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.

Laura Masterson | Jewelry Designer & Artist

I’ve never been a risk taker. I’ve never been the kind of person with the “need for speed” or the need to get my blood pumping. I’ve always stood in the shadows, kept a low profile, sat in the back of the room type of person. That was until I lost someone very dear to me in early 2019. Read more>>

Colton Kramer | Tattoo Artist

I chose a very niche career path, everyday I go to work it’s a risk. I don’t know if clients are going to be happy with the design I spent hours working on or if they’re going to keep coming back. Tattoos are a choice and I’m lucky people choose to get tattooed by me. I spent a few years trying to balance a corporate job during the day and tattooing in the evenings. Read more>>

Janice Ferrante | Oblique Design, Owner + Creative Director

I made a significant career decision by choosing a lifestyle change that came with the risk of losing my biggest client. For nearly a decade, I had been working as the primary agency for BMW of North America. However, I felt ready to leave my hometown in New Jersey and move to Boulder, Colorado, even though the client had cautioned that relocating might jeopardize our partnership. Read more>>

Samantha Anderson | Artist & Storyteller

Risk is inevitable. It’s part of our daily lives. We’re taking risks every time we make a decision. There is always a risk that another decision would have been the better decision. When we make decisions throughout the day we are slowly building our future while also sacrificing countless alternative paths. Read more>>

Shawna Henderson | Owner: Majestic Mountain Events and Breck Mtn Wedding

Risk has always been woven into the fabric of my life. As a youth, I craved the adrenaline rush of speeding down ski slopes, leaping off cliffs, and conquering daring mountain bike trails. Adventure sports were my playground, a constant battle against fear and a celebration of pushing limits. Read more>>

Kelsy Yates | Co-owner & co-founder of Police & Thieves Dispensaries

I think that anyone in cannabis must be comfortable with risk. Continually erratic market fluctuations, Kafkaesque legislation, and an untraditional work context are attached to the weed industry. There’s no getting around it. While my husband and I, who wholly own and run the company, have a decent level of structure and routine to our lives so that we can stay somewhat sane while we raise our children and run a company, we both are comfortable in certain level of chaos.  Read more>>

Molly Murray | Tattoo Studio Owner & Artist

Risk regarding business is often referring to investing in something before you know the return. In my own business, I view all the investments I make as investing in myself. And investing in myself doesn’t fall into the risk category because there’s an underlying certainty there is no such thing as losing. I’ll simply figure it out and keep moving forward. Read more>>