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.

Diana Whitcomb | | Co-Founder of WILO Collective and 2008 Olympian

I have always been someone who hasn’t shied away from risk and change. I started in gymnastics at age 7 and was pretty serious about the sport for 6 years, until I got too tall (haha). I would strongly attribute that experience to shaping my ability to stomach risk and trust the work and path leading to change. I think participating in such a disciplined and high-risk sport at a young age was important in setting me on a path for the future. Later in life, it allowed me to move across the country for college as a scholarship track and field athlete and take the risk to train intensely in that sport, ultimately leading me to the 2008 Olympic Games representing the USA as a Heptathlete. This mindset has transcended beyond sport and, in combination with good gut instinct, I know what feels right. As scary as it has been launching a new company and starting from ground zero, my belief and conviction are so strong it made the risk background noise. Read more>>

Bethany Gill | Digital Entrepreneur

By nature, I am not a risk taker. Sometimes though, risk finds you and you have no choice but to leap. In 2018 I suddenly became a single mom after being a wife, stay-at-home mom, and homeschooler for over 11 years. I was facing a future with three young children on my own with very little work-related skills and no significant work history. I was determined to be able to continue homeschooling my children and was unrelenting in my devotion to being with them as much as possible. It was a huge risk to start my own business. I was told by the court system, by my ex, my friends even, that it was an unsafe and unwise decision. But I knew it was my best option for an income that also gave me the freedom to be the mom that I had committed to being so many years ago. I started small, working multiple jobs to make ends meet, and eventually in the last 6 years grew my business to be what fully supports my family. There have been risks inside of risks, with pivoting in the business, clients that didn’t work out, paving my own way in a digital world that has opportunities beyond comprehension, and learning new ways to balance mom life, work-life, and now relationship life. All my risks have paid off every single time. I either moved forward, or I learned. Read more>>

Beth DeVerre | Master Stained Glass Artist

When I was younger I looked at risk taking to be walking across a rope bridge over a huge valley, hang gliding over a volcano, or jumping across a crocodile infested bayou. I didn’t really understand the risks I was taking when I started in my career. Read more>>

Sea of Doom (Kristin Scholz) | Artist

I am, and have always been, a creature of habit. Routine has been the structuring force of my life since childhood. My parents have always had a routine in which they follow (“Friday is Pizza Night” etc.), so, as a child, I followed suit. I followed this well into adulthood. While I always pursued my art and passions, I did so with the safety net of having a non-art related day job. The plan was that, one day, when my finances were just right, I would scale back to part time work and then eventually pursue art full time. Read more>>

Brett Rein | Therapist

Risk taking boils down to one question for me typically: do I feel that the potential happiness in the unknown is greater than the comfort I currently feel? That has meant different things at different times. The first risk I took came after reading the book “The Last Lecture” by Randy Pausch. The author was a Carnegie Mellon professor who was diagnosed with terminal pancreatic cancer. He gave his last lecture and wrote the subsequent book on how he lived his life until 47 rather than speaking about death. He shared stories including being an imagineer at Disney and winning the biggest prizes at the carnival. He said he wanted the book to be a blueprint on how to live life for the kids he was leaving behind. This encouraged me to begin living my life in that same manner. Read more>>

Chelsey Ray | Jewelry Designer & Photographer

Risks are pretty much what shaped my entire career so i’m very adamant about risk-taking. I am however, also passionate about waiting to make sure spirit is telling you to take the right risks. I feel like signs play a role in everything. If you are getting signs that point you in a certain direction, that’s where you should put your risks. I feel like the more you do this, the easier things will get and those “risks” will just feel like guiding roads from spirit. Read more>>

Engenius Beatz | Music Producer & Songwriter

Well, I believe risks are necessary, although uncomfortable. Getting to a greater position in life comes with a level of risk, but if we never take it, we will remain stagnant in the same place. I’ve experienced some of my greatest blessings because I was willing to take the risk for something different. I released my first single, featuring my now-wife, which was a risk because I didn’t see myself as an artist, just a musician and producer, but I did. My single “Prayed Up” by Engenius Beatz ft. Just Danielle is on its way to 1 million streams! Read more>>