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The Catch-22 Of Designing For Serendipity | Nomensa

The Catch-22 Of Designing For Serendipity

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6 minutes, 33 seconds

What is Serendipity?

The word “serendipity” was coined by Horace Walpole in 1754, when he wrote a letter about “The Three Princes of Serendip”. In this tale, three princes traveled around a land applying their wisdom to accidental events, making great discoveries “they were not in the quest of”.

This kind of discovery is behind some great scientific breakthroughs and inventions. Alexander Flemming, for instance, forgot to clean some cultures of bacteria before going on holidays, only to find these bacteria killed by Penicilin mould when he was back in the lab. Velcro was envisioned by George de Mestral after going for a walk in the mountains, finding cockleburs attached to his trousers and his dog’s coat.


Picture of small hooks in a Velcro strip

Velcro hooks


Serendipity can help develop new ideas in fields like science and art. These “discoveries by accident” are seen as a powerful tool in creative processes. But how can we design to add serendipity as a feature? How is online serendipity supported?

Boosting Serendipity Online

Nowadays we have access to online tools which try to generate “happy accidents”, basically helping users reach content they would  not find themselves (or didn’t even think of finding). We have identified three categories of tools supporting serendipity this way.


Curating involves selecting and organising objects for exhibition, normally at a museum. Facebook or twitter can be seen as a source of curated information. Contacts share links to media they are interested in, giving other contact access to potentially unknown but appealing content. Music services supporting social network interactions, like Spotify or iTunes Ping, let people recommend songs to friends.


Message and picture on Hikotoki, showing a writer writing in the morning.

Thoughtful ideas and experiences can be shared on Hitotoki.


Curation can also take place in non-social networks. The Hitotoki project gives anybody the chance to share tweets about throughtful experiences to inspire others. Google, on the other hand, ask professional editors to select pieces of news for their experimental “editor’s picks” box in Google News.

While curation is a great way to have access to valuable content, it is not clear whether it can lead to serendipitous events. Contacts in social networks are actually selected by the user’s personal preferences, narrowing down the variety of potential “curators”. In addition, curators select what to share according to their taste. All this removes the randomness necessary for a truly serendipitous experience.

Recommendation engines


Related artists section in Spotify

Spotify’s “related artists” feature


These engines supply recommendations based on conclusions drawn from data mining, that is, the automated analysis of large amounts of data using computers.

Pandora, for instance, perform a qualitative analysis of each song in their catalogue and then analyse songs using automated algorithms (as it was explained to The New York Times). This way, they can find similarities between songs and suggest customers new ones according to their taste. Other cloud-based services like Spotify or iTunes Genius also provide recommendations, possibly through data mining as well.

Recommendation engines can be used, like curation, to successfully expand our knowledge about a certain topic. However, by focusing on what can be analysed and compared,  they are constrained to finding patterns and similarities, possibly dismissing unrelated content that could lead to serendipity.

Random Access Tools


The Guardian Roulette

The Guardian’s random news reader


These tools are based on random access to content. ChatRoulette is one of these. This service randomly connects people who have webcams, allowing them to have conversation with people they would have never had the chance to have a chat with. With that idea in mind, The Guardian’s developer Daniel Vydra created a web page which presents a piece of news randomly selected from The Guardian’s archive.


Wanderfly homepage

Wanderfly and its random holidays planner


Wanderfly is a different take on holiday planning. Users fill in some details about their holidays, leaving other undefined (like the destination) or loosely defined (budget). With this information, Wanderfly look for cities, plane tickets and hotel reservations to offer different plans suiting the user’s requirements. While not completely random, it provides several degrees of freedom, leaving room for unexpected results.

Access to random content has been promoted as a way to experience serendipity. However, presenting people content they may not be interested in can backfire on the service. Users may end up feeling frustrated and bored, and therefore dismiss the service.

What’s Wrong With These Tools?

As we can see, it is not clear whether online tools can help boost the ratio of serendipitous experiences. Presenting related (recommendation engines, curation) or unrelated content (randomly) does not seem to provoke “happy accidents”. What is the problem, then? The biggest problem behind these failed attempts is intentionality.

Serendipitous events are “not sought for” or are found “by chance”. We may stumble upon interesting songs, pieces of news or movies using these tools, but we will be expecting it. By intentionally looking for these events using the aforementioned tools, it’s no longer an unsought event. A pure Catch-22 already known by designers.

So is there a way to make serendipity happen more often?

The Right Tools For The Right Task

Serendipity, according to the original definition by Walpole, is based on “accident and sagacity”. Researchers have structured a serendipitous event as a two-stage process: encountering unexpected information (related to a goal or not) and understanding this information to arrive at an insight.

These researches concluded that the first stage could be computer-supported by providing the user with relevant resources at specific points in the search for information. On the other hand, the second stage is an action taking place in the person’s brain. Therefore, it can’t be directly performed by computers, but they can help.

As Louis Pasteur stated, “In the fields of observation, chance favors only the prepared mind”. In order to arrive at an insight it is necessary to have a solid background of knowledge, so the observer is able to understand the importance of the unexpected information presented to him.

Social networks, curated content and random-supported tools are deemed as successful at increasing the amount of information that could lead to serendipity, but they serve another purpose. They are the tools needed to increase knowledge, to expand areas of interest, and to prepare the mind to be able to acquire insight from unsought events.


Designing to create serendipitous experiences seems to be barely possible. By choosing to use a tool to look for information or access any kind of media, we are already showing an intention to find it, removing the accidental factor that serendipitous experiences require.

However, we can actually design for serendipity, but not artifially producing serendipitous events. Instead, we can design to prepare the user to make the most of events that seem random and unrelated, but that could lead to great discoveries if they are associated with other ideas in the user’s mind. How can we help the user do this?:

  • Understanding the user’s background to know what information to show to expand their knowledge. New encounters in a certain field of knowledge can be thoroughly studied only if that field is fully understood.
  • Presenting relevant resources related and unrelated to the field the user belongs to. The exposure to relevant content from unrelated fields may encourage the cross-pollination of new ideas (like genetic algorithms, born from the interaction between Biology and Computer Science).
  • Helping the user look for information from different points of view. As scientist Marvin Minsky said, “You don’t understand anything until you understand it in more than one way”. Seeing a problem from different perspectives can lead to a deeper understanding and potential new applications (for instance, the wave-particle duality and their application in electron microscopy).

Developing our own skills and expanding our knowledge is still the way to go if we want to acquire insight from experience. Computers cannot replace humans in that process, but they can hopefully help people become better observers and better thinkers.

Keep your eyes open… and your mind, too!

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