Serendipity and the Zettelkasten

06 Feb, 2026

The term "serendipity" and allusions to serendipitous-like events are not uncommon in the zettelkasten scene, particularly in regard to the way insights are expected to reveal themselves through the connecting of ideas. Niklas Luhmann’s emphasis on unanticipated findings;¹ Johannes Schmidt's description of Luhmann introducing "chance" leading to "connections among a variety of heterogeneous aspects;"² André Kieserling comparing Luhmann's process to looking through a library for a specific text and stumbling on an even better one³ all do right by Horace Walpole's 1754 coinage and description of "serendipity" as being the result of both "accident and sagacity."⁴ Or to put it more common terminology, chance and agency. But, how exactly does serendipity show up when working with a zettelkasten, and how might it be assessed?

The Process Model of Serendipity

Between the years 2012 and 2019, academic researcher, Stephann Makri along with a number of colleagues, produced multiple studies on the serendipitous experience, interviewing and observing nearly a hundred interdisciplinary researchers and creatives on their experiences with the phenomenon, at the same time exploring the role design elements in bookstores and online spaces play in generating valuable and unexpected encounters with information.⁵ What emerged from this work was a conceptualization of serendipity that breaks from what passes for its conventional definition today, i.e., a "happy accident." Instead, Makri et al. found serendipity to be the result of highly engaged people actively wrestling with a variety of endeavors and projected outcomes.

To give shape to this finding, Makri and fellow researcher colleague, Ann Blandford, developed the "process model of serendipity," detailing how valuable, unexpected encounters result from the fulfillment of distinct stages of intellectual activity.⁶ These stages include:

• Making a connection
• Projecting value regarding the connection
• Exploiting the connection
• Recognizing a valuable outcome as a result of exploitation
• Reflecting on the origin of the outcome
• Considering the outcome as serendipitous

Together the steps play out as follows: Serendipity begins with a need—any intellectual problem in need of solving—leading to an attempt to satisfy the need through the making of a connection—finding some other thing (e.g., a piece of information, an observation, or a social encounter) with the potential to address the need, which in turn generates an idea, a possibility you hadn't considered. From there, the process becomes iterative and bidirectional. You project value forward, imagining what might come from pursuing this connection. You take action to exploit the connection to draw out its potential value. Then you reflect backward on what emerged, assessing both the value of the outcome and the unexpectedness of how you arrived at it. Only after you've connected, projected, exploited, and reflected can you make an assessment as to whether or not the experience was indeed serendipitous.

Makri and Bladford's process model is, essentially, a roadmap for understanding Walpole's appreciation of "accidents and sagacity." Let's look at how it squares with the work we do in our zettelkästen.

The Need for a Need

At the heart of Makri and Blandford's model is a counterintuitive insight: you need a need for serendipity to occur. This need might be well-defined—"I'm looking for a theoretical framework for my thesis"—or it might be vague—a general sense something is missing, a question you can't quite articulate. The need might even be unconscious, only becoming apparent when you stumble across something that later addresses it.

For zettelkasten users, needs take many forms. You may want to understand a concept more deeply, or need evidence to support an argument. You may want to connect two ideas, but only possess a vague sense of how. You might be actively pursuing the need—searching your zettelkasten for notes on a specific topic—or the need might simply lurk in the background of your thinking, ready to be activated when the right note appears. Makri and Blandford found this to be the case in their 2012 study:

"Most of the time, the need will not be actively pursued at the time the connection is made (or for connections that involve thinking back to things from memory, at the time the thing was originally encountered). Consider, for example, the examples from our interviews of finding information relevant for one research project while searching for information on another project entirely, or meeting someone with similar research interests whilst attending a conference that was seemingly unrelated to those interests. However, sometimes connections involving a mix of unexpectedness and insight can occur while actively pursuing the need (consider, for example, finding information from a previously unfamiliar domain that provides a useful theoretical angle for current work in-progress whilst conducting a general Internet search in the area)."⁷

The above maps directly onto many people's experience using a zettelkasten. You're reviewing notes on one topic when a note on something else catches your attention. You're searching for material to support a specific argument when you encounter a note that forces you to rethink the argument you're trying to make. Whatever the case, in order for serendipity to take place, you have to be working on something, thinking about something, needing something, even if you can't fully articulate what that something is.

Making the Connection

Having a need prepares you for the possibility of making a serendipitous connection, identified as the moment you recognize something has the potential to address your need in a way you hadn't anticipated.

The meeting of the need and the thing that satisfies it is key. For a connection to occur, two or more things must come into contact. In zettelkasten work, we typically talk about this in terms of intersecting ideas, where notes containing information that's mutually beneficial are brought into proximity with one another. It's not enough to have a single idea as insight doesn't arise from observing a unit of information in isolation, regardless of how profound. There must be context.

