Shoot your shot? Take a chance? Society bombards us with messages, phrases, examples and stories of how taking risk is the key to success, but is anything ever that simple? We asked some of the brightest folks we know to tell us about how they think about risk. We’ve shared their responses below.

Jill O’Leary | Owner/Chef

I am a true believer in that the only regrets you have in life are the risks you didn’t take! I’ve started three businesses over the past 22 years…the first one in Santa Barbara, the second in Fort Worth, and then my most recent launch here in Tucson. I never thought for a minute that I couldn’t make these businesses into successes. And I had to take the risk; otherwise, I would always wonder ‘what if.’ Read more>>

Shorty Greene | Mixed-Media Visual Artist & Educator

Risk has to be taken in order to gain anything worth having. I felt scared for a long time to take risks in my life and certainly in my career but it wasn’t until I took a big risk that I started to realize I was holding myself back. In 2008, I moved myself and my six-year-old daughter to Oakland, CA. I didn’t know anyone but I was determined to attend a school in San Francisco. It was beyond risky especially with the crime rate, lack of quality schools for a young mind, and no support system. I had to really trust the process and it was because of this risk I found so much reward and learned so much about myself. Read more>>

Divya Yoder | CEO

I never would have pegged myself as a risk-taker since I have been a planner my entire life, but starting a business is inherently risky. I feel like making the decision to move forward with my business was the biggest risk I’d taken up to that point. Funnily enough, now that I’m a couple of years into it, I’ve started taking more risks in both my professional and personal life. Read more>>

Zachary Wein | Founder of ZacFit

Risk Taking is Everything! In May of 2015, I packed up everything I owned into a Volkswagen Jetta and moved to Arizona (from Wisconsin) to officially start ZacFit. With no connections, no where to stay, no concrete or solid plan, just a whole lot of heart and the dream of owning a gym. With as risky as that was, I was 100% convinced that my dream would manifest. Read more>>