Applying Antifragile and Nassim Taleb’s Ideas to Education, Learning and Career

Okay this blog post is not like the usual stuff you get from me — it will probably require patience and note-taking. It corresponds with a mini-series on the With Joe Wehbe Podcast to do with Nassim Nicholas Taleb, whose books are pretty hard to read especially for young people!


Check out the podcast here — the Taleb series starts from episode 181.


I want to spend time on the podcast unpacking great thinkers about education, learning and careers and I wanted to start with Taleb.

Taleb is a very entertaining, intellectually sassy figure known in particular for his epic books and ideas on systems, philosophy, uncertainty and society; in particular Antifragile, Skin in the Game and Black Swan.

To be honest, I loved Antifragile but I find his writing style a bit drawn out for my liking — there is a bit of rambling but he is a very eloquent, sophisticated thinker.


Great, but what the hell does he have to do with education?

Well, that’s why I want to start with him. This is incredibly ‘meta’, but the reason why we should look at Taleb, and I’ll argue his book Antifragile in particular, is best answered by a quote from Taleb himself!

What one needs to know for a profession is necessarily what lies outside the corpus, as far away from the centre as possible.

This relates to what I’ve said and written about Without-The-Box Thinking, which is how I think about thinking. Long story short — our systems normally move away from the key problem they’re meant to solve, or service they’re meant to provide over time. They develop a sub-culture, and as that sub-culture becomes more complex, people zoom-in and lose sight of the big picture.

A very poignant example for our times — high school and university. We live in a time where it’s easier to setup (emphasis on setup) an online business than it is to get into a prestigious university degree. Of course the social life and resources at a college campus or university are still very attractive (shock horror, universities are bigger than the degree itself), the application of any learning in these places to the real world seems to be getting worse and worse over time, as the outside world evolves faster and faster. It’s almost as if these pieces have broken off from the everyday world and started their own journey of evolution, one discordant from other parts of society.

What do the leaders of these institutions do? They try their best, but there are constraints — the bureaucracy of boards, conflicting stakeholders, the parameters by which they get funding, and usually for individual leadership the desire to keep a position of status, authority or power. Over time, these become very powerful incentives not to make aggressive innovation and changes.

In 2018 I fired myself. The role was as Co-Director of a small nonprofit. I wasn’t paid for the work, we didn’t have a formal team, I’d only been doing it for two years and I had a separate business to lean back on — so it was easy in a situation like this to do the necessary thing. How does the CEO of World Vision, or the leaders of major schooling institutions and government bodies do this? Every possible self-preservation bias forbids it!

What they normally do is this thing I call ‘Outside-The-Box Thinking’, which is where the figures within a ‘corpus’ start making cosmetic changes, imprisoned as they are by biases and their echo chamber. In education it’s things like ‘we’ll setup startup incubators in our universities, we’ll put extra tutorials online, we’ll announce lifelong learning initiatives’. These changes are normally quite practical but they are never fast enough and do not change the premise underpinning the field, industry, institution, or outdated set of ideas.

Summarising this in one line, I’d say when things become outdated, it will take someone outside of the corpus, far away from the centre, to make the necessary innovation. This is the very basis of creative destruction.

So this point I make about Taleb is the point about why Taleb is so useful for thinking about education. Though he’s not commonly identified as an education thinker, though he’s not talked about at school leader conferences and isn’t making policy recommendations to education boards, his ideas are more useful to the future of education, learning and careers than 99% of the current discourse.

But why?


Drilling into Taleb’s significance

Now I turn to a very important theme — uncertainty.

Taleb is a former options trader and entrepreneur. He has a lot of exposure to and understanding of risk, uncertainty, and non-linearity. Most of his work unpacks the powerful forces of randomness and how human perception makes mistakes in trying to both reify and control randomness, as well as take credit for the random outputs of nature. (Definition of reify is here).

In one line: Things are random. Because we don’t appreciate the full extent of this randomness, all the things we do normally make matters worse! We punish ourselves (examples include the history of medicine, the state of economics and politics). We need to acknowledge this randomness to begin being productive.

This is not a widely adopted worldview. Look at Western Society, capitalism and mainstream education — the underlying code is not an emphasis on randomness, it’s a promise!

The story is ‘if you study here and apply yourself, you will get your just rewards. You will be successful, you will own assets, you will be fulfilled’. Such an idea is absurd — the reality is that chance and randomness (I’ll veer away from the word ‘luck’) have a much bigger part to play in our life outcomes than individual brilliance or control. Quite cunningly though, the mind constantly overestimates the role we’ve played in our success. I can’t promise you what the weather will be tomorrow, but because you are so desperate to know and plan, you still listen to the weatherman.

For example, ‘I studied at university, and I’m successful’ (insert definition of successful) ‘therefore university is good’, is just as erroneous a conclusion as ‘I didn’t study at university, and I’m successful, therefore university is bullshit’. There’s gaping holes in both, they’re both oversimplified, but obviously the former is a dominant narrative.

