Antifragility. It’s an awkward word but one that sinks in to your consciousness as you read “Antifragile: Things That Gain from Disorder” by Nassim Nicholas Taleb. As a big fan of The Black Swan by the same author, I eagerly devoured this book. It takes the findings of the Black Swan and projects it outwards in to a philosophical and pragmatic outlook on modern life. Taleb is a divisive, opinionated, funny and passionate writer and this book, like his last, seems to have settled in to place at the base of my spine where I will carry it forever.

So what does antifragile mean? Well if you have a linear scale with “fragile” on the left, the common thought is that “robust” sits opposite to that on the far right. However what Taleb introduced with the notion of the Black Swan and expands upon now, is that robust doesn’t exist as this polar opposite state to fragility. Instead, a robust system is one that protects itself against known dangers, but as a consequence is hugely vulnerable to Black Swan, or unpredictable, events. Taleb instead proposes the notion of antifragility as it represents both preparation for known fragility whilst also allowing for the unknown. Whether they be small, large or Black Swan sized setbacks, the antifragile person or organization is set up to roll with the punches and still come out fighting.

If you work in an agile software development environment, or are an entrepreneur, or work in an entrepreneurial environment, then you are probably seeing some key familiarities with your daily work-life. The much discussed innovators burden is that they need to accept failure more than success, because every setback propels you forwards in the end, so long as you learn from your mistakes and can keep going. Failures should be bumps on the road to success, not big gaping pot-holes from which you will never emerge. Taleb himself sees this correlation between antifragility and start-up, Agile business culture, so I wanted to share some of his nuggets of wisdom.

On Entrepreneurs & Start-Ups

To answer the question of where Taleb sits on the scales of opinion regarding entrepreneurs, I present exhibit A:

My dream—the solution—is that we would have a National Entrepreneur Day, with the following message: Most of you will fail, disrespected, impoverished, but we are grateful for the risks you are taking and the sacrifices you are making for the sake of the economic growth of the planet and pulling others out of poverty. You are at the source of our antifragility. Our nation thanks you.

His impassioned view of entrepreneurs and scrappy start-ups ties very closely to his views on education. He believes in trial and error, and people who forge a path with nothing or little to lose and a lot to gain.

No one at present dares to state the obvious: growth in society may not come from raising the average the Asian way, but from increasing the number of people in the “tails,” that small, very small number of risk takers crazy enough to have ideas of their own, those endowed with that very rare ability called imagination, that rarer quality called courage, and who make things happen.

Also that start-ups fertilize the soil on which the economy will continue to grow:

The fragility of every startup is necessary for the economy to be antifragile, and that’s what makes, among other things, entrepreneurship work: the fragility of individual entrepreneurs and their necessarily high failure rate.

Whilst also forging the path towards greater knowledge:

Entrepreneurship is a risky and heroic activity, necessary for growth or even the mere survival of the economy. It is also necessarily collective on epistemological grounds—to facilitate the development of expertise.

So foster that pursuit of trying new things and learning from your mistakes and failures:

my characterization of a loser is someone who, after making a mistake, doesn’t introspect, doesn’t exploit it, feels embarrassed and defensive rather than enriched with a new piece of information, and tries to explain why he made the mistake rather than moving on. These types often consider themselves the “victims” of some large plot, a bad boss, or bad weather.

On Innovation

In turn, innovation evolves out of this entrepreneurial, trial and error, antifragile spirit:

How do you innovate? First, try to get in trouble. I mean serious, but not terminal, trouble. I hold—it is beyond speculation, rather a conviction—that innovation and sophistication spark from initial situations of necessity, in ways that go far beyond the satisfaction of such necessity (from the unintended side effects of, say, an initial invention or attempt at invention) … The excess energy released from overreaction to setbacks is what innovates!

Also an interesting outcome of the antifragile thinking is that the best ideas should come via negativa:

we know a lot more what is wrong than what is right, or, phrased according to the fragile/robust classification, negative knowledge (what is wrong, what does not work) is more robust to error than positive knowledge (what is right, what works). So knowledge grows by subtraction much more than by addition—given that what we know today might turn out to be wrong but what we know to be wrong cannot turn out to be right, at least not easily.

And just like a good writer or programmer who enjoys removing words and code to reach a more elegant solution, Taleb quotes one of my favorite Jobs-ism’s:

Finally, consider this … saying from Steve Jobs: “People think focus means saying yes to the thing you’ve got to focus on. But that’s not what it means at all. It means saying no to the hundred other good ideas that there are. You have to pick carefully. I’m actually as proud of the things we haven’t done as the things I have done. Innovation is saying no to 1,000 things.

