In Pursuit of a Fifth Place

Grey Swan Guild
12 min readMay 24, 2024


Making better sense of the world requires a different type of space

Authored by: Sean Moffitt, Founder -Grey Swan Guild/ CEO-Cygnus Ventures

“Making your way in the world today, Takes everything you’ve got.
Taking a break from all your worries, Sure would help a lot.
Wouldn’t you like to get away?, Be glad there’s one place in the world…
Where everybody knows your name, And they’re always glad you came.
You wanna go where people know, People are all (not) the same.
You wanna go where everybody knows your name.”
Cheers” Modified Theme Song

It’s a core social motivation, humans want to go where their talents are appreciated, views are listened to, and that whether or not people know your name, or have just met you, they can find an enlightened space of kindred value. That’s what fifth places are.

In Cheers’ case (the song and 80s TV stalwart show referred to above), it was more likely set in a great local third place — the Cheers’ bar knit together by a love of a quick quip, Boston quotidien, the Red Sox and beer. There are many third places in the world, and comparatively fewer fifth places. Fifth places may be tougher to form and hold together, they don’t have all the laser-focused trappings and hard identity edges of other places. However, done well, these fifth places can provide transcendent benefits to its members. They offer up something distinctly different and something higher up the Maslow’s pyramid.

Let’s take a step back. What’s the backdrop behind all this talk about places? The triumph of humans is that we have succeeded despite fairly unimpressive abilities by nature’s standards. We are bottom percentile slow among the mammals, not particularly strong pound-for-pound, and require tonnes of energy and shelter to keep us alive. What we are however are smart and great collaborators. This is what separates us from most animals. The fact we can do it across distance without feeling threatened makes us unique (even our close cousin Gorillas struggle dealing with the foreign and unfamiliar).

Given our cognitive wherewithal, humans have been able to hold up. like spinning plates, many agglomerations of connections across our lives. And technology and the internet have brought connections even closer and more varied. As the age old African proverb states “If you want to go fast, go alone. If you want to go far, go with others.”

Over the last few years, I have had the privilege to lead a unique fifth place, an assemblage of professionals called the Grey Swan Guild. We have the shared mission to make better sense of the world. Over the years, it has moved from being a small experiment, to a tight knit treehouse of the willing, to a movement of passionate individuals, to a global community of great minds, to an aspiring network organization with high ambitions. But with a difference. We operate as “a fifth place” for people who decide to participate, collaborate and join with us.

What is a Fifth Place?

The idea and need for a fifth place is a fresh abstraction that suggests we need to have different spaces and environments in our lives to produce different types of personal and collective benefits. The membership, rules and composition of these places all engender different outcomes and affiliations, where form truly follows function.

I would love to be able to claim domain over the idea of different places in our lives but I came across this integral human need through the bottom of my coffee cup. Starbucks in its early days co-opted the team “a third place” from sociologist Ray Oldenburg in the late 1980s as a place beyond home and work where people could gather, relax and talk.

Starbucks has intentionally designed its stores with comfy seating, ambient music, relaxed atmosphere and some level of barista theatre, to embody the characteristics of a “third place”. In recent years, the Seattle siren has pivoted away from this experience via drive thrus, apps and other convenience-based measures focused more on commercial efficiency rather than instiling a sense of community. We shall see if this shifts pans out, but it has left room for other enterprises to occupy third places like Apple stores, Lululemons and various fitness, apparel and food stores.

Who knew other places existed too. The idea of distinct places in a person’s full life, their 168 hour week has more layers than three.

Let’s cover them all:

Five Places

A First Place — the inner hive of our lives where we spend our most time, among family and friends, typically in what we would call a house or home. Upwards to 100+ hours we spend each week in this enclave, providing us the essential human needs of confidence, support, trust and safety. When these ties are sufficiently strong, they provide us a springboard of other healthy assets as we gallop off to our other places.

For all their benefits, the challenges of first places are that: they are small in nature, you don’t get to choose them, they usually have a clear hierarchy, are part of a societal caste, have some (or a lot) of baggage, and many unshakeable beliefs despite evidence to the contrary.

