How to Take Risks Even When You’re Terrified of Failing

Taking risks is one of the most powerful ways to grow—yet it’s one of the hardest things to do, especially when the fear of failure looms large. Whether it’s pursuing your dreams, starting a business, or making a career change, the very thought of failure can paralyze us. But here’s the thing: every major opportunity and every breakthrough in life exists outside your comfort zone. In this post, I’ll break down how to take risks, even when you’re terrified of failing, and how you can take actionable steps to assess, plan, and leap with confidence.

Why Taking Risks Matters

Let’s face it: the biggest opportunities often come with the greatest risks. From landing your dream job to launching your own business, or even making a major life move like relocating to a new city—the common thread is risk. But here’s the paradox: we’re biologically wired to avoid risk. It’s a survival mechanism. The instinctive part of your brain is constantly asking, “What if it all goes wrong?” But here’s the crucial question to ask yourself instead: What if it all goes right?

I’ll give you a personal example. When I made the decision to switch careers, it wasn’t just about changing jobs—it was about aligning my work with my core values. It was a monumental decision, and believe me, I was terrified of failing. But that leap didn’t happen overnight. It took strategy, preparation, and most importantly, a shift in mindset.

Taking risks doesn’t mean blindly jumping into the unknown. It’s about being willing to step outside your comfort zone with a plan in place. It’s about trusting yourself and knowing that the only way to grow is by embracing the unknown.

The Power of a Safety Net

So, what gave me the courage to take that leap? The peace of mind that came from knowing I had a financial safety net in place. When you’re at the edge, ready to jump, the fear of failure is at its strongest—especially when you feel like you have everything to lose. That’s why having a solid financial cushion can make all the difference.

Here’s the thing: fear of failure diminishes when you know you have a safety net that will catch you if things don’t go according to plan. For me, that safety net was a 6-month emergency fund. The security it gave me allowed me to take the risk without panicking if things didn’t work out as planned.

Step one: Build your safety net.

Here’s how you can do that:

• Start small. Cut unnecessary expenses and reallocate them into savings.

• Automate your savings, even if it’s just $100 a month.

• Aim to build 3-6 months of living expenses in an easily accessible account.

This isn't just about having money in the bank; it’s about giving yourself the confidence to take risks without the constant fear of what could go wrong.

How to Assess a Risk (The SMART Framework)

Taking risks doesn’t mean being reckless. It’s about assessing the situation intelligently and making calculated decisions. Here’s a simple framework to help you assess risks more effectively: The SMART Framework.

1. Start with the Worst-Case Scenario:
   Ask yourself, “What’s the absolute worst that could happen?” Could you handle it if things didn’t go according to plan? If yes, the risk is likely worth exploring. The worst-case scenario is often much less catastrophic than we fear.

2. Measure the Opportunity:
   What’s the potential upside? Will this risk move you closer to your goals, or is it just a distraction? Evaluate whether the reward is worth the risk.

3. Align with Your Values:
   Does this risk align with the life you want to build? Is this opportunity in line with your long-term vision? If it checks the boxes, it’s time to lean in.

4. Ready Yourself for Growth:
   Growth doesn’t happen without discomfort. Accept that stepping outside your comfort zone means you’ll feel uncomfortable, but that’s the price of growth.

5. Take Action:
   Let’s break this step down into more detail.

Actionable Steps to Take Smart Risks

Taking action and therefore accepting and taking risks doesn't have to be all-or-nothing. Here are some actionable steps to help you take risks smartly, without being paralyzed by fear.

1. Start Small:
   You don’t have to quit your job right away to make a change. Start by testing the waters. Begin a side project, start freelancing, or take on a small project that challenges you. The key is to dip your toes in first, instead of diving in headfirst.

2. Find a Mentor:
   There’s a lot of wisdom in learning from people who’ve already taken the leap. Find someone who’s gone through a similar experience and ask for advice. Mentors can help you avoid common mistakes and provide you with the confidence to move forward.

3. Create a Backup Plan:
   Having a backup plan doesn’t mean you’re expecting failure; it means you’re preparing for potential challenges. Life doesn’t always go according to plan, and having a “Plan B” can help you stay calm if things don’t go as expected.

4. Focus on the Next Step:
   Instead of obsessing over the end result, break the risk into smaller, manageable steps. Focus on the first step, then the next, and so on. Taking risks becomes much less overwhelming when you focus on one piece at a time.

My Story – The Leap That Paid Off

Let me take you back to when I made the leap to change careers. I wasn’t just chasing a bigger paycheck; I was chasing something far more important: fulfillment. I wanted to build a career that excited me, something that aligned with my values and my long-term vision. But taking that leap wasn’t easy. It was filled with uncertainty and fear.

But because I had prepared—by building my safety net, seeking guidance from trusted mentors, and evaluating the risks—I made the leap with confidence. And let me tell you: it paid off. The growth, the fulfillment, the freedom I feel now—it was all worth it. The fear I experienced before making the leap now feels trivial compared to the rewards I’ve gained.

Closing Thoughts: Tie It All Together

Here’s the takeaway: Fear doesn’t mean you shouldn’t take the leap—it means the leap is worth taking. If you’re feeling fearful, that’s a sign that growth is just on the other side of that fear. Growth doesn’t happen in the comfort zone. It happens when you’re willing to stretch yourself, when you’re willing to embrace discomfort, and when you take risks with purpose and planning.

So, what’s the leap you’ve been too scared to take? What’s holding you back? I’d love to hear about it. Drop a comment below, and let’s talk about how you can take that first step toward a bigger, bolder future.

And if you’re still unsure about how to start taking smart risks, check out my previous blog post / video on “Why Your 20s Will Make or Break Your Future.” It’s packed with tips on building the kind of foundation that allows you to take risks with confidence.

Now, take that leap and trust yourself to handle whatever comes next. You've got this.