Hindsight & Retrospection

Grey Swan Guild
15 min readAug 23, 2022

Craft Building Series #41 — Looking Back Before Stepping Forward — A Curation, An Event and A Wisdom Summary

Author: Sean Moffitt, Co-Founder, Grey Swan Guild

“Hindsight is a great teacher, but it is also an unforgiving reminder of what could have or what might have been.” — Don Paul Aprile

We conducted an expert panel on the oftentimes weaker but no less potent sister of insight and foresight — hindsight. As much as many of us believe our world is riddled with unexplainable anomalies, notorious exceptions or significantly different futures, the truth is we know there is much that can be learned from our pasts to understand more deeply our now, project forward to a better future and take the moral high ground of humanity’s progress.

Some progressives believe that full histories need to be wiped out to establish new values, axioms and ways of running the world. Morally right or not, they would be setting fire to a lot of learning with it. The world has 7.7 billion people in it now, but 120 billion have ever lived on earth , nearly 16X our current world— surely we can learn lessons from their experiences. So let’s explore the value of hindsight.

I want to thank my fellow panelists Dave de Bakker, Julia Claeys Freeland and Louise Mowbray for their valuable contributions and dialogues to our discussion.

Our Discussion:

Join us for the hour back-and-forth discussion (a retrospective on retrospective — so meta): watch our recording here.

Watch our panel discussion: https://www.linkedin.com/feed/update/urn:li:activity:6959571772518121472

Glossary & Definitions:

Hindsight what happened? what can we learn? Understanding a situation(s) or event(s) after it has happened and finding out what can be absorbed. Generally, we feel a lot of wisdom, certainty and knowledge comes from hindsight in our lives.

vs. Insightwhat matters now? why is something happening currently or presently shifting? The skill and capacity to generate a deeply intuitive understanding of a person, thing or subject, typically in the current tense.

vs. Foresight what will happen? what’s next? The ability or process of forecasting, predicting or postulating what will happen or what could happen.

Data Analytics — Hindsight, Insight and Foresight — Patrick McDonald

Retrospectionwhat happened to me/we? what did I/we do? how could I/we have acted differently? The act of thinking about the past or something that happened in the past, particularly with a personal lens, with slightly different uses and meanings in:

  • medicine — outcomes specified at the beginning of a study by looking backwards at data collected from previous patients
  • software development — meeting held at the end of a software iteration — asking what went well/what could be improved/what went badly/docus for next period/sprint/month/quarter
  • popular culture — the events, happenings and topics that define a unique previous era, year or period across culture
  • the arts — commonly refers to art exhibitions or anthologies, assembled to look back at and individual artists career, movement or artistic periods.
Agile Development Retrospectives

“The most fertile source of insight is hindsight.”— Morris Kline

Pattern Recognition and Detection

Hindsight provides opportunity for pattern recognition and depends on the ability to see what is the same and the ability to see what is different. It depends on being able to make connections between different types of information and on being able to apply transformations to different types of data — spatial, temporal, auditory, linguistic and abstract.

Source; Ibbaka

Patterns make tasks simpler. Pattern recognition requires the repetition of experience. Discoveries and inventions-to-date are a result of the pattern recognition skills of humans. Humans have a tendency to see patterns everywhere. They are important when making comparisons, judgments, and acquiring knowledge; we tend to be uneasy with chaos and chance, just like the new citizen might be intimidated by a local tradition or a new worker might be disjointed by a new workplace culture.

Eight Analytical Approaches to Pattern Recognition (Source-Analytics Vidhya) https://www.analyticsvidhya.com/blog/2020/12/patterns-recognition-the-basis-of-human-and-machine-learning/

In looking at hindsight, we are considering not only things that are in our datasets, but also things beyond our datasets and observations and what may be going on inside our heads in processing hindsight (or in machine learning what’s happening in artificial intelligence).

“Hindsight is not only clearer than perception-in-the-moment but also unfair to those who actually lived through the moment.”
— Edwin S. Shneidman

Hindsight Bias

Hindsight bias is a cognitive bias (also known as creeping determinism or the knew-it-all-along effect) with the tendency to view events as being more predictable than they really are, of predicting the outcome of something that cannot really be predicted.

