The Making & Meaning of “Uncertainty” — The Opus for our Age

14 min readJun 21, 2023

Behind the curtain and the impetus for the making of our just launched book Uncertainty that makes better, bolder sense of the world

“Uncertainty is the engine room for forerunners — effective leaders of our more complex, superCAFFEINATED 2020s. Uncertainty captures the spirit of our current times and rises above the sub-factors of volatility, ambiguity or complexity. It expresses the authentic, dominant challenge and liberation of our times. Uncertainty is malleable as a term. It is wedged somewhere between manageable risk and uncontrolled chaos. It appears in inputs but is also reflected in outcomes. It taxes our rational minds, weighs on our emotional souls but also catalyze our ambitions. Uncertainty is the top level rung of our existential, professional dispositions and wicked problems, It manifests itself unexpectedly, changing our mindsets, decisions, values, behaviours and actions … but it doesn’t have to paralyze us.” — Sean Moffitt

This post takes us inside the curtain of how and why we built “Uncertainty: Making Sense of The World for Better, Bolder Outcomes”, the tome for this decade and beyond. As you read along, it behooves us to tell you five things in advance:

Buy it (it’s really good and helpful)
Learn about it (we have given you plenty of ways to experience it)
Provide your observations on uncertainty (we call these Weathervanes)
Join us for our 2023 Tour (the book is just the start of the movement)
Listen to our podcast (authors, editors and special guests)

January 21, 2022 — weeks after our Grey Swan Guild General Assembly where we voted on our 2022 ventures (our book ranked third among fifty), I had what I would term a casual “imagine if we could…” Zoom call with Gordon Withrow, one of our early Guild members and true leaders of from our satelite office in Ohio. Between geeking out on ice hockey and big hair metal bands, we realized we had an early shared ambition. The small ambition was to scout out the steps required, decisions to be made and considerations for our Guild publishing its first book (yes a real live book). The big ambition in the back of our heads was cranking up a thought leadership publishing house that could put our sharpest Guild members’ best thoughts on public display to the world ongoing. Thankfully, we ended up doing both.

Launching a book certainly wasn’t our most pressing venture ambition at the time. In the interim 17 months, we have launched a consultancy, hatched a research group, minted a futures/trend boutique, crafted a learning event series and beta tested and educational venture. Sometimes the fast moving turtle does beats the skittish hare. We have now crossed our first finish line(taking pause to celebrate).

A. Our UNCERTAINTY Publishing Timeline

“The solutions to uncertainty are to take the widest possible lens and adopt an expanded framework of methods suitable for the world in front of you. In times of uncertainty, the true, post-modern craftperson uses a range of disciplines and applies the largest possible latticework of frameworks.” — Sean Moffitt

If you are ever considering publishing a collaborative book yourselves, you might want to consider our timeline as a benchmark, particularly for a collective group of us that do full time “other things.” We did a lot of things right, a few things wrong. Here were our 25 biggest milestones:

Advance scout work and long advance planning — Jan-Sept’22
Tabling the plan and intent— Sept’22
Assembling the core team (started with 16 members) and setting up our guardrails — Oct’22
Making a call for authors (48 initial authors took up the challenge) — October 5'22
Editorial board assembled for the first time — October 10’22
“Uncertainty” mentioned as lead theme, it stuck — Late Oct’22
Weekly Operating team meeting with Editorial board (12 members) — Early Nov’22
Miro Board meeting — grouping shared ambitions — late Nov’22
Agreement to charter, principles and format of book — early Dec’22
Kickoff meetings with finalist authors — Dec 9 and 13th’22
Chapter Editor/Author meetings — Late Dec’22
Setting up a repository for initial submissions, style guidance for citations and action timelines/plan to publication — late Jan’23
Final drafts submitted — Jan’23 and extended — Feb’23
Project Triage “but I thought you were sending me your endnotes” — March/April’23
Copy editing at a chapter level — Mar’23 and full book level — May’23
Podcast interviews begin — March’23
Graphics & layout completed April’23
Commercialization plan — April’23 and execution — June’23
Combine chapters and send to formatting — May’23
Components Assembled and typeset May’23
External first reveal to our Guild members — May 25'23
Publish date — June 8'23
Full website launched — June’23
Uncertainty companion research project and advance review effort begins June 19'23
Launch Events — June 15th, 20th and 27th’23

Well here we are now. Our shared thinking was that there was no better vessel for Guild member collaboration to act as a vessel that publicly communicated to the world our tangible value than a book. Seventeen months later we have launched, our time is now.

Much appreciation to the editorial and design crew for stepping up nearly each and every Monday for the last six months (and some moments in between): Aaron Mikulsky, Angi English, Besir Wrayet, Deepshikha Yadav, Emma Withrow, Gordon Withrow, Deb Dimoff, Louise Mowbray, Nathan Gilliatt and Olga Howard.

