

Methodological note: capturing the unnoticed

To observe emotions and serendipity in “real time”, I developed a novel AI-assisted diary method with ChatGPT. 

What inspired me for this idea was my own experience, as I tried to remember and make sense of all the unexpected insights and random encounters I had, which was simply impossible. Life comes with so much noise oftentimes, and we, as humans, are often not even able to remember what we had for lunch the other day.

To reduce noise, I built a prompt that asked participants to document any kind of unexpected encounter and reflect on them. This method made such small moments recognizable for me as a researcher, and memorable for the participants. Some entrepreneurs later told me that the AI journaling changed their emotional awareness toward serendipity. They began to notice feelings they had previously ignored through the conversational mode with their ChatGPT dairy partner.

Author bio

Nele Marie Terveen is an Assistant Professor (Lecturer) in Innovation & Strategy at the University of Auckland, New Zealand, and is affiliated with Stanford in Professor Yi Cui's lab. In her research, she looks at complex problems, serendipity, and innovation, as well as ideation processes, specifically in the sustainability domain. She loves to explore novel phenomena through inductive and ethnographic study designs.

Further reading on this topic

Busch, C. (2024). Towards a theory of serendipity: A systematic review and conceptualization. Journal of Management Studies, 61(3), 1110-1151.

Engel, Y., Kaandorp, M., & Elfring, T. (2017). Toward a dynamic process model of entrepreneurial networking under uncertainty. Journal of Business Venturing, 32(1), 35-51.