Legend holds that Cornelius Vanderbilt had built a massive fortune in the steamboat shipping industry, but then realized the railroads were the way of the future and invested almost his entire net worth into railroads. The gamble paid off and made Vanderbilt one of the wealthiest entrepreneurs ever. But risks are inherently…risky. How do you think about risk and how has it affected your life and career? Some of our community favorites share their perspective below.

Paul Rohrer | Actor, Coach, Husband and Father

Risk is one of my favorite four-letter words. The other is “next”. The two go hand in hand. No matter whether a risk works out or not; I am always looking for the next opportunity or risk. Risk is becoming more and more, the way of the world for most people I am assuming all over the world. As a teen I would take dares. I was dared to mix applesauce in my chili at summer camp. A win. I was dared to cross over the Fox River which flowed under a railroad bridge that was below high tension electric wires that were below the girders I was to cross under the Dan Ryan Freeway. A near fatal loss. There were many other wins and losses as I grew, finally deciding that the greatest thrill of all was the dare to survive as an artist. An actor. Trusting in the self worth I nurtured doing tens of odd jobs growing up. Read more>>

Tyree Jones | Painter & Writer

I learned young that taking risks is essential when it comes to any type of forward progression. Looking back on it, I’ve always leaned towards riskier activities that required every ounce of dedication. If there wasn’t complete dedication on my part, then I would fail or be unsatisfied with the results. This mindset developed early in my teens when I began hurdling. I was told that if I stuttered, then the race was over. There was no time to second guess my decision and the only option that I had was to trust in my abilities and run over that hurdle as hard as I could. I fell hundreds of times, I fell at big meets in front of huge crowds and had the wind knocked out of me. After those disappointments I was always told that it was a part of growth, and that motivated me to go even harder over the next hurdle set in front of me. Read more>>

Eileen Roscina | Artist

I view risk as an integral part of my artistic career. I would not have advanced past a box of crayons without taking risks in my work. And this is all to say that it has not all been a linear path upwards – taking risks has resulted in many failures, and some successes, but it has moved the needle, and I have learned from each experience. I always try and remember to trust myself and that I will grow no matter what the outcome. Read more>>

Stacy Robinson | Artist & painter

I think being an artist is a blessing and a curse. Making art is my happy place to explore, create and communicate my thoughts and feelings. It feels like a spiritual journey in many ways. If a client/buyer or art enthusiastist connects with one of my pieces I’m overjoyed. But because this is my personal journey I often feel vulnerable and exposed. To present my work to the world requires risk. Risk of what others will think and risk of rejection. Being an artist can be lonely and frustrating, and exhilarating and pure joy. As I’ve matured as an artist I’ve become much more confident and appreciative for having the opportunity to share my work and am honored when a client hangs one of my pieces in their home. With risk comes great reward! Read more>>

Keppen Laszlo | Small Business Mastermind Consultant

As an entrepreneur, risk has always played a big roll in my life. I was always taught that Success Involves Risk. It wasn’t until I failed at this approach more than once when I realized, Success Involves CALCULATED Risk. There is a huge difference between the two. When I took a calculated risk approach, I begin to make sure I was happy with the upside but also, I made sure I could live with the downside. Whether it’s a new marketing plan, a real estate purchase, or taking over a hurting business, when the focus is on both the upside and the downside, it works out well more times than not. There are now several rules I follow to calculate whether I should do a deal or not. Once many years ago I wired a huge amount of money to an investor I had never met. I thought I did my due diligence, but little did I know, I was scammed – big time. Read more>>