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How to Get Comfortable Taking Risks (Even When It Feels Scary)

February 27, 20256 min read

Taking risks can be daunting. Whether it’s making a career change, starting a business, moving to a new city, or even just speaking up in a meeting, the fear of failure often holds us back. However, the ability to take risks is essential for personal growth and success. Getting comfortable with risk doesn’t mean eliminating fear—it means learning how to navigate uncertainty with confidence.

In this blog, we’ll explore why risk-taking is important, what holds us back, and practical strategies to help you step outside your comfort zone and embrace risk, even when it feels scary.

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Why Taking Risks Is Essential

Risk-taking is a fundamental part of progress. Without it, we would remain stuck in familiar patterns, missing out on opportunities for growth, learning, and transformation. Here’s why embracing risk is important:

1. Growth Comes from Discomfort

Stepping outside your comfort zone forces you to develop new skills, expand your perspective, and build resilience. Every great success story involves moments of discomfort that ultimately lead to growth.

2. Opportunities Come from Risk

Many of the best opportunities in life come from taking chances. Whether it’s networking with someone new, applying for a job beyond your qualifications, or launching a project, risk is often the bridge to unexpected rewards.

3. Failure Teaches Valuable Lessons

Failure is often seen as a negative outcome, but in reality, it is a learning experience. When you take risks and fail, you gain insights that help refine your approach for the future.

4. Confidence Comes from Overcoming Challenges

The more you take risks and push through fear, the more confident you become in your ability to handle uncertainty. Confidence is built through experience, not by avoiding challenges.


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What Holds Us Back from Taking Risks?

Before we dive into how to take risks, it’s important to understand what holds us back. Fear is often the biggest obstacle, but it manifests in different ways:

1. Fear of Failure

One of the biggest reasons people avoid risk is the fear of failing. The thought of embarrassment, financial loss, or wasted effort can be paralyzing.

2. Fear of Judgment

Worrying about what others think can keep us from making bold moves. We fear being criticized, ridiculed, or not fitting in.

3. Perfectionism

Perfectionism often leads to inaction. If we wait for the perfect moment or perfect plan, we may never take the first step.

4. Past Negative Experiences

Previous failures can make us hesitant to take risks again. We may develop limiting beliefs that convince us we’re not capable of success.

5. The Comfort of Routine

Staying in familiar situations feels safe. Even if we’re unhappy or unfulfilled, the known feels less intimidating than the unknown.

Now that we understand why we hesitate, let’s explore practical ways to become comfortable with taking risks.

A modern home office featuring a sleek wooden desk set against a breathtaking cosmic mural of a swirling galaxy in shades of blue, purple, and gold. Two minimalist black desk lamps and small potted plants add a functional and decorative touch to the workspace. Large windows allow natural light to fill the space, complementing the celestial-inspired design and cozy atmosphere.

How to Get Comfortable Taking Risks

1. Start Small

Risk-taking doesn’t have to start with a life-changing decision. Begin with small, manageable risks. Try a new hobby, speak up in a meeting, or introduce yourself to someone new. These small wins build confidence and prepare you for bigger risks.

2. Reframe Failure as Learning

Shift your mindset around failure. Instead of seeing it as a dead-end, view it as feedback. Every risk, successful or not, teaches valuable lessons. When you remove the pressure of perfection, taking risks becomes easier.

3. Visualize Success

Before taking a risk, spend time visualizing a positive outcome. Picture yourself succeeding, feeling proud, and enjoying the benefits of your decision. This mental exercise helps reduce fear and builds motivation.

4. Assess the Worst-Case Scenario

One way to reduce fear is to ask yourself, “What’s the worst that could happen?” Often, the worst-case scenario is not as catastrophic as we imagine. Understanding that you can handle setbacks makes risk-taking less intimidating.

5. Use a Risk vs. Reward Analysis

Before making a decision, weigh the potential risks against the potential rewards. If the potential benefits outweigh the risks—or if the risks are manageable—go for it.

6. Build a Safety Net

Taking risks doesn’t mean being reckless. Have a backup plan in place so you have security if things don’t go as expected. For example, if you’re starting a business, save some money beforehand or have a secondary income source.

7. Surround Yourself with Supportive People

Having a strong support system makes taking risks easier. Seek out mentors, friends, and colleagues who encourage and inspire you. Being around people who have taken risks and succeeded will boost your confidence.

8. Develop a Growth Mindset

Adopt a mindset that embraces challenges and sees effort as a path to mastery. The more you focus on growth rather than fixed outcomes, the more comfortable you’ll be with risk-taking.

9. Take Action Despite Fear

Courage isn’t the absence of fear—it’s acting despite it. When you feel fear creeping in, acknowledge it, but don’t let it stop you. Fear diminishes with action, and the more you push through, the less intimidating risk-taking becomes.

10. Track Your Progress

Keep a journal of the risks you take, the results, and what you learn from each experience. Over time, you’ll see patterns of growth, resilience, and success.

11. Celebrate Your Wins

Recognize and reward yourself for taking risks, no matter the outcome. Whether it’s treating yourself to something special or simply acknowledging your courage, celebrating small victories builds momentum.

12. Adopt the “What’s the Best That Could Happen?” Mindset

Instead of focusing on what could go wrong, shift your focus to what could go right. This change in perspective makes risk-taking feel exciting rather than terrifying.


Final Thoughts

Getting comfortable with risk doesn’t happen overnight, but with practice, it becomes second nature. The key is to start small, reframe failure, visualize success, and take action despite fear. The more risks you take, the more resilient and confident you become.

Life is too short to let fear dictate your choices. The next time you’re faced with an opportunity that feels uncertain, ask yourself: What’s the best that could happen? Then take the leap. You might just surprise yourself.

Are you ready to take a risk? Let us know in the comments how you plan to step outside your comfort zone today!

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Ree Denson

Digital Creator & Crazy Decision Maker 🎨🤯 helping creators turn bold decisions into unstoppable growth. Passionate about simplicity, fun, & empowering others to embrace daring choices with ease ✨💡. Founder of CRAZY DECISIONS™️, Crazy Decisions Email Club™️, & The CRAZY Column™️ 🚀.

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