Consider this: did Steve Jobs decide to be born in the shadow of Silicon Valley? Did he manage to plot his time of birth to coincide with Steve Wozniak, his Apple Co-Founder? Jobs was also cunning enough to get a tour of Xerox Park to steal from under their nose the concept for the modern computer. But as I always point out with my Thousand Doors concept, he could not have been certain as to what he’d find when he went to Xerox Park! He only knew once he saw it.

None of these three factors, which were three of the biggest factors in his ‘success’ or emergence, had anything to do with those abilities we naturally associate with success, IQ or individual ability. That is, they have nothing to do with the things we learn at school.

Why I shine a light on Taleb here is that he cultivates an awareness about this bigger picture reality. When people think about what they want to learn, they normally think about specific, ‘micro’ skills (my phrase, very experimental) — how do I design a website? How do I write better? How do I code? How do I write a cold email? How do I raise capital? How do I start a podcast? etc.

These are all very important, and the right micro skills can definitely have compounding returns, but it’s a classic 80/20 trade-off. If I were to introduce the concept of ‘macro’ skills, these would be things like the Bucket, the Thousand Doors, self-awareness, positioning, optionality and understanding the dynamics behind nature and people that actually deliver 80% of the results. Of course, macro skills are vague, intangible and high level, so it’s hard to create an education ‘system’ for them — as a result, we focus on the path of least resistance. We teach people the basics not because it’s better, but because it’s easier… easier to teach, and easier to sell.

Imagine I set up a school for children teaching them optionality, the positioning oneself for opportunity, the nature of reality, self-awareness, the importance of self-transcendence and emotional intelligence… how would I sell this to parents? My market would be limited to the sophisticated thinkers, perhaps high-functioning writers, entrepreneurs and investors — and not just any writer, entrepreneur or investor. I hope I would at least secure Taleb’s children, if he has any.

People have precisely the wrong narratives in their minds, and as a result, the real solutions look like jokes to them. Of course the best way to guarantee ‘success’ as most people vaguely define it? Be friends with the children of the country’s richest people. As long as you can read, write and think at a very decent level, you will go further than most Harvard MBA’s… this is the reality, but how do you design an education system for that?

Wink-wink, nudge-nudge, that’s the implicit version we have now, and the very point of the Harvard’s, Oxford’s and Cambridge’s of the world. It’s just not a socially acceptable narrative so it’s subverted and branded as something else.


Example time.

Liam Hounsell is the first person I asked to help me build The Constant Student Community. Did I do an international search, spend hours pouring over LinkedIn, search high and low and screen hundreds of applications to find the best most wonderful candidate possible? No. Why?

  1. Liam was available.
  2. We had already built rapport through a friendship.
  3. It was clear he had a lot of potential.
  4. He easily exceeded the basic requirements — my analogy for this is high jump — it doesn’t matter whether you clear the bar by a mile or a millimetre (mixing metric systems, how controversial of me!), what’s important is just that they clear the bar.
  5. The prospect of working with him gave me a whole-body-yes feeling.

Now poor Liam is dyslexic, which makes writing challenging. He’d never worked as a community manager before, never started a project quite like this before, didn’t have any sort of socially recognised qualification to do the role… and of course, neither did I. He had other things though — attitude, perspective, vision, and ultimately, was in the right place at the right time.

Taleb would get very cross with me if I were to cherry-pick data and examples, but I always make the opposite point before the haters say ‘that’s an isolated example’. Firstly, it’s not, and secondly, if it’s possible once, it’s able to be replicated. The 4 Minute Mile was achieved by one man first, a fellow by the name of Roger Bannister, before countless others started running a mile in four minutes — a feat that, before Bannister, was thought to be scientifically impossible.

Taleb is a great thought leader for the macro skills (again, I’m not sure we can even call them that!), by educating us on the dynamics of randomness, odds, and the dynamics, probabilities and asymmetry behind things. So, let’s get specific.


The best of Antifragile and applying it to education


Let’s apply Taleb’s amazing ideas to our lives, because they truly transform the way we think and approach our affairs. We’ll use the following format:

  1. Break down the most relevant themes into Taleb’s categories, metaphors and analogies
  2. Unpack why it’s relevant
  3. Unpack if/where possible how it can be applied to the career and thinking of someone embracing a higher leverage, more ‘Da Vinci’ version of themselves, especially showing how or where I’ve applied it myself.


Fat Tony Example & The Green Lumber Fallacy

Taleb uses a fake character in his books called ‘Fat Tony’ to demonstrate a lot of his points. Although Fat Tony is not highly sophisticated, fancy or theoretical in his style, he can overcome his shortcomings by being shrewd… and that’s just what he does.

The ‘experts’ are always making bets about what will happen in the future. Because Fat Tony knows that in general, experts are wrong, he creates a simple strategy: bet against the experts.

As a result, he becomes rich! With the paradigm of the ‘promise’ I referred to before (work hard, apply yourself, have a high IQ and you’ll succeed), this is a major contradiction. Is it a glitch in the Matrix?

Fat Tony reminds me of all the Australian-Lebanese men in my family, many who migrated from Lebanon without a ‘formal education’ and so, lacking qualifications for traditionally high-earning and high status professions, were drawn to construction and property development, where the barrier-to-entry was much lower.