The importance of relationality, reinforces an important point regarding where value resides in a zettelkasten. As Luhmann put it, "Every note is only an element which receives its quality only from the network of links and back-links within the system."⁸ Schmidt reinforces the point when he says, "There is hardly any informational value in the note on its own, it will only prove its informational value when it's connected with other zettel."⁹ These statement are in direct contrast to those who argue individual notes need be polished and "fully developed" to be valuable, that an ineffectual note is one that hasn't been thought through completely.¹⁰ All of which misses both Luhmann and Schmidt's point: a note's value emerges primarily from its relationships with other notes, not from the completeness of its contents.

Projecting Value

We make a connection between a need and something intending to satisfy it, because we perceive the connection as potentially valuable, projecting value forward in anticipation of it being useful sometime in the future. The projected value, however uncertain or small, is what motivates us to both make the connection and take advantage of it later.

But, projecting value is not a given. In order to perceive the potential value of a connection, you must first be mentally prepared to do so. Makri and Blandford's interviewees identified several factors that enabled them to project value forward, namely, being relaxed, alert, in a good mood, and/or willing to deviate from the work in front of them. When participants felt stressed, tired, or time-pressured, they were less likely to notice connections or their potential value. And, if they did notice them, they were less willing to exploit them (see below).¹¹

Being able to perceive the potential value of the connections you're making by maintaining an alert and flexible mindset has direct implications for how you work with your zettelkasten. Trying to force insight through note-making quotas and "discipline," especially when you're disinterested or mentally exhausted, can backfire, not because you can't physically perform the tasks, but because you're closed off to unexpected encounters that might take place in those moments. According to Makri, et al., serendipity benefits from you being focused enough to recognize significance, but possessing enough peripheral vision to notice what doesn't quite fit.

Exploiting the Connection

After making a connection and projecting its potential value forward, you must at some point take action, which will allow you to transform potential value into actual value.¹²

In zettelkasten practice, exploitation takes several forms. The simplest is articulating the connection itself—creating a link between notes with an explanation of why you've done so. But exploitation can go further. Structure notes and writing are tools for working out the implications of multiple connections, for seeing patterns across your network of notes.

Each round of exploitation—every time you reexamine, alter, and develop the work in front of you—reveals new possibilities, which in turn alter, even subtly, how you're approaching what you're working on. This is why doing something with your connections, even when you're unsure where they will lead, is essential. Valuable, unforeseen outcomes aren't possible through contemplation alone.

Recognizing a Valuable Outcome

In order for serendipity to have taken place, the connections you've made and the ways you've exploited them must result in a valuable outcome. No value, no serendipity. Additionally, this outcome will have had to address your need, but not in the way you anticipated.

In zettelkasten practice, valuable outcomes take a variety of forms: an insight that reframes your understanding of a concept; a structure note that reveals patterns across seemingly disparate ideas; a finished piece of writing that articulates something you've been struggling to express. Your outcome may be the one you intended, or something else entirely. Many are the times I set out to write one thing and ended up with another. Articles intending to be books ("Doing What Matters Most: Personal Project Management for the Burgeoning Homesteader"). Books intending to be articles (A System for Writing). Regardless of the outcome, it's the unanticipated nature of it that suggests it being the result of serendipity.

Reflecting on the Outcome's Origin

Serendipity is ultimately a subjective experience. To assess whether or not you've had a serendipitous experience, you must look back and evaluate the unexpectedness of how you arrived at the outcome. How did you make this connection? Were you actively searching for it, or did you stumble across it while looking for something else? Did the connection come from a source you expected, or from somewhere surprising? The more unexpected the path from origin to outcome, the more likely you are to consider the experience serendipitous.

In zettelkasten work, this reflection often happens naturally. You finish writing a section and pause to think about how it came together. You realize that a note you captured months ago—one that seemed tangential at the time—turned out to be central to your argument. Or you notice that a connection you made on a whim while browsing your notes became the foundation for an entire structure note. These moments of reflection reveal the serendipitous nature of your process.

Considering the Outcome as Serendipitous

The final stage is simply labeling the experience as serendipitous. Like so many of the stages above, this usually happens unconsciously. You don't typically stop and think "Aha! Serendipity!" More often than not, it's a quiet realization, a sense something valuable happened through a combination of chance and your efforts to capitalize on it.

In zettelkasten practice, this recognition serves a purpose beyond mere satisfaction. When you identify which of your processes led to serendipitous outcomes, you can cultivate those conditions. You may learn that browsing notes without a specific goal sometimes yields unexpected connections, or that having a strong agenda combined with a willingness to be surprised does the same. You might discover working when you're relaxed rather than stressed produces better insights. You may find the best articulated notes aren't always the ones leading to insight, so you give yourself a break now and again. Nothing about this awareness guarantees serendipity. By definition, you can't plan it. But, understanding the ways in which serendipity has arisen, can help you create the conditions for it to occur more often.

*If you enjoyed this piece, please pick up a copy of my latest book, A System for Writing: How an Unconventional Approach to Note-Making Can Help You Capture Ideas, Think Wildly, and Write Constantly. You may also sign up for my free newsletter HERE. To get my premium newsletter with all the insights, short essays, and zettelkasten scene weekly recaps, click HERE. To read more of my writing, click HERE. To learn more about me, click HERE. For my full website, click HERE.

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