7 Ways to be More Antifragile

A how-to guide for the real world

Shaw Talebi
The Data Entrepreneurs
6 min readJul 18, 2022

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Antifragile things benefit from uncertainty. In a world better characterized by uncertainty than certainty, being (at least a little) antifragile seems like a good idea. In a previous post, I introduced this idea of antifragility and mentioned 7 things that can make you more antifragile. Here, I will expand on these points and provide examples of each. Let’s get into it.

7 ways to be more antifragile (overview). Image by author.

Antifragility is an idea defined by author Nassim Nicholas Taleb (NNT) in his book Antifragile. Put one way, antifragile things have more to gain than to lose in the face of randomness. Therefore, this class of things loves uncertainty and disorder.

While this may sound abstract, there are concrete things we can all do to be more antifragile. Below I explore 7 paths to antifragility, and share illustrative examples of each.

1) More upside than downside

When you’re antifragile, you don’t need weather forecasts

At the core of anything antifragile is having more ways to win than to lose. NNT conveys this very plainly as having more upside than downside. Whether we like it or not, the world is more unpredictable than predictable.

While it may initially seem like we are doomed to be slaves to randomness, it doesn’t have to be so. If we have more upside than downside, then we don’t need to worry about predictability. It’s basic statistics. If things change at random, we will be better off in the long run, since we have more to gain than to lose.

(Contrived) Example: Let’s say we flip playing cards over one by one, and every time a non-face card comes up I pay you $1, but if a face card comes up you pay me $1. Clearly, it would be stupid of me to play this game, because if we go through the whole deck you will win (and I will lose) $36. The point is you wouldn’t care about predicting the very next card, you’d just want to keep playing as long as possible.

2) Options

Be stubborn on the vision, but flexible on the details — Jeff Bezos

When there is only one way in which you can win, you are fragile. On the flip side, if you have multiple routes to what you call “success”, you are antifragile. This goes back to having “more upside than downside.” And options are great way to do this.

An option is well.. optional. You aren’t obligated or dependent on it. This removes the need for predictability. When you have a lot of options, odds are at least one of them will work in whatever situation you find yourself in.

Example: One of the clearest option makers is cash. Cash can be translated into many different things: dinner, a house, a car, real estate, love, stocks, beauty, etc. If real estate is cheap you can buy it, if stocks crash you can buy them, or if your wife leaves you can order a new one online.

3) Bottom-up traditions

Listen to your grandma

A bottom-up tradition is a practice that is typically born out of trial and error. It is developed over time by people who actually do the thing. This is in contrast to top-down rules, which is when someone from up top (e.g. a king, CEO, academic, Burger King manager, etc.) makes a decision on how people should live their lives or do their jobs.

Okay so, how does this help us? One take is, be skeptical of top-down rules, because they tend to be fragile. If the context changes from when the rules were written, odds are the rules will fail. Conversely, don’t be so quick to dismiss your grandma. She’s seen things come and go, and what she carries with her has stood the test of time.

Example: A great example of this is acupuncture. This is an eastern health practice that has been done for thousands of years, however it has not been until recent years that western science has taken it seriously.

4) Failure (or mistakes or trauma)

There are no downsides in life. You either win, or you learn something

In of itself, failure isn’t antifragile. However, in moments of failure we have the opportunity to be antifragile. It’s simple, we take the bad (e.g. failure) and gain from it (e.g. learn something).

What this comes down to is inverting what would typically be considered downside (e.g. losing everything) into upside (e.g. coming back stronger). Taking this to its extreme, if you convert all your downside into upside, and maintain the upside you already have, you are antifragile by definition.

Example: An example of this (also discussed in the book) is post traumatic growth. This is a phenomenon where people who have endured traumatic experiences, are not damaged by it, but strengthened by it.

5) Staying small

The bigger they are the harder they fall. — Someone

This is based on a simple principle. The more you have, the more you have to lose. The inverse of that is, if you have nothing, what do you have to lose?

The bigger a system gets, the more fragile it (typically) becomes. One observation of this is in nature. Most species are much smaller than us (e.g. total mass of ants on Earth is about 10x the total mass of humans). And of the ones bigger than us, there are a lot more of us then them (e.g. we outweigh whales by about 10x) [Source].

Example: An example of this in the business world is a tech start-up. Software has ridiculously low overhead (i.e. you just need a laptop), and if you’re a small team, you can more readily adapt to changing technologies and industries than a large corporation. That’s perhaps why tech companies keep getting replaced by newer ones every decade or so.

6) Diversification

80–20 rule, but for everything

This goes back to having options. If you put all your eggs (i.e. money, time, energy, social capital, etc.) in one basket, you set yourself up to be fragile.

In the book, Antifragile, author NNT gives a concrete strategy for diversification, which he calls the barbell strategy. This is based on the 80–20 principle from Vilfredo Pareto’s work. This strategy prescribes that ~80% of resources are invested in safe, secure enterprises, while ~20% are devoted to more risky ones.

Example: What this might look like in the real-world is spending 80% of your time working a full-time job (40 hrs a week), then spending 20% of work time on a side hustle or start-up (10 hrs a week).

7) Independence

The three most harmful addictions are heroin, carbohydrates, and a monthly salary — NNT

Being dependent on anything makes you fragile. It just like having no options. If you are completely reliant on a particular job, person, market condition, habit/routine, social setting, electoral outcome, etc. to be happy (or successful), you set yourself up for failure.

Nothing lasts forever. Things will eventually change. Thus, the more you depend on, the more you stand to lose when change inevitably comes.

Example: Marcus Aurelius famously stated, “You have power over your mind — not outside events. Realize this and you will find strength.” This is a key aspect of independence. Realizing your lack of control over external things, and internalizing that worrying about things outside your control is a choice. With this mindset, you won’t be shaken by every little disruption in your environment.

[1] Antifragile by Nassim Nicholas Taleb

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