They could overcome being borderline illiterate and still make millions or tens of millions… that’s a lot of shekels. You can be a high school drop out and become a multi-millionaire through property. In fact my father’s best friend-turned-business partner is an incredible example of this — having dropped out of high school in year ten and first gone into his family’s business as a butcher, he later began working in property with my Dad and has done incredibly well (on any metric you might consider… not just income, but also autonomy, which is undervalued by most people).

No degree or formal education — just lucky enough to have access to the right people, and being more hard-working and more reliable than 99% of the people you meet. In Antifragile, Taleb talks about the Green Lumber Fallacy, a reference to a story in the book What I Learned Losing A Million Dollars by authors Jim Paul and Brendan Moynihan. In it a trader makes millions of dollars by trading in green lumber, which he assumes is ‘green’, when actually it’s just a term for freshly cut lumber (timber).

The narrator on the other hand has elaborate theories about investing but loses a lot of money. How can this be?

Again, it defies the logic we have about the ‘success’ narrative.

Choosing the right game for you isn’t half the battle in life… it’s got to be far more. Think bigger than career paths, and about choosing the metrics that matter.


  • I don’t buy into what authority figures say just because they’re authority figures. Experts are the go-to when you want to replicate exactly what they’ve done, or they have a framework that you can really personalise to your situation, but they don’t have ‘all the answers’ and are often dangerous when over-confident.
  • I don’t pay premiums for knowledge/information. To me, the investment is not well weighted to spend large sums on acquiring more information. It’s hard to get me to invest more than the price of a book — books tend to have been refined far more than other material, but even then, I’ve cut back on books lately. I do practice what I preach though, I think online communities are a much better opportunity and experience, because there’s more chance to get access to people. To me, it’s all about people. People have the biggest impact on your trajectory, not information.
  • I’m working on packaging things up and selling them through course-like formats but improving and optimising the experience and outcomes. This is because of ethics. I understand that others over-value knowledge, even though I don’t, so I’m trying to create a bridge for them to see this new perspective. Meet people where they’re at.


Fragility, Robustness and Antifragility

Damocles, the Phoenix and the Hydra are the three examples Taleb uses to break down the differences between fragility, robustness and antifragility.

Damocles is fragile: his life depends on a thin hair which holds a sword right above his head. So any little stressor to the thin hair might end his life.

Phoenix is robust: whenever he dies, he arises again from the ashes. So Phoenix doesn’t care about stressors—they can’t really harm him.

Now compare this to Hydra and her many heads. Whenever one of her heads gets cut off, two new grow back. Thus, Hydra is more than robust—she is antifragile. She is not indifferent to stressors, she actually loves them, because they help her become stronger.


We’ve talked about this briefly on the podcast before, but today I’ll add an important note — according to Taleb, no word like ‘Antifragile’ exists in our language. What does this mean?

Words symbolise narratives, ideas and concepts that we’ve found use for. Words don’t exist for otherwise random reasons. For example, in Nepal there was no real word for ‘time’. It was a fluid concept to the Nepalese, who were always late and didn’t keep to deadlines. It’s no wonder therefore that the country is less developed and less capitalist!

The absence of this word ‘Antifragile’ might suggest that we’ve failed to integrate this important idea of improving from volatility and stress in our culture. In the podcast episodes, Luke talks about thinking of the Antifragile concept in terms of words like ‘improve’ and ‘growth’, but neither of these is specific enough to mean getting stronger from stressors! That’s to say, though the pattern exists, we’ve failed to get clear on it in our culture on a very conscious level.

It is absent from many of our social institutions and societal systems. When you look at school as a system in my opinion it is a fragility factory, making people more afraid of failure and also far less autonomous, because they follow obedience. Where is the Antifragility?



  • On a systems level: Absence of the word in our culture might represent absence of our ability to cultivate it.
  • The most common reasons not to do something! People always insert an excuse or reason not to do something, never stating of course that they were fragile as a pose to robust or antifragile. Consider an actor that can’t handle rejection after going to audition after audition. This could be repurposed, from rejection to feedback, learning and improvement. If the audition is an opportunity for success, it creates tension and pressure, ‘will I get it?’. If the audition is a degree, a chance for feedback, it’s a different proposition. Of course, easier said-than-done, but being Antifragile is a good investment. I need to remind myself of this, it’s how I look at things, and it keeps me on the path of things that truly matter when the going gets tough. The ‘safe’ paths, in contrast, lead to destinations that seem boring to me.
  • Don’t invest in fragile things: Jeff Bezos famously said, people will never want slower, poorer service, and they’ll never get tired of cheaper prices. Amazon is built on principles like this, because they are so unlikely to change. So, it’s a pretty safe investment. I’m big on customer service, plus writing and podcasting as tools for expressing insights to me seems very ‘unfragile’.
  • Be in Antifragile games: Of course you can’t fake interest in things, but you can i) open your mind and ii) explore how to do what matters in a higher leverage and more antifragile or robust way. I made up for a slow start in my thinking about real estate — don’t be in the real estate game, be in the real estate innovation game, began a different model. The Constant Student model is deliberately chosen, because the main institutions we have now are fragile. When we come to talk about Peter Thiel, we’ll unpack his perspective that education is an inflated insurance policy, and that premiums are always inflated before disaster. Think about Zoom — Zoom was early mass market video-conferencing technology… the worse COVID gets, the better it is for Zoom. How can you do your own version of this?


