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.

Jonas Jungblut | artist

According to mountaineer Reinhold Messner bringing a device to call for help on an expedition makes it non-risky. If you are embarking on an adventure but can call for help, its not an adventure. Risk requires one to have the confidence to manage without knowing what form of hardship one will encounter. Read more>>

Pat Shen | Small Business Owner & Artist

I’ve always been the type to lean into risk, generally a jump-now-think-later kind of person. It hasn’t always served me well, but nine years into my business, I’m realizing how much we have to be willing to take those leaps in order to get anywhere. Read more>>

Holland Clement | Commercial Lifestyle Photographer and Director

I’ve admittedly never considered myself a risk taker – certainly not in the classical sense that often comes with a connotation of recklessness. Most of my risk taking from a business perspective has been calculated, considered over time, and weighed against a massive amount of introspection and purposeful self-awareness. Read more>>

Jason Williams | creator/animator The Storytime Show with Story J””

Every time I put on the fedora and stand in front of the green screen I risk making a fool of myself. As much as I’m on camera as Story J, I’ve never been fond of seeing myself on screen or being the center of attention. I always wanted to be a behind-the-scenes guy. Read more>>

Eli Prasit | Photographer & Videographer

As a photographer who took the risk of dropping out of college at 18 and leaving my hometown to chase my dream in Los Angeles, I believe that risk-taking is absolutely essential to achieving success in any field, especially in the creative industry. Read more>>

Laura Petkunaite | Wholistic Medicine specialist

I think that every decision we make in life has a risk, some of them small risk, some of their high risk. And depending on the outcome we are seeking we have to choose the level of risk we are taking. I believe that “big” things don’t come with small risk decisions. Read more>>

Adan Maldonado | Designer

Risk is basically the ethos of any Entrepreur; essentially you are betting on yourself (a good idea helps too, though that’s not as important). Sometimes it pays off and other times it doesn’t, but part of taking risks is knowing the lessons learned from failures are as valuable as the successes. Read more>>