On Risk Taking 

Risk taking is where the spirit of antifragility meets reality. There must be an acceptance of asymmetric payoffs:

To see why asymmetric payoffs like volatility, just consider that if you have less to lose than to gain, more upside than downside, then you like volatility (it will, on balance, bring benefits), and you are also antifragile.

As a product manager in software development, this quote rang so true about decisions our product team make daily:

In other words, if something is fragile, its risk of breaking makes anything you do to improve it or make it “efficient” inconsequential unless you first reduce that risk of breaking.

Taleb also proposes a heuristic against which to validate your ideas by using extremity of opinion, both positive and negative (of course):

consider this simple heuristic: your work and ideas, whether in politics, the arts, or other domains, are antifragile if, instead of having one hundred percent of the people finding your mission acceptable or mildly commendable, you are better off having a high percentage of people disliking you and your message (even intensely), combined with a low percentage of extremely loyal and enthusiastic supporters. Options like dispersion of outcomes and don’t care about the average too much.

It is also not about being right most of the time but instead being wrong with impunity and right that one time when it matters:

The frequency, i.e., how often someone is right is largely irrelevant in the real world, but alas, one needs to be a practitioner, not a talker, to figure it out. On paper, the frequency of being right matters, but only on paper—typically, fragile payoffs have little (sometimes no) upside, and antifragile payoffs have little downside. This means that one makes pennies to lose dollars in the fragile case; makes dollars to lose pennies in the antifragile one. So the antifragile can lose for a long time with impunity, so long as he happens to be right once; for the fragile, a single loss can be terminal.

On Education

Taleb is unforgiving in his assessment of the education system in the modern first world. The most powerful idea he presents is an assessment of the relationship of between education and wealth:

The implication is nontrivial. For if you think that education causes wealth, rather than being a result of wealth, or that intelligent actions and discoveries are the result of intelligent ideas, you will be in for a surprise. Let us see what kind of surprise.

I fully agree with this, now I read it, but I had never reviewed the relationship objectively in this way. Once you do, you see that entrepreneurialism and risk-taking in the US are the bases of future growth and wealth and it is this spirit that we should be fostering along with core STEM fields:

Many people keep deploring the low level of formal education in the United States (as defined by, say, math grades). Yet these fail to realize that the new comes from here and gets imitated elsewhere. And it is not thanks to universities, which obviously claim a lot more credit than their accomplishments warrant. Like Britain in the Industrial Revolution, America’s asset is, simply, risk taking and the use of optionality, this remarkable ability to engage in rational forms of trial and error, with no comparative shame in failing, starting again, and repeating failure.

And once again, what we see in software development so often now, is that some of the best developers are those passionate “amateurs” without the formal training:

Amateurs in any discipline are the best, if you can connect with them. Unlike dilettantes, career professionals are to knowledge what prostitutes are to love.

I just love that last line!

On Data

I found it very refreshing to read Taleb’s perspective on data, and particularly the dangers of big data. Working on the web you are constantly made-aware of the need to gather and use data to guide your decision-making. This is not something I disagree with per se, but something I am wary of, and Taleb captured my wariness in three words:

data increases intervention

Like a doctor who feels he must prescribe a pill in order to have a sense of agency in an uncertain situation, a product team will feel the need to constantly tinker with their product as a result of data, which is not bad in itself, but is compounded by the very quantity of data available:

In business and economic decision making, reliance on data causes severe side effects—data is now plentiful thanks to connectivity, and the proportion of spuriousness in the data increases as one gets more immersed in it. A very rarely discussed property of data: it is toxic in large quantities—even in moderate quantities.

So amid this large quantity of data, the real information can be lost, skewed or overlooked altogether:

Modernity provides too many variables (but too little data per variable), and the spurious relationships grow much, much faster than real information, as noise is convex and information is concave.

Going back to innovation via negativa, data should be used likewise:

Increasingly, data can only truly deliver via negativa–style knowledge—it can be effectively used to debunk, not confirm.

On Life

I will end with a more general quote, but one that demonstrates the underpinning of Taleb’s whole outlook and why this book just sang to me. The fact that life is about ups-and-downs. About failures and successes, and risks and rewards. To try and level everything out is to set yourself up for a bigger and more inevitable fall, like the economists who thought modern financial life had evolved beyond the boom-bust cycle just before the greatest depression in 60 years. There is no flat line through life, but if you are ready for the troughs and protected against the unknown, then the peaks will be all the sweeter and more lucrative:

The best way to verify that you are alive is by checking if you like variations. Remember that food would not have a taste if it weren’t for hunger; results are meaningless without effort, joy without sadness, convictions without uncertainty, and an ethical life isn’t so when stripped of personal risks