A Second Placesecond places have become a big part of our post-subsistence hunter/gatherer human age where we communed together for work among colleagues and co-workers for the purposes of esteem, purpose, income and challenge. In many situations, this might be termed a workplace (although as we all know in COVID, a workplace can be a fickle, omnipresent thing). For younger people, this might alternatively be the institution of a school. People gather together and build together in these environments to create things better than what they could create themselves. People can spend 10–70 hours every week in the second place of our lives.

For all their benefits, the challenges of second places are that: they can be impersonal, they can conflict with your first place values, they can have a hollow agenda, they can have organizational cultures that disdain new and different, they don’t particularly develop people well (anymore) and they have clear hierarchies not necessarily based on merit but on a complicated mix of tenure, relationships, buy-in and talent/perceived talent.

A Third Place — although Starbucks has popularized and commercialized it, we have always had third places where we would gather as local neighbors and citizens for collective stability, sociability, amenities and leisure. Whether its the local market, country fair, neighborhood cafe, local community centre or city theatre and events, important venues have established themselves as third places. For many of us, we can spend up to 30–40 hours each week in these community watering holes for all of their local (and now online) benefits.

For all their benefits, the challenges of third places are that: they are often hyper -local, lack central organization and coordination, are run by the whims of their owners or managers, and may lack a productive focus.

A Fourth Place — many of us occupy central roles within our respective industries and disciplines. Trade associations, professional networks, lobbying groups, federations, co-ops, chambers of commerce and conferences all provide avenues into shared benefit of similarly occupied partners. In a digitized flattened world, these fourth places may take on the role of online communities of similar professions. Across a range of competitively- and collaboratively-wried members, these organizations facilitate important within-industry benefits of visibility, connections, best accepted practices and knowledge (e.g. progressive tips/techniques). Episodic in nature, some of the most vested volunteers and key volunteer executives can find value in spending 10–20 hours in fourth places.

For all their benefits, the challenges of fourth places are that: they can be reactionary, a function of past (not future) success, reward size and stature over merit and effort, are frequently self- not world-motivated, and can be driven more by ego and vested interests than surfacing what’s accurate, authentic or truthful.

A Fifth Place fifth places are quite different and often underrepresented arenas where people can find others that they might not find in the regular course of their day-to-day, or even week to week activities. These entities cut across disciplines, geographies, industries and positions, and place all members on an even, flattish and valuable playing field.

Some of these collectives may be called societies, fraternities, sororities, movements, forums, foundations, or guilds (as in our case). These groups are much more mission-based and membership is more a function of what you believe in or aspire to, then what role you play or what you actually do in your personal; or professional life.

Fifth places provides windows into improving your skills (particularly those beyond your single domains), challenging you to wider and more expansive views, introducing leading edge thinking, perspectives and tools into your arsenal, and creating new-to-the-world ventures by collisions you might not ordinarily have in the other places.

Our Guild members suggest under the right set of activities and bandwidths, they would averagely want to spend seven hours a month with us, getting outside of their regular orbits. Some of our inner core would quite happily spend 80 hours/month co-vested with us, in return for their key motivational levers being pulled.

The Benefits of Fifth Places:

As one of my colelagues mentioned, our guild and fifth places, are like having the ability to get out of the fish bowl from time to time in order to know that you have actually been swimming in water. They can operate as important step backs for the critically thinking and introspective with at least six key advantages vs some of the other places:

