after this, you'll welcome obstacles
after this, you’ll welcome obstacles

“The general principle of antifragility, it is much better to do things you cannot explain than explain things you cannot do.” – Nassim Taleb

“Being an entrepreneur is an existential, not just a financial thing.” – Nassim Taleb

“They have turned the wolf into a dog and man himself into the man’s best domesticated animal.” – Friedrich Nietzsche 

The ideas in this post have been the most transformative in my life over the last couple years. I avoided writing about them because I didn’t feel I could. Finally, I feel that I’ve internalized, tested, and understand them deeply enough to communicate them with you.

This is a long post, but it could change your life and outlook in massive ways. I can say that without arrogance because these ideas aren’t my own, they’re Taleb’s.

Nassim Nicholas Taleb warned the world about the 2008 financial crisis before it happened. He didn’t predict it, per say, he just evaluated the financial system and saw how fragile it was.

The world is slowly beginning to admit how terrible we are at predicting the future. Stumbling on Happiness showed us that we can’t even predict what will make us happy in the future.

“Your mistake was not in imagining things you could not know—that is, after all, what imagination is for. Rather, your mistake was in unthinkingly treating what you imagined as though it were an accurate representation of the facts.” ― Daniel Gilbert, Stumbling on Happiness

I am going to do my best to share a new lens of the world with you and convince how powerful it can be in your life. This isn’t about wishful thinking or small self-help lifehacks. This is about looking at reality as the mess it is and learning to benefit from the chaos.

I’m not going to attempt to summarize Taleb’s books, it would be blasphemy. Almost all business books I read I feel fine sharing a summary, synthesis, and some quotes. That’s all they deserve. Taleb’s work is different. Reading his work, especially Incerto (containing The Bed of Procrustes, Fooled by Randomness, The Black Swan, and Antifragile) is an experience. This post will provide a powerful perspective shift and tools that you can begin using immediately. It will not replace the books in any way.

I’ve written skimmable articles before, this is not one of them. This stuff is too important to skim. I hope you take the time to read the whole thing. If you can’t read it now then skim it and bookmark it for later.

Here is an overview of what we’re going to be getting into:

  • What Happens When You Become Antifragile: The benefits I’ve found by adopting antifragililty.
  • Understanding Chaos: A look at some of the most important ideas from Fooled by Randomness and The Black Swan.
  • Taking the Antifragile Perspective: A deep-dive into understanding what antifragility is, why it’s important, and how we can begin to use it.
  • How to Become Antifragile: Specific ways to introduce antifragility into your business, health (personal, emotional, mental, physical), social life, society, etc…
  • Heuristics and Aphorisms: Some of the most powerful and useful quotes from Taleb.
  • A Final Note on Antifragility: Refocusing and getting ready to take action.

Our goal is presented by Taleb in the Prologue of Antifragile:

I want to live happily in a world I don’t understand.

We think we need to know what’s going to happen to be ready for it. We think we need to have a perfectly clear vision of what we want our future to be if we want to avoid being homeless. We believe experts when they bullshit us and themselves with comforting predictions that are ultimately worse than useless – they convince us that we can know the unknowable.

It took me a long time to accept that I can’t know what’s going to happen in life. It can be paralyzing to realize that what you’re doing might not work, that the economy is changing so fast you won’t be able to keep up, and that, no matter how well things are going, the shit will inevitably hit the fan.

Taleb opens Antifragile with the following:

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. …

The mission is how to domesticate, even dominate, even conquer, the unseen, the opaque, and the inexplicable.


Let’s find out.

Our hero
Our hero

[Note 1: All quotes without a name attached are Taleb.]

[Note 2: There are some complex ideas here, if you don’t understand something then keep reading – the next paragraph may explain it.]

What Happens When You Become Antifragile

I can only speak from my experience so really these things are what happened to me after I decided to become antifragile. I’ve only scratched the surface, by the way, every day I try to find new ways. The practices and heuristics that have made these possible are listed at the end of this article.

(Note: I’ve provided the tricks that I use to get these benefits in parentheses, I’ll explain them and others more toward the end of the article.)

  • I make better decisions faster. I use mental models and heuristics to keep me from making terrible decisions and to stop me from overthinking things. (Heuristic: the best choice is the one that remains for no good reason while other options have 2 or more reasons.)
  • I’m not scared of negative emotions (even fear). I have embraced my humanity and decided to use the whole range of my emotions. (Adjust activity to mood.)
  • I’m confident in not having an opinion. Being able to say, “I don’t know, and I don’t think you do either,” is amazingly useful for getting grounded in reality. (Focusing on creating potential opportunities and remembering predictions are useless.)
  • I was able to stay out of a salaried job even though all my entrepreneurial projects were “failing”. (Being more fearful of the fragile/dull life than failure.)
  • StartupBros is as successful as it is because of it’s antifragility. We don’t know what will work. We make a bunch of small bets (mainly blog posts) to find what you love and need – then we can expand on that later. We had no idea when writing our most successful posts that they would be successful. We had a heuristic (you, our audience, loves crazy-detailed posts that solve a problem while remaining deeply personal) but even with that we can’t predict what will work. We spread the posts as many places as we can get them. We try different topics. When something finally hits, like Will’s epic post on starting an importing company, we know to expand on it. (We test and leverage what works without staying too focused.)
  • Renewed focus on taking action. These ideas forced me to realize that over-planning is expensive, soul-sucking, and ultimately ineffective. Doing is cheap, effective, and tied to reality. (Maybe my most powerful heuristic: Begin doing the thing before reading about it.)
  • I do what I want to do instead of what I “ought” to do. The future is unpredictable, how you do something is usually a more sure bet than what you do. Doing what you want allows you to persevere longer than if you were going against yourself – that increases your chances of success exponentially. (Art is antifragile – passionate work.)
  • I consider other people’s incentives and what they do more heavily than what they say. If someone is being paid to have an opinion I don’t listen to it. If a person says, “This is what I do and it works for me,” I listen. This extends to avoiding exciting headlines, taking scientific studies about personal growth and creativity with a grain of salt, and asking, “What do you do when you’re in this type of situation?” instead of “What would you do if you were in my situation?” (Realizing that other people’s brains make the same mistakes mine does.)
  • I respect the aesthetic more. If something can’t be completely scientific rigorous then I don’t take on any obligation to make it make sense at all. (It’s about enjoyment, not optimization.)
  • I’m more patience. I realize that time creates opportunities and possibilities that don’t currently exist. I realize that that a failure, with time, looks like a stepping-stone to success. (Focus on the process and creating a stronger foundation instead of outcomes.)
  • I am more accepting of adversity in my life. I more easily embrace obstacles because I treat them differently. (I don’t control much but I will respect that which I can.)
  • I’m never late to things anymore. (Go early to create redundancy and opportunity for serendipity.)
  • I’m not duped by experts as easily. (Their incentives are off.)
  • I have more fun. (Fun is the single greatest life hack.)
  • I feel a deeper sense of purpose. (Because I’m focused on executing. And fun.)
  • I write better. (Because I realize rigidity is boring. And reading Taleb just makes you better.)
  • I eat better. (It’s not strict diet or terrible diet – it’s loose.)
  • I’m more fit. (Randomness in exercise is fun.)
  • I’m more human. (I don’t aspire to be an optimized robot.)

I know this sounds too good to be true. I’m not bullshitting you, though. These ideas have permeated through my entire life and continue to push farther and free my from bad ideas and stupid ways of living.

We are not looking for a cure-all here – we are moving beyond the cure-all.

We are not looking for a silver bullet because we realize there is no such thing.

Life is not what we expected. Life is almost all unexpected, actually.

Let’s learn to love our unknown fates.

Amor Fati!

Understanding Chaos

You get pseudo-order when you seek order; you get a measure of order and control when you embrace randomness. – Nassim Taleb

The mass of this book is going to focus on Antifragile, Taleb’s most recent, central, and applicable work. First, there are some important ideas to understand from his first two books in Incerto (basically, I’m not including his textbooks).

black swan

The Black Swan

Let’s start from Taleb’s (public) start.

Taleb became famous for predicting the 2008 financial collapse.

The only thing is, he didn’t actually predict anything.

In his books Fooled by Randomness (2001) and (more urgently in) The Black Swan (2007) Taleb warned that the banking system was fragile. That is, if some kind of shock happened it was primed for a meltdown.

He assessed the current situation to understand what was likely to happen later.

His term “Black Swan” was then spread all over the place and thoroughly misunderstood. You won’t make the same mistake.

Here are several key ideas from The Black Swan that will give us a solid foundation for antifragility:

Black Swans

A Black Swan has “rarity, extreme impact, and retrospective (though not prospective) predictability”. In other words: it “never” could happen, it changes everything, and everyone pretends like they saw it coming but didn’t.

Essentially everything we do from here is going to build on this idea.

Narrative Fallacy

We freak out if something doesn’t fit into a neat explanation. So we end up making stories for everything, even the randomness in our lives.

The narrative fallacy addresses our limited ability to look at sequences of facts without weaving an explanation into them, or, equivalently, forcing a logical link, an arrow of relationship upon them. Explanations bind facts together. They make them all the more easily remembered; they help them make more sense. Where this propensity can go wrong is when it increases our impression of understanding. – Nassim Nicholas Taleb

Taleb offers up a few ways to overcome the narrative fallacy:

The way to avoid the ills of the narrative fallacy is to favor experimentation over storytelling, experience over history, and clinical knowledge over theories. . . . Being empirical does not mean running a laboratory in one’s basement: it is just a mind-set that favors a certain class of knowledge over others. I do not forbid myself from using the word cause, but the causes I discuss are either bold speculations (presented as such) or the result of experiments, not stories. Another approach is to predict and keep a tally of the predictions.

Extremistan vs Mediocristan

The law of Mediocristan:

When your sample is large, no single instance will significantly change the aggregate or the total.

Compare this with the law of Extremistan:

[I]nequalities are such that one single observation can disproportionately impact the aggregate, or the total.

As the world moves faster and more areas move towards a “winner-take-all” system, Extremistan grows in influence. To get a better idea, let’s look at examples of Mediocristan and Extremistan:

Matters that seem to belong to Mediocristan (subjected to what we call type 2 randomness): height, weight, calorie consumption, income for a baker, a small restaurant owner, a prostitute, or an orthodontist; gambling profits (in the very special case, assuming the person goes to a casino and maintains a constant betting size), car accidents, mortality rates, “IQ” (as measured).

Matters that seem to belong to Extremistan (subjected to what we call type 2 randomness): wealth, income, book sales per author, book citations per author, name recognition as a “celebrity,” number of references on Google, populations of cities, uses of words in a vocabulary, numbers of speakers per language, damage caused by earthquakes, deaths in war, deaths from terrorist incidents, sizes of planets, sizes of companies, stock ownership, height between species (consider elephants and mice), financial markets (but your investment manager does not know it), commodity prices, inflation rates, economic data. The Extremistan list is much longer than the prior one.

Extremistan is where you will find the most catastrophic dangers and the most massive opportunities (especially if you take steps towards antifragility).

fooled by randomness

Fooled by Randomness

This is Taleb’s first non-technical writing so it ends up being more technical than either The Black Swan or Antifragile. Surprisingly, it makes it even more interesting in it’s own way.

There are a ton of great ideas but here’s the most important for us:

Lumpy Payoffs

We are wired for linearity. If you work hard on your business every day it would feel great to see progress every day. Unfortunately, that’s not how entrepreneurship (or life) works. Instead, you work your ass off for years and have nothing to show for it. You look crazy and you feel crazy. There’s no reason for you to continue. Then one day something clicks and you get slapped in the face with success.

For artists it’s the “overnight success” that took a decade. John Hamm got no work for 12 years then… Don Draper.

For the tech entrepreneur it’s often the acquisition or the first round of venture funding.

For StartupBros, it was launching our first product. We worked like crazy on this thing with nothing to show for it forever. People looked at us like we were nuts. “You…blog?

Now we’ll probably work another extension of time until the next big click. In a lot of ways, it’s back into the abyss of uncertainty.

“Our brain is not cut out for nonlinearities. People think that if, say, two variables are causally linked, then a steady input in one variable should always yield a result in the other one. Our emotional apparatus is designed for linear causality. For instance, you study every day and learn something in proportion to your studies. If you do not feel that you are going anywhere, your emotions will cause you to become demoralized. But reality rarely gives us the privilege of a satisfying linear positive progression: You may study for a year and learn nothing, then, unless you are disheartened by the empty results and give up, something will come to you in a flash. . . This summarizes why there are routes to success that are nonrandom, but few, very few, people have the mental stamina to follow them. . . Most people give up before the rewards.” Nassim Taleb, Fooled by Randomness

Keep in mind that your progress will not look like a nicely sloping line up and to the right. No, no. It’s going to flat line, dip, plateau, then spike.

Later we’ll talk about some tricks to hold out for the spike. Just being aware of this problem will sustain you for a while though.


So now you understand that:

  • The biggest catalysts of change in the world and our lives are Black Swans: you can’t see them coming (but have good explanations for them later), they happen once in a blue moon, and they change everything.
  • You (and everyone around you) is so desperate to create a cohesive narrative that you will make shit up to do so.
  • We spend most of our time in mediocristan but our lives are influenced more by extremistan.
  • Progress is rarely made linearly. Most of our work goes “unrewarded” but is silently building toward a breakthrough moment that makes it all worth it.

Now, the main event!

