Guild Pain Point #7 —Challenges

Grey Swan Guild
10 min readJul 30, 2024

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Wicked problems, sticky issues, world boulders, societal catalysts

Author: Sean Moffitt, Grey Swan Guild Founder and CEO, Cygnus Ventures

“Some problems are so complex, you have to be so intelligent and well-informed just to be undecided about them.” — Laurence Peter

Our Cygnus Sprints on-demand consultancy and advisory — disrupting how organizations solve their biggest challenges

Grey Swan Guild’s Seven Pain Points for Making Better Sense of the World

These are the seven things that confront our mission. We obsess about them. We strive to overcome them. We seek to navigate around them. We hunger to alleviate the bad consequences of them. They are pain points.

We are profiling our seventh and last one here — it is less an enemy and more of a catalyst for fresh new thinking that goes beyond what has come before. Some call these pain points wicked problems or sticky issues, we merely call this pain point Challenges (which of course exist only to be overcome!).

VII. Challenges

Challenges rise above the levels of mere problems or nuisances. Problems we can and will put up with and are more straightforwardly solved. Nuisances we either simply squash for good or avoid. Challenges are a different beast — complex, multifaceted issues that are enormous in influence, difficult to define, tough to avoid, and resist resolution for a variety of reasons (indicated in our facets of Challenges below).

The added complication is that big challanges often involve multiple stakeholders with divergent perspectives and vested interests, making them particularly challenging to address, especially if you only own one piece of the challenge solution pie. They frequently befuddle governments, institutions and organizations, preferring to deal with the symptoms of a challenge, but not directly the challenge itself. When tackled in a constructive, intentional way, challenges pursued can free up a lot of energy and productivity.

Rapid rise in popularity of Challenge-relevant terms: Sensemaking, Big Challenge, Wicked Problems and Unknown Unknowns (Source: Google nGram)

Our Guild’s very first big challenge we confronted was back in 2020 when we rallied a fervent group of 80 pioneering souls around the multi-headed nature of the pandemic, and what it meant for our current existence and many futures. Our intense focus on this effort become the central premise of our Guild’s first two years of operation, as the conclusion and potential solutions for COVID were still very much in doubt. Perhaps they still are?!

To borrow a startup term, our Guild has pivoted from this early 2020s decade seminal moment to address other foreboding challenges. Consider the rollout of our two year research and intelligence plan just announced this last week. We are now focusing on the many-tentacled challenges of: Uncertainty, AI Realities, Happiness, Resilience, Organizations Next, Knowledge & Decision Making, The Future of Cities & Living, The Future of Money and DeFi, The Regenerative Economy, Impending Grey Swans (possibilities, wild cards and extremes), The Regenerative Economy and Customer Shifts. No small problems indeed.

Our Guild’s 2024–2026 Intellgence efforts, declare your candidacy to participate.

Our Guild’s radar is constantly scanning, rating, ranking and evaluating the looming challenges of our world. We’re not content just considering why they happened, but also like to abstract and consider the actions and implications for people operating in the now. In fact, we have profiled and pulled together a Spinning Wheel Billboard list and app of the biggest 100 societal Big World Challenges below, culled from our universal bank of 300. These are the type of monumental issues that we conjure up when we think about out pain point of Challenges.

100 Big Societal Challenges — Grey Swan Guild. Spin that challenge wheel:

Facets of our Pain Point Challenges:

Frequently confronted in planning, policy and strategy work, big Challenges have some inherent characteristics to them that make them extraordinarily difficult and almost impossible to solve because of incomplete, contradictory, and changing conditions, requirements and stakeholders. These are often difficult to accurately map, identify and appease respectively. Sometimes teams and organizations try to piece out a challenge and solve some of its smaller pieces, but because of complex interdependencies, the effort to solve one aspect of a wicked problem may reveal or even create other associated challenges.

Although sometimes the source of these challenges are intentional and represent vested or established interests consciously sewing dissonance on the world, most of these colliding elements are neutral and benign in nature that compond when they combine with other factors. They can be justly characterized as chaotically dynamic, irresponsibly disorganized, or blindly, collectively malevolent in nature. We’ve defined the key 11 facets to consider when tackling big Challenges here:

