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Why am I writing this
Most people spend their lives making safe bets.
The problem? Safe bets rarely move the needle.
You can work hard for decades on a path that guarantees stability — but caps your upside.
Asymmetrical bets flip that equation: limited downside, uncapped upside.
They’re how creators, founders, and investors change their trajectory — without changing who they are.
1 Insight
An asymmetrical bet is any decision where the potential gain far outweighs the possible loss.
The beauty lies in the math of outcomes:
Worst case: you lose little time, pride, maybe a small investment.
Best case: it changes your life.
Start looking for these bets in your everyday life:
Publishing online (reputation upside, minimal cost)
Reaching out cold to people you admire (network upside, zero real risk)
Building a side project or newsletter (learning + leverage upside)
The most powerful asymmetrical bets are rarely financial — they’re social and creative.
1 Habit
Once a month, place one asymmetric bet.
It doesn’t need to be big or bold.
Just something that feels a little scary, a little uncertain, but could compound if it works.
Ask yourself:
“What’s the upside here? And what’s the real downside?”
If the answer is “not much” it’s probably worth doing.
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1 Story
In 1976, a young engineer named Steve Wozniak built a small computer in his spare time.
His friend Steve Jobs convinced him to sell it.
Wozniak hesitated — he had a stable job at HP. But Jobs pushed:
“What’s the worst that happens? We fail and go back to work. What’s the best that happens? We change the world.”
That’s an asymmetrical bet.
The downside was unemployment.
The upside was Apple.
The bet rewrote history.
That’s it for this week!!!
The people who win big don’t always work harder; they risk smarter.
Every once in a while, life hands you a door that only opens from the other side.
You just have to push — even if you’re not sure what’s behind it.
Make one asymmetrical bet this month.
It might not change everything — but it could.
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