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.

Lucie Van der Elst | visual artist, maker & miniaturist

That is such a wonderfully complex question! It feels a little weird to talk about risk-taking in these trying times, when uncertainty seems to lurk around every corner. Defining risk means you also have to define failure, and define success. Fear of taking risks means fear of failure. Does it also mean fear of success? First you have to set goals. Then think about what failure would mean in relation to these goals. It means different things for different people. Read more>>

Tim Smith | Visual Artist & Creator

I truly believe without taking big risks, you prevent yourself from growing as a person, and in my case as an artist. Recently I just took a huge risk. I resigned from my safe job a full time teacher- with a guaranteed salary and annual contract-to follow my dreams of becoming a professional full-time artist. There’s a saying I have heard before that goes “If you want big rewards, you have to take big risks.” I am not going to lie, it is scary. I have 3 young children, a mortgage, and bills to pay. Relying on myself and my creativity to pay the bills is a challenge sometimes. Read more>>

Ethan Maurice | Writer, Photographer, & Creative at Large

At the age of sixteen, I had a near-death experience that forever altered my relationship with risk. In our culture, we mostly think about risk in the form of fears about the future: we fear poverty, being alone, disappointing our parents, having low-social standing, and other variations of things not working out in the cultural definition of well in the long run. Read more>>

Tommy Rhyan | Photographer and Videographer

Risk has been a huge part to my career. I have lived in many states to pursue and try new parts of the media world. Each opportunity I was able to learn so many different avenues of the photography and videography world. Without risk, I would have never worked on set in the hills of LA or traveled to Poland for a TV show or even moved to Georgia to work for a YouTuber. I think risk was necessary for what I wanted to accomplish at let me have the portfolio I have today. Read more>>

Reed Woodford | Guide Service Owner

I think we have a pretty skewed vision of risk management here. Taking people into the mountains every day, there is inherent risk in that right? So we are used to it. The risk that comes with taking out a huge loan to buy a business feels a little different, that’s not a risk I’m used to taking every day so it feels scarier. Most people would probably just view that as part of life, for me though going rock climbing or skiing or even going for a long solo run in the mountains that feels more secure than a big loan with a variable rate. I guess risk is always on a scale and we are more comfortable with things that we do on a regular basis. Read more>>

Whitney Bradberry | Freelancer Marketing Strategist & Vacation Rental Host

The risks I’ve taken in my life are probably the things I’m most proud of. From leaving my family to move to Colorado to going freelance to buying a little a-frame cabin in the woods to turn into a vacation rental—I have always believed in following passions, even if that comes with some risk. In my experience, the more risks you take, the more you learn about yourself, and the easier it becomes to get comfortable with discomfort. Read more>>

Megan Brown | Pup Caretaker & Greeting Card Designer

Risk-taking is crucial to starting (and continuing to run) your own business. You’re constantly faced with decisions that require you to take a leap if you want to grow. I don’t think it gets easier over time to take risks in my business. Sorry, future entrepreneurs…it definitely can be scary! But that’s when I lean on friends and fellow small business owners for support and advice. I’ll also add that sometimes you just have to make the decision on your own and go with your gut. Read more>>

Sarah Rose Attman | Founder of Sarah Rose Events in Aspen

I don’t actively think about risk taking, but reflecting on my life and career I do, in fact, take a lot of risks. It was a risk to start my PR company at age 24 with no formal business or marketing education. It’s a risk now to be an event planner in Aspen. It’s hard to explain, but I take risks because I can’t not. They say people only move from the least uncomfortable place to the next least uncomfortable place. Not having these businesses was more uncomfortable than the risk of doing it/the fear of failure. Read more>>

Sarah Banker | Musician

Risk-taking is absolutely necessary for success, no matter what our goals, personal or professional. Risk is best applied in a healthy, balanced approach. For instance, when I left my hometown, everyone in my life (except my dad) warned me that I was making a mistake. I had it all, a loving family, a good job, and great friends but I was miserable and depressed, living with a dull ache that wouldn’t subside no matter how much I meditated, practiced yoga, and/or went to therapy. I needed to explore myself and my life. It was a huge risk, heading out by myself to pursue some sort of life with music.  Read more>>

Katie Pye | Friend mother artist

Uncertainty,doubt a passion and creative spirit don’t follow constructs of authority and conventional thinking .becoming yourself set’s you up for trusting and believing in your vision and it demands risk if that implies uncertainty difference to be original .the need to believe in our selves is a journey that unfolds when we take a risk because we have a longing to do or achieve something that take us out of our comfort and might no unfold as we hoped or imagined but its the knowledge that we gain from the experience that’s teachers us to have more confidence in taking risks , Read more>>

Suzy & Heather | Youth Life Coaches
As life coaches specializing in adolescents, we help young adults aged 14-24 build resilience and mental wellness to help AVOID mental crisis. Critical gaps in support exist for this age group that neither they, nor their parents may be aware of. We fill those gaps and help prepare them for life by building confidence and sharing important life skills they don’t teach in schools. It is this focus on life skills that sets us apart from other youth life coaches. There are many options for programs to keep young adults busy, but few that will have a long-term impact on their life like ours.Read more>>

Cooper Gunther | Owner of Denver Storm Door

In order to succeed at anything, you have to take risks, especially in business. Before I started Denver Storm Door I was working as a full-time electrician, and one day I decided that is not what I saw myself doing for the rest of my life. Immediately, I put all of my money and time into creating Denver Storm Door and risked everything I had, and so far it’s paying off. I’m 26 years old with my own successful business and I can’t wait to see what the future holds for Denver Storm Door. Read more>>