Executive Insider

How to Avoid Losing

It’s your lucky day! You meet a kind stranger who offers you your choice of a great deal, something for nothing. No tricks, really: you’re getting a free lunch. 

She gives you $45. Then, she asks if you want to keep that money, or give it to her in exchange for a coin flip, where if it’s heads, she’ll give you $100, and if tails, you get nothing.

Which do you choose? Do you want $45 in cold, hard cash in your pocket, or are you willing to take a chance with the coin flip? Decide before reading further.

When I present this scenario in my speeches to business audiences, about 80 percent say they’ll take the $45 from the kind stranger. I made that choice when I first learned about this scenario, and so do most people in studies of similar choices.

After all, the $45 is a sure thing. Wouldn’t I feel foolish if I took a risk and lost it all for just a chance at getting the $100? My gut reaction was to avoid losing out. After all, who wants to be a loser, right?

Well, let’s run the numbers. The chance of getting heads is 50 percent, so in half of all cases you’ll win $100, and in the rest you won’t win anything. That’s equivalent to $50 on average, versus $45.

Imagine you flipped a coin 10 times, 100 times, 1,000 times, 10,000 times, and then 100,000 times. At 100,000, on average you would get $5 million if you chose the coin flip for $100 each time, versus $4.5 million if you chose $45 each time. The difference: a cool $500,000.

Thus, unfortunately choosing $45 as my gift actually results in losing out. The right choice – the one most likely to not cause me to be a loser – is to choose the coin flip as the gift. Otherwise, over multiple coin flips, you’re pretty much guaranteed to lose.

But wait, you might be thinking: I presented this as a one-time deal, not a repeating opportunity. Maybe if I told you it was a repeating scenario, you’d have thought about it differently.

Here’s the problem. Research shows that our gut treats each individual scenario we see as a one-off. In reality, we face a multitude of such choices daily. Our intuition is to treat each one as a separate situation. Yet, these choices form part of a broader repeating pattern where our intuition tends to steer us toward losing money.

That gut reaction is called loss aversion, one of the many dangerous judgment errors that result from how our brains are wired, what scholars in cognitive neuroscience and behavioral economics call cognitive biases. Fortunately, recent research in these fields shows how you can use pragmatic strategies to address these dangerous judgment errors.

Your professional life – anyone’s professional life – is made of 100,000 coin flips. The stranger’s gift represents the series of opportunities we face in our lives, and we can either win $5 million or $4.5 million depending on the choices we make for each one.

The same applies on an organizational level. Let’s say your company has an annual revenue of $50 million, and a healthy profit of $7.5 million. Regardless of the choice you’re making, if other employees in your organization are going with their gut to avoid losses, and the company loses 10 percent of its revenue or $5 million per year, then two-thirds of your profit will be wiped out, leaving only $2.5 million.

Every day, you face a series of situations where you need to decide whether to take the course that feels most comfortable by avoiding losses, or the course that feels less comfortable and leads to more gains over time. We’re not talking about huge bet-the-company risks – which require a different approach – but the kind of small decisions that add up to large sums over time. If you just go with your gut instead of doing the calculations and going with the data, you are likely to lose much more money by not taking the course that feels most risky.

To prevent your intuition from leading you astray, adopt a policy of letting the data lead you, instead of relying on your intuitions. For each decision you face, envision it as a repeating pattern, instead of a one-time decision: run the numbers, account for the role of uncertainty, and take the course most likely to lead to the biggest profit.

Treating each choice as part of a broader pattern might feel counterintuitive, uncomfortable, and unsafe. Yet the course that feels most safe of avoiding losses is actually much more dangerous for your bottom line.


Written by Dr. Gleb Tsipursky.

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Dr. Gleb Tsipursky
Dr. Gleb Tsipursky is an internationally-renowned thought leader in future-proofing and cognitive bias risk management. He serves as the CEO of the boutique future-proofing consultancy Disaster Avoidance Experts, which specializes in helping forward-looking leaders avoid dangerous threats and missed opportunities.

A best-selling author, he wrote Never Go With Your Gut: How Pioneering Leaders Make the Best Decisions and Avoid Business Disasters (Career Press, 2019), The Blindspots Between Us: How to Overcome Unconscious Cognitive Bias and Build Better Relationships (New Harbinger, 2020), and Resilience: Adapt and Plan for the New Abnormal of the COVID-19 Coronavirus Pandemic (Changemakers Books, 2020). His writing was translated into Chinese, Korean, German, Russian, Polish, and other languages. His expertise comes from over 20 years of consulting, coaching, and speaking and training for mid-size and large organizations ranging from Aflac to Xerox. It also comes from over 15 years in academia as a behavioral scientist, including 7 as a professor at Ohio State University.


Dr. Gleb Tsipursky is an opinion columnist for the CEOWORLD magazine. You can follow him on LinkedIn. For more information, visit the author’s website.