The Daily Habits of Future Thinkers

Grey Swan Guild
11 min readJan 11, 2022


Sixty Things That Futurists, Foresighters, Forecasters, Trend Navigators and Strategic Planners Do … That You Might Not — Part I — Habits #1–30

“Practice isn’t the thing you do once you’re good. It’s the thing you do that makes you good.” Malcolm Gladwell, Outliers

A collaborative post by Sean Moffitt with contributions from: Alexander Kline, Dr. Anne Kyoya, Axel Gruvaeus, Bruce Wade, Chirag Tripathi, Claire Marshall, Heather Galbraith, Laura Cleries, Michel Maieta, Rob Tyrie, Stephen Steck and Sylvia Gallusser.

Ongoing Patterns of Possibility, Probability and Potential

The future thinking muscle — an enlightened brain — requires just as much habitual fitness as lungs might need constant challenge and toning for a marathoner.

We asked some of our member future thinkers, what made their 24 hour cycle come to pass when it comes to minting and perfecting their craft. Here were there answers:


Half the battle of “futur-ing” is adopting a resilient perspective to a future that could be much different to the present:

#1 Entertaining wild cards & possibility — asking yourself “what if” regularly and pursuing answers that may even be inconvenient truths or less than remote possibilities is a rare and noble pursuit.

#2 Think in time continuums & likelihoods — it’s not enough to consider probable, possible & near impossible scenarios, understand the time context and chances of occurrences happening — is this a sure thing? a remotely possible thing? or something in between? and when will this affect us?

#3 Have a beginner’s mindset — enter even familiar circumstances with the thought that you are going to learn something new, not just fit new wisdom into a pre-existing frame.

#4 Optimism & Can-doism — establishment people who have much to lose if your future scenarios are right may ridicule you as freaks and geeks; find ways to bridge gaps with these constituencies but also take the slings and arrows with a badge of honor, their voices may be louder if you are onto something real.

#5 Establish Status Quo Convention … then Find the Gap — enormous value is trapped in understanding the gaps between what is currently believed and what will soon be untrue — fortunes no longer get lost over decades, the arbitrage of future and foresight intelligence can be valued in days & weeks. Start new work with understanding incumbent thinking, chip away at its seams.

#6 Pursue Adjacent Rabbit Holes…Just Don’t Get Stuck There — pursuing and validating associations, and understanding second and third order impacts, is worthwhile pursuit, but also can lead to enormous time drains. Know when you have squeezed just enough juice from the future orange.

SUPPLEMENT: How much time do you spend explicitly (on average) improving your future thinking craft?

Sometimes dismissed as a lesser of soft social sciences vs. the hard and natural sciences: biology, physics, chemistry, as we can see my time invested, future thinking practitioners make a rivalling and considerable cerebral investment:


Why drink from the mainstream all the time, when you can go to the fountain source:

#7. Variety is the spice of the future mind — bring together shards of many disciplines, approaches, mindsets and insight sources under one umbrella; fusion and combination are powerful animators.

#8. Polarity teases out insight from the extremes — new ideas and innovation nearly always happen from the edges not from the mainstream (and invoking Hunter S. Thompson, can also tell you when you’ve gone too far), just know that edges take awhile a cross the chasm to universal popularity.

#9 Novel starting points and experiences — if you always do what you’ve always done, you’ll always get what you’ve always got. When approaching a new foresight situation, change the intelligence departure or intelligence journey embarkation point to produce a different revelation.

#10 History doesn’t repeat in the future ... but it does inform it — past performance is a powerful rudder to future outcomes. Newton’s law of motion has some applicability here — an object (and trend) in motion remains in motion at constant speed and in a straight line unless acted on by an unbalanced force (or influence). Don’t immediately dismiss or accept history, learn to navigate with it.

#11 Scan for multi-disciplinary signals- avoid the echo chambers — regularly swap and change up the influences in your life to avoid staleness and predictability, or you too will become the convention you rail against. Make it goal to meet new people each week.

