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.

Jenny Crawford | Landscape Designer

Entrepreneurship feels like taking one calculated risk after another. My first year of business felt like the majority of the risk-taking was on the financial side. I thought once I was more established I would experience other types of risk more often. Now that I am in my second year of business, I realize that the financial risks never stop. As your business grows you consequently make more investments and add personnel to meet demand. Every time I add a fixed cost or additional salary it feels so risky, since a strong client funnel is required to remain profitable. Read more>>

Warrior Queen Artist | Artist & Intuitive Yoga Guide

I see risks as faith, and opportunities for adventures. I’ve always been a curious kid and enjoyed the wonderment of what life has to offer even though taking a risk can be scary. I always come back to my breath so, before the leap, I breathe in and upon my exhale I surrender to trust. I would not be where I am today without trusting that there will be something magical on the other side. It’s letting go of the judgment of that something, to be good or bad, right or wrong, in pain or pleasure, in loss or gain. It is from this place of receiving what is, to just be, and then we can take whatever is on the other side of risk and allow it to be a return to our own truest self. Read more>>

Kaci Goff | Chef of Wolf and Woman

Risks are a part of life and it’s something I don’t shy away from. Stepping out of your comfort zone and what may be the safest choice isn’t necessarily the right one you must make for yourself. You have to do things that you can grow and learn from even if that means you fail. Every time you fail you are a step closer to success. Read more>>

Sham Blak | Entrepreneur

Big risk big reward! I think unnecessary risks are dangerous and costly, but calculated risks and gamble give you a high. It’s like you could lose it all in this one bet, but also you can win big too. I never let the idea of losing be the sole decision maker on the risk, but what do I stand to gain. I’d rather take a calculated “L” with some growth and knowledge attached to it, then say go rob a bank and have to go to jail for a long time. Read more>>