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.

Stephanie Hoyle | Entrepreneur, Experienced Marketer & Business Owner

In my career and life, risk-taking has always played a role. Sometimes the risk is bigger than other times, but I’m always analyzing and calculating the “what-if’s”. What’s the worst thing that could happen if I take this job, or what’s the worst thing that could happen if I don’t take this job? I like to look at all sides, pros and cons of a situation and assess the risk level. I make decisions quickly and always go with my gut. I live by a motto about failure and risk taking- “What if I fall? Oh darling, what if you fly.” It’s okay to try and fail because we learn. But if you don’t try, how is that going to make you feel? I always ask myself, if I don’t take this risk, and do XYZ thing, am I going to regret it? Am I okay with taking the risk and failing and learning from it? What if I succeed? You never know unless you try and taking a risk is the best way to learn. Read more>>

Michelle Blasen

I believe we are meant to live our lives taking risks and living in the unknown. Taking risks and living in the unknown go hand in hand. The only moment we truly ever have is the now. Living in the past holds us in depression and if we wake up each day choosing to live in the past we are living in a past state-never able to receive what the the present moment can give us. Living in the future creates anxiety, it doesn’t mean we can’t plan (we should), but living in a state of fear or worry only inhibits us from seeing the beauty and opportunities that are right in front of us. I have been a rebel about living the conventional way, it never appealed to me. I tried to fit the mold for years doing careers that I thought would make my parents happy or help me to fit into society. I always ended up leaving a job or career because I was miserable. I kept learning, switching careers, and diving into my own personal development. Read more>>

Thomas Harrison

As I define in my book INSTINCT; Tapping Your Entrepreneurial DNA to Achieve Your Business Goals, risk is actually ‘opportunity’. If you are honest with yourself, know why you want to start your own enterprise, why you want to change your career, what you want people to feel when interacting with you… risk is really opportunity. Because you have thought through the consequences. Read more>>

Michael Tiernan | Performer, Songwriter & Live and Virtual Event Producer

Life itself is all about risk. Without taking the bigger risks and deciding to take some leaps here and there, growth isn’t possible. In my music career, it was all about risk from the beginning – sort of a challenge to answer a call I felt in my heart to be an artist, which led me to quit my ‘safe’ job and plunge headlong into my music career. In the many twists and turns of my music career, identifying new challenges and taking risks helped me grow in ways I never dreamed of. It has been a wild path from growing my career as an artist, as a production company, to now in the Covid-age, shifting once again to the virtual world for performance, engagement, and connection through music. Read more>>

Diane Mandle

Life is full of challenges and with each challenge there is some amount of risk. I have always thought about risk being a challenge to reflect on what is important and true for me and how my taking the risk might affect others. Sometimes the risk is only personal: Shall I try a new food that looks weird? Sometimes it might affect others: Shall I move to California despite the wishes of my family? So each level of risk requires introspection. Risk is the opportunity for me to feel my own limitations and decide to push the boundaries or not. When I take the risk it means that I walk with some amount of fear or anxiety. That is something I call courage. Usually it strengthens me and inspires others. If the risk resulted in something negative, then I have learned something too- for the next time. Read more>>

Krystal Dyer | Artist & Teacher

I guess I have taken risks my whole career. I never thought about it that way but when you ask that question, and I think back, I have definitely taken risks to get to where I am today, and I still am. I took a risk of going to an art college out of state, right after losing my Mom, to be an animator, only because I wanted to do character design. I took a risk by accepting a job with Nickelodeon in NYC when I lived in Philly, and commuted by train daily. I took a risk in accepting a job after that, at Lockheed Martin, working on things I never knew an artist would work on, stuff I truly knew nothing about. I took a risk in accepting a job at Think Up Toy Design as a concept artist, animator, and voice over actor when I was not sure that was exactly what I wanted to do. Read more>>

Debbora Childress | Small Business Owner, Dance Instructor & Creative Director

I believe that in order to grow or move forward, you need to be willing to take a leap of faith. That leap of faith is called “risk.” Heading down a safe, known path is easiest; however, it might not enable you to fulfill your passion. In my case, being a single parent led me to stick to a known path. Then, my re-marriage allowed me freedom to look further and gave me the support I needed to finally take a risk and follow my passion. I have always known I would teach children. I pursued my college education in that direction. Combining my lifetime of dance training with my education seemed like a perfect fit. Leaving my full-time job at a community college to teach dance to children was a real “leap of faith!” I lined up a teaching position with a city arts program. That position fell through AFTER I left my secure employment. Read more>>

Daniel Travers | Multimedia Producer & Artist

Moving to California sixteen years ago from the Midwest was a big risk for me. I only knew one person and didn’t have a job, but had two college degrees, a little money saved up, and ambition. I’m now glad I did. Taking the risk to relocate to a more opportunistic location opened up new doors for me, It may be easier for some individuals to take risks given their situation, but I definitely think it’s something to seriously consider if you want to evolve both professionally and personally. You don’t have to move halfway across the country like I did to try something new you might not be comfortable with. Read more>>

Christopher Canole | Artist

Even though I had a successful career as a earth art sculptor including being New York City’s first Artist-in-Residence in the 70’s, I was seduced by Hollywood in front of and behind the camera for decades. On a sunny morning at the Pannikin Coffee House i La Jolla I decided to explore two dimensional art for the first time by drawing a postcard filled with images of fellow San Diegans. I printed up thousands of cards and handed them out free. Many cards reached people I never expected to meet or be hired to draw personal portraits including Barack Obama, Pope Francis, Smithsonian Air and Space Museum, International Olympic Committee and The Stan Lee Foundation. Most of my artistic time now is split between my drawings and appearing as Dude Vader at charity events. Read more>>