By far, the topic that comes up most in our conversations with entrepreneurs and creatives is risk. We’ve had conversations about risks that worked out and risks that did not. We’ve seen eyes light eye sharing about career-trajectory changing risks as well as folks sigh about the risks they wish they had taken. Below, we’ve selected and shared some of those thoughtful conversations.

Kathleen Culebro | Founder and Artistic Director of Amphibian Stage

Every attempt to create art has been risky. That means there’s a very high probability that it will fail. That’s the very definition of “risk.” And yet when it succeeds something truly transcendent is created for the first time ever. Read more>>

Cooper Neill | Freelance Photographer

As a full-time freelance photographer, I am my own business and stepping away from a staff gig with a newspaper to go out on my own was one of the riskiest things I could have done but sometimes you just have to bet on yourself. Read more>>

Camille Thompson | Choreographer, Creative Director, Business Owner

I would not be where I am today without the willingness to take risks. If we do not jump, we will never learn to fly. I feel that taking risks is important for growth in every aspect of life. We learn from these risks. Read more>>

Reece Fish | Artist & Counselor In-Training

By no means am I a master at risk-taking, but I’ve taken enough leaps of faith to realize that’s where the juice of life is. Over time I realized that comfort does not necessarily equal happiness. I enjoy kicking back on a Saturday like anyone else. Read more>>

Brandon Gibbons | The Gibbonses: Wedding & Event Entertainment

Taking risks is extremely important if you want to continue to grow and be successful in both your career and your life. Over the years we’ve worked in many different live performance markets, from cruise-ships to local bars & restaurants, national touring in support of our original music to weddings & special events. Read more>>

Daphne Anderson | Founder & Executive Director

I think about risk in a unique way; I consider it to be a planned inevitable. Because I accept risk as part of life and a necessity for success, I’ve taken it upon myself to get comfortable with the idea of risk and have my circle of trusted people with who I consult. Read more>>

Katie Mont | Designer & Marketer

Risk taking has played an extremely important role throughout my life and career. I feel like I grasped onto the value of taking risks early in my design career. I faced some adversities with my health while in college that led to me learning a few very important life lessons. Read more>>

Jordy Warren | Creative Organizer & Groovy Store Manager

Risk it all. I would not be where I am today if I hadn’t reached for the moon and lived life on the edge. Life is the best teacher, so live while you can. Read more>>

Sheridan Reed | Musician

I would definitely say I’m a risk taker, but I would say I take calculated risks. Rather than just going for something on a whim, I’ll do my best to set myself up for the best possible chances of success and minimal fallout or consequences if something doesn’t work out. Read more>>

Bryson Hennington | RnB Artist and Dancer

I think taking risk is one of the biggest components of growth. People think they know the outcome of something but once they try it they are completely blown away and wonder why they were so scared in the first place. I decided I wasn’t going to let the fear of not knowing control my life. Read more>>

Patrick Stockwell | Author & Instructor

For me, risk is an inherent component of success as a creative person. Since opportunities to push your work forward professionally are few and far between, it is often necessary to create spaces for yourself where you can share your work and, hopefully, make a little money while you’re at it. Read more>>

Misela Hrgota | Model, Legal Assistant, and Student

I think taking risks is important and helps with a persons growth, Personally taking risks has helped me get to where I am in life now. For me choosing to take risks has always been important because without doing that I probably wouldn’t have worked with so many great photographers, signed to an agency, or travelled to many cool places. Read more>>

London Lawhon | Singer/Songwriter

Taking risks are always scary, but the vulnerable space created by putting yourself out there in new and uncomfortable situations is where opportunities flourish. In my career, every risk has led to a lesson learned and more often than not a new opportunity for my music. Read more>>

Graham Jones | Singer-Songwriter

For an independent musician, risks are a major part of every step of the music-making process. There’s a risk in being vulnerable in your songwriting that you won’t be heard or accepted. There’s a risk in booking shows that no one will come listen. Read more>>

Pearlyn Lii | Artist & Designer

I’ve found that change is the only constant. I wanted my own business by 25. In my head, I had a soft deadline of sorts. And with a lick of foolish youth, I decided to leap into my own venture knowing that I would indefinitely sacrifice stability. The most thrilling part about being an entrepreneur is constantly leaping into the unknown. Read more>>

Myles Cordae | Facin Art

Taking risks, as it pertains to fear specifically, have shaped my entire career literally from the beginning. My art journey was birthed directly from me taking a risk to leave everything and everyone I have ever known in my life. Read more>>