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.

Kemet Ackee

Taking risks has been the heartbeat of All My Friends Are Rappers. From leaving the military and diving headfirst into fashion, to expanding into the craft beer world—everything we’ve built came from betting on ourselves when there was no safety net. I see risk as a necessary part of growth. It’s never about being reckless—it’s about believing in a vision strong enough to make the leap, even when the outcome isn’t guaranteed. Read More>>

Kimberlea Bass

In the world of art, risk is the very essence of creation. When I think about risk, I am reminded of Thomas Jefferson’s saying: “With great risk comes great reward.” In my journey as an artist, every decision I make carries a weight of uncertainty. Each mark in my sketchbook is a gamble—will it blossom into a masterpiece, or will it serve as a stepping stone to a valuable lesson? Read More>>

Sergio Gonzalez Jr

The greatest risk in life is standing still, afraid to take a chance. What’s truly at stake? Nothing compared to the regret of watching time pass you by. Life doesn’t pause it keeps moving forward, and before you know it, the years will have flown by. Imagine looking back at 60 and wishing you had dared to take those leaps. Every risk you take becomes a lesson, a stepping stone to growth. So, embrace the uncertainty, and remember: each step forward is a step toward becoming the best version of yourself. Slow motion is better than no motion. Read More>>

Erin Ainslie

Risk is scary, It has stopped so many people from changing the trajectory of their lives. I’m terrified of risk. I crave security. However, the life I want for myself and the life I believe God has in store for me, would not be possible without risk.

Throughout my life, I have chased passion over security. I chose careers in non-profits over stable STEM research facilities. I’ve done so because my personal fulfillment is found in impacting the world, other than having a stable and steady income. I have no regrets about any of the choices. Taking risks has paid off and allowed me to have a life where I feel satisfaction in my work. Read More>>

Andrew Juarez

I think risk has played a huge role in my journey—honestly, more good has come from taking risks than from playing it safe. Every major shift in my career happened because I stepped into the unknown. Like when I got laid off from my first marketing role—at the time, it felt like a low point. But if that hadn’t happened, I probably wouldn’t have gone all in on freelancing. That moment pushed me to bet on myself, and from there, things really started falling into place. Read More>>