B. Our Aspirations and Principles for UNCERTAINTY

“But nothing is solid and permanent. Our lives are raised on the shakiest foundations. You don’t need to read history books to know that. You only have to know the history of your own life.” ― Ron Rash, One Foot in Eden

We came up with five fundamental principles that our book should live up to, and we think it has:

A Grounded Vision
Uncertainty is visionary like science fiction, but grounded in what’s possible — this book aims to create clarity and decision-making confidence for any situation.
Whether there is a lack of clarity due to constant change or the multi-layered elements of uncertainty, proven sensemaking frameworks and methods are the bedrock that binds this work.

2. Expert Driven
Uncertainty is a real-life independent practitioner-thinkers guide of an all-perspective view to increase the reader’s ability in acquiring knowledge and expanding their perception, sense cognition and perception threshold practices, through real-world use cases and resources.

3. Relationship Building
Uncertainty is speaking to both executives and middle managers, this book exudes a friendly inviting tone. Humor and playfulness are used to make the reader feel like a partner while wrestling with big thorny problems.

4. Interlacing Frameworks
Uncertainty is a full-range of thinkers coming together from various disciplines to partner with the reader in creating innovative frameworks through the interlacing of existing frameworks, methods, and experiences.

5.Emerging Perspectives
Uncertainty is unexpected ideas and perspective-shifts reflect emerging diverse world-think. Interdisciplinary solution-smithing collectively helps the reader persevere and thrive in unpredictable worlds.

C. Success Criteria for the “Uncertainty” Book Contents:

“All acts of genius begin with the same premise, do not be constrained by your current reality” — Davinci

One of our editors Angi English shared one of these quotes and its early importance for us to break out of current and traditional patterns of thinking.

Through this lens we evaluated the author submissions against a criteria of:

☐ Calibre of topic — “this would be fascinating and broadly appealing”
☐ Calibre of submission — “this followed what we asked for”
☐ Calibre of writing — “this suggested strong writing & conceptual framework”
☐ Calibre of approach — “novel, interesting, fresh or new take on subject”
☐ Calibre of playbook element — “this would be an important and valuable artefact for people to apply our learnings”

We additionally overlayed:
☐ Balance out topics across chapters
☐ Balance out for gender and geography across guild

All thirty-six of our book’s submissions passed this litmus test. Since we hav taken off the last two criteria for our extended Wild Cards of Uncertainty, we expect even more people — 50 others — to add to our Uncertainty compendium in our digital collection over the next year.

Uncertainty — Intended Feelings, Emotions and Outcomes We Wanted To Impart

D. The What — We Intended this Uncertainty Book to Be…

“Although our intellect always longs for clarity and certainty, our nature often finds uncertainty fascinating.”― Karl Von Clausewitz

We want Uncertainty to be a fully balanced and professional perspective on the topic of uncertainty.

The Uncertainty Playbook is a future-forward collaborative work of thought-leadership, frameworks, approaches, and case studies aligned with the seven sprints of the Cygnus Sprints venture, providing leading practices exercised by members and guest associates of the Grey Swan Guild.

The Uncertainty Playbook will focus on mindset pivots, new approaches and strategies, including applicable tools and techniques to solve the issues at hand. The desired final product will include tangible, visual assets that can be exercised, and may take the form of a framework, a checklist, or a standard format used in business communication, as appropriate (e.g. 2&2, Civiat, Stepwise Approach, etc.).

The Uncertainty Miro board exercise — Reader intended experiences, emotions and outcomes

E. The Who — People this Uncertainty book was designed for…

“Navigating uncertainty and all its components. It’s the most difficult of all responsibilities. If that’s your struggle, this book helps you.” — Olga Howard

Uncertainty is targeting current and future practitioners, executives and curious others, that we may find around our professional worlds, within our 8,000 member Grey Swan Guild, or guided through our 70 member Cygnus Sprints consultancy.

Primary Persona: Leaders who are drivers of change in their organizations, largely practitioners in strategy, planning, change and innovation work, typically at the VP/SVP level, and serve as primary advisors to the C-Suite.

Secondary Persona: Guild members and Cygnus Sprints practitioners will be encouraged to resource The Playbook as a solid reference and development guide.

F. Historical Context — Why Uncertainty fits for this decade

“As you become comfortable with uncertainty, infinite possibilities open up in your life. It means fear is no longer a dominant factor in what you do and no longer prevents you from taking action to initiate change.”— Eckhart Tolle

Since the 1940s, there has been more scholarly and popular interest in uncertainty verus certainty (see visual below). Massive scale wars and sciety change have a tendency to do that.

The 1950s were about the boom, communism vs. capitalism, mass markets and civil rights.
The 1960s were about space, the Cold War and the Button, assassinations and flower power.
The 1970s were about oil, protest, equal rights and the green revolution.
The 1980s were about free markets, the fall of the Wall, globalization and the PC.
The 1990s were about internet, neo-liberalism, Y2K and Islamic militarism.
The 2000s were about 9/11, the rise of China, social media and economic meltdown.
The 2010s were about global growth, climate change, mobile and the Cloud.

It’s early yet, but with boundary jumping AI and tech, global warming, military conflict and a global pandemic to begin the decade, it’s not hyperbole to consider the 2020s as the decade of “Uncertainty.”

