The concept of Asymmetrical Upside is a mental model, or 'razor,' for decision-making, which is often used in the financial world.

It's a risk vs. reward analysis, where the idea is to look for opportunities with a much greater potential upside than potential downside.

Life is full of asymmetric opportunities, and if you start to apply this razor, it can significantly change the course of your life—as it did for me.

When I was younger, so much younger than today...

In 2010, I was a humble web designer working for a small company based in London. A new member joined our team. 

She was intelligent, vivacious and beautiful. 

So, naturally, I spent the next 18 months getting to know her and subtly hinting that I was interested.

I didn't see any sure signs that the attraction was mutual, so I didn't ask her out directly for fear of ruining what had become a valued friendship.

But then she made a shock announcement.

She was leaving the company in 6 weeks.

I had very little time to decide whether to make my feelings known, and how.

There's nothing like a deadline to focus the mind!

I found an excuse to invite her for dinner and decided I wouldn't leave without telling her how I felt.

At that point, I had little to lose.

So, over dessert, I clumsily told her that I liked her, which came as a massive shock to her. It seems I had been far too subtle after all!

Fast forward to today, and that woman is now my wife, and we have a beautiful family together.

Remember: “You miss 100% of the shots you don’t take.” (Wayne Gretzky)