Antifragile – Risk

Nassim Taleb antifragile risk chart


While this blog is ostensibly about Embracing Failure and Leadership and Management, the underlying common thread is the notion of “risk”. Notions, approaches and even philosophy about “risk” (or “probability” or “stochastic” processes) is also underpins Nassim Taleb’s “Antifragile”…

  • “I used the image of the barbell to describe a dual attitude of playing it safe in some areas (robust to negative Black Swans) and taking a lot of small risks in others (open to positive Black Swans), hence achieving antifragility. This is extreme risk aversion on one side and extreme risk loving on the other, rather than just the ‘medium’ or the beastly ‘moderate’ risk attitude that in fact is a sucker game (because medium risks can be subject to huge measurement errors)…Antifragility is the combination of aggressiveness plus paranoia” [ed. in poker, “tight aggressive”]
  • “If you take risks and face your fate with dignity, there is a nothing you can do that makes you small; if you don’t take risks, there is nothing you can do that makes you grand, nothing.”
  • “Instead of having all members of the staff on an airplane be ‘cautiously optimistic,’ or something in the middle, I prefer the flight attendants to be maximally optimistic and the pilot to be maximally pessimistic or, better, paranoid.”
  • Never ask anyone for their opinion, forecast, or recommendation, just ask them what they have – or don’t have – in their portfolio…Never ask the doctor what you should do. Ask him what he would do if he were in your place. You would be surprised at the difference.”

The vehicle of ‘risk’ is often ‘optionality’. It is a concept that often seems like the domain of hedge fund rocket scientists, but people execute “options” every day. Perhaps the largest “option” in one’s life is home ownership. My wife Lori and I have always felt that the greatest riches we could bequeath on our children were “options” in life. So we exposed them to much and tried to nurture as broad an array of skills and insights. Taleb observes…

  • “The option is an agent of antifgragility.,,’the right but not the obligation’…Most interesting options are free, or at the worst, cheap…Freedom is the ultimate option.”
  • You will never get to know yourself – your real preferences – unless you face options and choices.”
  • Like Britain in the Industrial Revolution, America’s asset is, simply, risk taking and the use of optionality, this remarkable ability to engage in rational forms of trial and error, with no shame in failing, starting again, and repeating failure. In modern Japan, by contrast, shame comes with failure, which causes people to hide risks under the rug, financial or nuclear, making small benefits while sitting on dynamite, an attitude that strangely contrasts with their traditional respect for fallen heroes and the so-called nobility of failure.”

Antifragile – Leadership and Management

Nassim Taleb antifragile leadership and management


I’m not the only one who talks about Embracing Failure along with Leadership and Management in the same breath. Not surprisingly, Taleb’s “Antifragile” had plenty to say on the subject of Leadership and Management. And like my perspective and link between the two subject, Taleb’s observations also pivoted on the notion of risk stewardship.

Contrary to the prevailing cult of ‘Leadership’, Taleb articulates strong advocacy for the power of effective ‘Management’ (ie. downside minimisation)…

  • “Of course a bonus system based on ‘performance’ exacerbates the problem [of focusing only on upside and not downside avoidance]. I’ve looked in the history for heroes who become heroes for what they did not do, but it is hard to observe nonaction…The corporate manager who avoids loss will not often be rewarded.”
  • “There is a Latin expression ‘festina lente’, ‘make haste slowly’…The Chinese thinker Lao Tzu coined the doctrine of wu-wei, ‘passive achievement.”
  • “The Romans revered someone who, at the least, resisted and delayed intervention. One general, Fabius Maximus was nicknamed Cunctator, ‘the Procrastinator.’ He drove Hannibal, who had an obvious military superiority, crazy by avoiding and delaying engagement.”
  • “Statement by the financier Warren Buffet that he tries to invest in businesses that are ‘so wonderful that an idiot can run them. Because sooner or later, one will.”
  • “If you ‘have optionality,’ you don’t have much need for what is commonly called intelligence, knowledge, insight, skills, and this complicated things that take place in our brain cells. For you don’t have to be right that often. All you need is the wisdom to ‘not do’ unilltelligent things to hurt yourself (some acts of omission) and recognize favourable outcomes when they occur.”

Business and life has been tainted by the ‘industrial’ mentality’ of the 20th century where the notion predominated that all outcomes could be engineered through process and planning. Over time, people found holes in their ability, but they felt that that their shortcomings were just gaps and that if they filled the gaps with more process, then the system would work. So process got layered with more process onto process with belts, and braces, and duct tape resulting in the large-scale megalith corporations that are designed to control every aspect of business outcome. The myth of the coin-operated spreadsheet.

The fallacy of this model is only now becoming apparent. The idea that one can create the perfect system blueprint following some PRINCE, ISO-certified recipe that ticks every boxes and accounts for every eventuality is widely discredited now. That approach is probably responsible for as many multi-million dollar project scrapheaps than successes. The software world has also moved sharply away from the “big bang” approaches of the 20th century to a more dynamic more of “Agile” development built around the notions of “iterate and improve.” Maybe that an apropos shorthand for “Antifragile” – “Agile”.