Taking the Antifragile Perspective

Antifragile triad

The Triad: Fragile, Robust, Antifragile

Before Taleb came along, we assumed that the opposite of a fragile thing is a strong (robust) thing. Fragile things break when something messes with them, robust things don’t. Seemed right.

Taleb takes it a step further: the opposite of breaking is being unbroken, it is getting better.

We are going to look at each corner of the triad in turn. First, an overview:

  • Fragile: Stuff that hates uncertainty because uncertainty means death. (A teacup or a kid raised by a soccer mom.)
  • Robust: Stuff that doesn’t care about uncertainty because it’s unaffected. (A steel block or a boring Buddhist.)
  • Antifragile: Stuff that loves uncertainty because it grows from shocks. (Human body or an aggressive Stoic.)

These are relative terms – some people are more antifragile than others. Also, they can apply to specific pieces of a system. You may have cancer and by physically fragile while your spirit remains antifragile. You may be a soldier or athlete and be physically robust, even mentally antifragile in dealing with enemies, but be emotionally fragile in relationships.

As we go into each, be thinking about what things in your life fit into each category. Is there a way you can make your life and the things in it less fragile? Your business? Your career? Your mindset? Your relationships? These principles apply everywhere.

tea cup kitty


You already know what is fragile: that teacup, a hanging chandelier, or a person lacking emotional intelligence.

The less obvious fragile things are those that we try to control too tightly. The soccer mom who is overly protective of her kid is making him weak. People who optimize their diet too carefully are prone to get sick when they can’t eat exactly what they need. Similarly, the person with an optimized schedule loses his shit when he has to improvise.

These last couple things point to a serious societal problem that you might be engaged in: optimizing everything and everything. Taleb calls these people “fragilistas”. These people are arrogant in that they believe they understand (and therefore can control) more than is possible.

In short, the fragilista (medical, economic, social planning) is one who makes you engage in policies and actions, all artificial, in which the benefits are small and visible, and the side effects potentially severe and invisible. – Nassim Taleb

Do you see how the narrative fallacy can fragillize you? A bad explanation can put you in serious danger.

A fragilista who believes he can predict things with certainty would not be able to hold out for the lumpy payoffs, would he?

If we think we know exactly what will happen then our chance of noticing serendipitous opportunities plummet.

Fragile things tend to be:

  • Huge. The Zeppelin blew up because of one tiny mistake. The whole banking system basically collapsed when faced with a relatively small shock. (Hint: startups and freelancers are antifragile.)
  • Desperate to be in control of everything – scared of the unknown. Parents who try to create the perfect child. Entrepreneurs who refuse to be flexible. People who think they can predict the stock market (or any market, for that matter). I fell into this category for most of my life. I was obsessed with the traditional self-help world and completely rigid with my plans. I freaked out when I was forced to face how little control I actually had in my life. A-type personalities are prone to this mistake. (Hint: Talking heads lie – and stop you from being open to improvisation.)
  • Overly optimized. The banking system failed because they were leveraged to the hilt. They were leveraged to the hilt because they believed in their own ability to predict the future too much. Governments with too much central control fail because of the same problem. They optimize to the point where any bump in the road destroys them. I’ve done this with: my schedule, my diet, my driving, my dressing, my bathing. (Hint: Maximizing the best things in life (happiness, purpose, relationships, and even money) depends on you committing to a non-optimized life.)
  • Rely heavily on outside help. The teacup that’s falling is screwed unless you catch it. The business with no money in the bank will need a loan when their biggest client drops out. Your friend who calls every time some minor drama happens to them. Yeah, they are emotionally fragile (and you should tell them that).


Robust things don’t care.

The following image illustrates the robust:

zero fucks spiderman

If things stay calm, it’s all good. If the shit hits the fan, it’s all good.

I always think of a steel block. Pretty much nothing is going to happen to it… whatever happens. It’s just going to keep being a steal block. If you drop it, it won’t break and it won’t grow (like an organic object might).

Taleb uses the Phoenix to help us understand robustness. The Phoenix burns itself up and is reborn just as it was before.

Just as it was before.

If it the Phoenix got stronger when it burned itself up then it would be antifragile.

I’ve found that, in many circumstances, robustness is a stepping-stone to antifrigility.

Sometimes before we can position ourselves to want the wildness of the future we first need to stop being scared of it.

There are certain cases where we’d rather be robust than antifragile, and there are some situations where we don’t want to be too robust.



You’re already antifragile. You put your body through pain when you exercise. You probably get vaccinations so your body grows stronger defenses. You have probably compensated for some of your weaknesses by growing past them.

Taleb uses the Hydra as a mythic representation of Antifragile. Two heads grow back each time one is cut off. It gets stronger when you attack it. (This is why existential crises and depression are never dealt with by a head-on logical front.)

Taleb presents some examples of antifragility:

“[Antifragility] is behind everything that has changed with time: evolution, revolution, political systems, technological innovation, cultural and economic success, corporate survival, good recipes (say, chicken soup or steak tartar with a drop of cognac), the rise of cities, cultures, legal systems, equatorial forests, bacterial resistance… even our own existence as a species on this planet. And antifrigility determines the boundary between what is living and organic (or complex), say, the human body, and what is inert, say, a physical object like the stapler on your desk.”

The simplest way I can express it:

Things that are antifragile have more potential for gain than loss when the unseen future becomes seen.

You don’t become antifragile by knowing more about the future. You become antifragile by being more ready for the future.

Antifragile things are often:

  • Organic. Not like USDA Organic, like biological organisms organic. Anti-bacterial soap has helped create super-bacteria that we can barely kill. They grew in the face of adversity. Certain medical procedures include breaking bones because they grow back stronger. Vaccines signal danger to our bodies so that we build up our immunities.
  • Fast. Antifragility often relies on our ability to seize opportunities as they come (or get out of the way quickly). The startup with 10 employees can completely change it’s business model in a week when they learn they are in the wrong market. The quicker boxer can create more opportunities.
  • Self-reliant. When you are cut your skin knows how to mend itself (note that the human body isn’t completely antifragile – aging makes us fragile). The (Stoic) philosopher can turn a negative event into an opportunity. The artist can be fueled by harsh criticism.
  • Redundant. Companies and people with extra cash can take advantage of opportunities that those strapped for cash can’t. The human body has two kidneys (and half of them have two testicles). If you plan on being very early you’ll never be late – and you’ll be open to serendipity.
  • Counterintuitive. If you want to feel like you know more about something the worse thing you can do is get a couple books on the topic – they will only show you how little you actually know. You can’t aim at happiness or purpose and get them. Many “irrational” traditions have nonobvious benefits that science can’t understand yet. For instance, the benefits of fasting have only been scientifically proven recently but they have been part of religious tradition for thousands of years. Redundancy can seem like a waste – until you need to use those extra resources.
  • Exposed to Positive Black Swans. Remember the extreme events from earlier? The ones we can’t predict? They can be negative or positive. Every artist’s big break came because they were exposed to a positive Black Swan. You never know when the thing is going to work (damn lumpy payoffs!) but you know that the more you expose yourself to the possibility of success the better chances you have of getting it.

Don’t worry if it hasn’t clicked. It will.

The table below will help us understand the relationship of the triad:

MythologySword of Domocles, Rock of TantalusPhoenixHydra
Black SwanExposed to negative Black SwansExposed to positive Black Swans
BusinessesNew York: Banking systemSilicon Valley: “Fail fast,” “Be foolish.”
Biological & Economic SystemsEfficiency, optimizedRedundancyDegeneracy (functional redundancy)
ErrorsHates mistakesMistakes are just informationLoves mistakes (since they are small)
ErrorsIrreversible, large (but rare) errors, blowupsProduces reversible, small errors
Science/technologyDirected researchOpportunistic ResearchStochastic tinkering (antifragile tinkering)
Dichotomy event-exposureStudying events, measuring their risks, statistical properties of eventsStudying exposure to events, statistical properties of exposuresModifying exposure to events
ScienceTheoryPhenomenologyHeuristics, practical tricks
EthicsSystem without skin in the gameSystem with skin in the gameSystem with soul in the game
Financial dependenceCorporate employment, Tantalized classDentist, dermatologist, niche worker, minimum-wage earnerTaxi driver, artisan, prostitute, f*** you money
LearningClassroomReal life, pathemata mathemata (learn by suffering)Real life and library
Political systemNation-state; centralizedCollection of city-states; decentralized
Social SystemIdeologyMythology
Post-agricultural modern settlementsNomadic and hunter-gatherer tribes
ScienceTheoryPhenomenology (direct experience)Evidence-based phenomenology
Psychological well-beingPost-traumatic stressPost-traumatic growth
Effect on Economic LifeBureaucratsEntrepreneurs
Reputation (profession)Academic, corporate executive, pope, bishop, politicianPostal employee, truck driver, train conductorArtist, writer
Reputation (class)Middle classMinimum-wage personBohemian, aristocracy, old money
MedicineVia positiveAdditional treatment (give medication)Via negativeSubtractive treatment (remove items from consumption, say cigarettes, carbs, etc.)
Philosophy/scienceRationalismEmpiricismSkeptical, subtractive empiricism
KnowledgePositive scienceNegative scienceArt
StressChronic StressorsAcute stressors, with recovery
Decision makingActs of commissionActs of omission (“missed opportunity”)
LiteratureE-readerBookOral tradition
BusinessIndustrySmall businessArtisan
FinanceDebtEquityVenture capital
GeneralLargeSmall but specializedSmall but not specialized
GeneralMonomodalBarbell [We’ll discuss these soon!]
Noise-signalSignal onlyStochastic resonance, simulated annealing
EducationSoccer momStreet lifeBarbell: parental library, street fights
Physical trainingOrganized sports, gym machinesStreet fights

You probably don’t have a totally clear picture of what antifrigility is yet. That’s fine. It’s a more difficult concept to grasp than most.

I only began to really understand antifragility when I started putting it into practice.

Let’s get into the actionable stuff now!

The Great Unknown

How Become Antifragile

Ah! Here we are, it’s time to get down and dirty. I’m going to provide you a bunch of ways you can start making yourself antifragile.

Life Decisions

[I]f you have more than one reason to do something (choose a doctor or veterinarian, hire a gardener or an employee, marry a person, go on a trip), just don’t do it. It does not mean that one reason is better than two, just that by invoking more than one reason you are trying to convince yourself to do something. Obvious decisions (robust to error) require no more than a single reason.”

We feel that we should make “plus and delta” lists like we learned in elementary school. We think we can find the perfect rational answer – even though the most rational answers are rarely the right ones for us.

So again, the heuristic:

If you have more than one reason to do something, don’t do it.

There is a fairly long (and interesting) explanation for this rule. If you’re interested, read on, otherwise, scroll on down.

Taleb’s fictional character Fat Tony and Socrates have a conversation about unjustified actions:

Fat Tony: ‘[M]y good Socrates, why do you think that we need to fix the meaning of things?’

Socrates: ‘My dear Mega-Tony, we need to know what we are talking about when we talk about things. The entire idea of philosophy is to be able to reflect and understand what we are doing, examine our lives. An unexamined life is not worth living.’

Fat Tony: ‘The problem, my poor old Greek, is that you are killing the things we can know but not express. And if I asked someone riding a bicycle just fine to give me the theory behind his bicycle riding, he would fall from it. By bullying and questioning people you confuse and hurt them.’

Benjamin Franklin and Charles Darwin were similarly tempted. John Kay shows both of their attempts and failures to rely on logic for their most important decisions in his brilliant book Obliquity:

Franklin explained his rule for making decision:

‘Divide half a sheet of paper by a line into two columns; writing over the one Pro, and over the other Con. Then, during three or four day’s consideration, I put down under the different heads short hints of the different motives, that at different times occur to me for or against the measure. When I have got them all together in one view, I endeavor to estimate the respective weights…. I have found great advantage for this kind of equation, in what may be called moral or prudential algebra.’

Charles Darwin attempted to follow Franklin’s rule when he set out the pros and cons of marriage in two opposing columns. A wife would provide “children, companionship, the charms of music and female chit chat.” She would be “an object to be beloved and played with” – though he did not seem to attach great weight to this, conceding only that a wife was in this respect “better than a dog anyhow.”

But Darwin also noted the disadvantages of the married state: the prospect of “being forced to visit relatives, and to bend in every trifle”; the “loss of freedom to go where one liked, the conversation of clever men at clubs.”

We snigger at the moral algebra of Franklin and Darwin. And so did they: Both men understood perfectly well that moral algebra is not how people really make decisions and that most people actually make judgments on more complex issues in oblique ways. Below his assessment Darwin scrawled: “It is intolerable to think of spending one’s whole life, like neuter bee, working, working – only picture to yourself a nice soft wife on a sofa.” He ends his notes, “marry-marry-marry Q.E.D.” The following year, he wedded Emma Wedgwood; the couple had ten children.

Franklin knew that moral algebra was generally a rationalization for a decision taken more obliquely. That is why as well as Franklin’s rule he set out what I earlier called Franklin’s gambit – “So convenient a thing is it to be a reasonable creature, since it enables one to find or make a reason for everything one had a mind to do.”

This cartoon sums up the idea well:

chart cartoon

Stop Trying to Be A Machine: Comfort is Not the Human Ideal

Most tourists don’t know how to travel well. They plan their vacation down to the hour. They try to maximize the fun they’ll have… and that invariably causes huge amounts of stress. It’s better to keep your options open.
Will and I went backpacking through Europe without a plan. We wandered through cities and then got on a train to go to the next country when we felt like it. We were able to wander and expose ourselves to fascinating opportunities that we could never have planned for. This is the only way to travel in my opinion. Otherwise you turn what could be magic into a trip to Magic Kingdom….