Don’t deprive things of stressors


Part I — Atrophy and Weaknesss

Taleb points out that depriving an entity of stressors leads to atrophy. This seems to be true across nature… the world is not run by programmed design! The greatest example is COVID.

He brings up historical figures like Marcus Portios Cato (aka Cato the Censor), a great Roman soldier, who had a great disdain for comfort of any form. Cato thought comfort weakened the will and was the path to weakness… what a simple but important point to emphasise. My three or so years in the nonprofit world led me to the conclusion that ‘the Western World optimises for comfort, rather than meaning’. If I were to update this, I’d say ‘the Western World optimises for comfort and status, rather than meaning’. Most people are most focused on their financial freedom and their place in our arbitrary social hierarchies.

Sebastian Junger’s book Tribe: On Homecoming and Belonging makes the point that affluence corresponds with (and not necessarily causes) higher suicide rates. Think about it — an increase in affluence usually corresponds with a decrease in interconnectedness. The fences get higher, your security gets more intense, your property gets bigger, and there is literally more space between you and your neighbours. You become more estranged, whereas in Nepal or a rural community, everyone is interconnected and co-dependent. Less comfortable, but more meaningful.

In this example — less community and interconnectedness leads to weakening of the spirit and will.

A small and simple example is the muscle. A muscle that is not used weakens and atrophies.

Another example of course is the spoilt child. Having been conditioned into expectancy by overprotective and overcompensating parents, expectancy becomes the pathway to dependency. A cat domesticated won’t survive when it’s released into the wild, but if it had been raised in the wild, it would have better prospects.


Part II — A stitch in time saves nine

Let’s take the same point and explore a slightly different emphasis. Let’s see why Taleb thinks we should be grateful to the Titanic.

As fatal as it was, we would have kept building larger and larger ocean liners and the next disaster would have been more tragic.



  • Alan Watts’ Chinese Farmer parable: don’t judge your small failures of successes, or large failures or successes. Perhaps spilling coffee on your trousers this morning making you late for a big meeting saved you being hit by a bus in your rush to work. But you will never know, and you will say, ‘Damn you God, damn you universe’, when God or the universe is standing there thinking, ‘fuck you, I just saved your life’.
  • The concept of ‘career risks’ is normally quite hysterical to me. When the risks you’re worried about are too small, it normally means you’re wading into way bigger risks. Maybe we can call this the risk see-saw. When you try to minimise the small risks, you maximise the large risks — and vice versa.
    • This is a whole point of its own. To most people, inconsistent income appears to be a pretty big risk. To me it’s a small risk. Hippies and tribal people don’t have consistent income, but of course, I like plumbing, power and shelter. By trying to remove the small risk of consistent income, I’d seek the most stable salary you can, but this creates bigger risks like being behind the ball with better opportunities, being able to take meaningful entrepreneurial risks and make a meaningful change in the world. There’s no way I can do that to such a magnitude from a bank job, and dying with a story I’m proud of is much harder. Helping people unlock their Da Vinci, and open the right Doors is at risk if I work a stable bank job. If I focus on reducing the big risks, which are that I won’t feel fulfilled, that I won’t enjoy the present, that I won’t help as many people I can to an acceptable depth, that I won’t create a story I’m proud of, leaves me open to the smaller risks, main one being short-term income, being able to see huge material progress in six months time vs. being patient for six years and so forth.
    • A quality question — what means even more to you than financial freedom, that doesn’t necessarily harm financial freedom?


Part III — Make your risks visible, receive, don’t hide from your feedback loop.



In this analogy, the banker seems to have a more secure setup. He gets a steady salary and comfortable desk job, whilst the taxi driver feels his stressors. When he doesn’t make income for a fortnight, he’s forced to reflect and try new things, like trying a new area to find more rides.

Fortunes reverse during the Global Financial Crisis. The banker is fired, having not realised because of his steady paycheck that he was not really needed. The taxi driver on the other hand is far less vulnerable to the GFC in this scenario.



All year the turkey thinks that things are great, that the farmer loves it, and there is no reason to suspect otherwise. Food intake increases, so things get even better… right up until… Thanksgiving.



  • There is a tension between our drive for status and those things which blind us from real risk. The game of ‘where do I want to be by a certain age’ for example is seductive, how do you overcome it? My solution so far has been, find the things that are even more meaningful than having prestige or being in a certain place by a certain age. Then they will push them down the hierarchy. Joey Diaz decided age thirty-one that he was happy to be broke for ten years if it meant he could go all-in on comedy. Always, always return to the Minimum Viable Lifestyle Concept.
  • Don’t hide from your feedback loop — manage it. If you never ask a girl out, if you never try to launch a new idea, you can’t take steps to improve. We’re looking for the way up the mountain that doesn’t involve us losing face or getting our hands dirty. Avoidance doesn’t necessarily mean removal, sometimes it means relocation of the risk to somewhere more dangerous.


