My 3-Step Antifragility Plan To Eliminate Career Uncertainty Forever

I lost my main job a few months ago, here’s how I’ll ensure it will never happen again.

James Presbitero Jr.
ILLUMINATION
11 min readNov 20, 2023

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Do you think your career is “safe”?

Maybe you have a pretty cushy job in an in-demand industry. Maybe you’re a high-paying freelancer or business owner. Maybe you’re an entrepreneur

(Yes, with all the sparkle, given how much that word is thrown around today)

Midjourney image generation by author.

Now, I’m going to try and destroy your hopes and dreams here for a bit.

Think about this: What exactly made you think it’s a job you’ll have forever? What makes you so sure?

Have you carefully considered your company’s organizational structure and thought — “Yes, I am safe, for there is no other one like me. Surely, this company will go to ground without my unreplicable expertise.”

Or maybe you’ve studied your industry top to bottom, analyzed your place in the billion-dollar global economy, and concluded “I have a place here, capitalism needs me.”

Or heck, maybe you’ve made something so unique, so valuable, and so irreplaceable that you’ve conquered the market. Made a new sustainable energy source lately? Created the cure for cancer? Maybe created sentient AI?

No?

Well then, my friend — you’re just like the rest of us: subject to the tyranny of life’s unknowns.

The Problem of Hidden Chaos

We don’t really know anything.

I lost my main job a while ago, because of something I didn’t know.

For some time, I moped and blamed myself. And while I did carry the responsibility, at the same time, life is irredeemably complex. There is so much information, so many things going on, all at the same time. Things slip by us all the time.

Whatever it is you think you know, it’s not nearly enough to get the entire global picture of it — not nearly enough to get a good idea of the “Grand Scheme of Things”. The way things actually are.

Oh, we have an idea of how things are. It’s a pretty illusion our brain uses to adapt to the modern world: focus on what’s in front of us and ignore everything else.

Some people would call it incredibly myopic and ignorant.

But I’d call it working. Because it works. It works really well. We only have an idea for a reason — it’s quite literally impossible to know everything, all the time. Our mental shortcuts make our lives livable.

But as much as I like to applaud human psychology for keeping us sane (well, relatively) it does admittedly get us into all sorts of problems.

Hidden chaos in everyday life

Let’s look at the job analogy again.

Let’s say you’re an online writer. Average dude, started writing right out of college, and has been earning pretty decent money.

It’s a pretty sweet gig, but there’s a kicker: it’s right about the end of 2022, and ChatGPT just released.

Midjourney image prompt by author.

Boom.

The AI tool goes viral in a couple of days, making ripples that are suddenly tsunamis. Meanwhile, some of his clients looked at him and thought, hmm, if a browser can do what he’s doing, he’s probably not worth much, and started paying less for more work. He lets go of them.

But a month in, and the influencers get to work. Titles like “Make $1000 with ChatGPT” or “Become a Millionaire with AI” flood the market.

More “writers” flood the industry, lured by the promise of easy money, ready to make sky-high promises they can’t keep. Now, it seems everyone and their grandma could write.

Pretty soon, all clients start going hmm.

They all look and you and say “I want you to write 2000 words of quality content in 30 minutes, using AI.”

Our writer protagonist tells them that’s impossible, they move on from him and find someone better at making false promises.

Now, he can’t let go of anyone. Now, he has to accept more trashy work for less pay. It’s a race to the bottom, and there’s nothing our poor writer dude could have done to prepare.u

More, AI completely disrupts not just the writing sphere — but soon, everything else. Image generation, web searches, computing, statistics, security, investing.

A wave of cascading effects, the end result of which is something unforeseen, but surely vastly different.

Photo by Steve Johnson on Unsplash

Introducing the black swans

In hindsight, there might have been tell-tale signs.

Maybe there was the odd tech blog covering language models some months back. Maybe there was even a documentary.

But heck, he was a regular writer guy, he had friends and a life outside of work and bigger problems than some niche blog post predicting something right out of a sci-fi movie.

Who cares about AI? No one. Until everyone.

And we can’t really blame our poor writer dude.

