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WiserWith and Designing for Serendipity

What Is WiserWith?

WiserWith (WW) is an evolving concept of an R&D project for creating a living, socio-noetic-technical platform co-evolving with its participants. I will be designed to support better sensemaking, wiser decisions, mutual learning, emergent collective intelligence, and generative serendipity among people, organizations, communities, and societal systems. 

To achieve these design objectives, the platform will use a combination of electronic, social, and inner technologies for Computer-Assisted Wisdom Development.

It will combine a “Software as a Service” (SaaS) delivery mechanism with a facilitation framework and processes baked into the software.

Much more than a technology platform, WiserWith will also be a living system of people using language, tools, and methods for augmenting their wisdom-guided individual and collective intelligence and capabilities. It will be a complex adaptive anticipatory system, not unlike a generative “Knowing Garden” introduced by Mark Szpakowski here, optimized to co-evolve with its user participants.

Modular structure

WiserWith will have three modules, one for each of the individual, group, and societal inquiries. Their development will be supported by our Generative Action Research methodology (outlined here), in each of the three areas.

The WiserWith product family will be clustered in three modules, distinguished by the scale of its users’ inquiry:

SoloQuesting, the individual inquiry module, GroupQuesting, the group inquiry module, and SystemQuesting, the societal inquiry module

The modules will be not only inter-operable but also, well integrated. The benefits of using more than one of them will be cumulative. Although any of them can be used by itself, the specific combination with the others is intended to lead to surprising breakthroughs in whichever domain they will be applied to.

For instance, systems change approaches developed with the help of transcontextual mutual learning, inspired by the prompts of SystemQuesting, will be more actionable when used by groups/movements that also QuestWith. In turn, the use of GroupQuesting will be more effective when the inquiry muscles of its users are trained by transcontextual learning prompts of SoloQuesting.

The focus of the latter is to empower the individual users to create continually growing value for themselves, including by inventing new uses. However,  its full potential will shine only when WW users aggregate in teams, communities, and larger networks and make themselves available to the larger, encompassing a range of benefits from GroupQuesting and SystemQuesting.

Designing for Serendipity

“Serendipity is crucial because it expands your horizons. You need that if you want to be free.” — Cass Sunstein

Expanding one’s horizons is one of the gifts that WiserWith intends to bestow on its users. It will do that in various ways and fostering serendipity is one of them. Its varied navigation paths, prompts, mental modeling tools, etc. “would present a wide array of information and viewpoints, rather than just re-enforcing a user’s opinion.” (Serendipity, in Wikipedia)

Serendipity, as a design principle for a living, socio-technical system of people using language, tools, and methods, will provide exposure to new ideas, surprising perspectives, and collision opportunities.

Collision density is a factor not only in the innovation propensity of cities and online co-learning and collaboration spaces, such as WW’s QuestWith and SystemShift modules will become but also, even in CogniSavvy, its individual inquiry module. To illuminate the role of collision in serendipity generation for individual users, I paraphrase two findings from Jane Jacobs seminal book, The Death and Life of Great American Cities.

  1. Each space within the WW environment must serve more than two functions so that they attract the user with different intentions at different times of the day or his/her life, and discover unsuspected connections. 
  2. WW modules, must be populated with dense intersections among use cases that give user opportunities to interact with something that s/he originally didn’t intend.

What fields of surprise do you want to scout today?

The Serendipity Generator

“Serendipity means an unplanned, fortunate discovery. Serendipity is a common occurrence throughout the history of product invention and scientific discovery. In recent years, the phenomenon has become a potential design principle in online activity for preventing filter bubbles and echo chambers.” — Wikipedia

 If “chance favors the prepared mind” (Pasteur), one can think of WW as a serendipity generator, using idea emergence. It’s a method designed to lead to the discovery of new meaningful connections between parts of our knowledge, forgotten inspirations, and freshly-noted reflections on books we read, conversations we have, or videos we watch.

We can also feed information into the serendipity generator, add tags and links, and watch how the knowledge graph is organizing them into patterns of unfolding connections. Those patterns are evolving over a period of time as shown in the snapshot from a 30-min video, generated by the Obsidian app that we plan to use for the core of WW.

No matter how powerful the connectivity features of the tool will be, it’s not by themselves that they will act as the serendipity generator. The users’ surprising discoveries due to linking one’s thoughts will be a consequence of the synergy between the software and the users evolving mind skills (supported by WW’s built-in guides and prompts to enhance their inner narratives).

The WiserWith concept draf is an invitation to those feel called by it. Here’s also more than 2 years research went to it and what is presented here come from a large volume of design notes, ready to  be turned into a design document. The invitation, at this stage, is not to those who have similar projects and want to blend theirs into this, but those who want to learn about and help manifest the potential of WW.