Surprises are part of life. You never know for sure what’s going to happen next. After all, we’re complex individuals interacting with other complex individuals within the complexity of nature.

If none of us know what will happen next, then why is it some people do well no matter what? Nassim Taleb would call these people antifragile, an idea explored in depth in his book ‘Antifragile: Things that gain from disorder.‘

Antifragile is the opposite of fragile

To understand antifragility, it helps to think about fragility.

Fragile things break when they are stressed or surprised but are fine when everything is the same. Think of glass or ceramics.

You might think the opposite of fragile is robust or resilient. Something that is fine no matter what happens, like a rock or diamond. But robust isn’t the opposite of fragile, because it doesn’t get better when stressed or surprised.

The opposite of fragile is antifragile. Things that get better when they are stressed. Thriving. Like muscles or a good pair of jeans.

Antifragility is beyond resilience or robustness. The resilient resists shocks and stays the same; the antifragile gets better.

Of course, there are limits to things getting better under stress. Too much weightlifting and you might get injured. Too much wear of your jeans and they break. While everything breaks eventually, the antifragile lasts far longer than the fragile.

Organic and complex

Something antifragile is often organic and always complex. Organic being the biological and natural. Complex being a system of things that interact with each other.

While complex, the antifragile is not usually complicated. Complicated systems are not only difficult to understand but also lack the interdependencies within a complex system.

With complex systems, interdependencies are severe. You need to think in terms of ecology: if you remove a specific animal you disrupt a food chain: its predators will starve and its prey will grow unchecked, causing complications and a series of cascading side effects.

Approaching work and life

I’d rather be dumb and antifragile than extremely smart and fragile, any time.

The fragile can break at any time while the antifragile can gain at any time.

Being antifragile is a more realistic approach to work and life. It acknowledges that we know surprises will happen, but we don’t know what they’ll look like or when they’ll happen. As Scott Sagan reminds us: “things that have never happened before happen all the time.”

So don’t bother trying to predict when surprises will happen (how can you with a surprise?), just focus on being prepared for surprises.

Avoid ruin and allow for gains.

First, remove fragility

The first step toward antifragility consists in first decreasing downside, rather than increasing upside; that is, by lowering exposure to negative Black Swans and letting natural antifragility work by itself.

Fragile and antifragile things respond differently to good and bad surprises. Fragile things have large downside but limited upside. Antifragile things have limited downside but large upside.

On our way to living an antifragile life, Nassim suggests we first remove fragility.

[I]f 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…

Simple test: if I have ‘nothing to lose’ then it is all gain and I am antifragile.

Second, adopt the barbell method

Then, add in some antifragility.

The best way to do this is using Nassim’s barbell method. Like the shape of a barbell, you have a lot of safe things on one end (robust) and some small risky (antifragile) things on the other end. This creates “extreme risk aversion on one side and extreme risk loving on the other, rather than just the ‘medium’”.

You’re protected from negative surprises, but you allow for rewards from positive surprises.

Third, embrace optionality

To get your barbell method working, you want to find things that let you benefit from good luck without losing from bad luck. Nassim calls these things options, which allows “you to benefit from the positive side of uncertainty, without a corresponding serious harm from the negative side.

Options take a long-term view

[I]f you make more when you are right than you are hurt when you are wrong, then you will benefit, in the long run, from volatility (and the reverse). You are only harmed if you repeatedly pay too much for the option.

For example, a book or pieces of an art are options

The number of persons who dislike the work don’t count – there is no such thing as the opposite of buying your book… and this absence of negative domain for book sales provides the author with a measure of optionality.

Apart from the time invested to make something useful, what’s to lose?

Finally, be a rational flaneur

So far, Nassim suggests we navigate through life avoiding fragility and finding antifragility in the form of options. He’s got a concept for someone that does this. A rational flaneur. They are

Someone who, unlike a tourist, makes a decision at every step to revise his schedule, so he can imbibe things based on new information… often guided by his sense of smell…

The flaneur is not a prisoner of a plan… [he] continuously – and, what is crucial, rationally – modifies his targets as he acquires information.

To update your path at each decision point you will want to avoid becoming locked in. Like getting needing a job when taking out a large mortgage. Maintaining options and flexibility gives you the ability to seize an opportunity when it arises.

That doesn’t mean never lock yourself in. In fact, Nassim notes how this approach does not work in relationships where one needs loyalty. What it does mean is thinking hard about going down a path that effectively locks you in.

This idea of navigating as a rational flaneur shows up in other places too. As discussed with Tim Ferriss’, for Jim Collins its the simplex method

Now as I navigate, it’s kind of like the Simplex Method in operations research where you find optimal by never really knowing what optimal is ahead of time. You do it by a series of iterative steps of the next best step.

Or, as Robert Greene describes in Mastery, it’s about maintaining flexibility and knowing when to settle

You are not wandering about because you are afraid of commitment, but because you are expanding your skill base and your possibilities. At a certain point, when you are ready to settle on something, ideas and opportunities will inevitably present themselves to you. When that happens, all of the skills you have accumulated will prove invaluable. You will be the Master at combining them in ways that are unique and suited to your individuality.

You may settle on this one place or idea for several years, accumulating in the process even more skills, then move in a slightly different direction when the time is appropriate. In this new age, those who follow a rigid, singular path in their youth often find themselves in a career dead end in their forties, or overwhelmed with boredom. The wide-ranging apprenticeship of your twenties, thirties or forties will yield the opposite—expanding possibilities as you get older.

Eithics, freedom and skin in the game

But above all, as you navigate life as a rational flaneur taking a barbell approach and seeking options, you must be ethical:

Thou shalt not have antifragility at the expense of the fragility of others.

If you’re unsure whether someone is behaving ethically, or talking without action, consider whether they have skin in the game. “The only true mitigator of fragility”.

To me, every opinion maker needs to have “skin in the game” in the event of harm caused by reliance on his information or opinion.

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.

Writing in an antifragile way

After reading Nassim’s book I decided pretty quickly to take his advice. While I’m still working on ways to remove fragility, I’ve finally started writing online.

In doing that, I’ll avoid fragilities in writing, like mistakes or unscientific claims. I’ll use writing as an option, where by taking time to write (the fixed downside) I make something that people might find useful (the potential upside). And I’ll maintain flexibility, posting on a website that I can take in any direction.

What’s to lose?

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