Hardly anyone ever prepares for the worst-case scenario. Hardly anyone ever thinks there could be a worst-case scenario.

And why should we? We’ve got other things going on.

This is the problem of hidden chaos. At any point, something somewhere could easily be in motion — something massive, highly improbable, and unpredictable. In his book, Nasim Nicholas Taleb, a prominent risk analyst and writer, called these Black Swan events.

Examples include the life-changing disruption we just witnessed, the rise of AI, but also:

Things are quite different for the Coronavirus pandemic.

Upon analysis, most experts say COVID wasn’t a black swan event, since history has been replete with examples of high-impact pandemics and people have indeed been warning of its possibility for years.

I don’t quite agree, though — experts may have seen it coming. But a normal person, like you and me? It was a sucker punch that came right out of the blue (But what do I know, right?).

All that to say — life is inherently chaotic.

If we won’t lose our jobs because of mundane reasons like company profits not being enough this quarter or our boss not liking us enough, it might happen because of a Black Swan Event. Something massive. Something unpredictable. Something life-changing.

Like, say, a recession. Or a global pandemic. Or an alien invasion.

Photo by Ani Kolleshi on Unsplash

The universe literally prefers entropy over anything else — everything is moving towards a state of greater and greater disorder. We just don’t see it.

Our heads are, proverbially, buried in the sand.

I know, because I was like that, too.

I’m not our writer-guy protagonist — but I was a writer and I did lose my main source of income, and there was no warning. (That’s a different story, you can read it here)

So I ask again: is your career safe? Probably not.

But we could be.

Enter the Concept of Antifragility

“What doesn’t kill you makes you stronger.”

Antifragility is the characteristic of something to benefit from chaos, uncertainty, and stress.

It’s a term coined by Nassim Nicholas Taleb in his book, Antifragile: Things That Gain From Disorder — contending that some things in nature actually need chaos and disorder to grow.

Antifragility is the opposite of fragility. Not “robustness” or “resilience.”

When something is fragile, it easily breaks when subjected to disorder.

When something is robust, it doesn’t break easily — but it does break at some point. When something is resilient, it bounces back to its original state after being broken. But it does not benefit from the experience.

Thus, these states are not opposites of fragility but are neutral states.

On the other hand, when something is antifragile, it actively gets stronger when it is subjected to chaos, uncertainty, and stress.

Image created by author.

This is an important distinction because antifragility is what I’m working towards — my ultimate career goal. Not just robustness, not just stability, but untouchability.

Recession proof. Market-instability proof. Life proof.

For me, this is the only way for my career to beat the uncertainty of life.

If I had been a bit more antifragile a few months ago, my entire financial structure wouldn’t have gone to the ground just from losing one job. If I was a bit more antifragile, I would have bounced back quicker — all the better.

That’s why I’ll ensure it will never happen again.

5 Characteristics of an Antifragile Career

To have a career that will beat recessions and instability and all the craziness of life, just think of the human body.

That’s right, the good ole skin suit.

Photo by dilara irem from Pexels.

You see, the human body is naturally antifragile. Think exercise, messy break ups, getting an education — all of these things are chaos and stress. And with the right dosage and application, they help us grow.

That’s why the best way to determine the characteristics of an antifragile career is to compare it to an organic system like our body.

1. Adapts to a variety of different conditions

Our bodies can adapt to anywhere on Earth — and even beyond.

Our careers should be just as flexible and adaptable. Antifragile careers aren’t “jack of all trades,” but they’re not savants as well.

They should be demanded across industries, mediums, and companies. But at the same time, they should be best-of-class, enough to command a premium.

2. Allows for continuous growth

Humans don’t stop growing.

Our cells are constantly repaired, new muscle fibers constantly form, and new neural connections are always being made. This way, biology ensures our bodies meet the everyday challenge of uncertainty.

Thus, your career shouldn’t be a “dead end.”

It should allow you to upskill and improve. It should have multiple paths available. It must trend upwards over time.

3. Endures a reasonable level of stress

Our bodies don’t explode from a single punch, die from a single fever, or crumple when we hit our toes on a table leg.

