How Calculated Risks Drive Business Growth

I’ll be honest—risk-taking doesn’t come naturally to me. My business partner, Jay Feitlinger, thrives in high-stakes scenarios. He’s bold, decisive, and unafraid of big moves. Me? I’m the spreadsheet person, the one double-checking every angle to make sure we’re covered before taking the plunge. According to Kolbe Corp, I scored a 9 on the Fact Finder scale. That assessment was the first big “aha” moment that highlighted just how differently Jay and I approach risk.

‍

This dynamic has been a gift, but I’ve learned that leaning too hard on caution can hold us back. True leadership isn’t about avoiding risk entirely; it’s about learning when to embrace it while keeping a steady foundation.

‍

Why Calculated Risks Are Worth It

‍

Playing it safe often feels, well, safe—but it can be the riskiest choice in the long run. Leaders who avoid risks miss out on opportunities to innovate. A Harvard Business School blog explains it perfectly: taking calculated risks allows you to learn from setbacks and iterate toward success.

‍

The idea isn’t to gamble recklessly; it’s to fail forward. Every failure teaches a lesson, and every lesson is a step closer to achieving your goals. Dan Sullivan and Dr. Benjamin Hardy’s book 10x Is Easier Than 2x drives this home. They argue that transformational growth requires bold decisions and a willingness to let go of what no longer works.

‍

The paradox? Staying in your comfort zone might feel secure, but it quietly stifles growth.

‍

Facing the Fear of Failure

For those of us who value stability, risks come with a mental checklist of “what ifs”:

‍

• What if it doesn’t work?

• What if we lose money?

• What if my reputation takes a hit?

‍

These fears tend to exaggerate the downside while ignoring the upside. Meanwhile, staying put creates the illusion of safety but erodes opportunities for growth. In reality, the cost of doing nothing can outweigh the cost of trying and failing.

‍

Practical Ways to Balance Risk and Stability

‍

If risk-taking feels unnatural, you can train yourself to approach it strategically. Here are some methods that have worked for us at StringCan Interactive:

‍

1. Start Small:

Before launching a new service, we test it with one client or internally. This allows us to gather insights and make improvements before committing fully.

‍

2. Set Boundaries:

Define clear limits for your time, budget, or resources. These guardrails make bold moves feel manageable.

‍

3. Learn from Every Failure:

Treat setbacks as opportunities to gather data. Reflect on what went wrong, why, and how to improve for next time.

‍

4. Build Safety Nets:

Risks are less scary with a backup plan. Create contingency strategies to soften potential impacts.

‍

5. Trust Your Team:

Collaboration spreads responsibility and brings diverse perspectives. You don’t have to take every risk alone.

‍

Our Journey with Calculated Risks

‍

Switching from Jira to ClickUp was one of our biggest calculated risks. It felt daunting—time-consuming, disruptive, and expensive. But by breaking the migration into phases, testing features incrementally, and keeping communication open, we made the transition successfully.

‍

Similarly, when it came to AI, we saw the risks of adoption—but also the risks of ignoring it. Over 18 months, we invested in learning and refining our processes. Today, we’re leveraging AI to work smarter and faster, proving that embracing change can be transformative.

‍

Risk-taking isn’t about throwing caution to the wind; it’s about finding the balance between bold moves and smart planning. If you’re hesitating on a big decision, start small. Test your courage this week by taking one manageable risk.

‍

What’s the worst that could happen? And more importantly—what’s the best?

‍

Ready to take calculated risks for your business?At StringCan Interactive, we specialize in helping leaders make bold yet strategic moves to drive growth. Let us help you build a plan that balances innovation with stability. Contact us today.