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.

Nathan Wannlund

Risk-taking for me is an essential part of growing as a person, and it expands the boundaries of what is possible. I have found, more often than not, internal risk calculations have major blind spots, which can make a decision look safer than it is or much more dangerous than it really is. I have a fairly high risk tolerance, which is important to know because it creates miscalculations if I am not careful. Truly knowing this and recognizing how it skews decision-making has been the hardest part, but the most important step forward in my career and life. I am still not perfect at managing this, even now in my 40s, but I can say with certainty I am much better than I was 10 or 20 years ago. Taking risks is the only way to change and grow— Read More>>

 Ilan Gutin

For me, risk has always been part of the process—both as an artist and as a curator. As an artist, taking risks has meant being honest in my work, even when it’s uncomfortable or hard to do. It’s meant experimenting with new mediums, sharing personal stories, or showing work that I wasn’t totally sure how people would receive. But every time I’ve leaned into that uncertainty, it’s led to growth and connection. Read More>>

Valerie Kinyon

For me, risk is at the core of every meaningful journey. It’s always been about trusting my gut — jumping in, getting messy, and figuring it out along the way. The key is simple: start before you’re ready. Too many great ideas stay stuck because people wait for the perfect moment. I’ve built my life and business by refusing to let fear or details hold me back. Growth doesn’t happen in your comfort zone — it happens when you bet on yourself, even when the path ahead is still taking shape. Read More>>

Cheryl Steffen

Looking back, I’ve always embraced risk. I grew up and went to college in Michigan, and the day after graduation, I packed up my car and drove to Southern California to be with my boyfriend. Though that relationship ended after a year, it sparked a new desire in me: to explore the world, even though I didn’t have the funds to do so. I figured the best way to make it happen was to become a flight attendant, so I pulled out the Yellow Pages and sent my resume to five airlines. After a few interviews, I received three job offers and chose the one that flew internationally. Within two months, I had packed my bags, moved to Minneapolis, and was traveling the globe. Read More>>