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.

Katy Foster | Stir Cooking School Owner

Taking risks is something that my parents really taught me and my siblings. My Dad’s an entrepreneur but took the leap to quit corporate America when I was in high school. Seeing that at a young age shows you how beneficial making choices for your own happiness and for your family can be. I truly believe if you’re not happy, it’s only your responsibility to take the risk and make a change. Read more>>

Bob Carmichael | Director/director of photography and photographer

I was very privileged to have had an opportunity during college to intern at KGO-TV in SF for three summers where I was allowed to observe and participate in all the components of a major city television station from spot sales to production. The year was 1967 when I started this program. Read more>>

Brienna Wagner | Creative Consultant & Designer

I think risk tends to have a negative connotation. I see risk as opportunities. I have taken many risks throughout my career and sometimes they work out and other times not. I never feel regrets about taking chances on things because right or wrong, good or bad, it always teaches me something new. Read more>>

Jenny Von Westphalen | Eclectic Entrepreneur

Risk is terrifying. It’s about being vulnerable to the universe and seeing how much maintenance is required to achieve the best outcome. I had to move away from my family home and start networking with new people that I’ve never met, all the while overcoming my severe social anxiety. Read more>>

Dinah Polhemus | Visual Artist, Student and Life-Long Member of the Cavity Free Club

I am usually hesitant on taking risks, I am generally “if it ain’t broke, don’t fix it” kind of girl, I wear my vans till they fall off my feet, then I get the exact same pair of vans to replace them. I patch up clothes instead of replacing them, I buy pants a size up “just in case”-so risks really aren’t something I naturally am drawn to. Read more>>

Glenn Maddocks | Skier, Coach, Founder and Dad.

The biggest risk in life is not taking any. Ever since I was a little snapper growing up on the beach in Australia, I’ve always been inquisitive, curious and wide eyed. My zest to seek answers, see where my family came from and to experience the roller coaster of life has always been omnipresent. Read more>>

Kate Petley | Visual Artist

As a visual artist, risk taking is built into each step. A willingness to continue working and risk total failure is important because mistakes might lead to a better outcome. Experimentation in the studio requires both risk and determination; Read more>>

Tennille Wood | Interior Designer

Many of my greatest successes have come from saying “yes” in my personal life and this carries over to my business. Saying yes led my husband and I to an opportunity to live and work in London and that experience informed the foundation of my style as an Interior Designer. Whenever I find myself in a rut, it’s often because I’ve become too static, routine or safe. Then it’s time to take a bigger risk. Read more>>

Liz Pearrce | Co-founder & CEO of Fresh Chalk

I’ve taken many so-called risks throughout my career and in my personal life. In my own narrative, though, I prefer to think of them as “big leaps.” These are life decisions based on gut instincts, eagerness to learn and try different things, and fear of regrets. Here are a couple big leaps I’ve taken along the way, and how they panned out: Read more>>

Matthew Tuzson | Singer / Songwriter

Risk risk risk, reward reward reward! The bigger the risk the bigger the reward. Nothing in life worth having comes easy, and I love betting on the unknown! Read more>>