Taleb warns against this touristification in all areas of our life:

This is my term for an aspect of modern life that treats humans as washing machines, with simplified mechanical responses – and a detailed user’s manual. It is the systematic removal of uncertainty and randomness from things, trying to make matters highly predictable in their smallest details. All that for the sake of comfort, convenience, and efficiency.

What a tourist is in relation to an adventurer, or a flaneur, touristification is to life; it consists in converting activities, and not just travel, into the equivalent of a script like those followed by actors.

There are powerful forces trying to convince you to become a machine. They will have you believe that you need to use their system to be happy, that you need to have a perfect success mindset to get anywhere, or give you a step-by-step method for never-ending happiness.

no thanks
no thanks

There is this belief that humans should experience only one emotion: happiness. You should find your passion and then eat this exact diet and never be angry.

So you medicate yourself to bring your emotions closer to the understood standard.

It’s bizarre to me how radical idea it is that you should treat yourself as the human you are. Taleb provides a helpful table to help us embrace our humanity:

The Mechanical, NoncomplexThe Organic, Complex
Needs continuous repair and maintenanceSelf-healing
Hates randomnessLoves randomness (small variations)
No need for recoveryNeeds recovery between stressors
No or little interdependenceHigh degree of interdependence
Stressors cause material fatigueAbsence of stressors cause atrophy
Age with use (wear and tear)Age with disuse (use it or lose it)
Undercompensates from shocksOvercompensates from shocks
Time brings only senescence (gradual deterioration)Time brings aging and senescence

How do we become more human?

We rebel against the justified life.

We understand that the best things are had obliquely. Try to be happier and you’ll become miserable.

How? Read something for no reason other than you are interested in it. Create art (poem, painting, video, anything) that nobody will ever see.

Let go of your goals for a minute and think about what you actually like doing.

You’re not here to check off items on a to-do list, you’re here to live.

“My life is not an apology, but a life. It is for itself and not for a spectacle. I much prefer that it should be of a lower strain, so it be genuine and equal, than that it should be glittering and unsteady.” – Ralph Waldo Emerson

Stoicism: Antifragile Perspective and Using Your Emotions

seneca hard things

This was one of the hardest lessons I’ve ever learned. When I got depressed I rejected it for the longest time. I fought it and fought it but it just got worse. I did this for nearly a full year. When I finally let go and began usingand accepting my depression (in writing, appreciating art, increasing empathy) it immediately began to dissipate.

You’ve got to use what you got – even if that’s a shitty mood. Stack the odds in your favor (exercise, eat well, talk to friends, watch a funny movie, sleep, meditate, etc.) but don’t freak out when you wake up melancholic.

Taleb suggests stoicism as a way to take advantage of your emotions, not eliminate them.

“… Stoicism is about the domestication, not necessarily the elimination, of emotions. It is not about turning humans into vegetables. My idea of the modern Stoic sage is someone who transforms fear into prudence, pain into information, mistakes into initiation, and desire into undertaking.

He then relates a couple tricks recommended by Seneca (my personal favorite Stoic):

“…to separate anger from rightful action and avoid committing harm he would regret later would be to wait at least a day before beating up a servant who committed a violation.”

Another popular Stoic practice is to practice “negative visualization”. That is, imagine the worst possible outcome. This makes you prepared for an outcome other than your ideal. It can also be a source of freedom: the worst that can happen is rarely as terrible as you think.

“…the key phrase reverberating in Seneca’s ouvre is nihil perditi, “I have lost nothing,” after and adverse event.”

Ryan Holiday’s book on Stoicism, The Obstacle is The Way, is titled after the sentiment written by the famous emperor Marcus Aurelius in his diary over and over again: “…the obstacle becomes the way.” A fire uses everything as fuel to grow stronger. Stuff like that.

Nietzsche sums it up with amor fati – love your fate.

You have to use everything. Every shitty thing that happens to you must be used to grow in some way. Every negative emotion you have can also be used.

Taleb expands on emotions:

I feel anger and frustration when I think that one in ten Americans beyond the age of high school is on some kind of antidepressant, such as Prozac. Indeed, when you go through mood swings, you now have to justify why you are not on some medication. There may be a few good reasons to be on medication, in severely pathological cases, but my mood, my sadness, my bouts of anxiety, are a second source of intelligence – perhaps even the first source. I get mellow and lose physical energy when it rains, become more meditative, and tend to write more and more slowly then, with the raindrops hitting the windows, what Verlaine called autumnal “sobs” (sanglots). Some days I enter poetic melancholic states, what the Portugese call saudade or the Turks hüzün (from the Arabic word sadness). Other days I am more aggressive, have more energy – and will write less, walk more, do other things, argue with researchers, answer emails, draw graphs on blackboards. Should I be turned into a vegetable or a happy imbecile?

Had Prozac been available last century, Baudelaire’s “spleen,” Edgar Allan Poe’s moods, the poetry of Sylvia Plath, the lamentations of so many other poets, everything with a soul would have been silenced…

If large pharmaceutical companies were able to eliminate the seasons, they would probably do so – for a profit, of course.

Another example: procrastination. There are a thousand articles teaching you how to stop procrastinating. We assume it is only evil. In reality, procrastination is our best teacher. Instead of fighting it, you can use procrastination as a tool to understand yourself better. What are the things you do when you’re procrastinating? They may be a strong indicator of what you actually enjoy doing.

This admission of this situation (our own human nature) can be expanded into understanding how to organize groups of people as well. Taleb:

Not seeing a tsunami or an economic event coming is excusable; building something fragile to them is not.

Also, as to the naïve type of utopianiasm, that is, blindness to history, we cannot afford to rely on the rationalistic elimination of greed and other human defects that fragilize society. Humanity has been trying to do so for thousands of years and humans remain the same, plus or minus bad teeth, so the last thing we need is even more dangerous moralizers (those who look in a permanent state of gastrointestinal distress). Rather, the more intelligent (and practical) action is to make the world greed-proof, or even hopefully make society benefit from the greed and other perceived defects of the human race.

The next step? Stop pretending you can predict the future.

More Options, Less Plans

“The fact that we often judge the pleasure of an experience by its ending can cause us to make some curious choices.” – Daniel Gilbert, Stumbling on Happiness

Options are things that you can act on but don’t have to.

The quick fix: Stop pretending you know so much about your future and structure yourself to take advantage of opportunities in the future.

Before we get into optionality and planning in personal life, let’s take a look through the lens of construction (there are important parallels):

[I]t is the size per segment of the project that matters, not the entire project – some projects can be divided into pieces, not others. Bridge and tunnel projects involve monolithic planning, as these cannot be broken up into small portions; their percentage costs overruns increase markedly with size. Same with dams. For roads, built by small segments, there is no serious size effect, as the project managers incur only small errors and can adapt to them. Small segments go one small error at the time, with no serious role for squeezes.

This is an idea that needs an explanation. Here’s what it looks like in my life:

I avoid jobs I can’t leave. I create work (and skills) that compound – writing, storytelling, marketing, video, helping people. I tell people “probably” instead of “yes”. I rent a home.

keep calm best laid plans

Let’s give Taleb the floor:

So let us call here the teleological fallacy the illusion that you know exactly where you are going, and that you knew exactly where you were going in the past, and that others have succeeded in the past by knowing where they were going.

The rational flaneur is someone who, unlike a tourist, makes a decision at every step to revise his schedule, so he can imbibe things based on new information, what Nero was trying to practice in his travels, often guided by his sense of smell. The flaneur is not a prisoner of a plan. Tourism, actual or figurative, is imbued with the teleological illusion; it assumes completeness of cision and gets one locked into a hard-to-revise program, while the flaneur continuously – and, what is crucial, rationally – modifies his targets as he acquires information.

Now a warning: the opportunism of the flaneur is great in life and business – but not in personal life and matters that involve others. The opposite of opportunism in human relations is loyalty, a noble sentiment – but one that needs to be invested in the right places, that is, in human relations and moral commitments.

The error of thinking you know exactly where you are going and assuming that you know today what your preferences will be tomorrow has an associated one. It is the illusion of thinking that others, too, know where they are going, and that they would tell you what they want if you just asked them.

Never ask people what they want, or where they want to go, or where they think they should go, or, worse, what they think they will desire tomorrow. The strength of the computer entrepreneur Steve Jobs was precisely in distrusting market research and focus groups – those based on asking people what they want – and following his own imagination. His modus was that people don’t know what they want until you provide them with it.

This ability to switch from a course of action is an option to change.

Some ways to increase your options right now:

  • Learn a new professional skill. If your company goes bust right now, would you be able to get another job doing exactly what you’re doing now? If not, you need to expand your skillset. This kind of learning can create asymmetric payoffs – skills often work together synergistically.
  • Side hustle. Work on something on the side. Again, if everything goes to shit it’s nice to have options.
  • Save money. It’s also nice to have options if things go well. Money in the bank gives you the option to take advantage of opportunities – be they investments or some amazing opportunity that requires you quit your job. Money in the bank also makes it easier to transition if everything goes to shit.
  • Go to parties. Opportunities often come in the form of humans – both personal and professional. One of the best ways to meet people is going to parties. I hate parties until I get to them, then they are always worthwhile.
  • Shift your perspective. I know. This is bullshit. But it’s also not. When you shift your perspective and become aware of more options, then you can take advantage of them. Train yourself to see your options and see what you could do to expand your options.

It wouldn’t be right to end this section without including Taleb’s four-rule summary of his chapter on optionality:

(i)Look for optionality; in fact, rank things according to optionality, (ii) preferably with open-ended, not closed-ended, payoffs; (iii) Do not invest in business plans but in people, so look for someone capable of changing six or seven times in his career, or more (an idea that is part of the modus operandi of the venture capitalist Marc Andreesen); one gets immunity from the backfit narratives of the business plan by investing in people. It is simply more robust to do so; (iv) Make sure you are barbelled, [Kyle: We will discuss barbells soon.] whatever that means in your business.

What this does, in practice, is shift your focus from right/wrong or true/false to benefit/harm, to payoff. Remember that it doesn’t matter how often you are wrong as long as your risks are small and your upside is potentially tremendous. Taleb laments our focus on true/false throughout history:

“The need to focus on the payoff from your actions instead of studying the structure of the world (or understanding the “True” and the “False”) has largely been missed in intellectual history. Horribly missed. The payoff, what happens to you (the benefits or harm from it), is always the most important thing, not the event itself.

Your most powerful options make look silly. The may be completely irrational. It doesn’t matter. You don’t need them to work every time, or even more than once or twice in your lifetime.

You can increase your options right now, no questions asked. You can’t, no matter how hard you try, know what the future will bring.


Poke and Prod

“The general principle of antifragility, it is much better to do things you cannot explain than explain things you cannot do.” – Nassim Taleb

It’s scary to do things that we can’t explain. Our every move is supposed to be justified. We need to be able to answer the question, “why?”

We need to have an excuse for every fuckup. That’s why we ask people for advice when we really know what we should do. We’re trying to spread the responsibility of failure around.

We’ve been scarred from people yelling, “What were you thinking?” when we messed up. We weren’t thinking. We were doing… and learning. We’ve been conditioned to only do what we have a good reason to do. Which means we ignore the greatest pieces of life.

The narrative fallacy not only tricks us into believing that there is a connected story behind everything – it also makes us think that the story came before the event.

“Evolution does not rely on narratives, humans do. Evolution does not need a word for the color blue.”

Taleb tells us that birds knew how to fly long before we were able to understand why they are able to fly. Humans have lived happily long before researchers breached the topic.

You were antifragile before you knew about antifrigility.

To help illustrate the power of doing things we can’t justify, let’s look at this table, titles “The Lecturing-Birds-How-To-Fly Effect Across Domains: Examples of Misattribution of Results in Textbooks”, from Antifragile:

FieldOrigination and Development as Marketed by Bird Lecturers [Or: Where they told us the innovation came from.]Real Origination and Development
Jet EnginePhysicists (busted by Scranton)Tinkering engineers with no understanding of “why it works”
ArchitectureEuclidean geometry, mathematics (busted by Beaujouan)Heuristics and secret recipes (guild)
CyberneticsNorbert Wiener (busted by Mindell)Programmers “wiki-style”
MedicineBiological understanding (busted by a long series of doctors)Luck, trial and error, side effects of other medicines, or sometimes poisoning (mustard gas)
Industrial RevolutionGrowth in knowledge, Scientific Revolution (busted by Kealey)Adventurers, hobbyists
TechnologyFormal scienceTechnology, business

Taleb uses cooking to help drive the point home:

[Many] recipes are derived entirely without conjectures about the chemistry of taste buds, with no role for any “epistemic base” to generate theories out of theories. Nobody is fooled so far by the process. As Dan Ariely once observed, we cannot reverse engineer the taste of food from looking at the nutritional label. And we can observe ancestral heuristics at work: generations of collective tinkering resulting in the evolution of recipes. These food recipes are embedded in cultures. Cooking schools are entirely apprenticeship based.

Taking action now is the best thing you do. You literally create new universes of possibilities when you start building something.

