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.

Zak St. John | Session & Touring Drummer

I think this is an interesting question that really applies to musicians and creatives. For most people in music and the arts, risk is a huge part of success. From my point of view, the majority of artists migrate to a center hub of work. By that I mean, Los Angeles, Nashville, New York, etc. That in itself, takes a huge amount of courage and commitment. I know it did for me. Read more>>

Hilary Sloane | Artist, photographer, journalist, creator

Being true to yourself is taking a risk. We may not be safe if we honor our desires and personal direction. I haven’t played it safe. And in hindsight, it’s not about winning or losing. There is no end to being true to yourself. There is only a continuous path of self-discovery. Read more>>

Alpha Patron | Music Artists, CEO, and Entrepreneur

Risk Taking to me is a doubled-ended blessing. As a shy introverted first generational African American kid growing up in the suburbs, I never really knew who I truly was and my purpose. I molded into being a product of my environment by pursuing a career and life that I wasn’t even 50 percent on board with in terms of my satisfaction. Read more>>

Waqqas | Artist

I think risk is a part of life, and the biggest risk lies in not taking the risk; Progression is nearly unattainable without risk, and as the saying goes, “with greater risk comes greater reward”. That said, it doesn’t mean to just jump into anything, but it comes down more to taking calculated risks. One of the biggest risks I’ve taken as an upcoming artist includes playing shows to open for major artists including Young Thug, Mozzy, and Fat Joe. Read more>>

Kay Keeks | Artist

Risk is something that I fully support. The right risks. Throughout my life I have always been the type to push the envelope and have more than not been met with the fear of others. Somehow that fear usually tells me that I’m moving in the right direction because playing it safe has never been my goal.  Read more>>

cassandra sue chavez | creativa behind monarcabox

The creative journey in its entirety has been a risk for me. I have often been comfortable as a “background character” rather than the “main character”. And putting my artwork and who I am out there for the world to see and/or critic is scary, it’s a type of indescribable vulnerability. So when presented with an opportunity that seems to be risky, or just out of my comfort level, I visualize a future-self, and if the opportunity would be in her best interest. And if so, I say “YES” before my overthinking or nerves get the best of me. Read more>>

Brett Cassort | Fine Artist

Risk has played a very big part in my life and my success as an artist and without it I would simply not be in the position I am today. After college back in New York I took a job at a hydro-electric facility up on the St. Lawrence River. I completed a 4 yr apprenticeship as a Millright Mechanic/Machinist and went on to do that for over a decade. At that point I was a self-taught hobby artist, drawing and painting, experimenting with different materials and medium in my spare time. I was very creative and worked with my hands in both my career and my artwork. Read more>>

Ezra Flores | Professional Dancer

The way I think about risk taking is being able to move past the fear of failing. If you keep obsessing over the “bad” that can happen, it can cause you to forego the risk that can take you to the next level. Read more>>

Lua Kobayashi | Artist

I believe risk is an entirely necessary part of the arts – without it, I don’t think it would be possible! As well as a very important part of living a full life. Read more>>

Darius D-Win” Winfield | Rapper & Designer

Risk-taking is essential for growth; though daunting, you can’t reap the rewards unless you venture outside your comfort zone. I’m only at my current success thanks to many risks I’ve taken. Risk-taking has been central to my life and career. Moving to Chicago was the most significant risk I ever took; recently graduating high school, working at Deveroes, and starting college at IUPUI, I didn’t hesitate to heed Prosper’s call and road trip up to the Windy City. Read more>>