Shoot your shot? Take a chance? Society bombards us with messages, phrases, examples and stories of how taking risk is the key to success, but is anything ever that simple? We asked some of the brightest folks we know to tell us about how they think about risk. We’ve shared their responses below.

Janet Ramirez

I truly believe if you’re not taking risks, you’re not really living. From joining the military at 17, to stepping into my first civilian job in completely new territory, and now transitioning into the beauty industry — risk has always been part of my journey. I’ll rather take risks and fail than play it safe and live with regret. Read More>>

Mary Hill

For me, risks are like death and rebirth, and it is a labor of love to die and to be reborn. Ego-dissolution is very painful, yet part of the initiation of transformation. Building a business, or an identity or a work of art, and then, letting it go, so that a new vision can explode into blossom, is terrifying and joyful.  Read More>>

Ana Maria Gower

Sometimes I feel like people overcomplicate the idea of risk. You hear people talking about managing it, hedging, and so on. And there is definitely a place for some sort of strategic thinking about risk. However, I think we often forget the heart of the matter. Read more>>

 Jonathan Flores

For me, risk has never been something to shy away from—it’s been the price of growth. I grew up watching my parents sacrifice everything so that my brother and I could have opportunities, and that perspective shifted the way I see risk. It’s not about gambling recklessly; it’s about honoring those sacrifices by betting on myself and creating something bigger than what was handed to me. Read More>>

Dayshawn Nellon

Risk is a part of who I am and how I move through both life and business. I put my last savings into Coffee Bae because I believe in this vision, and I don’t treat it like a side hustle — it is my career, my main focus, and the foundation of the brand I’m building. That decision is a risk, but it keeps me fully invested and intentional every day. Read More>>