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Tired of playing it safe? Learn how to take risks that pay off

July 20, 2022 - 15 min read


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Why is it important to take risks in life?

7 benefits of taking risks

Risk-taking on teams

​​How do you get the courage to take risks?

How to take calculated risks

When you think of risk-taking, what comes to mind?

Most of us immediately think of major risks, like jumping out of a plane or driving at break-neck speeds. In other words — risky behaviors. We tend to think of risk-takers as reckless, dangerous individuals, and we zero in on the potential negative consequences.

But in truth, risk-taking is highly subjective. Some people, like skydiving instructors or professional racecar drivers, take these kinds of risks all the time. They aren’t reckless. These individuals have calculated their risks, mastered the necessary skills, and created support systems to mitigate negative consequences.

Humans tend to apply this “life-or-death thinking” to other, less intense risks. We stress over asking someone a question, speaking in public, or asking for a raise. Cognitively, we know the level of risk isn’t the same — but it feels just as threatening. And that fear tends to keep us firmly in our comfort zone.

Author Robert G. Allen is known for saying, “Everything you want is just outside your comfort zone.” Put another way, everything you want requires some level of risk. Taking risks can be one of the most rewarding experiences in life, but it’s also one of the hardest to do well. But it’s not because success isn’t possible. Rather, the fear of failure often stops us from even trying.

Why is it important to take risks in life?

Have you ever heard of the principle of inertia?

People often explain the idea using Newtonian law: An object at rest tends to stay at rest, while an object in motion tends to stay in motion. When it comes to human behavior, this principle explains why it’s often easier to stay on the sofa and watch just one more episode (that autoplay feature is devious).

However, this also underlines the importance of risk-taking. When we get comfortable — whether in a role, a relationship, or a career — it’s easier to stay there. Our brains and bodies are wired for homeostasis (a state of relative stability). So when we feel comfortable, anything that takes us away from that state seems like a risk.

Unfortunately, just because we’re comfortable with our current state doesn’t mean that we’re thriving. In order to flourish, we need to have a sense of accomplishment and opportunities for growth. That means stepping out of our comfort zone. Homeostasis may be “comfortable,” but it’s also a fertile ground for languishing. Nothing’s wrong, per se — but we’re not growing and changing, either. 

Newton’s law of motion comes with a caveat — objects tend to stay in their current state, unless acted on by an external force. For people who feel stuck, taking the right kind of risks can be just the force they need to get moving again.

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7 benefits of taking risks

1. You’ll feel a sense of accomplishment

It might feel scary to start, but taking a risk — even if it doesn’t go exactly as planned — can be exhilarating. You’ll be proud of yourself for your bravery and courage.

2. Erase old stories

Sometimes, we grow up with beliefs or assumptions about ourselves and the way the world works that don’t serve us. We often stop questioning these assumptions as we get settled into our careers — but they may still be running the show. 

Taking risks can help you create evidence to disprove those old stories that may not be serving you anymore. Even if you wouldn’t change a single thing about your life, releasing those negative thoughts can be wonderfully freeing. 

3. You'll learn more about yourself

What do you like to do? What makes you happy? What are your values? If you were checking into a hotel at three in the morning and you didn’t speak the local language, and they didn’t have your reservation, what would you do?

Okay, that last one was a bit specific. But taking risks challenges you in big and small ways. As you have new experiences, you learn more about who you are and what drives your behavior. New challenges give out a chance to impress yourself and grow. 

4. Increases confidence

With each new challenge and risk, you’ll become convinced of your own ability to handle evolving circumstances. This will make you a more confident, flexible person and a better leader. Improved confidence (testedd through experience) can also have a positive effect on your decision-making skills. 

5. Opens up new opportunities

Stepping out of your comfort zone can lead to all sorts of new opportunities, both professionally and personally. You might find yourself opening your own business or becoming a trendsetter in your industry. 

6. Builds resilience

Taking risks can also help you learn how to handle adverse outcomes and setbacks, making you more resilient in the face of adversity. You’ll know that you can thrive no matter what happens, and become more adept at finding multiple routes to success.

7. No regrets

Finally, calculated risks are often worth taking, even if they don't always result in positive outcomes. Without taking them, we would never know what could have been. Risk-takers are often more satisfied with their lives and happier with themselves than non-risktakers.

Risk-taking on teams

Learning how to take risks as an individual can benefit your performance at work. In order for both small and large businesses to grow, they need to be comfortable managing risks, growing, and staying on their edge.

BetterUp measures Team Risk-Taking among our Members, since it influences so many other areas of personal and professional development. Compared to those who scored low, BetterUp members who report high levels of Team Risk-Taking report 47% more team innovation, 23% more goal attainment, 19% more engagement at work, and 10% more job satisfaction.


​​How do you get the courage to take risks?