The challenge is a person who is prone to hindsight bias might have a false sense of superiority, an overestimation of his intelligence or a false overconfidence about the effectiveness of his thoughts and decisions. This then propels them to take risky and ill-informed decisions which may have disastrous effects as we have seen in business, politics, sports, or medical practice, or even a jury’s judgments about a defendant’s past conduct.

Hindsight bias shows that we selectively recall information that confirms what we know to be true and we try to create a narrative that makes sense out of the information we have. When these bread crumbs are easy to generate, we interpret that to mean that the outcome must have been foreseeable. Research suggests that we have a need for closure that motivates us to see the world as orderly and predictable and to do whatever we can to promote a positive view of ourselves. Paradoxically, the technology we have at our fingertips may actually increase not negate our hindsight bias because of its availability and its oftentimes traits of being able to tell two stories.

Even though history deals in the facrs of what happened, there are three levels of hindsight bias that include:

Predictability “I knew that would happen” — focuses on the notion we personally could have foreseen the event

Inevitability “It had to happen” — centers on the belief that the event was inevitable

Memory Distortion “I said that would happen” — misremembers an earlier opinion or judgment

Interesting, research suggest older people tend to have a more magnified hindsight bias particularly as it relates to negative aspects of foreseeability and positive aspects of memory:

“Hindsight bias makes surprises vanish” — Daniel Kahneman

Hindsight & Retrospection Poll

Certainly a lot of our polled members consider Hindsight both a net positive and of strong value:

Hindsight was viewed by out respondents and panel as very valuable and perhaps an essential dance partner to other forms of ‘sight. Hindsight also involved applying new lenses to the past in order to explain, progress and push past challenges in the current or future. Despite overwhelmingly a negative valence in search engine results , negative connotations to hindsight were only a quarter of respondents.

“Hindsight does always serve the purpose of putting you in the right, and if you don’t have it, you find yourself very often in the wrong. “ — Roy Hodgson

What Can We Learn From Hindsight:

Hindsight is able to help current and futures by:

  • establishing cause and effects
  • understanding conditions and points of change and continuity
  • identifying turning points and “hockey sticks”
  • leveraging the past, proving meaning for the now and extrapolating to the future
  • being able to learn through the lenses of history and others

“Hindsight is notably cleverer than foresight.” — Chester W. Nimitz

The Benefit of Hindsight — Missed Turning Points :

Langar Research Associateds/ABC

Other interesting predictions that failed in hindsight:

  • in 1900, an American engineer predicted that by the year 2000 the letters C, X and Q would have become obsolete (because unnecessary)
  • Mosquitoes, flies and all wild animals would have disappeared;
  • Gymnastics would be mandatory for all.
  • the New York Times science editor was sure that by 2000 humans would eat sweets made from sawdust and wood pulp,
  • In 1966, Time magazine was certain that at the turn of the millennium, humans would travel on ballistic missiles
  • All viral and bacterial diseases would have been wiped out
  • Only 10% of the population would work
  • Drugs to regulate mood disorders would be widely available.

Oftentimes, we find major reasons for past predictions on the future that turned out to be far of the field goal posts : status quo bias, projection bias, linear and exclusionary thinking, confirmation bias, availability heuristics, sunk cost fallacy, the role of emotions such as fear and hope — but also simply lack of knowledge or a change in policy.

“Hindsight is not necessarily the best guide to understanding what really happened. The past is often as distorted by hindsight as it is clarified by it.”- — Amos Elon

Revisionist History

Even though it’s the title of one of my favourite podcasts, is Revisionist History something we actually want?

Revisionist history can have two skewing arguments that can upset people (e.g. somebody found guilty posthumously but can’t defend themselves), generate false histories or evidence (e.g. Jews did not die en masse/no holocaust, UFOs have/have not landed) or affect people’s identities (e.g. The U.S. military was right/wrong in Vietnam):

  • Historical revisionism, the reinterpretation of orthodox views on evidence, motivations, and decision-making processes surrounding an historical event
  • Historical negationism, the distortion of the historical record such that certain events appear to have occurred and/or impacted history in a way that is in disagreement with the historical record and/or consensus, and usually meant to advance a socio-political view or agenda.