Antifragile – Failure

Antifragile 2


Part 2 of reviewing Nassim Taleb’s masterwork, Antifragile, has to look at some of his insights into embracing failure itself.

He explores the subject on a personal and almost philosophical level…

  • “Provided we have the right type of rigor, we need randomness, mess, adventures, uncertainty, self-discovery, near-traumatic episodes, all these things that make life worth living.”
  • Nature loves small error (without which genetic variations are impossible), humans don’t – hence when you rely on human judgement you are at the mercy of a mental bias that disfavours antifragility.”
  • “My son, I am very disappointed in you. I never hear anything wrong about you. You have proven yourself incapable of generating envy.” [in response to a popular child that no one picks on]
  • Poverty makes experience.” – Publilius Syrus
  • “He who has never sinned is less reliable than he who has sinned once.”
  • There is no such thing as a failed solider, dead or alive (unless he acted in a cowardly manner) – likewise, there is no such thing as a failed entrepreneur or failed scientific researcher, any more than there is a successful babbler, philophaster, commentator, consultant, lobbyist, or business school professor who does not take personal risks.”
  • “A Latin saying that sophistication is born out of hunger (artificial docuit fames). The idea pervades classical literature: in Ovid, difficulty is what wakes up the genius (ingenium mala saepe movent).”


…as well as on a more professional and business level…

  • Firms become very weak during long periods of steady prosperity devoid of setbacks, and hidden vulnerabilities accumulate silently under the surface – so delaying crises is not a very good idea.”
  • “When some systems are stuck in a dangerous impasse, randomness and only randomness can unlock them and set them free…by a mechanism called stochastic resonance, adding random noise to the background makes you hear the sounds (say music) with more accuracy.”
  • “Not seeing a tsunami or an economic event coming is excusable; building something fragile to them is not…Focus on exposure to failure – making the prediction or nonprediction of failure quite irrelevant.”
  • In a system, the sacrifice of some units, that is, or people – are often necessary for the well-being of the other units or the whole. The fragility of every start-up is necessary for the economy to be antifragile, and that’s what makes, among other things, entrepreneurship work: the fragility of individual entrepreneurs and their necessarily high failure rate,”
  • “The engineer and historian of engineering Henry Petrovski presents a very elegant point. Had the Titanic not had that famous accident, as fatal as it was, we would have kept building larger and larger ocean liners and the next disaster would have been even more tragic.’”
  • “With bailouts, governments typically favour a certain class of firms that are large enough to require being saved in order to avoid contagion to other business. This is the opposite of healthy risk-taking; it is transferring fragility from the collective to the unfit.”


Nassim Taleb - Antifragile


  • Wind extinguishes a candle and energizes fire. Likewise with randomness, uncertainty, chaos; you want to use them, not hide from them. You want to be the fire and wish for the wind” – first line of Anti-Fragile

Antifragile” is the inspired word of Embracing Failure.

Many wise individuals embrace failure, but its prophet has to be Nassim Taleb. All of his works are imbued with its spirit, but his latest book ‘Antifragile’ makes the principle its very heart and core.

It’s not a perfect book. It employs lots of anecdote which is fine as illustration, but can lead to causation fallacy. I also feel that Taleb is a bit unfairly harsh on academia. His “History Written by the Losers” chapter is particularly slighting of models versus “tinkering”, but I don’t think you build a nuclear reactor by tinkering.

Where does one begin to share such a rich trove of insights? I’ve decided to do a bit of a Readers Digest selection of favourite excerpts for those of you who can’t get through the Bible-sized 426 pages (and that’s without the extensive appendices). But even then, there is so much to share that I am going to parcel it out in a few posts over the coming week.

I’ve chunked the citations into some of the more prevalent categories I use on the blog as well as added a few bits of commentary. The first post today focuses on defining the terms. Taleb not only provides helpful definitions and categorisations, but he also deftly coins new terms where nothing conventional fits (or an existing term is too laden is misconstruing semantic baggage).

Of course, the first one of all is the very concept of “Antifragility” itself…

  • Antifragile – “Some things benefit from shocks; they thrive and grow when exposed to volatility, randomness, disorder, and stressors and love adventure, risk, and uncertainty. Yet, in spite of the ubiquity of the phenomenon, there is no word for the exact opposite of fragile. Let us call it anti-fragile. Antifragile is beyond resilience or robustness. The resilient resists shocks and stays the same; the antifragile gets better…This property is behind everything that has changed with time: evolution, culture, ideas. Revolutions, political systems, technological innovation, cultural and economic progress, corporate survival, good recipes…, the rise of cities, cultures, legal systems, equatorial forests, bacterial resistance…even our own existence as a species on this planet..The antifragile loves randomness and uncertainty, which also means – crucially – a love of error, a certain class of errors. Antifragility has a singular property of allowing us to deal with the unknown, to do things without understanding them…We can almost always detect antifragility (and fragility) using a simple test of asymmetry: anything that has more upside than downside from random events (or certain shocks) is anti-fragile. The reverse is fragile.”

