The Pain Points for Making Better Sense of the World

Grey Swan Guild
8 min readJul 9, 2024

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The Seven Guiding Catalysts for the Grey Swan Guild

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

“Only by identifying their stakeholder’s pain points, can organizations and movements have real proof that they have the best solutions ready for the world.”

So we have been running a Guild for a number of years now. It’s full of passionate professionals and waves of activity. Tremendous energy gets spent on our various experiences, community activities, intelligence efforts and moonshot ventures. We are so grateful for a wave of authentically all-star professionals that we have come in contact with over the last four pandemic-infused years. This has to be a good thing, right?

In a fit of pensive sobriety, I step back and think that there must be some type of invisible hand that has gelled 10,000+ of us from around the world together in the spirit of understanding and making our professional worlds better (without a single dollar of marketing ourselves I may add).

People frequently play back our mission of “making better sense of the world together” as the rallying cry. That may be well and good but when you step down one level from that, what does that really mean? What are we actually solving for? What is the itch we are trying to scratch? What are the pain points we are trying to alleviate?

Paint Points — Grey Swan Guild

Pain Points at Work

We think we know our stakeholder’s pain points, but do we really? Pain points come secondhand for startups as they are usually the first slide indicated on their pitch deck. Entrepreneurs are driven by the need to tackle some imperfection with our status quo world at work. Their investors expect them to have a well articulated pain point. Sometimes these venture pain points can be small and lead to niche solutions, sometimes they are not immediately seen as valuable but turn into big solutions. Startups get pain points.

For some user experience (UX/UI) professionals, pain points are a staple first step of the design thinking experience where empathy is required in identifying the inconvenience or major issues of using a product before ever rectifying them. Getting after users’ pain points, can help deliver stronger desirability, viability and feasibility of a particular product, service or business model. Innovators and designers get pain points.

Perhaps this pain point identification is a little less clear and obvious for other types of organizations and people, including in our case, a Guild.

Pain points refer to specific issues encountered by stakeholders, both existing and potential, within the operating environment. Pain points can lead to negative experiences, influence decisions, poor knowledge and/or ill-fated behaviours and may dissuade people from making a preferred or correct action, staying loyal and connected to a community, or incorrectly interpreting the proper truth, meaning or interpretation. Defining the wrong or inconsistent pain points can cause drift.

With startups, the stakeholder involved is very clear and narrow — it’s the future customer. With larger company user experiences, the stakeholder may be well defined but the customer journey and touchpoints are much more splintered complicated. In a Guild like our Grey Swan Guild it’s a lot messier and more confusing, the stakeholder is a combination of our members and “the world”, and the touchpoints we have to alleviate them are a wide spectrum of member-expected and requested activities.

Pain Point Frequency Matrix — Landon Howell

Obstacles When You Have No Declared Pain Points

We have never codified our pain points. This has been a miss on our Guild’s part. From time to time, we have new waves of people that enter our Guild and despite best efforts, they struggle in trying to deliver against pain points that really aren’t relevant to our mission. It can be frustrating to both sides.

Sometimes people enter our Guild and love contemplating and recontemplating issues without ever arriving to an answer. They bang the drum of whatever single issue, single method or single frustration that has captured their psyche without ever getting to a convincing or improved point of view.

The Giving Pledge might be an example of an institution that has one single minded thing on their minds — get billionaires to give their majority of wealth to philanthropy. It’s simple. It’s great. It’s altruistic, but it’s not us. As much as the angst against the establishment and these single prism views stimulate conversation and a shared sense of frustration, this is more activism at best and ranting at its worst.

Sometimes new members arrive into the Guild wanting to push a particular agenda or dogma. It’s not entirely unexpected — I would wager 40–60% of the world’s research houses, big event series, foundations and associations have a vested interest in pushing and influencing a particular operating system or philosophy on the world.

World Economic Forum is a great example of a popular not-for-profit that although engaging in complex challenges, engages political, business, academic, civil society and other leaders of society to actually try to SHAPE global, regional and industry agendas. It may be noble, it may make headway, but that’s not us. In many cases, these institutions can operate directly opposite a mission of shining light on truths and perspectives, as objective findings that get surfaced may not be easily incorporated into their doctrinaire or unchallenged beliefs.

Finally, some strategists and marketers are hell bent for leather to choose among various specific audiences, down to some personalized human as our Guild’s target audience. As a recovering marketeer, I have seen the benefit from illustrating vivid singular customer personas (e.g. Sally is an aspiring 27 year old professional at a crossroads or Jeremy is a 43 year old grey collar worker at personal career pivot) but it’s usually to demonstrate the impact a brand could make in someone’s lives to those less informed.

Personas are oversimplifications of audiences that lead to oversimplifications of pain points. If you held a gun to my head, we have 50+ audiences in the Guild that carry with them over fifty plus different pain points. Not very actionable and ultimately blinding ourselves to the expanse of what our Guild could fulfill in its full spectrum of potential. We have more been knitted together not by what’s on a specific someone’s business card but what values they seek — in our Guild they are the ones of aspiration, collaboration, curiosity and purpose. These should be fueling our pain points. We need to identify pain points that rise to the level of our mission and values, not our titles and disciplines.

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

Uncertainty. Bias and Noise. Negativity. Superficiality. Silo Thinking. Ignorance. Challenges (big and wicked).

These are the seven things that confront our mission.

We obsess about them. We seek to overcome them. We seek to navigate around them. We seek to alleviate the bad consequences of them. Our Guild’s directions and activities should conclusively chase these down.

These pain points are not all unequivocally bad or evil in nature. Sometimes in specific environments they are actually necessary. But if you are trying to make better sense of the world, in the long game, these pain points do need to be dealt with.

Over the next few posts, we will profile exactly: what these pain points are, why they are important to tackle, how they manifest themselves, what key facets are part of them, and how the Guild actively responds to them through smarter intelligence, deeper experiences, elevating community and bolder ventures.

As a teaser, these are our seven pain points. Ourt next seven posts will tease out each of these pain points — describe them vividly, provide eleevn contributing facets and provide examples across the Guild on how we’re dealing with them.

The Seven Pain Points of the Grey Swan Guild

Grey Swan Guild — the Calls to Action

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

First, join our Grey Swan Guild Linkedin page Grey Swan Guild — we 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.

Grey Swan Guild Linkedin Page: https://www.linkedin.com/company/grey-swan-guild

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.

Grey Swan Guild Member Form — https://bit.ly/gsgsmemberform

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. https://bit.ly/lofsenseform

Grey Swan Guild’s Global League of Sensemakers form: https://bit.ly/lofsenseform

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.

Cygnus Venturist — Official Form: https://bit.ly/gsgventures

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 July. Here’s the link.

New Member Regatta — June’24 https://bit.ly/gsgjune24regattab

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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🦢