In markets, almost everything is cyclical. But few things are as consistently cyclical as volatility.
People forget that.
When the market goes months without moving, without shocks, the dominant narrative becomes that volatility is “dead.” That we’ve entered a new era of stability. That this time is different.
It never is.
The chart above makes it clear: every decade has its share of violent moves. Days with ±1% swings in the S&P 500, counted per decade. From the 1950s to today.
And while the numbers change, one thing remains constant.
Everything reverts to the mean.
In the 1960s, there were only 227 such days. In the 2000s, over 840. In this current decade, we’re already at 441, and it’s not over yet. The historical average? 507.
This matters. Because volatility isn’t noise. It’s the playing field of optionality. Without it, there are no dislocations. And without dislocations, there are no asymmetric opportunities.
And without asymmetry, there is no exponential wealth.
Nassim Taleb understood this better than anyone. Before he was an author, before he became a philosopher of uncertainty, he was a trader. In October 1987, during Black Monday, while the Dow Jones dropped 22% in a single day, he made between $35 and $40 million for his bank.
Not because he predicted it. But because he was intelligently exposed to positive asymmetry.
Cheap options. Limited downside. Controlled risk.
Unbounded upside.
That’s the real power of viewing volatility not as an enemy, but as fertile ground. Most people run when the market shakes. Those who think in asymmetries know that’s where life-changing opportunities emerge.
That’s why Taleb never bet on the middle of the curve. He bet on the tails. He didn’t try to be right, he built structures that would win big when others lost big.
And for that, you need a system with skin in the game. Portfolios that don’t depend on being right but on surviving long enough to be there when the system breaks. And then getting paid.
At Asymmetric, we do it through a simple framework we repeat again and again. Three boxes.
Core. Flow. Optionality.
The Core is untouchable. It’s your foundation. Bitcoin, gold, real businesses, land assets that endure with or without volatility. You don’t sell the core.
Flow keeps you free. Dividends, interest, rents, cashflow you can live on monthly without touching your core positions.
Then comes the most misunderstood, yet most powerful box: Optionality. It plays at the edges. It doesn’t need to be right, it just needs to be alive when everything else dies. This box can bleed for years… and still change your life in a single moment.
Let’s return to the chart.
If this decade is already nearing the historical volatility average, and we’re not done yet, there’s one clear message: the current calm is temporary. Mean reversion is inevitable. The tremors will return.
Because the system isn’t stable. The global economy is leveraged to the teeth. Central banks haven’t solved the structural imbalances, they’ve only postponed the pain. Narratives shift, but fragility remains.
The next shock will come.
And when it does, it’ll be too late to build margin, too late to stay calm, too late to improvise.
That’s why we build now. Not later.
You don’t need many events like Black Monday in your life. Just one. One that hits hard and if you’re positioned well, it can change everything.
That’s the beauty of optionality. It doesn’t require frequency. It doesn’t require volume. It only requires being prepared for the improbable.
And being prepared means having a system that holds. One that doesn’t force you to sell your best assets in the worst moment. One that lets you live calmly while you wait. Because waiting isn’t passive. It’s a strategy.
As Taleb puts it, “resistance to fragility doesn’t come from predicting what’s next, but from being ready for anything.”
Don’t invest as if you know the future. Invest as if the future is unbalanced and you can benefit when it breaks.
That’s the mindset.
Because when the day comes, and it will, when everything unravels, most will be out of the game. No liquidity. No margin. No plan. Forced to sell when they should be buying.
But not you.
You’ll have a structure. A solid base. A steady flow. And a loaded optionality box, ready to explode.
And maybe, that one day will be enough to change your life completely. Because when you invest through asymmetry, you don’t need to be right often. You just need to be present when the market gets it wrong.
And it always does.
If you want to see how this plays out in real-time, check out our breakdown in “300% Gains in a Week: My Asymmetric Portfolio Strategy Revealed”, published just a few months ago where we applied Taleb’s principles live and captured massive returns from market dislocation