#12 Distinguish between accepted wisdom and momentum — there are real truths and fake truths, dissect the difference. Propaganda, fake news, infodemics and wishful thinking are ubiquitous. Filter the noise from the signal, try to avoid the type one and type two errors in shifting times.


Future thinking is very similar to golf, just when you think you have figured the game out, it throws you for a loop. Always … be … changing … ahead of …the pace … of your … subjects of interest.

#13 Journaling — regularly documenting observations and insights can lead to a powerful trail of bread crumbs; future self journaling works because it creates conscious awareness around your behaviors and patterns. Establish time alone, cementing your observations of the day.

#14 Change The Process — the now popular trust the process edict suggests blind faith. Instead, constantly reorder and reinvent the process steps involved in your futures work to avoid the shortcuts, heuristics and sacred cows that lie within quasi-certain processes.

#15 Radar — always be intaking data and scanning for shifts. Ever notice how news articles, events and fashions have such short half lives — you need to constantly be processing the world around you to stay fluent. Before morning emails and meetings, read wide, make the linkages and find the threads.

#16 Rank Value & Importance — in any future analyses, there is the seed and root causes and then the symptoms, spurious correlations and red herrings, learn to differentiate them. Regularly stress test your significances and assumptions.

#17 Be the Multi-tool, don’t always be the hammer — future thinkers can get lazy and go back to the same well over and over, you should have command of 20+ tools in your arsenal and use them according to situation that presents itself.

#18 Lead other lives — cross-pollinate interests firsthand; remember the participant and observer power of ethnography and Edgar Dale’s cone of active learning. Doing can often be better than thinking.

VERBATIMS: What Daily Habits Do you Perform as a Strong Future Thinker?

Ingest media and content that isn’t remotely aimed at me, my demographic or personal value system. Stephen Steck

Creating polarity — taking in lots of signals and inputs intensely as well as scheduling “slack” to process. At a daily basis this can take the form of reading a wide array of newsletters, journals and such and then making sure to take the time to take a walk in silence in the afternoon. Axel Gruvaeus

Brailling the signals from the non-mainstream, Spotting the aberrations —important ripples and deviances from the norm, and projecting the future with this knowledge. Sean Moffitt

Reading and listening to the news, scanning for signals, engaging with my futurist community, reading and watching fiction/science fiction, reading essays, writing thoughts, articles, producing scenarios. Sylvia Gallusser

Ask people about how they imagine the future. Claire Marshall

As a general comment I think in this age of information overflow and attention-grabbing deliberate de-connecting is necessary. Making space for ones own thoughts should be a priority for all creative work I believe, and today this takes some effort. Axel Gruvaeus

Read , Write , Reflect , Rethink and coffee. Morning journal. Multi source news cycle to lay the groundwork. And another coffee. Rob Tyrie

Not daily but do I look at various sources — including Smart Cities Dive, Ark investing, Nature briefing, MIT Tech Review, dezeen, Bloomberg city lab etc. Heather Galbraith

Perusing job listings from leading companies to see what trends and innovations they are trying to adapt. Stephen Steck

Subscriptions to secondary sources, book reading in different disciplines. Laura Cleries

Reading, Reflection on wild cards and emerging occurrences/issues and writing. Dr. Anne Kyoya

Reading, exploring, people and voices. Michel Maieta

Reading, meditation and teaching. Bruce Wade

Even 30 minutes of Meditation helps a lot to focus more on visionary ideas and future trends. Chirag Tripathi

Creating future space to explore — a big room, multiple screens, big manilla sheets to domain map beyond the pixels of a screen, music that makes you think, coffee or lemon water, rewards every hour. Sean Moffitt

Writing. Alexander Kline


When we say new space, we mean your physical space, your mind space, your sensory space, your psychological space & safety blankets:

#19 Evidence Walls — create the 360° view — You are your view — how you arrange, connect, group and select what goes on your board affects your conclusions. Attack your quarry like a CSI veteran finds his/her criminal.