Starting something is not an event; it’s a series of events. You decide to walk to Cleveland. So you take a first step in the right direction. That’s starting. You spend the rest of the day walking toward Cleveland, one step at a time, picking your feet up and putting them down. At the end of the day, twenty miles later, you stop at a hotel. And what happens the next morning? Either you quit the project or you start again, walking to Cleveland. In fact, every step is a new beginning.” –Seth Godin, Poke the Box

Another benefit of continuously taking action is that you stop needing other people to tell you you’re doing a good job. When you focus doing your work as well as you can then it’s the work that matters, not how the work is received. Taleb expands on this:

“There is another dimension to the need to focus on actions and avoid words: the health-eroding dependence on external recognition. People are cruel and unfair in the way they confer recognition, so it is best to stay out of that game. Stay robust to how others treat you.”

This is also why it’s so important to have your own measure of success. Warren Buffett calls it his “internal scorecard” and credits it with helping him in thinking independently even when it looked to the rest of the world that he was wrong.

Action is often the answer you were looking for. There is no intellectual answer, you must experience the thing. You must try it out for real, not in the abstract.

You know what this means, don’t you?

You have no excuse not to follow your whims, your urges, and your interests. They may not last, they may not be big – but they will show you possibilities that you would never have known of if you didn’t follow them.

Heuristic: Try as many things as you can and keep your risk low.


Via Negativa

“Nimium boni est, cui nihil est mali.” – Ennius

“The good is mostly in the absence of the bad.”

If you want better health, quitting smoking is going to help more than eating organic. (Actually, reducing chronic stress will be better for your health than eating organic as well.) The first step to wealth is lessening your debt. You focus more by decreasing distractions.

When I’m feeling unmotivated, I know I need to get rid of the things stopping me, I don’t need to add anything to my life.

Taleb describes why we should worry about being less unhappy, not more happy:

[H]appiness is best dealt with as a negative concept; the same nonlinearity applies. Modern happiness researchers (who usually look quite unhappy), often psychologists turned economists (or vice versa) do not use nonlinearities and convexity effects when they lecture us about happiness as if we knew what it was and whether that’s what we should be after. Instead, they should be lecturing us about unhappiness (I speculate that just as those who lecture on happiness look unhappy, those who lecture on unhappiness would look happy); the “pursuit of happiness” is not equivalent to the “avoidance of unhappiness.” Each of us certainly knows not only what makes us unhappy … but what to do about it.

We are always told to do something about it and so we feel like every problem is fixed by adding things. Buy a new product to fix your self-esteem. Buy a new supplement to fix your energy levels. Hire more people to increase production.

It is often more effective to take the causes of the problems away. Stop hanging out with people that make you feel shitty for not having that new product. Stop staying up so late to fix your energy levels. Eliminate inefficiencies instead of making another hire.

You don’t become more productive when you add items to your to-do list, you become more effective when you force yourself to prioritize the single most important item.

Paul Graham, the founder of Y Combinator, and Robert Green, the author of Mastery, discuss via negative:

Paul:  I wrote essays because I didn’t understand about blogging. I had never done it, and I knew these guys did this thing called blogging, but I didn’t really care about it.

Robert:      You tend to always put these in the negative form.

Paul:           Okay. Well here’s a positive way. I deliberately ignored these things because I knew they weren’t interesting. You can do a lot by avoiding bad as opposed to seeking good.

Robert:      Yeah. And it’s a positive avoiding bad. It’s a choice.

Even Warren Buffett and Charlie Munger’s investment strategy is about avoiding bad decisions, not making good ones. Peter Bevelin has distilled their wisdom beautifully in Seeking Wisdom. The following quotes have been pulled from there, starting with Buffett:

Easy does it. After 25 years of buying and supervising a great variety of businesses, Charlie and I have not learned how to solve difficult business problems. What we have learned is to avoid them. To the extent we have been successful, it is because we concentrated on identifying one-foot hurdles that we could step over rather than because we acquired any ability to clear seven-footers. The finding may seem unfair, but in both business and investments it is usually far more profitable to simply stick with the easy and obvious than it is to resolve the difficult.

jolly buffett

Buffett goes on to provide a specific example of this in the management of Berkshire Hathaway:

We basically have the attitude that you can’t make a good deal with a bad person. We don’t try to protect ourselves by contracts or all kinds of due diligence – we just forget about it. We can do fine over time dealing with people we like and admire and trust.

And the bad actor will try to tantalize you in one way or another. But you won’t win. It pays to just avoid him. We started out with that attitude. However, one or two experiences have convinced us even more so that that’s the way to play the game.

It’s not just about avoiding external problems – it’s also about realizing how limited your own mind is. It’s about setting yourself up so you don’t have to make a lot of good decisions. Buffett explains:

Charlie [Munger] and I decided long ago that in an investment lifetime, it’s just too hard to make hundreds of smart decisions. That judgment became ever more compelling as Berkshire’s capital mushroomed and the universe of investments that could significantly affect our result shrank dramatically. Therefore, we adopted a strategy that required our being smart – and not too smart at that – only a few times.

If you’re interested, here is an assortment of Taleb’s fragilizers collected by Todd Becker at Getting Stronger (I’ve included the ones I disagree or have no idea about, the list is controversial to say the least):

  • Antiobiotics
  • Cortisone shots
  • Sunscreen
  • Toothpaste
  • Fruit (except for ancient ones)
  • Child Psychiatry
  • Cushioned Running Shoes
  • Supplements
  • Hormone Replacement Therapy
  • Lobotomies (This was normal once…)
  • Disinfectants
  • Soy Milk
  • Any drink except water, wine, coffee.
  • Air Conditioning
  • Antioxidants
  • Anti-Inflammatory Medication
  • Iron Supplementation
  • Excessive Hygiene
  • Cow’s Milk (For those of Mediterranean or Asian descent – he believes our origins matter.)
  • Antidepressants
  • Eye Glasses
  • Vitamin D Supplements.



Use Acute Stressors

One of the biggest mistakes we can make is to aim at comfort in our lives. Short bouts of intense stress are phenomenal for our health – physical, mental, and emotional.

When we endure intense stress for a short period of time, we grow back stronger than we were. It activates our antifrigility.

Working out is the most obvious example. It’s similar in work. There is amazing fulfillment to be had by losing yourself in intense work. Compare the exhaustion of an entrepreneur who just launched a new product to the exhaustion of the accountant. Chronic exhaustion is miserable, acute exhaustion followed by rest is great.

Science has found there are great benefits to fasting. It makes your body more ready to digest food when you do eat. It has positive benefits across the board.

Some other acute stressors that I have found to be great:

  • Cold showers. They reduce depression, burn fat, increase willpower, and invigorate you.
  • Work all night and then sleep 12+ hours the next day.
  • Go to a concert. For someone who doesn’t often go to concerts, it’s intense.
  • Risk social rejection. Pushing into the fear is exciting and expands your comfort zones.
  • Compete.
  • Read ideas that are different than your own. The stress of reading a smart person disagree with you makes you intellectually stronger and humble.


Redundancy increases our options and decreases our chances at being harmed by the future. Ironically, creating redundancies means that we must consciously become less optimal.

We can’t know what will happen in the future so we want to be ready to take advantage of as many outcomes as possible.

Here are some examples:

  • Get there early. You don’t have to worry about traffic and you have a chance to explore the area. Taleb even wrote The Bed of Procrustes by getting places early and wandering around.
  • Cash in the bank. For individuals and businesses, you can take advantage of more opportunities if you keep cash in the bank.
  • Buy books you won’t read right away. Having the option to read a different book at any time is awesome. Your unread library is actually more valuable than your read library.
  • Have more than one person to vent to. If you rely one person to talk through things with, they may get fed up. It’s better to be able to talk with different people about things.
  • Multiple streams of income. You are fragile if you are only making money from one place. This is true even for entrepreneurs – if one client determines your whole business you’re in a bad spot. You want to be able to survive getting fired or a client finding another provider.
  • Do a lot of work. If you are a writer you should be writing more than you’re supposed to be. If you’re an entrepreneur you should be delivering more than the customer expected.
  • Multiple skills. Robots and software are pretty much replacing everybody. Make sure you have more than one skill. Also, having multiple skills has a synergistic effect that creates a killer competitive advantage.
embracing extremes


“So just as Stoicism is the domestication, not the elimination, of emotions, so is the barbell a domestication, not the elimination, of uncertainty.” – Nassim Taleb

This is one of the most powerful strategies to create antifrigility. It is especially dear to my heart because I hate “either/or” decisions. Creating barbell strategies means embracing two extremes and using them to your advantage. It’s playing it safe while taking extreme (yet small) bets.

Here is Taleb’s definition from the Antifragile glossary:

Barbell Strategy: A dual strategy, a combination of two extremes, one safe and one speculative, deemed more robust than a “monomodal” strategy; often a necessary condition for antifrigility. For instance, in an occasional fling with a rock star; for a writer, getting a stable sinecure and writing without the pressures of the market during spare time. Even trial and error are a form of barbell.

The idea is that the mediocre is… mediocre. It’s better to spend time with professors and janitors than pseudo-intellectuals. It’s better to read academic papers and pulp novels than best-selling pop-psyche books that have nothing new to say.

Taleb explains barbells another way:

[T]o see the difference between barbells and nonbarbells, consider that restaurants present the main course, say, grass-fed minute steak cooked rare and salad (with Malbec wine), then, separately, after you are done with the meat, bring you the goat cheese cake (with Muscat wine). Restaurants do not take your order, then cut the cake and the steak in small pieces and mix the whole thing together with those machines that produce a lot of noise. Activities “in the middle” are like such mashing.

He goes on to describe the barbell that airlines use to create safe and pleasant travel:

In risky matters, 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.

Taleb provides a few examples:

Do crazy things (break furniture once in a while), like the Greeks during the later stages of a drinking symposium, and stay “rational” in larger decisions. Trashy gossip magazines and classics or sophisticated works; never middlebrow stuff. Talk to either undergraduate students, cab drivers, and gardeners or the highest caliber scholars; never middling-but-career-conscious academics. If you dislike someone, leave him alone or eliminate him; don’t attack him verbally.

bear barbell

More examples should clarify:


“And professions can be serial: something very safe, then something speculative. A friend of mine built himself a very secure profession as a book editor, in which he was known to be very good. Then, after a decade or so, he left completely for something speculative and highly risky. This is a true barbell in every sense of the word: he can fall back on his previous profession should the speculation fail, or fail to bring the expected satisfaction.”

This could also mean keeping your day job while moonlighting at a startup. You get to keep your job security while exposing yourself to massive upside if the startup takes off.


“This is what Seneca [the great Stoic philosopher] elected to do: he initially had a very active, adventurous life, followed by a philosophical withdrawal to write and meditate, rather than a “middle” combination of both. Many of the “doers” turned “thinkers” like Montaigne have done a serial barbell: pure action, then pure reflection.”


“If you put 90 of your funds in boring cash (assuming you are protected from inflation) or something called a “numeraire repository of value,” and 10 percent in very risky, maximally risky, securities, you cannot possibly lose more than 10 percent, while you are exposed to massive upside.”


I love to read and process information. People put massive effort into books. Thinking through an idea in excruciating detail and then bringing us the best of it. Or researching someone’s life and bringing us back the most important parts in the form of a story we can use to help guide our own life.

All this input allows me to understand the world in a way simultaneously more subtle and more wide than before. Knowledge, even as widely available as most of it is, is still power.

But it’s important to frame that input. I go through periods of only reading massive amounts. I take in amazing amounts of information without creating anything of my own. I begin to lose sight of my own ideas, my own understanding, and how this information is actually serving me. When these periods come, I put myself through an Input Deprivation Week. I don’t take in any information, I only create. (I’ve prescribed it here before and people have found a lot of success with it.)

This barbell of info in/info out allows me to take in a torrent of data without risk getting frustrated by not using it. The week reframes the information, pushes me to make connections between the information I had been taking in, and generally makes me more mindful.

Creative Work

Work intensely and rest completely.

[I]f I have to work, I find it preferable (and less painful) to work intensely for very short hours, then do nothing for the rest of the time (assuming doing nothing is really doing nothing), until I recover completely and look forward to a repetition, rather than being subjected to the tedium of Japanese style low-intensity interminable office hours with sleep deprivation. Main course and dessert are separate.

Indeed, Georges Simeon, one of the most prolific writers of the twentieth century, only wrote sixty days a year, with three hundred days spent “doing nothing.” He published more than two hundred novels.


Taleb advocates going for long, slow (very slow) walks most days with sporadic bursts of sprinting. Then once in a while going to the gym and lifting as heavily as you possibly can.

The hardest thing for the gym-freak to do is take a day off. Working out every day leaves no time for the body to repair and (antifragily) get even stronger because of the previous workout.

This recovery period is key to any barbell that requires intense exertion.

Personal Risks

“Let us take a peek at a few domains. With personal risks, you can easily barbell yourself by removing the chances of ruin in any area. I am personally completely paranoid about certain risks, then very aggressive with others. The rules are: no smoking, no sugar (particularly fructose), no motorcycles, no bicycles in town or more generally outside a traffic-free area such as the Sahara desert, no mixing with Eastern European mafias, and no getting on a plane not flown by a professional pilot (unless there is a co-pilot). Outside of these I can take all manner of professional and personal risks, particularly those in which there is no risk of terminal injury.

Social Policy

“In social policy, it consists in protecting the very weak and letting the strong do their job, rather than helping the middle class to consolidate its privileges, thus blocking evolution and bringing all manner of economic problems that tend to hurt the poor the most.”


Taleb recommends ignoring the doctor unless you are in a life-or-death situation, then try anything.

