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Chance It! Why Risk Pays Off

Posted on June 13, 2024 by James Harold Webb

As I reflect on my journey as an entrepreneur, there is one essential trait that got me to where I am today: the willingness to take chances. 

Now, with a lifetime of experiences behind me, I can confidently say that embracing risk has been one of the cornerstones of my success. In this blog, I’ll share why I firmly believe that taking on risk isn’t just a gamble—it’s a path to success and fulfillment.

Big Risks, Bigger Rewards

All entrepreneurs have a personal relationship with risk based on how much they can tolerate. For example, some people avoid risk. These individuals don’t often make it big, but because they have a low risk tolerance, they also don’t have a lot to lose. Others are all too eager to take risks and hope their huge swings will lead to perfect home runs. A high risk tolerance like this can lead to devastating losses or avalanche wins. 

Finding a middle ground somewhere between these extremes is ideal. I’ve learned that playing it completely safe doesn’t pay off—in life or business. I have a medium-high risk tolerance myself. Sure, there are moments to be conservative, but breakthroughs can only be reached if you’re willing to risk what it takes to get there. My risky moves have resulted in wildly successful business ventures, life-changing relationships, and a life beyond what I’d imagined for myself.

Vision Can Help You Take the Leap

Opportunity and uncertainty are almost always coupled. The key is being able to see when an opportunity might just be crazy enough to pay off. There have been many crossroads in my life where I chose risk because I had the ability to see what

could be just on the other side. One instance was when I met my second wife in the workplace. She was related to my boss, and I knew starting a relationship with her would put a lot on the line.

We took our time to develop our relationship privately. My vision of our life together is ultimately what pushed us to make our love public and face any consequences that might follow. It was one of the scariest moments of my life showing up to a company function hand in hand with her, but we were rewarded hundred-fold with a beautiful life together until the day she passed away. Once you have the vision, it’s just a matter of deciding. 

Make a Decision and Own It

I’m blessed with the innate ability to make a decision. When others waiver, risk-takers need to be able to seize what’s presented to them and move forward. Taking chances requires the ability to decide something and stick to your guns. Leave doubt at the door and replace it with a healthy dose of faith.

Being able to make the call confidently is also useful in weeding out risks that aren’t for you. Opportunities will come your way that just don’t fit—risks you shouldn’t take on. When this happens, you can decide to pass them up and never look back. Don’t waste time regretting big risks you didn’t take. 

Just keep your eyes peeled for the next opportunity worth risking it for.