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.

Hailey Van Wormer | Founder & CEO

Risk has been a huge part of my life, both personally and professionally, for as long as I can remember. Choosing to be an entrepreneur means bringing risk into your everyday life, and to do it well, you must learn to face risk consistently without letting it deter you. Regardless of your career path, I don’t think there is a way to escape risk. In fact, I believe risk presents an incredible opportunity, and with great risk comes great reward. As long as you’re willing to learn from your failures and risk in general and approach it with the right mindset, then really it’s just an opportunity. Read more>>

McKenna Ashcroft | Wedding Photographer

I have always been a huge risk taker. I dream extremely big and then I just jump and expect the net to appear and catch me. For the most part, things have worked out and the things that didn’t work out were great lessons for me. I remember when I left my 9-5 to take my business full time. It was a huge risk but I am so glad that I did! Read more>>

Amin Najem | Music Artist

I’ve always been a rather play it safe kind of individual. I usually view things with logical weight. Yet, when I decided to do music, I knew it was a risk. I figured that with the right determination, work ethic, and perseverance I would see it come to fruition. Risks are inevitable, but only when you take them can you earn great rewards. That’s my philosophy in this process. Read more>>

Fawn Racoma | Chef owner operator

Risk: What an interesting concept. Risk is defined as “exposure to the chance of loss” but so quickly forgotten is that it is equally tied to an “exposure of the chance of success” . There is no predetermined outcome when you consider risk. It is purely gauged on your willingness to take a chance and create. Risk to me is synonymous to vulnerability. Both concepts are nothing without their forefront feeling; COURAGE. You can not take risks if you do not make yourself vulnerable and you can not be vulnerable without first being courageous. This is where the true sweet spot for creativity and innovation has the ability to manifest. Read more>>

Jess Amrich | Landscape + Lifestyle Photographer

Risk taking has played a huge role in my life. I’ve been exploring different mediums since I was a child and when I realized I wanted to pursue a career in the arts, I knew I was going to have to take a big risk. After college, I spent many years in Connecticut feeling out of place and working to build someone else’s dreams, wishing everyday that it was my own. I would use my vacation time to road trip across the country and as soon as I returned home, I would daydream of the west again. I had a van that was already converted into a camper for short trips but I always wanted to travel full-time in it. I let every excuse stop me from doing what I actually wanted… Read more>>

Victoria Pinney | Abstract Oil Painter

I am by nature a shy person and putting my art out into the world was, and is, huge for me. Engaging with public – painting in public in a open studio! – is way beyond my comfort zone. Exposing my heart and soul to strangers scrutiny is a daily risk for me. Read more>>

Hali Murray | Content creator

“I would rather play risky than withhold safe security”. There have been a lot of instances in my life where my perception of risk would isolate me from potential rewards. I was so afraid of growing as a person and taking challenges offered to me because I was terrified of the “what if’s” like “what if it doesnt work out” or “what if it screws me over” but I slowly started to evolve into the person I have always wanted to be- careless. Not careless in a bad way, but careless in the most accepting way you could imagine. I have come to terms that everything we do in life can either turn out to be the best decision ever or the worst, but if you never explore those chambers, you will never know what that potential holds. Read more>>

Ashley Steele | Founder & CEO of Obtain Creative

I grew up thinking if I just “followed the rules” my life would turn out just fine. I quickly found that having a “check list life” is not a way to live (in my opinion) and often keeps us away from a truly incredible one. I like to look at the big decisions in my life through a lens of calculated risk. You won’t find me jumping out of an airplane for the sake of it. Heh. But you will find me deciding to start a digital marketing firm in the middle of a pandemic when options were looking less than rosy. Read more>>

Lauren Richardson | Jewelry Designer

It’s a risk to start your own business, but what about the risk of not pursuing your dreams of not finding happiness? A year and a half into what I thought was my dream job, I realized the 9-to-5 world wasn’t for me. The entire office seemed to live for the weekend, myself included. Sunday nights and Monday mornings filled me with dread. I lacked motivation. So, I asked myself: Why? Why do our lives revolve around waiting for 5 pm on Friday, only to unwind for two days and do it all again? Read more>>

Ashley Brauer | Hair Extension Specialist

Risk can be used as a great motivator! For me, the fear of failing is what kept me going. We moved to Denver in the middle of the pandemic, not knowing anyone. The only way to build my business/clientele was to set my sights on the end goal, & keep hustling till I got there! Read more>>

Tani Stanko | Barre Instructor & Studio Owner

There’s a quote about risk taking that I’ve always loved, “If it scares you and excites you at the same time, you should probably do it.” I truly believe that taking risks can be so rewarding. I honestly didn’t ever consider the idea of actually being a small business owner, now that doesn’t mean I didn’t dream of opening my own dance studio my whole life, but the idea of actually being the owner wasn’t ever really present. When I opened Raise The Barre Fitness, I was terrified, I thought about all the reasons why I shouldn’t do it first… my “excuses”. Read more>>

Lucas Onorato | Welder / Fabricator & Sculpture

I believe that risk is probably the most important factor in starting your own business and is a necessity. Risk is was drives me to do more with my business and motivates me to produce products that are of excellent quality and something that will make my clients happy. In my mind risk keeps me true to my mission and holds me accountable for the things that I produce, as well as giving me a kick in the pants to make sure that the risk was worth it. Read more>>

Oscify | Emcee, Vocalist, & Composer

I’ve always danced to the beat of my own drum, but when it comes to improvisations, there are no mistakes. Playing it safe may yield guaranteed results, yet the danger of experimentation is often a path to great art. Where diligent attention to detail can showcase skill, wild paint splatter demonstrates emotional passion. Risk taking in art can often hold keys to greatness Read more>>