Doctors are incentivized to do something about the problem – even if that means a dangerous surgery that isn’t totally necessary. Or prescribing pills that have known and unknown side-effects more serious in the long run than the short-term problem they are fixing.

Do nothing until you must do something. Then do that something with intensity.


I have a massive amount of acquaintances (who I normally refer to as “friends”) and a tiny group of friends. I like to expose myself to as many as people as possible yet remain extremely selective in who I let in.

This allows me to be exposed to all sorts of people and benefit from diversity without stretching my attention to thin.

Create Your Own

The real value here isn’t in the specific examples but in the strategy. Spend time creating barbells in your own life. Protect yourself from catastrophe but expose yourself to certain discomforts and small risks that provide opportunities for extreme upside.

signal and noise

Vigilantly Avoid the Noise (ie News, Newsfeeds, Unusable info..)

I was taught the importance of this early in my trading career. I mainly used patterns to make trade decisions (this made me a “technical trader”) and had to constantly fight the urge to make my trading system more complex. The best systems are simple, as we saw before.

In a way, Warren Buffett’s investment strategy (discussed earlier) is so successful because it avoids the dangers of noise. The simplicity of the system only responds to truly important signals. Actually, Buffett has said that his worst investment mistakes have been due to a lack of a signal. During these periods he would get bored, look too closely, and respond to what would normally be noise.

Instinctively, we feel we should be able to avoid reacting to noise. This is a dangerous assumption to make. Noise can rapidly dilute good judgment. Taleb explains how noise is amplified:

Say you look at information on a yearly basis, for stock prices, or the fertilizer sales of your father-in-law’s factory, or inflation numbers in Vladivostok. Assume further that for what you are observing, at a yearly frequency, the ratio of signal to noise is about one to one (half noise, half signal) – this means that about half the changes are real improvements or degradations, the other half come from randomness. This ratio is what you get from yearly observations. But if you look at the very same data on a daily basis, the composition would change to 95 percent noise, 5 percent signal. And if you observe data on an hourly basis, as people immersed in the news and market price variations do, the split becomes 99.5 percent noise to 0.5 percent signal. That is two hundred times more noise than signal – which is why anyone who listens to the news (except when very, very significant events take place) is one step below sucker.

It’s impossible to make good decisions and have a solid understanding if the majority of information we take in is bullshit. It’s also emotional terrorism on yourself to constantly check how many people liked the post you just made, how many views your blog post has had, and how happy you are each hour.

I tend to be significantly more clear-headed when I check Facebook twice than the days where I check it twenty times.

Taleb expands on the psychological impact of noise:

[W]e are not made to understand the point, so we overreact emotionally to noise. The best solution is to only look at very large changes in data or conditions, never at small ones.

He then expands on why we don’t need to:

Just as we are not likely to mistake a bear for a stone (but likely to mistake a stone for a bear), it is almost impossible for someone rational, with a clear, uninfected mind, someone who is not drowning in data, to mistake a vital signal, one that matters for his survival, for noise – unless he is overanxious, oversensitive, and neurotic, hence distracted and confused by other messages. Significant signals have a way to reach you.

There is a sea of “experts” and other assholes trying to convince you that you need their product. That they have packaged up the answer you’ve been looking for. That “if you don’t read this now you’ll never be happy, successful, or have sex. Ever!”
Then there is the news trying to freak you out about everything even though it will never change your life at all. Then there is the culture and the bullshit “art” that’s promoted every week.

One way to cut out the noise is considering age:

“Gott made a list of Broadway shows on a given day, May 17, 1993, and predicted that the longest-running ones would last longest, and vice-versa. He was proven right with 95% accuracy.”

The shows that have been successful the longest will probably last the longest starting now. So the books that have been around for thousands of years will probably be read thousands of years from now. The ideas in those books have proven useful to humans through all ages.

Speaking of books, they will certainly outlast ereaders. Pens will probably outlive styluses. Cars will be driven after we give up on hovercraft. This tendency for things that have lasted a long to time to last much longer is known as the Lindy Effect. It’s a powerful tool to think clearly around the noise of change. Taleb explains another reason noise can have such great pull on our minds:

“We notice what varies and changes more than what plays a large role but doesn’t change. We rely more on water than on cell phones but because water does not change and cell phones do, we are prone to thinking that cell phones play a larger role than they do.”

In summary:

“I just want to understand as little as possible to be able to look at regularities of experience.

So the modus operandi in every venture is to remain as robust as possible to changes in theories…”

Again, you don’t need a more detailed fitness plan, you need to go to the gym and eat less sugar.

There is immense power in the inputs you allow into your brain. It’s worth only allowing things that are worthwhile.

heuristics dilbert

Use Heuristics – A “Best Of” List

“Rules are for the obedience of fools and the guidance of wise men.” – David Ogilvy

We’ve already discussed a bunch of heuristics throughout this article. Heuristic, as an adjective, is defined as, “using experience to learn and improve.” This means that it’s a rule-of-thumb to follow but not put all your faith in.

It’s a way to quickly make decisions that will, in the long run, put you ahead.

Heuristics help stop you from making terrible mistakes by filtering out the crap. They help you take more bold action by assisting with decision-making.

The following is a list of my favorite aphorisms and heuristics from Taleb. They’ve been pulled from all over his works (though mostly Antifragile).

There are a ton of them here; it’s worth reading them all but selecting only one or two to take with you. I’d recommend writing one down and keep it with you. Knowledge is useless if it remains intellectual, you need to apply it to see it’s power.

I have added a note in italics to frame each aphorism as well as making bold the ones which have found their way most deeply into my life.

Antifragile Aphorisms and Heuristics

Why we want advice. “When we want to do something while unconsciously certain to fail, we seek advice so we can blame someone else for the failure.”

What advice to take. “Never ask anyone for their opinion, forecast, or recommendation. Just ask them what they have – or don’t have – in their portfolio.”

Courageous admission of ignorance. “It takes a lot of intellect and confidence to accept that what makes sense doesn’t really make sense.”

Fear of ignorance. “Under opacity, incomplete information, and partial understanding, much of what we don’t understand is labeled “irrational”.”

Bureaucratic babying. “The weak cannot be good; or, perhaps, he can only be good within an exhaustive and overarching legal system.”

Measuring money insecurity. “You can tell how poor someone feels by the number of times he references money in his conversation.”

Why wealth? “I wonder how many people would seek excessive wealth if it did not carry a measure of status with it.”

How hard do you hit? “What counts is not what people say about you, it is how much energy they spend saying it.”

BS friends. “Supposedly, if you are uncompromising/intolerant with BS you lose friends. But these are very good friends to lose. For you also make friends.”

Ask for others’ perspectives. “It is easy for others, but not for you, to detect the asymmetry between what you gain and what you give by doing, writing, or saying.”

How to lose an argument. “The first one who uses “but”, has lost the argument.”

Virtue vs Honor. “Virtue is a sequence of small acts of omission. Honor and Grandeur can be a singly gutsy, momentous, and self-sacrificial act of commission.”

Destructive learning. “To understand how something works, figure out how to break it.”

Delivering good/bad news. “Bring the good new in trickles, the bad news in lumps.”

Interestingly virtuous. “It takes a lot of skills to be virtuous without being boring.”

Metaphors matter. “Atheists are just modern versions of religious fundamentalists: they both take religion too literally.”

What are you making now? “There is no more unmistakable sign of failure than to that of a middle-aged man boasting his successes in college.”

They can’t think more money will make them happy. “One of life’s machinations is to make some people both rich and unhappy, that is, jointly fragile and deprived of hope.”

Silent rejection is more powerful than spoken. “You can almost certainly extract a “yes” from someone who says “no” to you, never from someone who says nothing.”

Beware too much comfort. “High Modernity: routine in place of physical effort, physical effort in place of mental expenditure, & mental expenditure in place of mental clarity.”

Vulnerability is strength. “It is a sign of weakness to avoid showing signs of weakness.”

Just do it. “Life is about execution rather than purpose.”

The unjustified life. “The general principle of antifragility, it is much better to do things you cannot explain than explain things you cannot do.”

Freedom is unjustified. “The ultimate freedom lies in not having to explain “why” you did something.”

Unjustified rules. “The rules you explain are less convincing than the ones you don’t explain – or have to explain.”

Winding paths vs straight shots. “For a free person, the optimal – most opportunistic – route between two points should never be the shortest one.”

Saying “Fuck you.” “a – You are free in inverse proportion to the number of people to whom you can’t say “fuck you”. b – You are honorable in proportion to the number of people to whom you can say “fuck you” with impunity but don’t.”

Mindless motivational Facebook posts. “When you cite some old wisdom-style quote and add “important truth”, “to remember” or “something to live by”, you are not doing so because it is good, only because it is inapplicable. Had it been both good and applicable you would not have had to cite it. Wisdom that is hard to execute isn’t really wisdom.”

Personal passions. “It is perplexing, but amusing to observe people getting extremely excited about things you don’t care about; it is sinister to watch them ignore things you believe are fundamental.”

The dark side is human, too. “If you get easily bored, it means that your BS detector is functioning properly; if you forget (some) things, it means that your mind knows how to filter; and if you feel sadness, it means that you are human.”

What price have they paid? “What we commonly call “success” (rewards, status, recognition, some new metric) is a consolation prize for those both unhappy and not good at what they do.”

Agility in living. “Life is about early detection of the reversal point beyond which belongings (say a house, country house, car, or business) start owning you.”

Teleological fallacy. “The first, and hardest, step to wisdom: avert the standard assumption that people know what they want.”

Quiet truth and loud lies. “People tend to whisper when they say the truth and raise their voice when they lie.”

Unpaid respect. “A good man is warm and respectful towards the waiter or people of supposedly lower financial and social condition.”

Incentivized bullshit. “Journalists cannot grasp that what is interesting is not necessarily important; most cannot even grasp that what is sensational is not necessarily interesting.”

First rid yourself of self-harm. “Injuries done to us by others tend to be acute; the self-inflicted ones tend to be chronic.”

Ditto. “We often benefit from harm done to us by others; almost never from self-inflicted injuries.”

Intellectual knowledge isn’t knowing. “Just as eating cow-meat doesn’t turn you into a cow, studying philosophy doesn’t make you wiser.”

The honest mirror. “Success in all endeavors requires absence of specific qualities. 1) To succeed in crime requires absence of empathy, 2) To succeed in banking you need absence of shame at hiding risks, 3) To succeed in school requires absence of common sense, 4) To succeed in economics requires absence of understanding probability, risk, or 2nd order effects and about anything, 5) To succeed in journalism requires inability to think about matters that have an infinitesimal small chance of being relevant next January, … 6) But to succeed in life requires a total inability to do anything that makes you uncomfortable when you look at yourself in the mirror.

Selling votes. “A prostitute who sells her body (temporarily) is vastly more honorable than someone who sells his opinion for promotion or job tenure.”

Balls and Brains. “Those with brains and no balls become mathematicians, those with balls but no brains join the mafia, those with no balls and no brains become economists. And those with brains and balls become artisans/entrepreneurs.

Timidity wastes horsepower. “Intellect without balls is like a race car without tires.”

Tic-tok. “Accept the rationality of time, never its fairness or morality.”

Shadows piquing interest? “People are much less interested in what you are trying to show them than what you are trying to hide.”

Participate. “Did you notice that collecting art is to hobby-painting as watching pornography is to doing the real thing? Only difference is status.”

Duty. “Real life (vita beata) is when your choices correspond to your duties.”

Smiling salesmen. “If you detect a repressed smile on the salesperson’s face, you paid too much for it.”

We can see your status-seeking. “Anything people do, write, or say to enhance their status beyond what they give others shows like a mark on their foreheads, visible to others but not to them.”

Author’s barbell. “I was told to write medium sized books: The 2 more successful French novels in history: one is very short (Le Petit Prince ~80 pages), the other extra long (Proust’s Recherche, ~3200 pages), following the Arcsine law.”

Get bigger. “Authors deplete their soul when the marginal contribution of a new book is smaller than that of the previous one.”

Mixing two wrongs doesn’t make a right. “In a conflict, the middle ground is least likely to be correct.”

Use the religion/philosophy you need now. “The ancient Mediterranean: people changed rites as we do with ethnic food.”

The words or the person? “We tend to define “rude” less by the words used (what is said) than by the status of the recipient (to whom it is addressed.)”

Confusing the secondary for the primary. “Studying neurobiology to understand humans is like studying ink to understand literature.”

“In theory…” “The only people who think that real world experience doesn’t matter are those who never had real world experience.”

Mechanized humans. “Automation makes otherwise pleasant activities turn into “work”.”

Cost vs value. “I recently had a meal in a fancy restaurant with complicated dishes ($125 per person), then enjoyed a pizza afterwards (straight out of the oven), $7.95. I wondered why the pizza isn’t 20x the price of the complicated dish, since I’d rather have the former over the latter.”

Transcendence. “Contra the prevailing belief, “success” isn’t being on top of a hierarchy, it is standing outside all hierarchies. Or, even better, for those who can, not being aware of, or not giving a f**** about hierarchy.”

People with people. “A happier world is one in which everyone realizes that 1) it is not what you tell people, it is how you say it that makes them feel bad, 2) it is not what you do to them but how you make them look that gets them angry, 3) they should be the ones putting themselves in a specific category.”

How to know not to do something. “Any action one does with the aim of winning an award, any award, corrupts to the core.”