A sampling of others that he has either defined, re-defined or lifted from obscurity include…

  • Mithridatization – “Let us call Mithridatization the result of an exposure to a small dose of a substance that, over time, makes one immune to additional, larger quantities of it. It is the sort of approach used in vaccination and allergy medicine. It is not quite antifragility…but we are on our way.”
  • Hormesis – “A word coined by pharmacologists, is when a small dose of a harmful substance is actually beneficial for the organism, acting as a medicine.”
  • Percolation Theory – “It is the system and its fragility, not events, that must be studied – what physicists call ‘percolation theory.’ In which the properties of the randomness of the terrain are studied rather than those of a single element of the terrain.”
  • Losers – My characterisation of a loser is someone who, after making a mistake, doesn’t introspect it, doesn’t exploit it, feels embarrassed and defensive rather than enriched with a new piece of information and tries to explain why he made the mistake rather than moving on. These types often consider themselves the ‘victims’ of some large plot, a bad boss or bad weather.”
  • Stoicism – “The key phrase reverberating in Seneca’s oeuvre is ‘nihil perditi’, “I lost nothing,” after an adverse event. Stoicism makes you desire the challenge of a calamity…Stoicism is about the domestication, not necessarily the elimination, of emotions…My idea of the modern Stoic sage is someone who transforms fear into prudence, pain into information, mistakes into initiation, and desire into undertaking.”
  • Strategy – “It turns out, strategic planning is just superstitious babble.”
  • Negative description – “Via negative does not try to express what God is…It just lists what God is not and proceeds by the process of elimination.” [metaphysical Sudoku].
  • Subtractive epistemology – “The greatest-and most robust-contribution to knowledge consists of removing what we think is wrong…So knowledge grows by subtraction not addition.”
  • Innovation – “People think focus means saying yes to the thing you’ve got to focus on. But that’s not what it means at all. It means saying no to the hundred other good ideas that there are. You have to pick carefully. I’m actually as proud of the things we haven’t done. Innovation is saying no to 1,000 things. – Steve Jobs”
  • Herosim – Heroism is the exact inverse of the agency problem [ie. “Other People’s Money” accountability]: someone elects to bear the disadvantage (risks his own life, or harm to himself, or, in milder forms, accepts to deprive himself of some benefits) for the sake of others…In traditional societies, a person is only as respectable and as worthy as the downside he (or, a lot more, than expected, she) is willing to face for the sake of others…The robustness of society depends on them; if we are here today, it is because someone, at some stage, took some risks for us.
  • Pseudocourage – “Comes from risk blindness, in which people underestimate the odds of failure.”
  • Option = asymmetry + rationality

Embracing Suffering, Desolation, Sickness, Ill-treatment, and Indignities

Friedrich Nietzsche birthday


  • “To those human beings who are of any concern to me I wish suffering, desolation, sickness, ill-treatment, indignities – I wish that they should not remain unfamiliar with profound self-contempt, the torture of self-mistrust, the wretchedness of the vanquished.” – Friedrich Nietzsche

The author of one of embracing failure’s most popular tag lines – “That which does not kill us makes us stronger” – was born 170 year ago today. Nietzsche’s embrace of failure extends well beyond a catchy turn of phrase and was central to this multi-faceted philosophy. The quote above is taken from Alain de Botton’s chapter “Consolation for Difficulties” (in his book “The Consolations of Philosophy”) which focuses on this perspective of Nietzsche.  Nietzsche was indeed one of the oracles of embracing failure.

Nietzsche also shared another philosophical perspective with this blog – a dichotomy between two opposing forces that invariably intertwine, Apollian and Dionysian. Though Nietzsche’s duality pivots more on the structure vs. freedom axis while Leadership and Management pivot more on upside vs. downside axis of risk.

Embracing Help


October is Breast Cancer Awareness Month. It’s an anatomical failure that I have covered so many times that I have now introduced a “cancer” tag for it on the blog.

So how does one embrace something as horrid and tragic as breast cancer? For starters, you can be inspired by the upbeat attitude of Deborah Cohan’s flash mob video and the friends who supported her. Sometimes embracing that help can be less easy than it appear as Karen Perry described in her family’s two-pronged cancer battle…

  • “’People are always asking to help,” she said. “The hardest thing was to accept that help. You think you can do it all on your own.”

Worshipping Failure

Nixon McInnes Church of Fail


The “Church of Fail” seems like my kind of Sunday (or ever day) devotional…

  • “’Dearly beloved, we are gathered here today to confess and celebrate the failures of ourselves and our colleagues.’ Welcome to the Church of Fail. It’s the invention of NixonMcInnes, a 15-person social-media consultancy in Brighton, England. The exercise was conceived three years ago at an off-site, as groups of employees brainstormed ways to improve the business. "One group decided they wanted to make it OK to fail, because the more we fail, the more we can innovate and succeed," says co-founder Will McInnes.”

Get every new post delivered to your Inbox.

Join 136 other followers