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.

Marquesa Ukawilu | Wedding Planner and Event Stylist

I recently recognized a significant risk aversion in my personal and professional life. When presented with new opportunities, whether in business or family matters, I meticulously analyze every aspect to ensure minimal risk. However, I understand that significant rewards often require calculated risks. Read more>>

Day Ra

I like to think about risk as like a mountain; ever changing and confusing. If you want to climb that mountain you have to understand that there is no easy way up. Some people will try to climb with their safety gear close by to catch them if they fall. I’d prefer to go all the way to the top with no safety gear on. The greater the distance from the ground the more it shows me how far I have to get to be at the top. And if you fall that’s okay because falling is something you’ve done since you learned to walk. So get back up keep climbing and when you make it to the top you’ll see that you made it there in half the time it took you playing it safe. Read more>>

Ayesha Youngblood

As a Licensed Professional Counselor, I view risk not just in the traditional sense of making big, bold moves, but as a deeper, more nuanced concept. I believe that risk, at its core, is about being vulnerable, stepping outside of your comfort zone, and embracing the possibility of growth. In this sense, I see risk as a tool for transformation, a necessary element of progress that invites change and fosters resilience. Read more>>