  • Fifth places can go anywhere more easily, pursuing value across industry-based, discipline-centric, geographical and cultural frontiers based on the needs and desires of ther champions and members, not the handcuffs of a board or executive
  • Fifth places appeal and connect more fluidly with individuals from diverse cultures and backgrounds with an unparalleled opportunity for personal enrichment; they transcend boundaries of our own experiences, enabling us to explore, question, push past paradigmatic hurdles and ultimately evolve as individuals.
  • In an increasingly interconnected and uncertain world, fifth places afford the opportunity to interact with people from diverse cultures and backgrounds, that with digital connections have never been more accessible. Through our interactions with others, we have the chance to learn, grow, and foster a stronger sense of communities of multidisciplinary practice.
  • Fifth places have value in objective synthesis and integration — with all the information at a person’s disposal on their fingertips, you still have people who are ignorant to reason and thnking, and having no idea how to integrate whatever they have discovered, fifth places can build paths to literacy, fluency, mastery and enlightenment.
  • Fifth places stem the tide of AI and advancing technology — the worlds of GPT and generative AI have enormous efficiencies and basic value but lack the nuance to deal with less constrained, complex, less clear and or less repetitive challenges; fifth places allow forward thinking conceptual knowledge to thrive being able to postulate scenarios, transfer knowledge, sensemake new developments, wayfind and sensegive to unfamiliar situations, and define leading edge breakthroughs for yet-to-be defined challenges and/or addressed pain points.
  • Fifth places spur transitions — other places have harder edges where the cost to entry or exit are prohibitively large (e.g. being shunned from a family, needing to move across the country, prohibited from working in an industry), fifth places can more easily play a role in supporting personal shifts by having less convention, baggage and positional authority allowing people and professionals to learn and naivgate through their liminal lanes

Grey Swan Guild and Fifth Places

Grey Swan Guild aims to create a compelling fifth place environment or space, beyond the home, workplace, local community, and industry, that facilitates connection, learning and collaboration among its members in a distinctive way.

The “fifth place” frames our position as a novel networked concept in building value distinctively from amongst the litany of research houses, media entities, government task forces, event groups and not-for-profits that may do similar intelligence, experience-based, community bonding and venture-backed things with a different motivation and operational nature at heart.

We have purposefully designed our guild as a fifth place:

  • We have a higher purpose mission that drives all of existing and prospective members — making better sense of the world — frequently this is something not achievable or promoted well in the other places for the sake of established identity, politics, culture or convention
  • We have lighter identities — given most people’s unfamiliarity with fifth places, people always ask the defining question of second-to-fourth places when they encounter us, who are you? and what do you do? We use whatever choices we make about what we do as enablers not handcuffs, allowing the opportunity to bring to life grassroots efforts that may fall outside of some tighter definition of strategy, equities or brand. It’s a bit messy, and we’re okay with it.
  • We attract multiple types of people — many startups from second places might focus on one single audience to build and nudge out their existence — it’s a smart company approach but not so smart for fifth places. To appeal to our disperse mission, we attract a broad expanse of minds and makers encouraged to operate outside their specialities and collide ideas, a group we call (pun slightly intended) 50 Shades of Grey Swans thinkers and do-ers.
  • We have light structures — we don’t have a governance board, we have a working Quickening group; we don’t have a long set of principles, we have four values, we tried to introduce harder-edged principles and guardrails, and they were rejected. The front row of the collective votes on key mandates of the Guild each year. In a pure relationship of reciprocity, the more effort you put into fifth places as individuals, the more you get recognized, the more influence you get, and the more value you derive.
  • We appeal to multiple interest areas — many institutions in fourth places, surgically concentrate on one industry focus area or professional group. This may be smart initial strategy but they frequently struggle to expand beyond the cell they put themselves in, at some later stage. Instead, from the very start, we have canvassed the interests of our members beyond their tightly bordered disciplines and industries, and reconciled on twelve core subject matters that captivate our membership. Although always with a multidisciplinary lens, we have themed our next year’s operational calendar based on these disperse but related interests:

What are your fifth places that you have joined or want to be part of? Care to share some of their journeys? Let’s amplify this idea of fifth places and define a different way to run the world.

There are about 27+ different ways to participate in the Grey Swan Guild

Make better sense of the world ● Host events ● Attend events ● Go deeper on analysis ● Meet & commune ● Steer & advise ● Learn, relearn & unlearn ● Localize Guild efforts ● Write ● Onboard ● Geek out ● Converse ● Connect deeper ● Forge peers ● Contribute to a movement ● Consult/advise ● Author & publish ● Research & investigate ● Mint foresights & futures ● Mentor & empower youth ● Distill methods & frameworks ● Discuss ● Inspire ● Develop craft ● Design & visualize ● Evaluate uncertainty ● Read & share opinion ● Journal ● Solve wicked challenges ● Catalyze ventures — what is your making sense appetite?

Three official routes to get involved:

Join as an official member:

Become a global sensemaker:

Catalyze a Cygnus Venture:



Grey Swan Guild

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