Leap Day of the Swan — February 29, 2024

Grey Swan Guild
6 min readFeb 21, 2024

A-Once-Every-Four-Years Discussion Forum, Time Capsule and Compilation — Join Us.

The Olympics happen every four years. Elections tend to happen every four years. A big Star Wars film nearly every four years. UN Climate conferences otherwise known as COPs, once again every four years. Apparently even Bitcoin, despite its relative youth, have fluctuating cycles that happen every four years.

Perhaps it’s no strange coincidence many large events take stock of the world every four years. These quadrennial events inventory the four years that have just past, understand and perform deeply in the present, and pivot to contemplating what might happen over the next four year orbit.

In 2024, we have been afforded this once-every-four-year celestial opportunity granted by the only somewhat off kilter Earth’s orbit around the sun — some extra time to audit the lives around us and muse on its bigger questions. Consider it a little bit of a CTL-ALT-DEL of our Grey Swan Guild world. Consider it our Leap Day of the Swan,

Introducing Leap Day of the Swan — February 29th, 2024

On the cusp of the fourth year anniversary of our Guild, we are hosting a three hour Leap Day of The Swan event on Thursday, February 29th at 10am EST/7am PST/4pm CEST/5pm SAST/7pm GulfST/8:30pm IST/11pm SGT. Here’s some of the salient details

The Why:

It’s a great natural milespost in our lives to get some brilliant minds together to understand deeply what we’ve gone though, what’s happening now and consider what’s next … as our event’s tagline suggests A Look at Today and A Leap into Tomorrow

The Who:

We are looking to engage one hundred (100) of our top Guild minds, and perhaps even some new faces, to spend three hours of cognitive, interactive and fun energy with us, and find intrigue in considering implications, consequences and actions around some of our bigger questions as we sit in 2024. You will all be credited for your contributions.

The How: We plan on hosting a discussion in seven instalments that mark the quadrennial:

  • Connection — Personal Futures 2028 — get people interacting and sharing about where they will be in 2028.
  • Fun — Leap Day Bingo — see if we trip over some buzz words of our deeper now and emerging future.
  • Pulsecheck — Leap-tradamus Predictions — we’ll ask a few pivotal and fun questions where we will be in 2028
  • Going Deep — A Wrap Discussion on Remote Work — we’ll explore interactively what might have been the biggest legacy from our pandemic-laden last four years — call it work from home, remote work, distributed organizations — and where does that leave us now — a pre-wrap of our favourite articles of great, good, bad, ugly and tapestry aspects about this topic will follow later this week
  • Perspective in Context — Headline Chasing Trivia — the best futurists are also historians, we’ll offer up the best headlines from the last 100 years of Leap Days and you tell us when it was, or what is was about.
  • Casting Forward — Futures Wheel Time Capsules (see below)— casting forward to the next four years of the 1st, 2nd and 3rd order impacts of the work-from-home genie being out of the bottle — we will be sending each of our attendees an advance brief ahead of the event
  • Synthesis and Lasting Artefacts — Leap Day Wrap Up Report — we’ll consolidate discussions, opinions, Future Wheels and polls, not only on work-from-home subject. but we’ll also be asking a select few attendees to provide their best glimpses on the next four years of : AI & Emerging Tech, Climate & Environment, our Geopolitical World and Mental Health & Wellness, publishing a summary report, and then meeting again four years from now to convene around a retrospective before pivoting once again to another four year future. After all, making sense of the world has no finish line.

The Where:

Pre-register here — our session will be hosted and recorded on Zoom and Miro.

The When:

February 29th — Leap Day of course — starting at 10am ET/7am PT/4pm CEST and going for three hours.

Seven Reasons to Join Us February 29th:

Here are seven good reasons for being one of our hundred Leap Day fo the Swan attendees.

#1 A high caliber and interactive discussion on one of the biggest changes to our Society and Professional Culture — remote work.

Our research indicated more than anything else remote work acceptance has changed our last four years and will continue to do so over the next four. Let’s step back and discuss.

#2 Contemplate where this could all go — The Futures Wheel

We’ll be breaking out into four hives to discuss four key aspects of remote work, distributred teams, flextime and work-from-home and where this could all go with our Futures Wheel tool. Get familiar with a great strategic planning tool and invest in identifying the four year probabilities, preferabilities, possibilities, wild cards, extremes and consequential effects of all these WFH aspects.

#3 Let’s have some fun and interaction

Leap-tradamus, Leap Day of the Swan Bingo, Personal Futures 2028 and Headline Chasing Trivia 2028. Let’s let down our Guild hair and play! In doing so, also get a chance to win our guild’s Uncertainty book- Updated Edition and the theme of our GSG Book Club’s March book discussion The Coming Wave.

#4 Producing something together — a Leap Year Wrap Up Report

We’ll be producing a synopsis of the event with some follow up that will function as a a four year time capsule, milepost and foresight publication. if you already know you’d like to contribute to our report, join here.

#5 Connect with One Hundred Smart Thinking & Doing Others

We will be providing a forum to meet new people, all making a big dent in their respective professional spaces. Strong peership, camaraderie and professional networks happen in the guild like no other place.

#6 Don’t be an ostrich, be a Grey Swan

Open your mind up to our Guild’s fifth place — a place beyond your personal, professsional, community and industry life, that explores deep questions, considers big uncertainties, postulates unknown futures and chases Grey Swans.

#7 We’ve bought you sometime

Make this your once-every-four-year check in with some brilliant minds. 2024 has give us an extra 24 hours, let’s make good use of it.

Seven Leap Day of the Swan Actions:

#1 Pre-Register for our event here: https://bit.ly/leapdayoftheswan

#2 Visit here for more details: https://www.greyswanguild.org/leapdayoftheswan

#3 Join our Guild: https://bit.ly/gsgsmemberform

#4 Read our forthcoming Wrap of articles & perspectives and forthcoming pre-brief on how our three hours will fly.

#5 Open mind, share wisdom, attend February 29th

#6 Contribute after the leap day to our March Report.

#7 Rinse and repeat, meet you February 29th, 2028.

Google Doodle Leap Day 2020 (Hops)
Google Doodle Leap Day 2016 (Leap Rabbits)
Google Doodle Leap Day 2012 (Barber of Seville and Frogs)
Google Doodle Leap Day 2008 (Korean Indepoendence)
Google Doodle Leap Day 2004 — Frogs



Grey Swan Guild

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