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.

Loan Kieu | Boutique Owner & Entrepreneur

Every decision we make in life is a risk. The results of those choices may impact us positively or negatively. There is something scary about the unknown and deciding to take that risk or not. It took me a while, but I’ve decided that I don’t want to look back and wonder ‘what if’. I was an elementary teacher for eleven years and deciding to give up what defined me all those years was extremely difficult. Imagine choosing between your calling and your dream. It was the biggest risk I’ve taken in my entire life; going from something I loved to perusing something new and uncertain. In the end, it’s all about taking the chance; go on that trip, eat the cake, buy the shoes, and take the risk! Read more>>

Sissy Martin | Fashion & Still Life Photographer

I think taking risks is crucial to attaining the life you want for yourself. I remember when I was making the decision to quit my full time job to pursue photography and I was so nervous. I had a role I really grew into with amazing coworkers and then I had the fear if photography would really work out for me. The wise man that my dad is sent me this message right before I put in my two weeks, “If this is what you want, go get it and never look back. If not don’t do it and just keep working there. There’s risk to all you do, but you have to weigh the risk against the reward. If you’re realistic about each then you will make the right decision.” So I did, I left my job and have been freelancing for the past 7 months and it did turn out to be the best decision for me. I’d rather try my best and fail than wonder what could have been the life that was waiting for me. Read more>>

Helen Buck | Visual Artist

Taking risks means weighing a number of factors. Sometimes those factors are incomplete or unknown and require a gut check without acting on impulse. I’m not afraid to take a risk or a chance on an opportunity. The important thing for me has always been, to begin with, as much information as I can garner and then make a decision. In this way, I lessen the risk factor but there is always a risk. It’s as if there is a built-in momentum once I make the leap and take a risk; like there is magic in that step. It may be a daring and undaunted step but it’s a start. The first time I approached a fine art gallery, I did exactly what you are not supposed to do. I walked into the gallery, introduced myself, and asked if I could have the opportunity to show my work there. Read more>>