Taleb’s recipe for innovation

According to Taleb, innovation does not come from:

  • Academia.
  • Sciences (Soviet-Harvard Delusion he calls it).
  • Formal education — I understand why, this creates box-thinking.
  • He argues it’s from entrepreneurship… especially our collective failures.

He thinks we should have ‘World Entrepreneurship Day’ where we celebrate failed entrepreneurs who bravely show us what won’t work — I can definitely see this. I’ve studied, I’ve excelled at formal schooling, then I’ve applied myself in entrepreneurship and frequently failed. As Taleb says, a book on failure will never sell as well as a success story, but it’s more useful. He cites the exception… that book ‘How I lost a Million Dollars’.

I don’t know if the best way to look at these things is as fully discrete entities. Entrepreneurial spirit is more important than trying to be an entrepreneur. You can apply entrepreneurial spirit to academia and science, just as you can business projects, the reality is that because of the cultures most people in these fields don’t.

He also points out that so many ‘discoveries’ are accidental!


List of ‘Accidental Discoveries’

  • Chemotherapy: US ship carrying mustard gas off coast of Bari bombed by Germans in 1942, helped as observed effects on those onboard ship with liquid cancers. But, illegal due to Geneva Conventions, so it was hidden from records by Churchill and others.
  • The Therapeutic Revolution in post-war years: James Le Fanu noted that the change at this time was brought about by doctors recognising that randomly chemistry would deliver results.
  • Coca-Cola began as a pharmaceutical product
  • Tiffany & Co started life as a stationary store
  • Raytheon made first missile systems, but started in refrigerators!
  • Nokia began as a paper mill!
  • Avon started out in door-to-door book sales!

It’s crazy to think how big a role randomness plays. It fosters a new perspective — take lots of shots, be in the right positions, don’t be obsessed with the story of your brilliance!


Lecturing Birds How To Fly


The greatest problem in knowledge is the “lecturing birds how to fly” effect.

Let us call it the error of rationalism. In Fat Tony’s language, it would be what makes us the suckers of all suckers. Consider two types of knowledge. The first type is not exactly “knowledge”; its ambiguous character prevents us from calling it exactly knowledge. It’s a way of doing thing that we cannot really express in clear language, but that we do nevertheless, and do well.

The second type is more like what we call “knowledge”; it is what you acquire in school, can get grades for, can codify, what can be explainable, academizable, rationalizable, formalizable, theoretizable, codifiable, Sovietizable, bureaucratizable, Harvardifiable, provable, etc.

The error of rationalism is, simply, overestimating the role and necessity of the second type, the academic knowledge, in human affairs. It is a severe error because not only much of our knowledge is not explainable, academizable, rationalizable, formalizable, theoretizable, codifiable, Sovietizable, bureaucratizable, Harvardifiable, etc., but, further, that such knowledge plays such a minor life that it is not even funny.

We are very likely to believe that skills and ideas that we actually acquired by doing, or that came naturally to us (as we already knew by our innate biological instinct) came from books, ideas, and reasoning. We get blinded by it; there may even be something in our brains that makes us suckers for the point.


Another point Taleb makes — ‘no one learns their mother tongue from a textbook’. This comes back to my argument around macro skills… the most important things are not learnt through any formal system, which is ironic. The low hanging fruit is often the best fruit, the problem is that our social games have been built around the hard-to-reach, albeit inferior high-hanging fruit.

I make a joke about the Spanish Teacher-Spanish Facilitator Paradox. No Spanish teacher ever tells you to go to South America or Spain to learn Spanish, but this is the most effective way to learn. True fluency is hard, and the quickest way is to immerse oneself in the environment. If they came to me, then unfettered by any biases (I have no careerism or identity to uphold, nothing to sell) my mind is more free to go direct to the best possible solution, which is, ‘if you really want to learn it, and aren’t looking for some fluffy hobby, go to the country’. The irony is, the only thing I know how to say in Spanish is necessito ir al bano (I need to go to the toilet).

This debases our entire paradigm around experts and teachers. If I sell a writing course, and you come to me wanting to improve as a writer, there are a map of scenarios we can map out to make this interaction as fair and productive as possible:

  1. Scenario 1 — I’m desperate for money. In more cases than not, I will encourage you to buy the course, without little regard for whether you need it or not.
  2. Scenario 2 — I have other income/ am not desperate. In this case I have more mental freedom to think about your needs — but also, there is no harm in getting another sale.
  3. Scenario 3 — My strongest drive is ego and status. In this scenario, though I might have financial freedom and breathing room, my personal need to ‘be the best writing authority’ or the ‘world’s best writing teacher’, or even more simply to feel successful and avoid a sense of rejection creates a bias to sell the course no matter what, if the course is something I find my sense of worth attached to. This normally does not get discussed or thought about when people say ‘I’m not in it for the money’.
  4. Scenario 4a — My priority is helping writers and I’m not in a position of financial desperation. In this situation, my course is just one potential resource to help a specific type of writer at a specific stage where I can most effectively help people. When you inquire about the course, I take the time to understand whether my course is for you or not. If it isn’t, I recommend the best available action.
  5. Scenario 4b — My priority is helping writers, but I’m financially (or status) desperate. This is an interesting scenario for the vendor selling the service. In general, a clever operator might still look past their short-term needs to get sales because they understand the longer-term benefits of branding and reputation. Genuine customer service and empathy builds strong relationships — telling someone that your course might not be for them could turn that prospect into someone who refers three others, even if they don’t buy it themselves… because of trust, which is the hardest thing to create in a transaction. This will of course depend on multiple factors… e.g. how easy it is to determine how much the course is appropriate or inappropriate for the person.


