Medium All-Stars of The Month — Grey Swan Future + Sensemaking Scan

5 min readDec 23, 2021

We have been scanning the world out there for great thinkers and their content which make sense of today’s challenges and next Grey Swans.

Author: Sean Moffitt

Here is our list of thirty (30) brilliant thinkers for December’21:

Design Thinking/Design Thinkers:

Some evergreen posts here but still resonate five-six years later:

Christina Wodtke — How I Stopped Worrying and Learned to Love Design Thinking

Dan Nessler - How to Apply a Design Thinking, HCD, UX or Any Creative Process from Scratch

Santhosh Gandhi — Futures Thinking and Design Thinking Simply Explained

Dan Nessier — Design Thinking Process Diamonds

Frames & Conceptualists:

A smorgasbord of resources on ensuring your arguments, challenges, opportunities and problems have the right filter form the get go:

Maja Voje — 90 Free Growth Hacking Tools and Frames

Enrique Martinez — Frames (#16 in a series)

Robert Skrobe — A Simplified Approach to Design Think Problem Framing

Systems & Complex Thinking:

In a world full of complexity, it’s great we have systems thinkers among us to simply our lives:

David Thiel — Five Books for Developing Systems Thinking

Thomas Oppong — How Systems Thinking Can Simplify Your Life

Leyla Acaroglu — Tools for Systems Thinkers: The 6 Fundamental Concepts of Systems Thinking

Tools of a System Thinker from Disruptive Design

Business Models & Value Generation:

The future is more about configuration than inventions, these alchemists have brought their wisdom together:

Bruno Aziza — How to Make Better Business Decisions

Daniele Catalanotto — Turn Your Resources Into Revenue

Scott Clary — Revenue Model Options: 10 Revenue Generation Techniques For Digital Businesses

Scott Clary — Business Models by Revenue Type and Monopoly

Perspective & Ways of Seeing:

What’s that old adage, change your perspective, change your mind:

Kate Rutter — Sketch Things Better with the 7 Ways of Seeing

Jose Caballer — 3 Ways of Seeing Brand Patterns

Volkan Yucel — John Berger, Ways of Seeing

Volkan Yucel — John Berger’s Ways of Seeing

A Beginner’s Mindset and Learning:

If your mind is empty, it is always ready for anything, it is open to everything. In the beginner’s mind there are many possibilities, but in the expert’s mind there are few:

Zita Fontaine — How a Beginner’s Mindset Can Help to Thrive as a Writer

Christine Denker — Get a New Lease on Your Career with a Beginner’s Mindset

Steve Davies — Are We Getting Dumber?

The Flynn Effect — Steve Dennis & Our World in Data

Future Thinking & Foresight:

The future has been sped up and Grey Swans are everywhere. Time for a healthy dose of futures thinking (and make it relevant and practical):

Amy Webb — How Futurists Cope With Uncertainty?

Ximena Vengoechea — How and Why To Do a life Audit?

Paul Higgins — Bringing Future Thinking into Strategy

Output to Ximena Vengoechea’s Life Audit

Regenerative Systems & Sustainability:

In order to support our soon-to-be 10 billion people, we better start getting systems that regenerate to work:

Laura Winn — Applying Regenerative Thinking to Systems Beyond Place

Rosana Rezende —Regenerative Systems for a Possible Future

Desiree Driesenaar — Business Models: from Linear to Circular to Regenerative

Regenerative Systems of a Brewery — Desiree Driesenaar & Ask Nature Nuggets

Creativity and Invention:

Creativity is about connecting things. When you ask creative people how they did something, they feel a little guilty because they didn’t really do it, they just saw something. It seemed obvious to them after a while. Let’s make it obvious to all:

Valentina Salvi — The Master Ideation Toolbox

Josh Spilker — 11 Best Books on Creativity for 2021

David Kadavy — Arrange Your Time and Tasks According to These Seven Categories, and You’ll be a Creativity Machine