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:


Fragile Robust Antifragile
Mythology Sword of Domocles, Rock of Tantalus Phoenix Hydra
Black Swan Exposed to negative Black Swans Exposed to positive Black Swans
Businesses New York: Banking system Silicon Valley: “Fail fast,” “Be foolish.”
Biological & Economic Systems Efficiency, optimized Redundancy Degeneracy (functional redundancy)
Errors Hates mistakes Mistakes are just information Loves mistakes (since they are small)
Errors Irreversible, large (but rare) errors, blowups Produces reversible, small errors
Science/technology Directed research Opportunistic Research Stochastic tinkering (antifragile tinkering)
Dichotomy event-exposure Studying events, measuring their risks, statistical properties of events Studying exposure to events, statistical properties of exposures Modifying exposure to events
Science Theory Phenomenology Heuristics, practical tricks
Ethics System without skin in the game System with skin in the game System with soul in the game
Regulation Rules Principles Virtue
Epistemology True-False Sucker-Nonsucker
Financial dependence Corporate employment, Tantalized class Dentist, dermatologist, niche worker, minimum-wage earner Taxi driver, artisan, prostitute, f*** you money
Learning Classroom Real life, pathemata mathemata (learn by suffering) Real life and library
Political system Nation-state; centralized Collection of city-states; decentralized
Social System Ideology Mythology
Post-agricultural modern settlements Nomadic and hunter-gatherer tribes
Knowledge Academia Expertise Erudition
Science Theory Phenomenology (direct experience) Evidence-based phenomenology
Psychological well-being Post-traumatic stress Post-traumatic growth
Effect on Economic Life Bureaucrats Entrepreneurs
Reputation (profession) Academic, corporate executive, pope, bishop, politician Postal employee, truck driver, train conductor Artist, writer
Reputation (class) Middle class Minimum-wage person Bohemian, aristocracy, old money
Medicine Via positiveAdditional treatment (give medication) Via negativeSubtractive treatment (remove items from consumption, say cigarettes, carbs, etc.)
Philosophy/science Rationalism Empiricism Skeptical, subtractive empiricism
Knowledge Positive science Negative science Art
Stress Chronic Stressors Acute stressors, with recovery
Decision making Acts of commission Acts of omission (“missed opportunity”)
Literature E-reader Book Oral tradition
Business Industry Small business Artisan
Finance Debt Equity Venture capital
General Large Small but specialized Small but not specialized
General Monomodal Barbell [We’ll discuss these soon!]
Noise-signal Signal only Stochastic resonance, simulated annealing
Education Soccer mom Street life Barbell: parental library, street fights
Physical training Organized sports, gym machines Street 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, Noncomplex The Organic, Complex
Needs continuous repair and maintenance Self-healing
Hates randomness Loves randomness (small variations)
No need for recovery Needs recovery between stressors
No or little interdependence High degree of interdependence
Stressors cause material fatigue Absence of stressors cause atrophy
Age with use (wear and tear) Age with disuse (use it or lose it)
Undercompensates from shocks Overcompensates 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:


Field Origination and Development as Marketed by Bird Lecturers [Or: Where they told us the innovation came from.] Real Origination and Development
Jet Engine Physicists (busted by Scranton) Tinkering engineers with no understanding of “why it works”
Architecture Euclidean geometry, mathematics (busted by Beaujouan) Heuristics and secret recipes (guild)
Cybernetics Norbert Wiener (busted by Mindell) Programmers “wiki-style”
Medicine Biological understanding (busted by a long series of doctors) Luck, trial and error, side effects of other medicines, or sometimes poisoning (mustard gas)
Industrial Revolution Growth in knowledge, Scientific Revolution (busted by Kealey) Adventurers, hobbyists
Technology Formal science Technology, 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



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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

  • Avatar for Kathy Wittes Kathy Wittes says:

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

  • Avatar for Hydra wannabe Hydra wannabe says:

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

  • Avatar for Liz Moscrop Liz Moscrop says:

    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

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