When will anyone who teaches a degree in business, marketing or entrepreneurship say to an uneducated young student, who is happy to enroll in the degree that they should just go and learn by some other means.

Then who to trust? Who to listen to?



  • I focus on Scenario 4 in all my dealings. I look for people who interact based on Scenario 4 to work with, people who can be genuine despite the other distractions, who can make an interaction as much as possible about generous sharing of value, especially those who can transcend ego and limiting stories.



The best philosophers were not academics, but had another job, so their philosophy was not corrupted by careerism.” – Nassim Nicholas Taleb


Taleb defines careerism as “The debasing of knowledge by turning it into a competitive sport”. It’s a term that’s been introduced elsewhere, that seems to pursue career metrics like advancement, power and prestige irrespective of actual performance. Perhaps we can think of it as the game of the career, like someone who plays sport or sings for fame, not because they love doing it.

I tend to scoff at careerism because it leads to layer of fat in society. I hate the word ‘career’ — I only use it in my writing to the extent that is a signal for those who might benefit from the ideas I try to explore and deepen.



  • I don’t wed myself to any single job title — I first noticed the benefits of this when, working on a nonprofit in Nepal, my colleagues and I were able to be more creative because we didn’t have the constraints that came with trying to satisfy a career in international development. My thinking is, the world is a place with problems, value to add, and experiences to create. Respond to that with the best tool within my toolkit, work with the people who have that tool, or figure out what, if it is beyond my current toolkit, is worth learning and growing into.
  • I’m not purely a writer, even though this is my favorite thing to do. This is due in part to financial realities, and I’d rather my writing not have that sort of pressure on it.
  • I keep a healthy distrust when I look at people and think they’re careerists. That’s because, I fear they’ll compromise quality and the truth in the interest of winning a career game for it’s own sake. I saw this a lot in the international development world, and it definitely exists in entrepreneurship and education. Where there is a conflict between the people we can help and the story we want to tell ourselves, we remain chained to the story.


Black Swan Events

How would you define a swan? Let me guess, white and fluffy is a part of the picture — the Black Swan is a metaphor used by Taleb to refer to unexpected but highly significant events. It was previously thought that black swans didn’t exist, because almost all swans seen were white, so this is where Taleb’s concept comes from.

Specifically, and I quote (from Wikipedia, hate all you want, it was broken down well)

  1. The disproportionate role of high-profile, hard-to-predict, and rare events that are beyond the realm of normal expectations in history, science, finance, and technology.
  2. The non-computability of the probability of consequential rare events using scientific methods (owing to the very nature of small probabilities).
  3. The psychological biases that blind people, both individually and collectively, to uncertainty and a rare event’s massive role in historical affairs.

Firstly, once the black swan is encountered, an entire system of logical thought is undone, e.g. ‘all swans are white’. Their is a second-order effect here, being that any logical conclusions made from the old system are also wrong.

What we call here a Black Swan (and capitalize it) is an event with the following three attributes.

First, it is an outlier, as it lies outside the realm of regular expectations, because nothing in the past can convincingly point to its possibility. Second, it carries an extreme ‘impact’. Third, in spite of its outlier status, human nature makes us concoct explanations for its occurrence after the fact, making it explainable and predictable.

I stop and summarize the triplet: rarity, extreme ‘impact’, and retrospective (though not prospective) predictability. A small number of Black Swans explains almost everything in our world, from the success of ideas and religions, to the dynamics of historical events, to elements of our own personal lives.

— Taleb, Nassim Nicholas  The Black Swan: the impact of the highly improbable


For example, Fukushima was designed to handle the worst earthquake that had ever been recorded. The problem was, one even worse came with the 2011 tsunami. More here.

Takeaways for me are, we don’t prepare for big risks that are predictable because they haven’t happened before. The second takeaway is, big unpredictable events come and can happen at any time, how do we make our systems as robust as possible?



  • Worrying about things without taking proactive steps is quite foolish and is a mismanagement of energy. No one is worried about the things that they can’t conceive of, that are actually worse than the things we do worry about. For example, I am not worried about a terrorist attack tomorrow, and if that were to happen, I’d be kicking myself for all the time spent worrying about bullshit.
  • Stop whinging about COVID, which is to say, stop whinging about external factors. Things are the way they are, which is not a call to say that we are helpless, but rather, our power comes from the adjustment and adaptation we make to the reality presented. ‘I can’t go to the party, what opportunity does this create?’ The Slingshot Principle.
  • “It’s better to be a soldier in a garden, than a gardener in a war.” goes the Chinese proverb. The problem is that no one wants to disrupt their current lifestyle because of threats that might come, but I kind of do! COVID helped to make me even more adaptive and able to deal with setbacks. This was an accidental benefit of taking a more entrepreneurial path where, as with any adversity, you become more battle-hardened. I always say, ‘you are the size of the challenge with which you face yourself’. I can deal with information that shifts my worldview, perspective, how I need to be approaching things, even life. I think that lightness is an advantage, I don’t have my feet planted in the ground.


