What if everything we were taught about goals, control, and planning works exactly backwards?

Late February 2022. My wife and I are celebrating our first wedding anniversary. A few days later, everything falls apart. Remember that feeling? When in a single week, years of work collapse. Markets, clients, relationships, plans — all wiped out. And you sit there thinking: okay, I'll just make a new plan. New spreadsheets, new goals, new steps. Reality will cooperate.

It didn't.

I'd read Taleb's Antifragile long before that. At the time — just an interesting book. But when everything started crumbling, I came back to it, and it hit differently. It explained why my approach to problems wasn't working.

Since then, antifragility has been my operating system. Business, relationships, health, planning. It helped me come out of that crisis stronger than I was going in.

In this post, I'll explain what the idea actually is, why almost everyone gets it wrong, and how I specifically apply it.

So what is it, exactly?

Nassim Taleb — former trader, mathematician, philosopher. In 2012 he wrote Antifragile, and the core idea is simple. Almost frustratingly simple.

There are three types of systems.

Fragile — breaks under stress. Glass drops, it shatters.

Robust — withstands stress. Plastic drops, nothing happens — but it doesn't get better either.

Antifragile — gets stronger from stress. A muscle grows after exertion. The immune system strengthens after illness. Bone heals denser after a fracture.

Powerful idea. Everyone's heard of antifragility, many discuss it, few understand how it actually works in practice. Taleb himself writes densely — 600 pages of philosophy, statistics, and personal grievances toward academics. And the idea sounds too simple: "get stronger from stress" — okay, but what do I do Monday morning?

I spent several years figuring out how to apply this in my business, relationships, and daily decisions. I've distilled it into a few principles that actually work.

Why everyone gets this wrong

Want to liven up any dull dinner party? Say the word "antifragility." Within thirty seconds, everyone's debating portfolio diversification, risk hedging, options, black swans, blah blah blah. We're all traders at heart, apparently.

Taleb came from finance, but antifragility is a property of any system. Your body, relationships, business, career — all of it can be fragile, robust, or antifragile. If you reduce it all to a stock portfolio, you lose the most valuable part: the ability to rethink how you live and make decisions every day.

The second problem is deeper. Say you've grasped that antifragility goes beyond investing. Then what? The book gives you philosophy but no instructions. No "10-step antifragile life checklist." Taleb would say any such checklist is itself fragility. And he'd be right. But people need somewhere to start. Some set of decision-making rules. These are the ones I've developed over the years.

Principle one: don't get wiped out

Antifragility only works under one condition — you stay in the game. Taleb calls this the "absorbing barrier": it doesn't matter how antifragile you are if you've been zeroed out. A dead trader doesn't come back.

What does getting wiped out look like? An event with no path back. Five types: physical death, irreversible loss of health, prison, total loss of capital, complete isolation. You can lose clients and find new ones. But if you've destroyed your health, ended up in prison, or cut yourself off entirely — there's nothing left to rebuild from.

So what do you actually do?

Once a month I sit down and go through each type of wipeout. I take one — say, death — and ask: if this happens, what's most likely to cause it?

Example. I'm 41. I live in Southeast Asia. Real risks: cardiovascular (age, weight, stress), cancer (age, genetics), motorbike accidents (here, that's statistics, not hyperbole).

Each event has a low probability. Each has irreversible consequences. So the goal is to eliminate the risk as close to zero as possible. Regular checkups. Weight reduction. Insurance. Always wear a helmet. Basic hygiene.

Then take the next type — capital loss. No safety net? Dependent on a single client? Drowning in debt? Write it down, act on it. Repeat next month. That's the cycle.

Why doesn't anyone do this? Because low probability feels insignificant. So what, 0.1%. So what, 15 extra kilos. The core mistake: people focus on probability and ignore consequences. Low odds of a total wipeout. Game over.

Principle two: subtract, don't add

Via negativa — one of the most underrated principles in the book. Removing what harms you is always easier than launching something new.

The classic example is health. The two interventions with the greatest impact on lifespan: quit smoking and lose excess weight. Running, vitamins, meditation — maybe 1x. Stopping what's killing you — 100x. Via negativa in its purest form.

I have a monthly review for this. What did I do last month that I don't need to do next month? I'm looking for one thing: whatever is draining energy disproportionate to the result. AI agents help me collect the data now. The tool is secondary — the question is what matters: what do I need to stop doing?

A project that leaves you wanting to lie down after every call? Cut it. Scrolling Reels until 3am, eyes burning, thumb moving on autopilot? Turn it off. Networking events that have never produced a single project? Done.

Starting something new always costs resources with uncertain returns. Stopping something with negative ROI returns resources immediately. Right now.

If you're digging a hole, before you climb out — just put down the shovel.

Principle three: the barbell isn't conservatism

The barbell strategy is the most well-known principle from the book. And the most misunderstood. People hear "90% into safe, 10% into risky" and only remember the first part. Safety net! Stability! Conservatism! The barbell becomes an excuse to do nothing new.

The barbell is about balancing two extremes. 90% protected. And 10% — mandatory, regular investment in what might return 10x. Every month. No postponing.

I fell into this trap myself for a long time. I focused on the safe side, while experiments existed only in my head. "I'll finish current projects first." Current projects never end. A barbell without the high-risk side is just irrational caution. You survive but don't grow.

Personal example. My last salaried role was at xHamster, where I led analytics. I held on to it until the end. It had been draining my energy and attention for a long time, but the salary kept coming in, and that felt like safety. I had my own projects on the side but could never properly invest in them — the job took everything. Then I got fired. My income grew significantly. Resources freed up for sources I'd been starving for years.

Here's the trap: employment feels like safety. But a single income source is actually maximum risk concentration. The barbell looks different: work a job, but invest in opportunities. A side project, consulting, a product, a skill. Right now, while things are stable.

Most experiments will fail — that's fine, the downside is small. But one in a hundred will return enough to cover everything else. If you're not making small bets — you're not antifragile. You're just paranoid.

Chaos isn't the enemy — it's the fuel

Everything I've described is a thinking system. At its core is a simple premise: chaos is the normal state of reality. Plans will break. Clients will leave. Bodies will get sick. The question is when, not if.

Most people build their lives as if chaos shouldn't exist. When it arrives — panic, frustration, an attempt to regain control. Antifragility means accepting chaos and building a life where random events work in your favor more often than against you.

Client says no — you sharpened your offer. Experiment failed — you got data. Got fired — resources freed up. It's a different default setting. It doesn't always work. But more often than when I tried to control everything.

Instead of a conclusion

Remember the question at the beginning — what if everything we were taught about goals and control works backwards?

For me — yes. The guy in late February 2022 who was drawing up yet another plan was fragile. One hit and everything collapsed. The "I'll predict the future and prepare for it" approach made me vulnerable to exactly what I couldn't predict.

Three principles that changed that:

Eliminate wipeout. Once a month, go through the risks that could end the game. Low probability, irreversible consequences. Eliminate to zero.

Subtract, don't add. Find what's draining your resources and energy. Removing is easier than launching something new.

Make small bets. Regularly invest a small portion in what could return disproportionately.

Taleb wrote 600 pages. I fit it into one post. He'd say I oversimplified. And honestly, he'd be right. But a simplified version you actually use beats a perfect one you read and forgot.