- PlayWinWealth
- Posts
- Black Swans, Inverted
In partnership with
A lot of modern life is built on a quiet assumption:
that tomorrow will look roughly like yesterday.
The problem is that the events that matter most don’t respect that assumption.
This idea sits at the center of the work of Nassim Nicholas Taleb. Taleb isn’t famous for picking stocks or forecasting markets. He’s known for studying risk, uncertainty, and asymmetry — especially the kinds that don’t show up in models.
His core insight is simple:
The biggest drivers of outcomes are rare, extreme events we don’t see coming.
Black Swans
Taleb popularized the term Black Swan for these events.
A Black Swan is:
Rare
Unpredictable
High impact
Obvious only in hindsight
Financial crises. Pandemics. Sudden technological or geopolitical shifts.
What matters isn’t how often these events happen.
What matters is that when they do happen, they dominate everything.
Years of steady progress can be wiped out by a single bad break.
How People Actually Lose
Most people don’t fail because they’re reckless.
They fail because they optimize for a world without surprises.
They build systems that look great in normal times:
Smooth returns
Stable income
High efficiency
Low volatility
And then one abnormal event hits.
The issue isn’t bad luck or bad forecasting.
It’s fragility — being positioned in a way that only works if nothing goes wrong.
You don’t get punished for being wrong frequently.
You get punished for being wrong once, at the wrong moment.
The Inversion
Here’s the part that’s easy to miss.
We make the same mistake on the upside.
Just as we underestimate rare, catastrophic risks, we also underestimate rare opportunities with massive upside.
These don’t look like Black Swans while they’re forming.
They look:
Slow
Uncertain
Boring
Indistinguishable from many failures
When they work, we call it luck.
But structurally, they’re the mirror image of disaster.
You Don’t Need Likelihood — You Need Exposure
A common mistake is thinking these upside outcomes need to be likely to matter.
They don’t.
They only need to be possible and asymmetric.
One investment that compounds for decades.
One skill that scales beyond your time.
One relationship that changes your trajectory.
Most attempts won’t matter.
One will outweigh all the rest.
How to Position Yourself
This leads to a simple framework.
On the downside:
Avoid ruin
Build margin of safety
Don’t be fragile
On the upside:
Create optionality
Accept small, contained failures
Stay exposed to convex outcomes
The goal isn’t prediction.
It’s positioning.
The Point
In a world shaped by rare events:
Consistency isn’t the same as safety
Volatility isn’t always danger
Optimization often increases fragility
The smartest strategy isn’t guessing what will happen next.
It’s building a life and portfolio that:
Survives the bad breaks
And benefits from the good ones
You don’t need many wins.
You just need to stay in the game long enough for one to matter.
This Week’s Affiliates
You could be wasting hundreds on car insurance
If your auto insurance rate went up in the last 12 months, check this before paying your next bill! All you have to do is enter your zip code and car info to find better insurance options. You could save up to $600 per year!
Homeowners: Don’t miss winter insurance savings
EverQuote is designed to make your seasonal insurance refresh effortless.
Fast Process: Skip repetitive forms and get matched in minutes.
More Ways to Save: Compare rates from both national and local carriers.
Winter-Ready Coverage: Enter the holidays with clarity and confidence.
And for homeowners, the benefits can go even further. Many qualify for lower auto insurance rates, and reviewing your options now can lead to real savings before winter weather peaks. With EverQuote, checking those potential savings takes only moments.
Whether you’re hauling gifts, driving through snow, or gearing up for the new year, now is the perfect time to ensure your coverage keeps you protected—and your holiday budget comfortable.