A lot of people think that self-confidence is the key to taking risks, but that's not always the case. You’re not more likely to take risks because you think you can’t fail. It’s actually more about having confidence in the outcome. You know that even if things don’t do perfectly, you have the resources to manage failure. 

Building a support system

When you're taking risks, it's essential to have a supportive network of people around you. These people can help you stay motivated and encourage you when you're feeling afraid. They can also help you assess whether a particular risk is worth taking. 

For example, if you are thinking about applying for a new role, your support team will help you identify the job you want and prepare for it. They can give you feedback on your strengths and areas for development. They can help keep you focused when doubt creeps in. These people play the roles of risk assessment, cheerleaders, and coaches.

With the right support system, risk-taking becomes much easier. For example, those racecar drivers are fully aware that driving at such high speeds is dangerous. They don’t do it thinking that they’ll never crash. In fact, professional drivers crash a lot. In 2019, NASCAR reported an average of three crashes per race.

Zoom out on any competitive racetrack, though, and you’ll see coaches, mechanics, and emergency medical technicians on standby to provide immediate support to injured drivers. Look at the vehicles themselves, and you’ll find safety features that don’t exist in commercially available cars. If your goal is to race professionally, crashes are part of the job. Your support system provides the tools to mitigate the risk of a negative outcome.

Working with a coach can help you build the confidence to take more risks. But a coach also can help you determine which risks to take, and when the right time is to take them.

How do you know when you should take a risk?

When I think of weighing risks, I imagine an old-fashioned, balance scale, weighing the pros and cons. 

As I consider what should go on either side, I don’t think of the best-case or worst-case scenario. I think about who I’ll become by taking the risk. I think about whether the potential benefits are worthwhile, and whether I have the tools to deal with failure.

The best risks to take are the ones that bring you into closer alignment with your values and desires. For example, you might be taking a risk by changing careers. But if the potential outcome is less financial stress, more opportunities to do meaningful work, and better work/life balance, then it’s a step worth taking.

That leap of faith — whether or not it results in the desired outcome — brings you closer to who you want to be.


How to take calculated risks

Risk-taking doesn’t mean “winging it.” The better you prepare, the better your chances of success the first time around. Here are 4 steps to take better, calculated risks that have the best chance of paying off:

1. Develop a system for evaluating your risks

When it comes to taking better risks, it’s important to be thoughtful and strategic. Consider what you have to lose and what you have to gain. Weigh the pros and cons. Talk through your reasoning with a coach or trusted friend.

Remember that you’re not evaluating your risks by extremes. You’re looking for the best way to reach a successful outcome. Successful people consider many different paths forward, and choose the one most in alignment with their values and goals.

2. Make time for Inner Work®

There are two components to risk: emotional and systematic. The emotional part often takes place unconsciously. There are certain things that we can’t even think about because they feel so scary. Those probably aren’t the best risks to start with, but they’re helpful to be aware of.

The more you systematically approach your risks with a strategy in place for managing them, the more comfortable you’ll be thinking through those emotionally triggering risks. A coach can help you unpack what you’re afraid of and when the right time to tackle it is.

3. Start small

You don’t have to take huge risks all the time. Building the habit of taking small risks can pay off big as well.

If you’re the type of person who automatically equates risk with danger, try changing your definition of risk. Think of it instead as anything with the potential for uncertainty. You can increase your risk tolerance in small ways, which can build the muscle to think through — and eventually take on — bigger risks. 

What constitutes a small risk? Look for anything that’s out of your comfort zone. If you always order the same coffee, try getting something new. If you always go to the same place for vacation, try somewhere new. If you’re considering a career change, try taking a class first. These might feel like small steps, but they’ll help you get comfortable with being uncomfortable.

4. Redefine failure

Don’t be afraid of failure — it’s part of the process. If you’re not failing, you’re not trying new things, and you’re not growing. The trick is to learn from every outcome. Many times we learn just as much — if not more — from failure than we do from success. A study of Olympians found that, years after they competed, silver medal winners tended to be happier and more resilient than gold medal winners.

Feel the fear — and take the risk anyway

When you first start learning how to take risks, it might be that everything feels scary. But that’s okay. Your brain is trying to keep you safe. You’ll have to prove to yourself that risk-taking doesn’t need to be threatening — and that it can even be fun. 

There are endless possibilities in the world, and the best way to figure out what risks are right for you is to tune into your intuition. Don’t be afraid to experiment. Even if something doesn't work out as planned, you'll learn from it and grow as a person — and that will help you build self-trust. Whether you’re moving to a new city, starting a new job, or launching a new business, you’ll know that you can handle whatever comes your way.

Weighing “good risk” is personal, but you don’t have to do it alone. Reach out to BetterUp for support in both small and big risks. A coach can provide you with a new perspective and the support you need to take smart risks.

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Published July 20, 2022

Allaya Cooks-Campbell

BetterUp Staff Writer

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