If your career folds at the first sign of economic instability, then you’re probably on the wrong path for antifragility.

You have to be sufficiently in demand even if the general economy is feeling a crunch. Ask yourself, “Will I be among the first people to be let go in the next pandemic?”

4. Positions you to benefit from instability

Within reason, human bodies grow stronger from stress.

Antifragile careers don’t just resist stress — they benefit from it.

You have to be someone who can make a lot of money or have a lot of options in times of market disruptions.

5. Conforms to a “barbell strategy”

The barbell strategy is a risk management approach characterized by extreme risk aversion on one side and extreme risk-taking on the other, completely avoiding the middle ground.

It’s called the barbell because it’s like having weights on both ends of a barbell, with minimal exposure to the middle.

Image created by author.

If you want a bulletproof body, you would do well in applying the barbell strategy

Engage in heavy weight lifting (extreme risk-taking) paired with recovery and low-impact exercise like swimming or yoga (extreme risk aversion).

The same can be applied to our careers.

A Roadmap to How I’ll Become Antifragile

Now that I’ve identified what makes an antifragile career, here’s what I’m going to do to achieve it.

Step 1: Cultivating an antifragile mindset.

To build an antifragile career, I need to start by developing a mindset that embraces uncertainty as a fact of life.

I must:

  • Embrace challenges as opportunities for growth.
  • View setbacks as stepping stones.
  • Look at failures as data points.
  • Actively learn from all experiences, and
  • Build a mentality that flourishes in dynamic environments.

Step 2: Increasing options and minimizing vulnerabilities.

A buffer against “the worst case scenario.”

This involves strategically diversifying my financial and skill portfolios to shield myself against the unpredictability of the economic landscape.

Here’s how I plan to achieve it.

  • Store money to create financial redundancy. I’ll build a financial safety net by saving an emergency fund and investing wisely.
  • Minimize career fragility. I’m diversifying and deepening my skills to avoid over-specialization. This way, I wouldn’t rely on a single job, industry, or economy.
  • Cultivate multiple streams of income. Currently, I’m diversifying my income streams and incorporating side projects, freelance contracts, and jobs.
  • Building a personal brand. Having a robust brand showcasing my skills, experience, and expertise opens doors to various opportunities, giving me more options.
  • Separate my value from my time. Shifting from a traditional time-for-money mindset is the ultimate antifragile move, which could involve creating scalable products, passive income streams, or leveraging technology to maximize impact.

Step 3: Utilizing a barbell approach to income generation.

By maintaining a stable, low-risk income source alongside ventures that embrace uncertainty and potential high returns, I can create a resilient system that not only withstands disruptions but capitalizes on them.

Extremely risk averse on one side:

I want a stable foundation with a reliable, low-risk income source. This provides a consistent financial base, allowing me to weather economic downturns without significant disruption.

Extremely risk-loving on another side:

Explore entrepreneurial ventures, high-yield opportunities, and mindful networking to pursue potentially lucrative endeavors.

This side provides balance by introducing high-risk elements that can provide substantial rewards.

Eliminate Career Uncertainty Forever

Midjourney image generation by author.

Are you someone who wants their career to start out right?

Are you a new professional just realizing the fickle world of economics and career progression?

Are you an entrepreneur wanting to build a resilient business that withstands market fluctuations?

Are you a freelancer who longs for ever-elusive career stability?

Are you considering a career change and entering unfamiliar territory?

Or maybe you’re just tired of all the preachy Twitter bros saying the only way to survive is to make 100k every month?

Wherever you are in your career path, you’re sure to deal with uncertainties — not just from things you know, but even from an entire world of stuff you have no idea about.

The universe, after all, prefers chaos.

But … so can you.

We humans don’t just have antifragile bodies. We have the unique ability to choose antifragile paths. We can’t change the universe, we can’t stop chaos — but we can choose to capitalize on it through the following.

  1. Cultivate an antifragile mentality.
  2. Increase my options and minimize vulnerabilities, and
  3. Utilize the barbell approach to income generation.

This is my simple mission to create a strong path for myself, and maybe for others.

How about you? What are you doing to be more antifragile?

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