Understanding things by layers

Restaurants on their own are quite fragile, but the restaurant industry as a whole is quite robust. If you were to invest in a single restaurant, it would usually be risky. If you were to invest in a cross-section of the restaurant industry, you would be in a much safer position.

This makes me think about the Thousand Doors concept — if you’re twenty years old, at a crossroads and don’t know what to do next with your early adult life, the one thing you know is that making no decision will leave you in the Room you’re in now and likely not making much of yourself.

Though any one decision you make next might not be a great one, continuing on that journey of always taking the next challenge and opening the best Door for you at the next juncture means you will end up somewhere remarkable, even though you have no idea where or what that is or looks like!

Takeaway — you can be much surer of indexed investments, in big picture perspectives, than one off ‘micro’ opportunities or decisions.

On the flipside, Taleb also says ‘it’s easier to macro bullshit than it is to micro bullshit’. It’s easier to tell an oversimplified story about a large trend, like making up statistics that apply to large sections of the population. But if you think about it, averages are always made up of the specific stories of sub-groups. For example, 6% of the nation is unemployed — okay, that’s not so bad! But if you look at it, there is one suburb with an unemployment rate of 60%.



  • Don’t buy into these lumped generalisations and statistics you see thrown around by political activists, lazy scientists and the media.
  • You want to understand something, best way is to be there. Focus on the specific story, not the generic narrative e.g. ‘young people don’t read’, if I’d held this belief I wouldn’t have done 18 & Lost? So Were We. It’s bullshit of course, the truer line is, ‘most young people don’t read often’, but I’m disproportionately interested in the small percentage who do read overall.
  • Keeping faith in the big picture — gives me the persistence to ride over the bumps and twists along the journey. I know that by continually taking big shots and placing asymmetric bets, I only need one to come off and compensate for the other benefits and rewards, which admittedly are still the less substantial like external world recognition, more attraction to my work, financial benefits, future opportunities and more. The contrast is that mindset that says ‘I’ll only do this if I know it will work’ — all we can do is use the process that reduces risk and improves the chances of criteria being met. For example, writing a blog to test ideas before devoting time to a full book, validating your startup idea before spending too much money or time building it out.


Definition of a loser

My characterization of a loser is someone who, after making a mistake, doesn’t introspect, 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.


Furthermore, he says they make out they are some ‘victim’ of a larger plot, their boss, the weather or some other external force.


  • I just need to remember this more often!


Don’t expect plaudits for bringing the truth

Taleb tells us the story of Ignasz Semmelweiss — saying that the Austro-Hungarian doctor is a true hero, having noticed that hand-washing was needed to stop so many child-bearing mothers from dying from infections. He was laughed at and ridiculed by the medical association and eventually put in an asylum! He died under sad circumstances, and his advice was only adopted years later!



  • To me the Semmelweiss story is all about leadership — these stories are inspirational. To me, they prompt us to overcome the traditional bullshit success markers like status, awards, even approval from one’s peers if it means standing up for what you believe in. This is not our expectation in society, we don’t hold such a high bar for one another — we think it’s perfectly adequate to aspire to a mortgage. If I spend twenty years trying to get financially independent alone, will that come at the cost of something far more meaningful?



Pretty much everything suffers from excessive meddling — politics, medicine, you name it. A key example is education.

If you go through Taleb’s ideas, even though he does not come to us as an education thinker, you find they fit nicely with the great education philosophies of the past. If you were to design a school based on these ideas, there wouldn’t be much meddling, there wouldn’t be formal classrooms, times and lesson structures, or even the usual didactic emphasis. It would require us intervening far less… human institutions regularly make the mistake of meddling too much and intervening too much to try and control the outcome.

So often teachers and educational theorists must be thinking about what more we can do to change education, but it’s the wrong question. The real question is, what do we need to stop doing?

There’s a very entertaining video of Taleb criticising the Gates Foundation for their plan to eradicate mosquitos. The video is titled ‘The Gates Foundation Is Repeating The Errors of Mao’ and explains how under Mao Zedong, China killed off sparrows so they wouldn’t eat farmer’s crops.


The unexpected consequences were that sparrows ate insects, and insects ate more of the crops than the sparrows did. Whoops — the result was famine. It turns out that the sparrows, who took a little bit of tax for a significant but unheralded role of keeping insects at bay, were well justified. The lesson is that nature is complex and has intricate second order effects that ‘the best of us’ like Bill Gates overlook. The rule-of-thumb when entering a new ecosystem, like a deserted island, is to avoid tinkering with the wildlife, because you’re not in a position to know the second order (or Thousand Door) effects, the chain reaction you could set off. Who’s most likely to do this? Probably experts who think they know-it-all, because unlike a regular all-round idiot, they have the ability to cause damage on scale. The exception of course appears to be Mr. Bean, who can set off a chain reaction of this magnitude too.