What you actually say. “When you say something you think you are just saying something, but you are largely communicating *why* you had to say it.”

What happens when you bitch. “Complaints don’t deliver complaints, they mostly reveal your weakness.”

Weak wanting. “Envy, like thirst for revenge, is the wicked person’s version of our natural sense of injustice.”

Honor defies envy. “It takes some humanity to feel sympathy for those less fortunate than us; but it takes honor to avoid envying those who are much luckier.”

Good books. “A good book gets better at the second reading. A great book at the third. Any book not worth rereading isn’t worth reading.”

Money-talkers. “Money corrupts those who talk (& write) about it more than those who earn it.”

If they don’t go for the jugular, they don’t know where it is. “Nitpicking is the unmistakable mark of cluelessness.”

Simple problem solving. “General Principle: the solutions (on balance) need to be simpler than the problems.

Thankful complaints. “Humans need to complain just as they need to breathe. Never stop them; just manipulate them by controlling what they complain about and supply them with reasons to complain. They will complain but will be thankful.”

Ideals. “Erudition without bullshit, intellect without cowardice, courage without imprudence, mathematics without nerdiness, scholarship without academia, intelligence without shrewdness, religiosity without intolerance, elegance without softness, sociality without dependence, enjoying without addiction, and, above all, nothing without skin in the game.”

Bad math. “Thinking that all individuals pursue “selfish” interest is equivalent to assuming that all random variables have zero covariance.”

Enemy of an enemy can be your enemy. “I feel robbed by those who make money with no skin in the game (Rubin, Geithner, and bankers) but I despise attacks on inequality based on envy.”

Essentials, and deprivation. “Every human should learn to read, write, respect the weak, take risks in voicing disrespect for the powerful when warranted, and fast.”

Undirected gratitude. “The most important aspect of fasting is that you feel deep undirected gratitude when you break the fast.”

School vs life. “In real life exams someone gives you an answer and you have to find the best corresponding questions.”

Meeting-lovers. “Anyone who likes meetings should be banned from attending meetings.”

Assholes & Angels: Part I. “Every asshole is an angel somewhere.”

Assholes & Angels: Part II. “Every angel is an asshole somewhere.”

Asshole “experts.” “I wonder why news suckers don’t realize that if news had the slightest predictive and non anecdotal value journalists would be monstrously rich. And if journalists were really not interested in money they would be writing literary essays.”

Ivory prison. “In the days of Suetonius, 60% of prominent educators (grammarians) we slaves. Today the ratio is 97.1%, and growing.”

Aim at nothing to produce your best. “A writer told me “I didn’t get anything done today”. Answer: try to do nothing. The best way to have only good days is not to aim at getting anything done. Actually almost everything I’ve written that has survived was written when I didn’t try to get anything done.”

Different gods for different needs. “Paganism is decentralized theology.”

Existential Crisis Syndrome. “[T]he simpler and more obvious the discovery, the less equipped we are to figure it out by complicated methods.”

Targeted boredom. “The trick is to be bored with a specific book, rather than with the act of reading. So the number of pages absorbed grow faster than otherwise.”

Boredom as a guide. “Avoidance of boredom is the only worthy mode of action. Life otherwise is not worth living.”

Academic forgetfulness. “An academic is not designed to remember his opinions because he doesn’t have anything at risk from them.”

Words. “As in anything with words, it is not the victory of the most correct, but that of the most charming – or the one who can produce the most academic-sounding material.”

Trust. “[N]ever trust the words of a man who is not free.” [As an aside, I believe StartupBros has done so well so fast partly because we didn’t need it to work. We avoided monetizing it for a long time because we wanted to focus only on giving without trying to extract any value out of the thing. This has allowed us to keep our content honest, interesting, and supremely useful – we don’t hold anything back.]

Final Note On Antifragility

This has been a lot of information. Too much for a single sitting. Remember that this is meant to be a resource. Not something you go to once but something you come back to again and again. I wrote this as a resource for myself to return to when I need to find Antifragile wisdom.

The whole point here is that you don’t need to understand it all – you need to act more bravely. You need to transform these ideas into actions and, better, habits in your life.

I urge you to take a single idea from this post and put it into action in your life. Make a habit out of it.

We are drowning in too many ideas with news feeds full of bullshit promises. People post all the time about the power of simplicity but keep their mental lives chaotic. It’s impossible to implement many ideas at once, you’re going to fail if you try that. Pick one strategy and practice it for a week.

Remember that the idea is not to be able to know the future better, but instead our aim is to be more prepared for whatever the future brings.

The world is full of people pretending to know the answers to unanswerable questions and future outcomes of unpredictable events. They are persuasive and comforting – don’t believe them. Confidently call bullshit. Not that they’re definitely wrong, but that they might be wrong.

Above all, focus on potential payoff – not being right or wrong.

“Suckers try to win arguments, nonsuckers try to win.”

“The general principle of antifragility, it is much better to do things you cannot explain than explain things you cannot do.”

– Nassim Taleb


Avatar for Kyle Eschenroeder
Kyle Eschenroeder

Thanks for taking the time to read this! Let me know what you think - the good, the bad, the ugly - in the comments below.

I'm an entrepreneur (more in the StartupBros About Page) in St. Petersburg, FL

64 comments add your comment

  1. Thanks for inspiring me to take some risks in order to move on from things that aren’t working for me.

  2. Really interesting stuff, with deep ideas behind it. Thank you for putting it together.

  3. Just read this and loved it. You all may have moved on by now, but it’s a shining light to where I’m at today. Thanking you x

  4. Great post Kyle. Great job. Missing other parts that Nassim uses, Danny Kahnamen’s many biases, Nassim and him are very similar and friends, Bent’s work on Project Management and the great Murray Gill-Mann. He ties in complexity, which integrates it all, Nassim is a big fan of Murray and calls him the greatest scientist alive, which he is.

  5. Good read. The point that hit me most was how detriment (fragile lol) self-imposed “perfect” schedules are. Took notes of many other interesting points, and will drop by few more times to digest the rest.

    • Nice! I’d love to see your notes 🙂

  6. This reminds me of the woods behind my house, there are large trees that have stood for years and at the edge of the woods there are those small saplings that I have continuously run over with the lawn mower but keep coming back. If I were to take a chainsaw to the big trees they would likely die, but the small trees that have been brutally hacked every week have grown to accept this and have claimed there place through true struggle. I would much rather be a gnarly, hardened sapling than a large tree that can be destroyed by a small storm.

  7. Wow. Holy shit, what an article. I had just started reading “Thinking, Fast and Slow” by Daniel Kahneman, only to stumble upon this article just a few hours later the same day (yesterday). Such an unusual coincidence… Have you read “Thinking, Fast and Slow”, Kyle?

    A lot of these concept really hit home for me. I myself have changed a lot in the past 2-3 years (for the better), and the points that you (and Taleb) are making here probably have the potential to be massive catalysts of additional positive change in my life. The Barbell Strategy is especially interesting. I’ve adopted some of the strategies listed, for example lifting as heavy as possible and then resting as hard as possible, avoiding all kinds of pills and medication unless really necessary (taking supplements though), trying to consistently take cold showers, fasting/feasting, etc.

    So yeah, I strongly believe in the “go hard, or not at all”-way of living. Doing things with half-intent is just sucking value from others and sucking the soul out of yourself. On a somewhat related side note, I think that one of the problems with being paid by the hour as an employee is that you just gotta fill in your eight hours a day and make it appear as if you are busy – rendering full-intent work redundant (unless it’s something you ACTUALLY enjoy doing, which is unfortunately seldom the case). When you get paid by effort and intent is when you will have more incentive to do what you want, I think.

    Interesting heuristics as well. Some of my favorties:

    * “Fear the fragile/dull more than failure.” – I do, even more so now.

    * “Begin doing before reading.” – I think this one is underestimated. I spend way too much time reading up on stuff in before hand. Nothing was ever created by a person mindlessly always following someone else’s lead.

    * “Seeking order leads to pseudo-order. Embracing randomness leads to order.” – I won’t comment on this now, but spend some time reflecting on it. I think it’s too important 😀

    * “It it better to do things you cannot explain than explain things you cannot do.” – I always laugh, cringe, or do both, when I see fat nutrition/health/fitness-“experts”. Seeing a skilled artist create something is on the other hand amazing.

    Apart from being super interesting and double-plus-goodly awesome, this post was a fucking quote machine – in a non-mindless way, of course. “… rebel against the justified life.”

    Superb. Thank you for the value and motivation, Kyle.

    • Thanks for the kind words Alexander, I’m grateful you found the article and dug it 😀

      I’ve read Kahneman’s book and actually used it a bit here… but didn’t pull heavily from it. (Same for The Signal and the Noise, You Are Not So Smart, and Poor Charlie’s Almanack… the thing was already too freaking long lol)

      Barbelling life is awesome, I love the ones you’ve picked! I’ve been using supplements as well but I’m tempted to get off of them. Do you know anything about the negative effects people have been finding?

      Totally agree on your career idea! That’s why StartupBros exists… there are few things that upset me more than able people in jobs that incentivize you to choke your soul. It’s just shit management. It’s amazing to me how many successful businesses survive hiring creative employees and then doing everything they can to make them LESS effective.

      Great heuristic selection man, I hope they stay with you!

      • Thanks for the answer, Kyle!

        ON BOOKS
        “I’ve read Kahneman’s book and actually used it a bit here… but didn’t pull heavily from it. (Same for The Signal and the Noise, You Are Not So Smart, and Poor Charlie’s Almanack… the thing was already too freaking long lol)”

        I thought so. I’ve added Anti-Fragility and The Obstacle is the Way to my book list, guess you gave me three more books I’ll have to look up there… 😉

        I haven’t heard about potential negative effects of supplements, but a whole lot on positive effects. So I can’t answer you question… but I would be VERY interested if you’d find an answer to that question. I mean, maybe we’re all doing it all wrong.

        ON JOBS
        Agreed. I’m so happy I ‘know’ all this at a young age (19). I have made a promise to myself that I will not trust anyone else to prepare a career for me, i.e. I don’t trust my college education to give me a good/educative/fun job, nor will I ever trust pension money to provide for me when I’m older (not to mention that the whole notion of retirement is kind of lame, only implying that work is tiring and rest is energizing). Fear the dull more than failure! 😉

        • Which supplements are you doing it wrong with? (I’m assuming you know Mansal at the hacked mind? He’s got a ton of good stuff on that.)

          Fear the dull more than failure… true hell is dull failure lol.

          I’m looking forward to seeing you build SwoleMind, let me know how I can help when you need it

          • That’s what I would like to know! The ones I am taking on a regular basis are omega-3, vitamin D in the winter, creatine, sometimes caffeine before lifting, L-glutamine when fasting (as Ludvig recommended), and I put collagen hydrolysate (gelatin) in my tea sometimes. However, for the last 5-6 weeks I have barely been taking any supplements without noticing any difference. I believe that at some point, supplements become just redundant micromanagement, especially when you already got momentum from taking action. But I don’t know, I shouldn’t say too much about this.

            Yea, I’ve followed Mansal a bit, read some of his posts and listened to some of his podcasts. It seems obvious that supplements are a good thing, at least on a nutritional level.

            I haven’t posted anything on SwoleMind in two months (been totally occupied with learning programming), but currently trying to work out a new post. Avoiding cliché content is hard sometimes.
            Thanks, Kyle!

          • Yeah I can barely tell the difference with most supplements, except the ones that are probably terrible for me… like pre-work out, intense nootropics, the intense stuff.

            I wouldn’t necessarily avoid cliche content at first, especially if it’s stopping you from posting. If you actually want to make SwoleMind into something, right now it’s about consistency and getting used to making content.

          • Yea, same here. Caffeine (sometimes with L-theanine) is the only thing I notice, but that’s pretty obvious.

            I guess you’re right about creating content, consistency is key. Thanks man.

          • Consistency is nice… but it’s not even enough anymore. Nowadays you got to do something ridiculous, promote the hell out of it, and get lucky to make it lol.

  8. kind of ..fully immersed in the mobile lead generation arena..not really sure though about my place and unique advantage yet. Learned a hell of a lot in the last 7 months or so. Slowly gaining the confidence (at least on most days) to try unique concepts and approaches. Right now though solidly stuck in mediocre territory ..and hate it with a passion 🙂

    • I doubt it’s as mediocre as you think if you’re trying different things and learning… maybe mediocre results, but that’s temporary.

  9. All I can say is ..glad to have found this … currently in the midst of one of those “let’s go for it ” transitions in my life and still stuck at the “plucking along ” stage without seeing the breakthrough.

    My barbell is very very heavy on the risk side side at the moment since I followed Cortés ship burning model. Felt good at the time ( still does actually ) . It definitely has helped to increase my stoic capacity .. briefly interrupted by intense bouts of fear 🙂

    But so far in my last 55 yrs. things always had a tendency to work out just fine..and it was never a ” according to plan ” solution. So I assume in the end this time won’t be any different.



    • Burned ships 😀 I’ve done quite a bit of that as well! I do like taking away subpar choices… even if that means taking away plan b.

      Is Desmira the thing you’re going for?

  10. It’s easy for people to get ingrained in the day to day ‘rat race’ and not be interested in seeing what’s happening ‘behind the curtains’. You check off things from your daily task list, go to bed and repeat it again ad nauseum. And quite frankly, at various times, I find myself in the very same daily routine where you can’t see the big picture.