“I have no desire to suffer twice, in reality and then in retrospect.”― Sophocles, Oedipus Rex

How to Get Better at Hindsight & Retrospection

  1. Review past actions and decisions.

Summarize after a period of time:

  • What did you do wrong? What should you have done?
  • What did I do right? What should Ikeep doing?
  • What lesson do you want to take away? What will you do differently?
  • After deciding on the best course of action, how can you improve it further?

2. Every evening review your day.

Ask yourself questions such as the following.

  • What did I accomplish today? What choices did I make?
  • What could I have done differently? What can I learn from today’s events?
  • What opportunities did I encounter? Did I rationally respond or emotionally react to stressful situations?
  • How should I change to make further progress? How do I feel about today?
  • Are my feelings based on reality or false assumptions? What should I do differently or what can I improve on tomorrow?

3. Keep a journal.

Putting things in writing when the hindsight happens, makes the thinking concrete. As you do so, you will develop hindsight and foresight while gaining insight. List the factors that made you consider something and include your suspicions, your hunches, your feelings and proof. Here are a convenient list of 12 apps.

4. Examine the evidence.

Just because you think or feel something, by itself, does not make it true. Find retrospective support, even if in other geographies, situations or industries to support points focused on what next.

5. Analyze Outcomes

On a periodic basis, compare what you thought might happen and what actually did. Account for the discrepancy and consider factors that may have led to the same or different choice.

6. Make it Real.

Scrutiny of pasts is great and future action items but may gather digital dust. Integrate retrospection into core of operations or activities.

7. Practice Prospective Hindsight (or pore-mortem)

Look back to the past from the future and do the important devil’s advocate work without the normal resistance or defensiveness,

“The real trick in life is to turn hindsight into foresight that reveals insight.” — Robin S.Sharma

Resources — Hindsight & Retrospection

New Your Times’ Headway’s Hindsight: https://www.nytco.com/press/the-new-york-times-launches-the-headway-initiative-which-aims-to-explore-the-worlds-challenges-through-the-lens-of-progress/

“Hindsight. It’s like foresight without a future. “— Kevin Kline


We may have invented a term “KINDSIGHT” during our session above. Julia Freeland mentioned being able to not penalize or criticize ourselves personally for what we failed to do in history that with hindsight’s advantage, we would avoid doing in the future. Louise Mowbray added making ‘friends with the past’. Beyond a Danish four-piece band or Robert Zuckerman book, there were no strong mentions for a word kindsight that could eventually mean being kinder to our previous selves.

“We all pine for a time in life when things were simpler. Even when they weren’t necessarily simpler, hindsight makes them look a lot simpler. The reality of it was that it wasn’t.” — Ben Gibbard

Being Ahead of Your Time?:

Many of us who take extended views of different time periods or complexities don’t exactly represent the orthodoxy of our times; it can be challenging for us living in the current age but can only be helped in hindsight, oftentimes when it is too late to affect or influence the world.

Jimmy Carter was seen to be an amazing person and very solid politician but was unelectable in 1980 losing in a formidable landslide to Ronald Reagan based on the economic, military, Middle East and social upheaval and energy crisis of the late 70s. Carter very accurately summed up the American crisis of confidence of no longer being able to call the shots around the world, but recognized the voting public of the time could only digest so much within their current worldviews.

“Hindsight is the historian’s necessary vice.” — Hilary Mantel

The Four Turnings — A Cycle of Hindsight:

While writing Generations, William Strauss and Neil Howe described a theorized pattern in the 80–90 year historical generations, noticing cycles of generational events which they call turnings. In their follow up book The Fourth Turning, they describe a four-stage cycle of social or mood eras which they call “turnings”: “The High”, “The Awakening”, “The Unraveling” and “The Crisis” that can be used to interpret patterns of hindsighy.

High — the First Turning
According to Strauss and Howe, the First Turning is a High, which occurs after a Crisis. During The High, institutions are strong and individualism is weak. Society is confident about where it wants to go collectively, though those outside the majority center often feel stifled by the conformity. The First Turning in the US was the post–World War II American High, beginning in 1946 and ending with the assassination of John F. Kennedy on November 22, 1963.

Awakening — the Second Turning
The Second Turning is an Awakening. This is an era when institutions are attacked in the name of personal and spiritual autonomy. Just when society is reaching its high tide of public progress, people suddenly tire of social discipline and want to recapture a sense of “self-awareness”, “spirituality” and “personal authenticity”. Activists look back at the previous High as an era of cultural and spiritual poverty. US’s most recent Awakening was the “Consciousness Revolution,” which spanned from the campus and inner-city revolts of the mid-1960s to the tax revolts of the early 1980s.

