Using Antifragile Concepts to Thrive in an Uncertain Future

Learning and implementing Antifragile's skills and strategies are more critical than ever to get stronger and increase stamina for change.

Written by:

Paul D. Roberts

Be Courageous Insights Blog Antifragile

Using Antifragile strategies, companies can both protect their business and take advantage of new opportunities in an unpredictable future.

In 2021, I wrote about how the world – companies and people alike – are ascending a massive mountain of change. 

Here it is, two years later, and it appears the mountain has gotten even taller and steeper.  Technologies like AI are infiltrating many jobs, with much more to come, not to mention all the unpredictable firsts that inevitably arise. To thrive, we must build even greater strength in our foundation while retaining the ability to bend and grow with change. Or be left behind. 

With all the unknown, one thing we can count on is the mountain of change will get bigger. We’ll be climbing steeper roads than ever before. But this is a good thing if you consider the alternatives. There are many incredible opportunities for you as a person and business to see gifts and opportunities in this journey.  

To get more robust and increased stamina for change, learning and implementing the skills and strategies of Antifragile is more critical than ever. 

What is Antifragile?

Antifragile is the opposite of fragile, and it doesn’t just mean being resilient and robust but addresses the actual benefits of stress and disorder. The concept was introduced in Nassim Taleb’s book,
“Antifragile: Things That Gain from Disorder. The approach has two key elements (which is why Taleb calls it a “Barbell Strategy”).

The Antifragile “Barbell Strategy”

Fortify your business.
Fortifying your business means openly and courageously exploring critical weak spots of your current business in a volatile world with extreme disruption (like a pandemic, accelerating Artificial Intelligence, or unsolved SDGs). It means focusing on weaknesses with accelerating consequences (i.e., consequences that worsen disproportionately as they grow.) 

The goal of fortifying your business is to build protective innovations designed to ensure disruptions don’t upend the business.

Raiding parties to the future, or “going a Viking.” “Going a Viking” is designed to embrace uncertainty and take smart options on possible futures with massive upsides. 

The goal is to take advantage of opportunities in an uncertain future by creating significant returns from products, services, and technologies while not betting the farm on them. 

The “Suckers Bet” is an integral part of the strategy, which dictates not to take bets in the mediocre space – the space between keeping safe and betting on a massive upside (hence the barbel). 

Both ends of the barbell require creating a safe questioning environment and a culture that fosters courageous and model-challenging thinking and action.

Reflect on your last 2-3 years: 

  • What fragilities did you and your company live through? 
  • What did you learn? 
  • What could you have done to take advantage of the change you experienced? 
  • What options/bets do you wish you had taken?

Companies have to be ambidextrous. Antifragile is an and system. You have to fortify your company’s core and “go a Viking” to look for opportunities in the future. Focusing too much energy on one means you miss opportunities on the other. Start with fortifying the castle – You have to survive to thrive.

How to begin implementing Antifragile strategies in your business 

1) Fortify the Castle: Begin by taking stock of your current situation in the context of the world you’re in. Ask yourself and your teams, “Where are we over-exposed? Where are our fragilities?” Use the tool below for more critical questions.

Identify where you could incur disproportionate damage – i.e., if a particular service, product, technology, or trend changes by 2X, the damage to you will be 4-5X+. Then take actions to limit or eliminate your exposure.

2) Raiding Parties to the Future (“Going a Viking”): This is where courage comes in. The potential of your future is linked to the degree of your courage. Ask yourself and your team a few questions:

  • What is the courage needed here?
  • If you get creative, where is there a potentially massive upside?
  • List all of the possible large upsides that you could take an option on. You could be well-positioned to take advantage of new products or services, markets, technologies, systems redesign, or pivots. 
  • Be ethical – it’s not about exploiting.

Then, lean in and act so that you still survive if it doesn’t pan out. Find a way to take an option. Experiment, and be ok if the experiment doesn’t pan out. Learn and move to the next experiment. This requires a courageous, safe learning culture.

Courageous Action is the central tenet of an Antifragile strategy.


Antifragile Strategy Worksheet

Thriving in uncertainty requires ensuring your business not only survives but takes bets on the massive upsides of change.

Example of Antifragile strategy in action


Unpredictable first/change: Artificial Intelligence

While many knew that Artificial Intelligence was about to explode on the scene, many felt blindsided. Its pace is incredible.

“Fortify the Castle” “Go a Viking / Raid Parties to the Future” 

Accept what global AI leader Andrew Ng says: “AI is the new electricity.” 

It will be in everything; it will transform every industry.  

Courageous creativity is critical. 

Ask: How am I going to use this differently than everyone else? What can we now do with AI that we couldn’t do before? What new things can we do with this powerful technology to create value (beyond efficiency and task substitution)?

Realize that you won’t have a place at the table if you don’t use it.Think of AI as a new tool, like a jigsaw. Unlike a regular saw, a jigsaw enables you to cut fancy shapes, make a puzzle, and make interesting designs.

Optimize efficiency. 

Today AI is focused on replacing current work/tasks. Suppose you have a presentation to make and spend forever doing it traditionally. Someone else is likely using AI to create better presentations faster. Don’t get left behind.

Discover what your competitive advantage with AI will be.  
Ask: What do I want to coordinate at a massive scale, make stronger, optimize, predict, create/design/invent, synthesize/simulate, discover?Ask: What proprietary databases can you assemble in a specialized area to create new knowledge?

Whether you’re facing challenges with AI, burnout, glocalization, hybrid times, confusion on roles, new systems, and technologies, lead with antifragile strategies to survive and thrive. 

We know it’s not easy; that’s where we can help; reach out! 

Sign up for our monthly newsletter, The Bridge, for more courage in your inbox.


Corporate Fragility


Most of us agree that we are really only at the tip of a massive amount of change. The 2020s will be the decade of challenge for the globe.

Corporate Fragility


Most of us agree that we are really only at the tip of a massive amount of change. The 2020s will be the decade of challenge for the globe.

Let's Get Started!

Courage my Challenge

The Bridge

Sign up to our monthly newsletter “The Bridge” and receive inspiration and practical tools to courage your future. 


0 M


Courage the Future

Crafted with 🖤 by Be Courageous Digital, San Francisco
©2017 - 2023 - All Rights Reserved.