1942 — The crossroads of certainty and uncertainty Google nGram

G. A Blue Ocean of Uncertainty Grey Swans

When we first considered the notion of titling our book Uncertainty, we considered some of the books that came before us (some we would highly recommend).

Happily we discovered two things:

the volume of books (and notably popular books) produced on uncertainty was much lower than some of its kindred peer subjects like innovation, futures, complexity, change or disruption, there was an avenue
the positioning space for books that took a practitioner, multi-disciplinary approach with a professional, company-wide and team-based lens to uncertainty was still fallow, there was an opening

Uncertainty was our first name and it has stuck and grown in our estimation the more we have lived with it.

H. A Group Committed to Navigating Through Uncertainty (not drowning in it)

From the very beginning we were focused on creating a book that lit up paths to solutions and not getting stuck on why we arrived in the frenetic, stressed out and uncertain post-pandemica world we exist in today.

The distinctive value and higher ground of Uncertainty the book is in dealing with and embracing uncertainty, not in bemoaning it, casting blame or belabouring how uncertainty happens. Thus, we were quite intentional with our inclusion of our book’s tagline “Making Sense of the World for Better, Bolder Outcomes.” Uncertainty derives out of our four imperatives of thinking AND doing AND acting AND changing.

With that in mind, we asked our contributing authors three key questions as we initially canvassed their interests.

What category of article would you like to write about?

Although we had a wide berth of interest across our chapters, leadership, sensemaking & strategy were the most popular submissions

2. How would your article most help the reader navigate through complexity?

Once again we received a broad array of reader helps but: a) a fresh or unique perspective; b) a better revolutionary approach; and c) a marked change from status quo thinking were tops.

3. What core playbook element (tangible solution) will be included in your submission?

A full spectrum of playbook elements were suggested (and can be evidenced in the final book). Tops among these tangible article pieces were: a) a new framework or model, b) a process flow or roadmap; and c) a customizable tool and canvas. Games or applications (darker red in visual below) received strong write-in ballots.

I. What’s Inside the Book

The structure of Uncertainty was framed very much on the focus and domains of our pre-existing on-demand consultancy and advisory group Cygnus Sprints. We have a set of authors (more than half of them are first-time published authors) who are steeped in not only thinking deeply and conceptually about topics but also in their real life professional application.

Here’s the containers they wrote to, with editors identified and dedicated for each chapter:

Introduction to Uncertainty (13 parts)
Leadership & Uncertainty (8)
Technology & Uncertainty (5)
The Marketplace & Uncertainty (6)
Scanning & Uncertainty (6)
Sensemaking & Uncertainty (5)
Strategy & Uncertainty (12)
Innovation & Uncertainty (8)
Discovery & Uncertainty (8)
Transformation & Uncertainty (8)
Conclusion and The Conversation Continues… (4)

I’m personally very grateful for all the contributing authors that made it into book and our Wildcards of Uncertainty. Of our 8,000 different Guild members and a couple of hundred of people who expressed an early inkling to write something, you were the ones that not only made a great first impression, but also had the resilience and moxie to see it through. Fortis fortuna adiuvat.

J. Uncertainty — By The Numbers

“The way a leader or organization goes about making sense of the environment in which they operate has changed. There are new tools, techniques and behaviors that allow us to thrive in the current environment without being torn down by the noise of the day, These methods and practices get to to the heart of the opportunities before us and allow for rapid action to implement solution sets which can move smart organizations forward.” — Gordon Withrow

410 pages of fresh perspectives and pathways through Uncertainty
11 chapters covering the gamut of an uncertain professional world
36 segments (contributed article pieces) written with purpose and intent
120,000 words, sweated over, agonized with and landed on
380+ references — we have researched this topic in-depth
50 all-star contributors plucked from our Guild-ed world (aka Golden Swans)
11 member rock star editorial team (aka Platinum Swans)
27 Uncertainty Hall of Fame finalists — we are nominating the top authors about some aspect uncertainty — the giants that have come before us (more on that later)
17 months in the making — 9 smooth and relaxed months, 5 planned and methodical months and 3 frenzied and hurried up months
20 events & experiences — scattered throughout the year to support our book dare we say movement — here’s our tour
20 ways to still get involved: discover, read, review, listen to our podcast, become a Navigator, author a Wild Card, chip in a Weathervane, join the Uncertainty tour, attend the Masterclass, celebrate with our bookfest, nominate a Hall of Famer, Guild up, start Cygnus Sprinting, geek out on methods, hire us, get us to speak, become involved in our sequel(s), book club — here is our central website hub for a greater breakdown
11 key forces that make Uncertainty more vexing and more important than ever before (forget VUCA introduced in the 1980s, we call it CAFFEINATED for the 2020s)
80+ visuals of evidence, frameworks and canvases (guaranteed to be used in your workplaces)
2 — we have both formats — color paperback and e-readers (ask us about other formats and languages down the road as we detox from these first launches)
1 — one mission — making sense of the world and turn it into better, bolder outcomes

What to Do Now:

The conversation is just getting started around Uncertainty. We’ll keep it simple for now (although we plan on 20 ways to get involved in our Uncertainty movement dow the road). Here’s how to participate in it right now: