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.

Aaroosh Kohli

I have always been more of a risk-taker in most of what I do. My career in film/TV was always a risk, especially given that I have a degree in Economics and come from a family of bankers. I can attribute a lot of that to the privilege my parents afforded me throughout my life by supporting me in whatever I wanted to do.  Read More>>

Kimberly Ryan

Risk plants you square in the space where success or failure are a heartbeat away. Risk brought me two children adopted internationally, a mid-life career change, and a business where my presence can tip the scales for someone else in an outcome. Read More>>

Gregory DeAnda

My life and career are defined by taking risks. I’d describe myself as a calculated risk-taker. I understand that being stagnant is, for me, a form of personal death. I need to challenge myself, and those challenges often come with risks. But I’ve learned that if I’m truly following my heart and I genuinely believe in what I’m doing, then it doesn’t feel like a risk at all. It’s a lesson, no matter the outcome something I can grow and learn from.  Read More>>

Thomas Diehl

When I look back on my career, I see that risk has been at the center of everything I’ve done. Moving to California to pursue landscape design was a leap — there was no guarantee of security, but I knew plants could be my medium as an artist. I’ve always seen myself as much a visual artist as a designer, and the challenge has been creating opportunities for people to trust me with their spaces so I can express that vision.  Read More>>

Pepe Del Rio

For me, risk isn’t about gambling—it’s about conviction and unlocking your full potential. I started my career in private equity, a path of stability and predictability. But I realized that if I only optimized for safety, I’d never build something truly transformative—and I could easily get stuck in the comfort of that path. Read More>>

Ingrid Giovanie

I do nothing in this life but take risks. I wear my heart on my sleeve and bet on no one but myself, and I am always grateful anytime anyone considers me for their projects. Several of the roles I have participated in acting or songs I’ve sung on stage have been unconventional, taboo, or downright in-your-face. I find risk taking to be liberating. Many times, I get nervous before taking a risk, and each time I take it, I am glad I do. It helps me grow as an artist and as a human being. Read More>>