    But once one has taken the time to step back and put some reasoning into his existence, it’s hard not to go back to the daily routine with the big picture in mind: Once you’ve heard the music it’s part of you forever. Ideas are like ultra powerful viruses: the mere fact of describing them or even merely alluding to them initiates their viral propagation.

    It’s interesting to me to see the different ways we use our creativity to express this ‘big picture view’, that realization that stems from taking a step back from your daily routine. Your essay, Kyle, is fantastic in that is allows us to see this ‘big picture’, but through a different set of eyes than our own: yours!

    A while back, I felt the urge to express my perception of these truths about life and it took the form of 4 pictures that I painted on a wall in my house. They were a simplistic/rudimentary way to describe 4 forces/values that are critical in my (our?) life: Share, Now, Risk, New.

    * Share is the energy to give back from our experiences. If we do everything in a vacuum, we are missing out on a great opportunity: the opportunity for our life to become viral. Not necessarily on a large scale, but even at the micro level, this propagation is essential.

    * NOW! This is the time to act. If something is worth doing, there’s no reason to delay it further. Most people get stuck in the day to day and never get to the important stuff: “NOW” is the only time these important things should live in

    * Risk represents stepping outside of our comfort zone and doing things differently. In essence it is setting ourselves up for failure. Through these abnormal/different/novel/disruptive actions, ideas and opportunities will emerge and in one way or another, we might come out stronger/better/faster. But one thing is for sure, we will come out differently (an essential aspect of anti fragility)

    * New! is the variation, the novel approach that is essential in our existence. The other 3 aspects get painful if there is no innovation, creativity, novelty in their undertaking. ‘New’ is the spice in this dish. It is what keeps things interesting even when facing adversity. It is what makes the process self iterating.

    I have not ready any of Taleb’s books yet, but for me, Antifragility originates from those 4 structural pillars: they enable it, reinforce it and even go one step beyond: they make it go viral!

    Seek change NOW, and share your experiences!

    Thanks for a great post and for great perspectives!

    • Thanks for such a badass comment, Eric!

      I love The 4! Do you still have the paintings? Are they still hung up? I’d love to see these things!

      One of the wild things to me is how similar all these methods are. Your four are different than Linus’ (his:(1) There is no external authority; (2) Nothing ever goes wrong; (3) The next step is the only step; (4) Memento mori), yet they lead to a remarkably similar life. Not in content but in posture: one that allows us to positively add to and alter the world around us. One that can overcome the chasm of doubt – existential and otherwise.

      I’m fascinated by HOW people cement ideals in their lives – do you have a ritual that you follow to remind yourself of these daily? (Looking at the paintings, going through a list, ….)

      • Indeed it was Linus’ comment that motivated me to share this. Very interesting how ideas take different shapes yet convey a very similar base meaning.
        For me, I was so ‘gong ho’ about these 4 concepts that I painted them in my home office… As in permanently. 4 large frames of about 10 sq.ft. each. And a few years ago, well, we moved! I have no idea if they still stand there, but I suspect they didn’t survive too long: It’s not like they were Picassos or anything!

        I did not create them for the world to see, but because 1) I had to express them , and 2) as a daily reminder to myself, my family, coworkers, etc, as to the values that are important to me. So for many years, it was the first thing I saw when I started my day, and the last one I left the office with. But now, they only live in a few electronic photos that are occasionally shared. The values are still there, but the paintings are not.

        I have not re-painted the frames. For me, the culmination of these values took a very tangible form a few years ago that I am still living to this day! My family and I changed everything in our lives, and now, everyday we wake up in an environment that remind us of those 4 values.

        What does antifragility look like in your home? Do you have a daily routine/reminder/object that keeps the concept omnipresent?

        • I want to see this pictures! Will you share them with us here? Or feel free to email them… even the Importing Empire group would dig them 🙂

          That’s such an awesome example of using art/design to make massive shifts in the way a group of people can live. Businesses rarely use tools to that effect, even families rarely do… it’s a shame we don’t take time to commit to shared values with the people we most love. BUT YOU DID! That, sir, is a book.

          That’s a great question. I don’t have any physical objects that are there explicitly to remind me of antifragility (Will and I have 3 Startupvitamin posters hanging up: “Get shit done”, “Think Bigger”, and “Are you being productive or just busy?” and I have a sticker on my laptop “Alway deliver more than expected”, so there ARE certain things). My lifestyle and habits are reminders of antifragility: the decision-making heuristics, the cold showers, the fast/feast eating, the piles of books everywhere… all sorts of stuff. It’s been so front-of-mind for me that it’s actually the one thing I least need reminders of. What I DO want to introduce are physical reminders of certain aspects of antifragility and other philosophies. Some things I’ve considered: painting “amor fati” on a large canvas and putting it in front of my bed, an ouroboros tattoo, a painting of seneca, a painting of a skull… Alain de Botton’s Religion for Atheists has me wanting to ritualize certain habits. This is something I’ve been thinking about a lot… and probably won’t be able to help but post about here in the next couple months.

  11. Finally! I made it to the end. Took me 3 days and a traumatic experience with Animal Control to get through all this! The fact that I stuck with it, and came back day after day until I finished pretty much says it all! I usually give up 50 characters into a 140 character Twitter post! I’ve never read anything by Taleb, but none of this information seemed new. I don’t mean that as a criticism. What I’m saying is that I felt like after reading this, a lot of the ways that have always “done life” were affirmed and finally clearly articulated! I found my self saying…”yes…Yes….YES…” in agreement with every sentence! (Expect for the procrastination part. Procrastination is TOXIC in my life!)

    Now I have a word for how I try to live: antifragile! Thanks for writing!

    • Thanks for the awesome comment, Morgan! It’s weird how seeing your beliefs put into words and relabeled can be such a powerful experience.

      It’s awesome to know you 🙂

  12. Wow!

    I still can’t believe i found this blog. There is so much information, knowledge and insights! I think I found the Starupbros 5 days ago and I can’t stop read it. Starupbros is not just one of this standard bussines blogs that basicaly, using the initial quotation of the post, “explain things that they cannot do”. I feel like I found the golden mine of the internet. Not just because of the knowledge that each of you teach us here, but because you put us in contact with certain ways of thinking that I would not even know that exist(this post is one good example).

    So, I would just want to say thank you for creating this amazing enterprise, that is helping me so much.

    (By the way, sorry for the english. I know I probably, in at least a couple of phrases, if not more, i looked like one caveman writing. So, yeah, english is not my first language).

    • I’m so glad you’re finding the site useful, Luiz! I’m interested, what IS your first language?

      Looking forward to having you in the community 😀

      • Haha
        Thank you, Kyle. My first language is the Portuguese, I’m from Brazil.

  13. BOOM!

    10/10 Kyle. (Yeah, you’re a ten!)

    Queue long-ass comment:

    “Keep in mind that your progress will not look like a nicely sloping line up and to the right. No, no. It’s going to flat line, dip, plateau, then spike.”

    –I think that this phenomenon also has a lot to do with how the brain takes on habits. How it goes through the “competence ladder.” (going from unconscious incompetence to unconscious competence)… That last step, when you get the habit and you automatically do things well, that comes VERY suddenly. You often don’t notice it.

    “In short, the fragilista (medical, economic, social planning) is one who makes you engage in policies and actions, all artificial, in which the benefits are small and visible, and the side effects potentially severe and invisible. ”
    – Nassim Taleb

    –From a political standpoint, this is why democracy is so flawed. The masses just wanted to be kept safe. And what do they want to feel safe from? Whatever threats they can ANTICIPATE, not the black swan events. Which is what they SHOULD, preemptively, be hedging themselves against to their best abilities. But no…

    Instead they are willing to give up their freedom and rights for stricter regulations that will “supposedly” make “them” safer. Except there is no them. Society is made up of individuals, and when the freedom of the individual is taken away, incrementally of course, society just gets LESS safe. So, the fragilistas (most people) end up harming themselves with their own ideas.

    “If you have more than one reason to do something, don’t do it.”

    –This sounds really clever… But is it really? How does Taleb know this? Can you give some example(s) where this has proven particularly useful?

    I can understand that it may be a good heuristic for avoiding post-rationalizing your decisions and talking yourself into thinking that you “should” do something;

    Haha. Damn, Darwin was a badass. Preferring to pursue studies of evolutionary biology and speaking to “clever men” over ladies any day of the week.

    Interesting to hear. It’s kind of the same thing for me. But slightly less extreme. I will admit that I am addicted to reading books and taking notes.

    Not sure I agree. I think procrastination can serve a good function for highly intelligent and accomplished people. But for the average joe, it’s just a bad habit that has been conditioned over time. How does the typical person procrastinate? By masturbating, watching TV, playing video games, or checking social media.

    I was wondering when you’d make a reference to that. It fit in so well here!
    Paraphrase: “If you can avoid common mistakes, you’ll do better than most people.”

    Taleb is a genius. But I am not taking his gym advice. He’s on point about fasting, cold showers, etc… All those things help you break out of homeostasis, and grow stronger via hormesis.

    Funny about Taleb’s medical advice. I think he’s right about it, but he’s talking about American doctors. In Sweden it’s the opposite. The doctors will try to reject you even if you have a serious problem, and if you somehow can convince them that your problem is serious enough to require medical attention, they will just do the safest/cheapest thing possible. It’s complete crap. But, it’s mostly governments subsidized.

    “Rules are for the obedience of fools and the guidance of wise men.” – David Ogilvy

    –Great quote. Losers follow rules made by others, without questioning. Winners questions rules, and create their own based on trial and error.

    I strongly recommend you watch this talk with Daniel Kahneman and Nassim Taleb. They discuss antifragility. It’s long: 1h 17 min. I don’t many YouTube vids, but this one was worth it.

    • You made me bust out my text editor to reply to this. Impressive!


      (I’m only responding to disagreements because, well, they’re more fun/interesting 🙂 )

      - I always think of sudden consequence as a “click”. It’s the moment where enough of a skill has been internalized to leave the conscious mind completely out of it.


      “If you have more than one reason to do something, don’t do it.”

      For me, it’s proved effective. Taleb cites a couple examples where he’s used it but, after this article, I’ve put Antifragile away for a while 😉

      For me, it’s the best way I know of “following my heart”… because I don’t really know how to follow a heart.

      A lot of times it’s the thing that has been nagging me for a long time but I avoid to do other things that “make more sense.”


      - This article. I’ve been avoiding it forever because I knew it would take a long time, I probably would do it badly, and there is NO demand for this kind of shit man.

      I have a list of 5 other articles that make much more business-sense to have published. There are few good business reasons to do this article. But I’ve been wanting to do it forever, and I couldn’t stop thinking about it, so I did.

      - I went to a 6-week film program. There were no great reasons for me to do so other than I have this nagging feeling that I wanted to learn film. It would have made more sense for me to go to a writing program or nothing at all. Now that info is going to become extremely useful as we bring StartupBros into video.

      - I have no great reasons to be with my girlfriend. I’ve dated a lot of other girls that made much more sense, that fulfilled many more of my checkbox-requirements I have for a mate. But the idea of being with this girl just nagged at me. She stood on her own for no rational reason, and she’s the best choice by far. (Same with friends, the more reasons you have for being with them the harder you’re trying to like someone you actually don’t.)

      - I do this all the time to make decisions. It’s my best tool for avoiding leading a rationalized (dishonest) life.


      The key is awareness. Do you go to research as procrastination? Are you taking in information to FEEL productive when you should just be reading for pure pleasure?

      Consciousness of the relationship to info is the aim for me.


      Right. They can learn a lot about themselves if they take note of what they do before they procrastinate. Not all procrastinating is productive, but awareness of it can be.


      Yeah, those boys are my favorite kind of simplicity. I’ve been tearing up Bevelin’s other stuff, too. And just ordered Poor Charlie’s Almanac… so excited. Farnam Street ran a great article on differentiating b/w loser’s and winner’s games:



      Fascinating! So, in some ways, an underfunded medical program could be helpful lol.

      Unfortunately, government-medicine in the US usually means MORE abuse and useless visits.


      HOLY HOLY HOLY great interview find! I haven’t been more excited about watching a conversation in a long time. I actually started pulling from Thinking, Slow and Fast but this thing was just starting to get even more bloated. Thanks for that.

      And thanks a TON for the thoughtful comment man. I really appreciate having to dig in deeper to ideas and question ideas I hold.

      • Thanks for the equally insightful answer, Kyle!

        “For me, it’s the best way I know of “following my heart”… because I don’t really know how to follow a heart.”

        –That makes sense.

        “This article. I’ve been avoiding it forever because I knew it would take a long time, I probably would do it badly, and there is NO demand for this kind of shit man.”

        –So true. So sad.

        “Now that info is going to become extremely useful as we bring StartupBros into video”

        — Awesome to hear.

        “It’s my best tool for avoiding leading a rationalized (dishonest) life.”

        — Alright.

        I now understand the meaning of that aphorism a lot better. Thanks.

        • Aphorisms are tough to get to hit home man, but when they do… KAPOW

  14. Powerful stuff. Especially loved your insights about embracing depression.

    And making fewer decisions. Often, I feel guilty going for the “Low Hanging Fruit”. But it is so obviously right in front of me, I can’t help it.

    If nothing else, Buffet will help me feel less guilty. :p

    • Good Guy Buffett, always offering consolation to the lazy lol

  15. Holy shit.

    This is almost spooky. Like you’ve taken my experience of life over the past ~7 years and broken it down in neatly arranged points. It crystallizes a lot of the things going on in my head that I have a hard time explaining to others, and things I’ve observed and realized from my own experience. I never read Taleb’s books, but this is my life almost down to the paragraph.