Unraveling — the Third Turning
The Third Turning is an Unraveling. The mood of this era they say is in many ways the opposite of a High: Institutions are weak and distrusted, while individualism is strong and flourishing. Highs come after Crises, when society wants to coalesce and build and avoid the death and destruction of the previous crisis. Unravelings come after Awakenings, when society wants to atomize and enjoy. They say the most recent Unraveling in the US began in the 1980s and includes the Long Boom and Culture War.

Crisis — The Fourth Turning
The Fourth Turning is a Crisis. This is an era of destruction, often involving war or revolution, in which institutional life is destroyed and rebuilt in response to a perceived threat to the nation’s survival. After the crisis, civic authority revives, cultural expression redirects towards community purpose, and people begin to locate themselves as members of a larger group. The previous Fourth Turning in the US began with the Wall Street Crash of 1929 and climaxed with the end of World War II. The G.I. Generation (born 1901 to 1924) came of age during this era. They say their confidence, optimism, and collective outlook epitomized the mood of that era.. The Millennial Generation (born 1982 to 2004) show many similar traits to those of the G.I. youth in: rising civic engagement, improving behavior, and collective confidence. Julia had also noted, perhaps instead of war, maybe our recent global pandemic marks a pivot into this current fourth turning.

“Life can only be understood by looking backward; but it must be lived looking forward.” — Soren Kierkegaard

If I Knew Then What I Know Now…

A really cool chalkboard wall in Carlsbad California …hindsight can be instructive and emotional. Give it a watch.

“The problem is when you are writing something in retrospective, it needs a lot of courage not to change, or you will forget a certain reality, and you will just take in consideration your view today.” — Boutros Boutros-Ghali

Multiple Pasts

Our Grey Swan Guild panel arrived to the conclusion that we may want to come together and look at multiple pasts. If we believe we have agency over our futures and potentially have many probable, possible, improbable and preferred futures, we might also be able to interpret history with the lens of different peoples’ probable, possible, improbable and preferred pasts. Give it a thought.

“History will be kind to me because I intend to write it.”-Winston Churchill

What’s Next in the Grey Swan Guild — Craft Building Series #40, #42, #43

“Never deprive someone of hope; it might be all they have.” — H. Jackson Brown, Jr.

Event: Hope, Faith & Courage
Date: Friday, August 26th, 2022 1pm ET/ 5pm UTC.
Forum- Clubhouse: https://bit.ly/gsgcraft42hope

“I engage in the use of game theory. Game theory is a branch of mathematics, and that means, sorry, that even in the study of politics, math has come into the picture. We can no longer pretend that we just speculate about politics; we need to look at this in a rigorous way.” — Bruce Bueno De Mesquita

Event: Game Theory, Risk and Reward
Date: Monday, August 29th, 2022 5pm ET/ 9pm UTC.
Forum- Guildmaster Roundtable : https://bit.ly/gsgcraft40gametheory

“There are many counterintuitive and surprising ways companies can boost users’’ motivation or increase their ability by understanding heuristics — the mental shortcuts we take to make decisions and form opinions”― Ryan Hoover,

Event: Heuristics, Probabilities and Mental Shortcuts
Date: Monday, August 29th, 2022 7pm ET/ 11pm UTC.
Forum- Guildmaster Roundtable : https://bit.ly/gsgcraft43heuristics

Cygnus Ventures-on-Go

We want to create a different immersive type of experience for making sense of the world. One of our upcoming ventures is our “Making Sense Masterclasses” that are ambitious enough to consider 50+ learning experiences focused on making better sense, transforming and creating impact from our past, present and future.

If you have an interest in directing, leading, planning , commercializing or curating the new frontier of learning, let us know here: become part of our Masterclass development team: https://bit.ly/gsgmasterclasses

Become part of our Masterclass development team: https://bit.ly/gsgmasterclasses

Grey Swan Guild

Making Sense of the World’s Biggest Challenges and Next Grey Swans — through content, experiences, intelligence, learning, community and ventures 🦢. Come see what we are all about: https://www.greyswanguild.org/




Grey Swan Guild

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