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.

Alex Harbart | Founder

I think risk is always a factor in the decisions you make in your personal life or career. I believe It’s always important to be able to identify the risks in any situation when making a decision, especially if the decision that will effect an outcome that’s unknown. Read more>>

Ashley Ionetz | Co-Owner and Lead Photographer/Videographer

When I was younger, I (Ashley) was not a risk taker. I followed the rules and did what I thought everyone expected me to do. I went to school and got an office job at an automotive company but I always had a passion for photography and videography. Read more>>

Sydney Webb | Model & Constant learner

As a model, risk is a big part of the job. You take risk in working with new photographers, other models, makeup artists, designers and the list continues. However, risk is what makes the career exciting. Meeting and working with new people can be as exciting as it is scary. Read more>>

Robert Laubacher | Landscape Photographer

I always have been a calculated risk taker. For thirty years I was a firefighter in the heart of New York City. It was a job I loved. While I saved people, I also saw many others succumb to flames and smoke. Read more>>

Megan Bendtzen | TheDoctorofFun.com

“I don’t think people will like that…” “You probably shouldn’t do that…”
“Nobody’s ever done anything like that before…” Read more>>

Tyler Harding | Graphic/Digital/Apparel/Decor Artist/General Manager

Risks are an important part of running a business. The amount of risk you are willing to take is dependent on your outlook on your business and the timing of your desired milestones. Read more>>

Crystel Becker | Photographer

Thinking back to three years ago and starting my photography business, just a few weeks after graduating nursing school, the biggest driving factor was: what is there to loose? Read more>>

Ariel Wright | Artist & Astrologer

When I think about risk, I think about the definition of my whole life! I personally have always taken big risks throughout my life for a multitude of different reasons. Read more>>

Dan Hillenbrand | Serial Entrepreneur & Modern Cowboy

I have always had a very high tolerance for risk, almost to a fault. Being willing to take risks is where I grow and I have learned to be comfortable, being uncomfortable. It has also taught me to accept the consequences as many times ideas do not turn out the way you planned and you need to pivot. Read more>>

Lara Gruden | Professional Triathlete

In order to be successful in life/career, I truly believe that you have to take risks. To be at the top you have to take risks. It comes with a big responsibility and you have to feel comfortable and confident when tackling life with this mindset. Read more>>

Scott Kemper | Landscape and Travel Photographer

Taking measured risks throughout my life has enhanced my journey and played a part in where I am today. I’m not talking “crazy” things, but things that took me out of my comfort zone. Read more>>

Jess Najera | Plant Stylist & Plant Care Expert

I think every decision you make has the possibility to be a risk based solely on the unknown circumstances that come with each decision. For myself personally, taking risks is the only thing that has gotten me where I am today. Read more>>

Nicolai Myers | 90kg Worlds Strongest Man, Veteran, Pilot, Business Owner, Do-er of things

I think risk taking is necessary for growth. Whether it’s calculated or all caution is thrown to the wind. You either win or you learn at the end of the day. Read more>>

Kimberly Vieyra | Curvy Model & Latina in Tech

Risk is scary. Risk is the unknown. As someone who is a planner by default, making risky decisions about anything in my life causes some level of anxiety. I, however, believe that taking risks in life is absolutely necessary. Read more>>