#20 Domain Mapping — before wayfinding the solutions, create the universe of the known and potentially unknown — are you analyzing just a thin slice or the full cake? You’ll never know until you’ve explored all your subjects’ pockets and perimeters.

#21 Future is Fusion — 1+1=3, 3+1=9 —futures are a collision of uncertain forces. A balanced perspective is necessary. For example, the Futures Triangle offers us a compelling view that balances the weight of history, the push of the present and the pull of the future; too often we settle on one or two views.

#22 Sensory Triggers — hearing, small, sight, taste & touch springboards — stimulating senses triggers multiple parts of the brain and leads to creativity and conceptual breakthroughs. How can we smell and taste the future?

#23 Sleep Solutions — the power of naps, recovery and waking diaries — we are just figuring out the powerful impact sleep has on thinking; synthesis happens while you sleep, you may even be able to have pre-cognitive dreams

#24 Keep a Misfit Toys Pile — yesterday’s trash could become tomorrow’s vintage — think about the occasions where you had a tangibly great idea but in the wrong time, with the wrong situation or stakeholder; keep a running list to repurpose in the future in your files. Here’s 7 reasons why.


Futures thinking requires malleability and a paradox of people skills. We need the curious minds, but people that can act. We need it to be a social process, but with strong individual passion & ownership. We need advanced thinkers, but open minds. We need diversity, but not to defend a pre-existing position. We need creative tension and conflict, but the ability to work effectively in groups. It’s a difficult balancing act:

#25 Teams & Community, Socialize but Don’t Compromise — know when your future odyssey is a collaborative one and when it needs some personal TLC. Sometimes your best ideas and intelligence come from powerful first impressions, ensure you hold onto that magic as others may try to sand down those sharp distinctive corners.

#26 Masterminds — Peer to Peer, Idea Genesis & Co-Creation — some of these people are not like the others. Embrace a personal board of future thinking advisors that light up your blindspots without negating your unique perspectives. As a CxO, this is particularly true of your executive boards, build them future worthy.

#27 Children - The Unvarnished, Unjaded, Curious Mindbut why dad why? but how come mom? Kids (and new minds generally) provide a unique opportunity to see the future differently without much baggage. Look at UNICEF’s effort among 2–12 year olds in foresight.

#28 Flexibility > Expert better ability to see new dynamics at play — currently established industry or subject matter experts usually have many tentacles in early and late majorities of marketplaces, and may be among the most powerful to reject your pioneering and early adopting perspectives. Seek out the stretchable minds and change-ready allies on a regular basis.

#29 Diversity of Minds — ways of thinking, ways of doing, genders and cultures — there is more to diversity than meets the eye, there are inherent & acquired differences. Too much diversity, conflict may get buried and you may never get to true agreement; too little diversity, and you get groupthink, expert overconfidence and miss out on the robustness of our future thoughts. Ensure your top 20 influences each month have the right type of diversity.

#30 Honesty leading to Creative Conflict, Productive Tension and Greater Self-awareness — there is a zone of good conflict that should be aimed for — too little honesty and you get safe, hierarchically-driven ideas, too much honesty and you get impassible friction and loss of trust . Getting to honest perspectives, self and team-awareness of biases, shaped by different world views, invariably leads to better received ideas and more accurate intelligence. Practice creative conflict regularly, get good at its nuance.

BONUS: When is your best investment in future thinking done?

It would appear future thinkers are more late night inclined and less regimented in when and how they find solutions.

Next week, we will provide our follow up part 2 — thirty (30) additional daily habits and tips of future and foresight thinking in the following 5 categories:


First forget inspiration. Habit is more dependable. Habit will sustain you whether you’re inspired or not. -Octavia Butler

Grey Swan Guild — Join our 50 Shades of Grey Thinkers

Hopefully some of you will think about joining our collective that tries to make sense of the world and the future, as a habit.

We are a post-modern version of the Guild — these are some of the people we are:

Consider Joining a Grey Swan Guild Venture

We have 12 ventures blooming and a few waiting in the wings. Come join us on the experimental quest.



Grey Swan Guild

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