  • Sheer Complexity + Uncertainty: big societal challenges can involve numerous variables (knowns and unknowns), information & data overloads, and unpredictable outcomes, making them hard to analyze, process and manage comprehensively.
  • Sketchy Framing: big challenges can lack a clear and definitive problem statement; an ask-think-do loop can be created because the challenge is too difficult to firm up because the information needed to understand the challenge depends upon one’s idea for solving it.
  • No Challenge Finish Line: there is no clear point or “”stopping rule” at which a challenge’s solution is achieved, making it hard to know when the problem is “solved” (e.g. climate change is one of biggest examples — is +1.5° Celsius the goal or avoiding an apocalypse?). Efforts to address the problem can only and always be improved, and at some point can suffer from problem solve fatigue from not arriving to a fianl outcome.
  • Murky Interpretations: challenges often lack clear unequivocal right and wrong, and more deal in better or worse (or less worse); therefore the nature of these challenges operate with no finite set of solutions and with decidedly different emphasis on progress criteria.
  • Long Progress Paths: there is usually no magic bullet theory or immediate experiment that can be produced and measured to intervene on the challenge; any forays into the challenge may delay progress given their unintended and unforeseen consequences on the nature of the challenge itself. Thus, policymakers and organizations often prioritize short-term gains over long-term solutions.
  • Conflicting Stakeholder Interests: different and often many groups have opposing priorities, perspectives, cultural beliefs, and misaligned incentives, making agreements unlikely and consensus difficult.
  • Holistic Testability: every potential solution to a challenge pursued is a distinct comprehensive effort; each attempt therefore represents one self-contained experiment that is tough to piggyback on for applicable learnings because of the complex and evolving nature of the underlying challenge.
  • Contextual Uniqueness: each challenge is unique to the environments it’s found; solutions that show progress in one situation may not work in another due to specific variables that are different; this issue can be confounded by human factors of those involved (e.g. risk aversion, resistance to change, and cognitive biases) that can impede recognition of the progress being made to address complex issues.
  • Lack of Owner & Resource Limitations: frequently, there is no one true owner of the problem — making it difficult to coordinate effective learning and responses across different levels of governance and sectors; this can lead to lack of accountable progress and tracking, and also fall short of threshold financial, human, material resources, knowledge or data required to address these challenges.
  • Emerging Technological Impacts: rapid and disruptive technological advancements can outpace regulatory frameworks, societal adaptation and research trajectories, creating new problems or exacerbating existing ones even when they represent progress or new insights on the challenge.
  • Clumsy Globalization: given the Increased interconnectedness and interdependence of challenges and their effects, the ability to find local solutions is compromised, the inability to govern global solutions makes progress difficult to scale and the lack of strong collaboration among interested national and multinationmal parties leads to fragmented efforts, inefficiency, and duplication of work.

The Guild’s Response to Challenges:

Unlike many institutions, the Guild has both the mission and talent that actually enjoys the process of considering big challenges. One of our key advantages is rooted in our name itself (i.e. Grey Swans essential mean improbable but major developments that have the potential to cause great opportunity or calamity).

The Guild is able to contemplate big challenges because we’re able to embrace possibilities at all levels — what is probable, possible, unmanageable, and almost unthinkable? It’s how many of us are wired and distinguishes us from large chunk of knowledge workers and their companies who prefer to work in stark certainties and absolute confidence.

Given the experience and executive-level composition of our membership, we are able to entertain the notion of knowing when we did not know solutions to challenges subjects from our past histories. This talent shows up in:

  • Experiences — GSG Book Festival: the Guild hosts a 12 episode December annual event that celebrates over a dozen authors who have produced leading edde works that challenge our world views through a holistic literary look at major and valuable professional subject matters, across a range of domains.
  • Intelligence — Weathervane Reports: we conduct a minimum of three primary research efforts every year that put a premium value on whether we have adequately shown the interrelated relationships, systems-coherency, friction points, clashes, causes, factors, contextual-awareness, liminal-sense, cultural-savviness and industry-specific implications to our full work.
  • Community — Ateliers: Our Guild provides the platform for expert members to run workshops named Ateliers that translate and transfer their expertise to or members on big chalenges (e.g. Atelier #4 emerging technology workplace impacts) and unusual world challenges (e.g. Atelier #9 — space exploration).
  • Ventures — The Compass and Compendium : our ambitious attempt to take down the blinders, conventions, lexicon and frameworks of various disciplines and place them in a common translatable platform. We are building a platfiorm that visually maps over 750 frameworks, furnishes a recommendation engine to methods (based on the objective nature of a challenge) and provides an expert wiki authored by global experts that have used the frameworks in real life settings.

Read up on the other Pain Point posts

The Pain Points for Making Better Sense of the World

Guild Pain Point #1: Uncertainty

Guild Pain Point#2 : Bias & Noise

Guild Pain Point #3 : Negativity

Guild Pain Point #4 : Superficiality

Guild Pain Point #5 — Silo Mentality

Guild Pain Point #6 — Ignorance

Grey Swan Guild — the Calls to Action

If you have an interest in responding to uncertainty, our pain point chasing and our particular Guild view on the world. You have a few options.

First, join our Grey Swan Guild LinkedIn page Grey Swan Guildwe post daily, usually surfacing interesting observations that respond to our pain points, giving you a first view of what’s upcoming, telling you how to get involved, or recapping what cool things we have just done.

Secondly, if you want to get higher up on our radar and profile your interests, declare your intentions and potentially take on a leading or contributing role in the Guild, there is only one way to do it. Become an official member. Here’s the form.

If your enthusiasm still remains whetted, and you love going below, around and above the surface of our world’s biggest issues, become part of our standing panel of 400+ analytical and observational minds. Become a Global Sensemaker. Here’s the form.

Not satisfied with just thinking, but would rather solve these pain points too. We have designed a ventures wing to our guild called Cygnus Ventures that has embarked upon twelve different ventures to get after solutions and opportunities that tackle making better sense of the world through our well-defined pain points. Become a Cygnus Venturist. Here is the form.

Trying to find the central thread and on-ramp to participation and still have questions? Each and every month, usually in the first week of the month, we host new member onboarding Regattas, where we meet you face to face and share in why we exist, what we do, who you are, explore some interactive queries and answer every one of our queries. Join us at our next regatta in August. Here’s the link.

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Grey Swan Guild

Making Sense of the World’s Biggest Challenges & Next Grey Swans — curating and creating knowledge through observation, informed futurism, and analysis🦢