View All Articles

How to Get Comfortable With Taking Risks

Taking risks isn’t exactly fun (at least not for most people), but it’s a necessary part of life. In fact, risk is pretty much built into every aspect of life. Dating is a risk, starting a new job is a risk, creating something is a risk. Anything we do that we haven’t personally tried and tested presents a risk. It might work and bring us happiness and success; or it might not work, and leave us feeling like we failed. 

But if risk is unavoidable and necessary, how can we get more comfortable with taking risks? If there’s a lot on the line, how can we overcome fear of failure and take the risks we need to take?

The value of risk

Some people are natural-born risk-takers. They challenge the status quo, stare down obstacles, and explore new possibilities and opportunities. 

The rest of us (yes, us—I count myself in this group) are a little more “security-oriented.” It’s not that we don’t respect or even admire risk-takers; it’s just that we appreciate stability and comfort. It’s nice to feel like you’re in control, at least when it comes to some things.

The truth is, both types of people are extremely valuable to the world and society as a whole. Risk-takers change the world, and non-risk-takers keep the world safe. 

But just as risk-takers need limits (i.e. they shouldn’t take 100% of the risks they face, 100% of the time), non-risk-takers need to be willing to take risks from time to time.

Which begs the question: why? Why don’t we all just play it safe, all the time? Why don’t we stick with what we know—the things we’re good at, the things we’ve succeeded at before, the things we know will work? Why don’t we just make the best of a situation?


Big risk can lead to big reward

While big risks can potentially lead to big disappointment, they can also lead to big rewards. If you want the payoff, you have to take the risk. 

Risks lead to growth

Taking a risk will either pay off or it won’t, but either way, experiences help us learn important lessons that will inform our decisions in the future.

Taking risks inspires creative thinking

When you’re trying to make a risk pay off, you’re likely to stretch your creative muscles to look for ways to make it work. When there’s a lot at stake, you’re more willing to do the creative work required to find innovative solutions that will lead you to success.

Risk reveals values

What you’re willing to risk can say a lot about what you value. If you’re ever trying to figure out what you really care about, think about the risks you’ve taken. What were you trying to gain, and what were you willing to put on the line?

Risk builds self-confidence

When risk ends in a positive way, it can boost your self confidence. When you see that your willingness to take the risk (and your willingness to put in the work to succeed) have paid off, it can give you more confidence in your decision-making abilities and creativity.

Risk helps you avoid regret

Research suggests that it’s more likely that you’ll regret not doing something than that you’ll regret doing something, even if the thing you do doesn’t go well. After all, if you never even try, you’ll never know how things could have gone. 

In short, learning to get comfortable with taking risks can help you as you work to create the happy life you want to live. It can help you grow in meaningful ways. It can help you learn lessons you may never have learned otherwise. These rewards, and others, make risk worth…well, the risk. 

“If there’s even a slight chance of getting something that will make you happy, risk it. Life’s too short, and happiness is too rare.”

A.R. Lucas

How to get comfortable with taking risks

Whether you’re a risk-taker or not, there are some things you can to do help yourself feel more comfortable taking risks on a regular basis.

Develop a growth mindset

A growth mindset is all about hope, improvement, effort, and growth, rather than outcome and performance. If you have a growth mindset, you reward yourself for trying, regardless of whether or not you succeeded. 

A growth mindset helps you let go of perfectionism and fear of failure. It helps you be more willing to take risks because you recognize that even if you fail, you can still learn and grow. 

Developing a growth mindset is all about embracing challenges, recognizing learning opportunities, and recognizing and accepting your imperfections. If you’re able to do those things, you’ll be more comfortable with taking risks. 

“What’s the worst that could happen?”

Anxiety and panic are rooted in feeling unsafe. In fact, panic attacks often stem from feelings of danger, even to the point of feeling like death is imminent. But the truth is, most of the risks you take are not going to put your life in danger.

If you’re considering taking a risk, ask yourself: “What’s the worst that could happen?” Allow yourself to really be honest about your worst fears and explore the potential negative outcomes of taking this risk. Maybe you do feel like your life could be in danger. Perhaps you think the risk could lead to financial ruin. Or maybe the future of a relationship is on the line.

Allowing yourself to think of the absolute worst-case scenario can help you keep the risk in perspective. After all, the worst-case scenario isn’t all that likely to actually happen. Plus, imagining the worst-case scenario can also allow you to imagine how you would respond to that scenario, helping you prepare for the worst, even as you hope for the best.

Design.org Shop

“What’s the best that could happen?”

Just as it’s useful to think of the potential downsides of a risk, it’s also beneficial to think about the potential upsides. What do you have to gain if things go well? How could that change your future? How could it help you “create happy” in your life? 

The risks you take could end badly, but they could also end well. Allow yourself to envision what could go right and how it could change your life for the better. Use that information to help inform your decision of whether or not to take the risk.

Compare the risk to your values

The risks you take should be based on the values you hold. You’ll likely be willing to take more risks if they could help you reach a goal you really care about, or support a cause you really believe in. Realizing that the risk you’re considering aligns with your values can help you feel more comfortable taking the risk, as it’ll help you live a more authentic life. 

“Do what is right, not what is easy.”

Roy T. Bennett


Practice taking risks. The more you practice, the easier it will get. Practice listening to your gut and following your intuition. Notice which risks you’re comfortable with, and what types of risks scare you more. Give yourself permission to fail. Give yourself credit for trying. 

Managing risks in a smart way

“I don’t believe in taking unnecessary risks, but a life without risk isn’t worth living.”

Charles Lindbergh

Getting comfortable taking risks is important, but it’s also important to take risks in a smart way. Remember: risk matters, but security does, too.

Here are some quick tips for making sure you’re managing your risks intelligently.

  • Understand the risk. Do research. Get informed. Don’t jump into something blindly. (If there’s financial risk, assess your finances. If you’re basing your decision on certain information, make sure that information is valid. And so on.)
  • Don’t take risks for the wrong reasons (reasons that don’t align with your values).
  • Be clear headed when you decide to take a risk (e.g. not under the influence of alcohol, not in an emotionally-compromised state, etc.).
  • Accept input from experts, friends, or family members you trust.
  • Have a backup plan.
  • If the potential reward doesn’t really matter to you, the risk is probably not worth it.
  • Be honest with yourself about any possible red flags you see.
  • Don’t be afraid to say “no” if you feel pressured into a decision.

Getting comfortable with taking risks can serve you well in life. Risk can play a big role in helping you create happiness—in your career, in your relationships, in your personal development, and more. Be willing to take (smart) risks, and you’ll open the door to the potential rewards. 

Risk on!

“Create happy” in your life (for free!) with Design.org.

(1) Take our free assessment. (2) Start receiving free, personalized coaching messages. (3) Increase your capacity to “create happy.” Are you ready? Start today!