Another example is the Dracthen Experiment run in the Netherlands, where most traffic signs were removed. The result? An increase in road safety! Another example is the Fabian Society in Britain, a revolution who decided, quite out of character as far as revolutions go, not to take action and show well-exercised restraint.

For example there’s a story of Taleb at a dinner party with all these people bickering about education.

I once ran into Alison Wolf at a party (parties are great for optionality). As I got her to explain to other people her evidence about the lack of effectiveness of funding formal education, one person got frustrated with our skepticism. Wolf’s answer to him was “real education is this,” pointing at the room full of people chatting.


Risk, Not Education, And Knowledge Is Overvalued.

Continuing from the above point, at another dinner party Taleb was in heated argument with guests about education. All but two people seemed concerned by bad math levels in the USA — Taleb, and the head of the New York City School System. In Taleb’s mind, the risk-taking culture in the USA is more important than math levels in determining the nation’s wealth.

Teach people all the arithmetic you want, but if they’re not willing to take ‘risks’, they won’t progress much of anywhere, no matter their field or domain. That entrepreneurial spirit is what moves society forward, finds new discoveries, creates brave figures who are willing to defy the narrative of their times, and who grow by combating stressors. Their risk is visible, and they are less interventionist.

There is little people need to objectively ‘know’, apart from these higher level concepts about the nature of… well… nature. Before I had a shot at classifying this as those obscure ‘macro skills’ that few people learn, and fewer still learn in any structured way.

Domain-specific and job-specific learning can come when engaged in the discipline, when taking risks.


Application of these:

  • Don’t get obsessed with meddling! E.g. with Constant Student, the real question is, ‘how do we help people help other people? How do we make this run without us?’ and have found that we so often go overboard preparing workshops or programs that don’t work as well as simply arranging breakout rooms or leaving people flexibility.
  • It’s a classic ‘less is more’ philosophy that gets applied across life.
  • Scott McKeon — ‘the only risk is not taking risks’.



If you “have optionality”, you don’t have much need for what is commonly called intelligence, knowledge, insight, skills and these 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 unintelligent things to hurt yourself.

This is powerful because it’s a very different success narrative, and this is something that few people consciously cultivate, but it represents what most people would really benefit from.

He gives the example of bumping into a friend in London and being invited to a dinner party. ‘Come if you can make it!’ says the friend. He reflects on how beautiful this is — he is able to go if he pleases, but he is not obligated.

The example Taleb gives in the book is from Thales of Miletus, an old Roman I believe, who made a fortune taking out an option on an olive field. An option in financial contexts is normally reserving the right, but not the obligation. He raised a small amount of money and put down deposits for oil fields around Miletus, and at low rents so that his cost was low. Then, when summer came around, olive presses soared. The modern equivalent is having 1%, rather than 70% of your wealth in some sort of cryptocurrency. It could pay off big, but if it doesn’t, there is no major loss to you.

Aristotle wrote about Thales as if he were a visionary and predictive master based on this transaction, but Taleb suspects otherwise. Taleb suspects Thales was just aware of his ignorance, and figured ‘why not’ with regards to the olive fields, if it were to cost him so little.



  • I put a lot of attention toward increasing and improving the options I have available to me. If you don’t have the Doors, you can’t open them, and that doesn’t mean gathering as many ‘Doors’ or opportunities as possible. For example, I am placed in fields where I can participate in a cross-section of projects without commitment or obligation. For example ghost writing, investing, startups, marketing work, these are situations where one can consult, contract or invest a small amount first, before getting more involved. But if you’re not in the lobby, you can’t go to the higher floors, I guess a lot of conventional workplaces make you get in the lift and go straight to the top floor with them.
  • If I hadn’t taken notes on Antifragile for example, I don’t have the option of doing this podcast series or blog post on it as easily. At the time, I got this sense — this is good insight, refining and organising this neatly will have some sort of advantage in future, even if I don’t know specifically what it is. It’s worthwhile gathering it at the expense of what else I could be doing with this time.
  • Another example, Gabby Monardo the youngest author of 18 & Lost? So Were We, I love her story as an example. I met her at a podcast launch, that’s why she was able to get involved in the book. If you don’t expose yourself, you have zero options. You take a few simple steps, this changes dramatically and you have an oversupply of options — good problem to have because then you can get filtering but also keep contacts for the long-term. Dig your well before you’re thirsty.


TLDR from Taleb

Don’t try to isolate things from natural failure. Accelerate them. Fatality is what’s to be avoided, not failure, and to avoid fatality, we must be experiencing ‘failure’.


Confused? Lost? Mind-boggled? Don’t forget to check out the podcast episodes for what is hopefully a more digestible version of these ideas, episode-by-episode!

1 Comment

  • Duncan Gleeson
    August 1, 2022

    It is “as opposed to,” not “as a pose to”…as you have written.


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