Taking a Risk or Being Risky?
David Freund

Recently, while leading a training session, one thought kept coming to mind: the importance of taking risks.

I must admit that I’m naturally a conservative person. I like having a plan, understanding it, and then working it. Uncertainty makes me uncomfortable, and if I’m not careful, I can quickly imagine everything that could go wrong. Some call that catastrophizing. I call it something I have to work hard to overcome! By nature, I don’t enjoy taking risks. Here’s what I’ve come to realize: If we never take a risk, we’ll never discover what we’re truly capable of accomplishing.

Two quotes stand out: “If you’re never in over your head, how do you know how tall you are?” and “If you’re in over your head, it doesn’t matter how deep the water is. Just swim!” Both remind me that growth requires us to move beyond what’s comfortable and familiar.

But there’s an important question: What’s the difference between taking a risk and simply being risky? Taking a risk is calculated and intentional. We’ve done our homework, considered the possibilities, and prepared ourselves to move forward despite uncertainty. Our purpose is clear, and we’ve considered ways to minimize the consequences if things don’t go as planned.

Being risky, on the other hand, often comes from a lack of preparation. We move forward without considering the consequences or understanding our exposure. Planning doesn’t eliminate uncertainty, but it helps us manage it.

However, there’s another question worth asking. What’s the risk of doing nothing? Sometimes we focus so much on what might go wrong that we overlook what we might lose by playing it safe. Opportunities pass us by, our growth becomes stagnant, and our potential remains undiscovered.

I remember facing this decision when I left my position as president of Selflock Screw Products to join MACNY and help transform its training department. I was leaving an established corporate career and the security that came with it to pursue something with no guarantee of success.

For someone who likes certainty, this was no small decision. After much thought, prayer, and conversations with my wife, something became clear. This wasn’t simply a risk I was willing to take. It was a risk I needed to take. I was trading the relative guarantees of my corporate career for the possibility of something much more significant. An opportunity to invest in people, develop leaders, and help others discover their potential.

Did I know everything would work out? Absolutely not. But I had done my homework, sought wise counsel, and developed a clear sense of purpose. I was taking a risk, but I wasn’t being reckless. Looking back, I’m reminded that sometimes we need to leave something good to pursue something greater. Had I let my desire for security drive that decision, I would never have discovered what was possible on the other side of uncertainty.

Isn’t that often the challenge we face as leaders? Organizations don’t grow, people don’t develop, and meaningful change rarely happens when everyone insists on staying within what’s familiar. I’m certainly not suggesting we throw caution to the wind – but even after we’ve planned and prepared, uncertainty will remain. At some point, we must stop planning and start moving. Taking a risk isn’t about being fearless. It’s about being prepared, having a purpose, and moving forward even when the outcome isn’t guaranteed.

So, let me leave you with one question: What opportunity for significance might you be missing because you’re holding too tightly to the security of what you already know?

Sometimes, we simply need to get into the water and start swimming.