Are You Taking Enough Small Risks?

This is the twelfth piece to be published on the Get The Guy blog from my brother Stephen. Steve helped co-write the Get The Guy book and is a wealth of knowledge on dating and relationships.

Today’s article covers the missing piece a lot of women need to begin taking action (and risks) in their love lives. We hope this leads to a shift in mindset. Enjoy!

Enter Stephen

You’ve read a lot of advice.

You’ve read techniques for meeting more guys, improving your relationships, getting the right mindset and you’ve delved into the psychology of attraction.

Knowledge is everywhere and freely available. A lack of knowledge is not what holds us back from the love life we want.

What holds us back is a simple truth: Doing stuff for our love lives can suck a lot of the time.

Doing work on our love lives can feel difficult, silly, distracting (from other urgent goals), unnecessary, frustrating, futile and often unfair. This makes it extremely hard to motivate ourselves to take action just for our love lives.

This has always puzzled me. If you took a survey, nearly everyone would agree that the quality of their life would be immeasurably improved if they felt completely happy in love. So why wouldn’t we be motivated to take actions that would dramatically increase the odds of its attainment?

I was recently reading the book Thinking Fast and Slow by Daniel Kahneman, and one of the chapters helped me figure out a plausible answer.

In one chapter Kahneman covers the idea of LOSS AVERSION.

Loss Aversion says that human beings are much more motivated to run away from losses than they are to pursue potentially large gains.

For example, a momentary spell of social anxiety is likely to prevent us from speaking to an attractive stranger at a party, even if the potential gain from taking that single action is enormous. It’s the same with a potential career gain that could offer enormous fulfillment, but we shy away from the opportunity because we risk getting rejected in an interview.

It’s terrifying how much Loss Aversion can affect our results in our career, our business, our love life, basically any aspect of our life that involves even the slightest element of risk.

Worth a gamble for love?

Kahneman gives a simple example to illustrate the power of Loss Aversion: Suppose you are offered a gamble on the toss of a coin: If it comes up heads, you win $200, if it’s tails, you lose $100.

Most people are so averse to loss that they wouldn’t take the single bet.

That part seems fairly rational though. No-one wants to risk losing $100 on a single coin toss.

But here’s the problem with applying this same logic to our love lives: loss aversion only makes sense if we have one opportunity. But it makes no sense if we have dozens of opportunities!

Most of us find it hard to take small individual gambles in our love life. For example, we don’t want to go on that date or flirt with that guy, or even to ask that guy how his night is going, because even though we would gain hugely if it came out positive, we also subject ourselves to a sting of disappointment and minor social embarrassment.

Thus, we are loss averse in love.

But this is because we put so much pressure on one opportunity, we don’t only have one person to speak to, one job to apply for, or one person to date who could potentially disappoint us. We have dozens if not hundreds of opportunities.

What Kahneman proves in his book is that the more opportunities (or coin tosses) we have, the more ridiculous and irrational it is to be LOSS AVERSE, because the losses become smaller and smaller, and the potential gain becomes bigger.

For example, let’s return to our coin toss scenario. Suppose you are offered not one coin toss, but TEN.

That’s TEN coin tosses in which, each time, you can either win $200 or lose $100.

On average mathematically, this makes it extremely unlikely we would lose any money, and the potential gains are enormous.

And yet, the sad part is, people will still remain loss averse, because they only consider each individual opportunity, instead of thinking of them as an aggregate of opportunities.

Traders in large financial firms are often taught how to combat loss aversion through a technique call broad framing. This requires us to stop focusing on the results of every individual transaction, and instead look at our rate of success as a running total over time.

You don’t need every individual transaction (or in our case, social interaction) to be a massive gain. Because one big win (i.e. meeting one amazing person, making one big transaction) will immediately outweigh all of the little hiccups experienced on the way.

And this is how we need to always approach gambles in life. Each individual gamble doesn’t matter. As long as we stand to gain more than we lose, and the losses won’t cause us to go bankrupt, we should always be willing to take the smaller risk.

Incidentally, in our love lives this makes even more sense, since in the modern world we have a nearly infinite number of people to meet, date, interact and converse with, and the losses from one interaction going badly are tiny.

With this in mind. Here are three questions to ask yourself if you feel you need more of a risk-taking mindset:

1. What small risks are you currently not taking?


It might be trying to express yourself more honestly, perhaps saying a more flirty line to a guy instead of just hanging back in “friendly conversation” mode. Maybe it’s touching more in conversation. Maybe it’s starting more conversations. Maybe it’s risking being vulnerable and telling a guy how you feel and connecting with people.

Make a list of three and keep it simple. Then resolve to take more risks in that area.

2. How much of your energy and time are spent avoiding losses vs. pursuing large gains?


Most large gains in life will always require us to face setbacks, potential rejections, and a good dose of negative feedback.

But if we are able to accept this and face them head on, we stand to win enormously. It’s not true that you have to risk big to win big, you just have to be willing to take small risks more frequently.

3. Can you think of something you enjoy in your life now that you owe to taking a small risk?


This question will help prove to yourself the value of taking small risks.

Perhaps you once made a decision to put yourself forward at a networking event and ask someone for a job. Maybe you approached a person your admire and they responded warmly to you. Maybe you spoke to a guy at a bus stop, or tried to push a business negotiation one step further than you thought you could. Maybe you said yes to taking a trip and ended up finding the place you want to live.

Start looking for them, and you’ll see the opportunity for taking small risks everywhere.

Where do you need to take more small chances? Let me know in the comments below.

P.S. For all economists and behavioural psychologists reading…regarding any mistakes I’ve made in the theory or examples presented in this article, I implore you, show mercy.


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Photo credit: Marcell Dietl

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