September 18, 2023

The Art of Asymmetric Bets

READ Time -
1.5 minutes

We all have a comfort zone. A “safety bubble”, if you will.

When you’re a solopreneur, this bubble might seem like a great place to hang out. A safe space to reduce risk and increase your chances for survival.

But here's the truth: your comfort zone can become a cage.

When you're too scared to take risks, you miss out on opportunities — opportunities that could completely change your business and your life.

If you've passed up opportunities recently due to fear, maybe it's time to make a list and reevaluate them.

Could they be worth revisiting?

Calculated Risk Doesn’t Mean Gambling

Being bold in your choices doesn't mean throwing caution to the wind.

It means weighing the pros and cons, and making informed decisions. When faced with a decision that feels risky, doing a simple cost-benefit analysis can be a game-changer.

List out the potential gains and losses and let the facts guide your choice.

Your goal is to find small risks with asymmetric upside.

Asymmetric Upside: When the downside is limited, but the upside is unlimited.

The Transformative Power of Asymmetric Upside

Back in 2018, I took what seemed like a small risk.

I started writing on LinkedIn, sharing my thoughts about business. There was a small risk involved: My CEO or teammates could have viewed it as a distraction give I was employed at the time.

So I mitigated that risk by having conversations with people to let them know why I was doing it and how I thought it could also benefit the company.

The risk was low. But the upside was extremely high.

This little bet snowballed into a $4.7 million business over the next 4.5 years and led me to create The LinkedIn Operating System, which is the most-enrolled course on using LinkedIn for audience & business growth.

The funny part? This was one of about 8 asymmetric bets I tried in 2018. The rest failed.

But that one didn’t. And it was life-changing.

Learning Through Each Step

Every decision offers a lesson, whether it pans out as expected or not.

'Failures' provide invaluable insights that can shape how you make future choices.

After each project or decision, you should conduct a post-mortem analysis to learn what worked and what didn't. Then use those insights for future decisions.

For example, one of my failed bets was called, “Tales from the White Board”. A short YouTube series where I tried to explain how technology companies grow.

It didn’t work because I didn’t like being on camera and I didn’t enjoy scripting out videos. I sucked at it.

So I made a simple note to myself: Don’t make those choices in the future. It even goes into my mantra, “…do very little of what I hate.”

Aim for a Life of Asymmetric Bets

Make it a point to identify one asymmetric bet you can make in your business this month.

It could be an investment, a new project, or even a new connection.

The higher rewards and lower risks mean fewer regrets and a life you won't look back on with 'what-ifs.'

Good luck out there.

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