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.

Kaeyla Noble | Multimedia Creative

There are so many things around us that communicate to us that we aren’t enough, we can’t do it, and we shouldn’t do it. Taking a risk as an artist is ultimately standing up for yourself and your purpose. Read more>>

Cara Cummings | Artist, surface designer, gardener, and educator

I have a tendency to do things out of order. I went back to college when my kids went to school, I finished graduate school when I was 40, and I decided to completely switch careers when I was 50. Read more>>

Susan Wasinger | Designer, Author, Painter

In business, “risk-taking” is often confined to putting your financial well-being in peril. However, career “risk” can also mean boldly striking out on a new, untried career path; mastering an untested skill set; Read more>>

D’Vontre Dotson | Owner Of Designer Streetwear Label, T’FUŁA Attire®

From my experience risk are essential to level up your business and your lifestyle. As an entrepreneur you are already taking a risk by starting up a business because statistically 45% of new companies fail within the first 5 years, Read more>>

Christopher Taylor | Photographer

How do I think about Risk: Risk is a tricky subject. I think most of us understand the concept of making a “risky decision,” but I believe that many of us are misled by the traditional notion of Risk and how it plays a role in our overall life. Read more>>

Eli Ellis | Professional Highliner/Adventure Athlete

Adventuring in the mountains is all about risk management. I’m always riding the line of pushing myself hard, but not so hard that I can’t get out of a dangerous situation. Read more>>

Jennifer Seybold | Nonprofit Executive & Mom

I think we talk about risk a lot when we talk about big success stories. It’s become a huge topic in business and it’s become somewhat synonymous with those who enjoy business success. Read more>>

Joshua Bredl | Fighter & Wizard

I love risk, I thrive in risk and find power in it . I feel like the more risk you take the less it seems a risky at all, I’ve become so used to risks and adversity that I find myself always taking risk. I wouldn’t have done half the thinking I’ve been able to accomplish without risk. Some people even call me BIG RISK. Read more>>

Brady Granquist | Founder of Light House Mushrooms and Crypto Enthusiast

You have to risk security for freedom. A lot of people aren’t willing to use their time and money without a guaranteed result at the end. Although I believe, if you don’t risk time and money, Read more>>

Ericka List | Photographer

Sometimes it just starts by taking that first step. I started out as a landscape and abstract photographer. If you mess up, you just take another shot. It’s no stress, Read more>>

Jason Seward | Wedding Photographer & Entrepreneur

Calculated risk is necessary for growth. Looking back at my life and career, I can pinpoint decisions with varying levels of risk that have led me to where I am today. Being originally from Halifax, Nova Scotia, Canada, I left everything behind in 2005 to move to South Korea to teach english. Read more>>

Andrew and Misty Modrzejewski | Chef and Restaurateur

I feel like risk taking is a necessary step to growing and furthering yourself both professionally and personally. The fear and uncertainty are what forces you to grow. One quote that I personally love. “if you don’t take risks you will always work for someone who does” Read more>>