We asked some brilliant folks from the community to talk to us about how they think about risk and the role risk has played in their lives and careers.

Kyle Gardner | Actor, Videographer & Editor

Risk taking is more of a feeling to me. But when I think about risk, I ask myself what do I stand to win and what do I stand to lose. The rewards of taking a risk keeps me intrigued. But when I think about what I stand loose, inevitably doubt and fear creeps in the equation. In the past, I would’ve let fear of failure determine my decisions in life and my career. So in 2014, at twenty years old I took a risk for the first time in my life. I wanted to purse a career in film and moved to Rome, Italy for college. Read more>>

Ashley Bates Bates | Professional Organizer and Designer

Taking a risk was truly the only way I got a reward in my business. Before I started OCD, I was the Director of Marketing for Dunkin Donuts. I loved being creative in my role there, however starting my own Organizing and Design business was my dream since I was a little girl. My mom was an Interior Designer and I would watch her and think to myself “One day, I want to make homes beautiful like this,” (so I guess you can say I was born with it, and it runs in my genes.) With that being said, during Covid the restaurant world was shutting down, and I knew this was my time to start OCD. Read more>>

Denzel Demby | Designer and Entrepreneur

For me taking risks does not fit my personality. I’m a meticulous individual and everything has to be planned out perfectly. I don’t care if it’s planning my day or my work week, everything had to fall into place. My desire to have my own business pushed me to take more risks. You can plan your business with a business plan, or a marketing plan but ultimately we don’t know what the future holds. Watching other well-known entertainers and entrepreneurs such as Gary Vee, Steve Jobs, Steve Madden, and Tyler Perry inspired me to think outside the box. Sometimes everyone will not see or understand your vision and that’s ok. When I was in high school, I always dreamed of attending business school and starting multiple businesses. I loved fashion and jewelry as a child and being a black young man from the south, that was not common. Read more>>

Courtney Vrablik | Executive Director of The Store

I find risk taking to be as critical an element in leadership as any other characteristic. Perhaps it becomes easier with experience because I have a wider base of knowledge to draw from. However, in hindsight, I can honestly say the biggest, most exciting changes in my life–both personally and professionally–have come from making a leap into the unknown and taking a chance. For example, my initial foray into professional pastry came from answering an ad for a lower level position. Within five months, I was not only the manager but Executive Pastry Chef for a major corporate entity. The calculation was that by getting my foot in the door, I could compensate for my lack of previous experience by showing what my capabilities were. Read more>>

katherine wagner | CEO, Business Council for the Arts

Such an interesting question! Here is a counter-question: is it possible to have risk without opportunities? Throughout the hour, day, week and year opportunities come and go. Periodically, I take stock of opportunities that surround me at that moment (street racing could be an option, never selected, but jumping out of a plane was). Being mindful of their fleeting nature – some never to reappear – is the way I’ve approached risk. Taking stock of opportunities that exist in a particular moment in time – even writing them down – has been a good guide for me, both personally and professionally. For me, the act of writing is an essential part of planning, What is planning for the future but a series of assumptions and risks built on each other? Read more>>