    Maybe this will be of value to you. Some time ago, I came up with 4 guiding principles (perhaps you’d think of them as heuristics). They came to me in the middle of the night, forcing me to get up and get them on paper…

    Everything in my life has been reduced to these four things:

    1. There is no external authority. (Meaning: most people live their lives through the eyes of others, not realizing they themselves are the ultimate, supreme, sovereign authority in their lives… related to this article’s point of “why we seek advice.” One of the strongest urges among most people is to abdicate the responsibility for their own lives to some external agent. Parents, school, “the system,” the guru, etc. People will go to extreme lengths in order to avoid being an actual person in their own right. “Think for yourself, or not at all”)

    2. Nothing ever goes wrong. (If you believe things do go wrong, it means you are in conflict with reality. The tsunami that wipes out a village is not “wrong.” It just is. The ocean is never wrong. You can’t argue against the ocean. If you believe it is bad or wrong, it just illuminates your own bullshit. Embrace reality, love your fate, and understand that anything that happens is the best thing that could possibly happen. It doesn’t matter how bad it seems in the moment, because you cannot predict the future. You can’t see the whole picture. The event that seems so horrible in the moment is like a single thread interwoven with many others in a large canvas called Your Life. And just because you can’t see the whole picture doesn’t mean it’s not there to be seen.)

    3. The next thing is the only thing. (Again, you can’t predict the future. Nothing good that has ever happened in my life has come out of “making a plan and executing”. I don’t make plans. I don’t know where my life is going. That’s the point. I just focus on the thing in front of me – the next thing – and trust that whatever thing that will show up after that is going to be infinitely better than whatever I could have conjured up in my head and planned my way to on my own. More importantly: if I DID try to plan my way to success, I would be closed off to the opportunities that would otherwise present themselves…)

    4. Memento mori. Remember you must die. (Awareness of death is the same as awareness of life. If you are not aware of your death, you cannot be aware of your life. Close your eyes and focus on your breath. Understand you’re never getting those breaths back. The clock is ticking. There’s an invisible expiry date stamped on your forehead. And it’s closer than you think. Severe accidents we think only happen to “other people” are just around the corner; you could get hit by a bus tomorrow afternoon. And even if you die of old age, it’s much closer than you imagine. Certainly, you’ll realize this at 85, reflecting on how you always thought you would have more time. Accept and embrace the fact of your own death. (And forget any “how many people will show up at your funeral” bullshit… NEVER do anything based on other people’s validation…))

    That’s it. Fantastic post.

    • First of all, Magnetism was great. I tore through it in 2 sittings.

      “Magnetism: “He has the power to influence others with the delight he takes in himself.””


      I love your 4 principles. If you haven’t read (or reread) Emerson’s Self-Reliance… well, you’ve got to for #1.

      #2 reminds me of my mantra “amor fati”. Nietzsche: “My formula for greatness in a human being is amor fati: that one wants nothing to be different, not forward, not backward, not in all eternity. Not merely bear what is necessary, still less conceal it—all idealism is mendaciousness in the face of what is necessary—but love it”

      3 and 4 are great too, presence of mind and appreciation of impermanence… magic stuff.

      I’m curious – how do you keep these principles in front of you daily/hourly? I’m getting interested in ways to deeply ingrain ideas (aiming for religious-level faith).

      Thanks for the love! Glad you dug the post Linus.

      • That’s a good question. I never really bought into the whole “creating systems in your life” thing that every blogger and his dentist is doing. Methodically following and implementing new habits, morning routines etc. Doesn’t work for me or align with how I see the world.

        My time management system essentially boils down to: I do what I feel like doing when I feel like doing it. If something needs doing, I trust there will come a time when I feel like doing it. If such a time doesn’t come, then it doesn’t get done and didn’t need doing.

        Sounds weird and counterintuitive, and the only reason it would ever work for anybody is if they have moved away from living their lives from a place of fear. Fundamentally there are two possible “operating systems” for human beings: fear or gratitude. If you are still in fear this absolutely doesn’t make sense. If you are in gratitude, this is natural and effortless and works amazingly well.

        All this to say: these four principles are what I’ve arrived at after thinking hard about this kind of shit for the better part of a decade, lol. I just think about it constantly. I don’t go out of my way to try to ingrain things in my brain.

        Things appear in my head, uninvited. I watch them and observe, and let them live or die on their own. Some ideas are antifragile and they just dig deeper roots for themselves as time goes on.

        • I fall into the same camp of doing what I want when… usually it’s based on what I can best do with the mood/energy I currently have.

          Alain de Botton’s Religion for Atheists has me wanting to create rituals though. Reminders of key ideas and rituals to ingrain them. It’s an immediate version of institutionalizing ideas – taking them out of books and out of us and injecting them into environments.

          It’s great how when you begin studying anything it becomes impossibly complex, then, after a while, if you keep pushing through, it becomes simple again. Smart-simple instead of stupid-simple. I wonder how much more your 4 principles mean to you than they could do anyone else. They recall a long process that was unique to you. Of course they’d be powerful for anyone to embody…

          Antifragile ideas embed themselves, indeed!

          What have you been working on?

          • You’re definitely right about that. I think most people never get to grasp anything at a high level. Reduction to the essentials is really only possible when you really know what the hell you’re talking about. You start by learning the fundamentals and you think you get it. Then you spend a couple years diving into something and come back to right where you started, now with a whole new perspective of what those fundamentals really mean…

            There’s a lot of people who would read your comment about things becoming smart-simple and think they know exactly what you’re talking about when, in reality, they haven’t the slightest clue…

            And yes, absolutely, I can’t imagine someone reading over my four little principles and inferring the same meaning and value out of them as I do. That’s why you can’t blindly follow and trust anyone else’s rules. If someone wants to become a “sovereign person” in their own right, not only should they make their own rules, they kinda have to.

            I’ve been up to lots of stuff! How come I don’t have y’alls on skype yet? Email me?

          • “… they kinda have to.”

            Indeed, sir.

            Looking forward to talking with you!

            (Just emailed you)

  16. I have to admit that I still have to finish reading your blog post but… you had me at the real beginning! Bought that book, already have it in my Kindle atm…
    Thanks for the great suggestion-s, see you in the Antifragile Heaven 😉

    • This is a great primer for the book, I think you’ll only like these ideas more and more 🙂

  17. Wow, Kyle. This was very well done. Read the entire post from beginning to end, to honor the efforts of you and Nassim Taleb.

    One part that really struck me was the quote: “We often benefit from harm done to us by others; almost never from self-inflicted injuries.”

    I have a tendency towards the masochistic side of “No Pain, No Gain,” and I’m wondering if I do a lot of self-harm. Possibly. This is a HUGE perspective shift.

    Maybe I don’t need to purposefully harm myself? Maybe other people will do it, and I will grow stronger from that, without purposefully arranging my life to make it as miserable and painful as possible?

    It seems that I really want to become antifragile, so I set up an extremely painful life for myself, not trusting the Universe to bring me pain in all of its randomness.

    Strange world we live in. I love it! Especially when things start to click, and you stop resisting the pain so much.

    • Thanks Josh, I’m loving your site now. Great series on writing. “To a novice, obstacles are enemies. To a writer-craftsman, obstacles are allies.” Nice, have you read Ryan Holiday’s new book? It’s pretty much just about that lol.

      I think that if you have the opportunity for self-harm then you aren’t pushing hard enough.

      If the world isn’t giving enough resistance then it’s your job to go harder, not create problems for yourself.

      Easy said, terribly hard to do.

      The only way to “work against” yourself that makes any sense to me is covered in the “acute stressors” section. So I work against my muscles when I work out so they can get better. I work against my desires all the time (fasting, cold showers) in order to build willpower. But other than specific situations where you know you’ll grow… there’s no reason for it.

      Like you said, life serves up all the stressors we need lol

      • Kyle, I think you hit it right on the head. Too much free time on my hands leads to masochistic behavior that harms me…instead, I need to channel that into greater challenges. Time to read some more Warrior Mindset books, and really go much harder in my business pursuit (and becoming a writer-craftsman).

        I’ve heard much about Stoicism and Ryan Holiday, though I haven’t read the book yet. I’m currently reading a bunch of books, and one of them is Meditations by Marcus Aurelius. Interesting mindset; I also like the Samurai mindset and the ethics of Bushido.

        I must trust life to deliver the right pain, and the BEST pain for my situation. I am learning to see Pain as my greatest ally. Apathy and Stagnation are the enemies.

        • Pressfield’s The Warrior Ethos is a really fast, really badass read for the warrior mindset.

          I just finished Meditations, pretty great but gets super repetitive. That is actually interesting in itself though because you can see the exact things that this ruler had to keep reminding himself of in order to keep his sanity.

          One thing I noticed in your comment is the emphasis on finding new things to read… it sounds like you might benefit in a huge way from taking an Input Deprivation Week and focus on taking action on (and discovering what) you already know.

          I hope you’ll pardon the unsolicited advice! I just see a similarity in the way I normally talk when I’m frustrated by feeling like I need more information when what I really need is to DO shit.

          Let me know what you think!

  18. Epic post. Thankyou. I will definitely refer to it over time, and think deeper about many sections to absorb it the best I can. It really blew my mind, as I have been aiming to be more planned, more organised, more predictive, forecasting my wealth/budgets etc, and have felt it has been to my detriment. Now I feel like I struggle to make small decisions, what brand of razor to buy? what drink shall I order?…

    This is timely too, as my job finishes in about 2 weeks – so I will hope to implement some of this in my life.

    Just reinforces that there are so many great minds out there, and that our human existence has been brought up on mostly solid bullshit.

    Cheers, Lee.

    • Hey Lee,

      I think we talked awhile about an entrepreneurial venture of yours – how is it going?

      Glad you liked the post! I really hope you implement the ideas in your life in a real way. They’re SO helpful it’s absurd.

      • Hi Kyle, you have a good memory! Since last time, I had resigned from my job, (government) and moved to Canberra, my partner got work here as a student counsellor first, then I got a job as a ‘data manager’ at a not-for-profit organisation, but the place got the chop because of the new federal budget here in Australia and I finish soon.

        So I am currently looking for another job, and again also considering my web businesses and whats involved. – Ive been doing quite a bit of reading, but still yet to commit for various reasons. At this stage I am going to try and build “something” of value as a side venture/hobby/business…That way my risk is low, but can get an indication of what works etc.

        My partner has her website going, (now a side project for her) but no income attached yet. Will just keep it bubbling along for now, as she works on an ebook to sell via the site


        I’ll let you know when I get my sites and business ideas ready to roll 🙂

        Cheers, keep up the good work.

        • Thanks for the update, Lee!

          I’m curious – what information can we provide that would most help you with your business now?

          (Feel free to comment here or email.)

  19. Solid post Kyle, this took me a while to read and process having to reread several parts… Certainly more of a resource rather than typical blog post. I love your philosophical views and hunger for life, similarly I enjoyed your section in Self Made U.

    My life got so much better when I unconsciously began doing antifragile things and adopting a more anti fragile lifestyle. I finished up my academic life and began doing the things I truly wanted to. Slowly the depression and anxieties of bullshit academic life lifted and I saw things in a new clarity. This clarity is MY clarity and it involves doing what I enjoy and taking action with tenacity.

    Shout out to all the folks out there who have gone through their personal hell and came out stronger. Negative emotions, illness, disease, hardship etc. Can all be used to learn about life and get better. Some people will forever be fragile wage slaves and I feel bad for them. Who on their death bed wants to utter the words “I wish I did that…” Cheers to the brave folks out there failing, flailing and struggling through the meandering path we call life. Chaos seems to be the only true constant and entrepreneurs leverage it.

    • Amen!

      I’m happy you dug the book, too!

      (Love your site btw 😀 )

  20. Very detailed and useful post. The hard work pays off in that the content is very valuable and appreciated. There is some stuff here and there that I don’t agree with but the overwhelming majority of the concepts are new to me and very enlightening. I didn’t know about Mr. Taleb before this article. Thank you, Kyle!

    • Awesome Mario! I’m glad a lot of the ideas were new for you!

  21. You know, some things just make you say…. hmmmm, never thought of it that way before.

    After taking 2-1/2 hours to read this (yeah, I read slow—what about it?!?), I’m saying… hmmmm, never gonna think the same way again.

    Where does a punk kid (and I mean that in just the nicest way possible), learn to be so, what’s the word I’m looking for? Oh yeah, so heuristic, when an old guy like me is still struggling to find his own way?

    I liked the read. My mind is officially blown!

    • hahaha I read slow as well, I’m honored you took the time!

      And I’m grateful it could help change your thinking, even in a small way

    • Often it is. Sometimes, more is more – redundancy! lol

  22. Impressively comprehensive post Kyle!

    I’ve read Anti-Fragile, and also loved it. It was very high value for being a ‘not-so-difficult’ read. Your post is much easier to understand!

    Thank you

    • It’s funny how Taleb’s work has gotten more and more friendly for the non-technical reader. The first book was a textbook on using options. Then Fooled by Randomness was his first work meant for mass consumption but it’s still extremely technical. Black Swan a little less. He was getting comfortable being non-technical by the time Antifragile came.

      Thanks for the comment man!

      • What year was this written? Other bloggers can’t cite you without a year!

        • 2014, but most would anyway 😛
          I’m looking forward to reading your piece!

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