Legend holds that Cornelius Vanderbilt had built a massive fortune in the steamboat shipping industry, but then realized the railroads were the way of the future and invested almost his entire net worth into railroads. The gamble paid off and made Vanderbilt one of the wealthiest entrepreneurs ever. But risks are inherently…risky. How do you think about risk and how has it affected your life and career? Some of our community favorites share their perspective below.

Megan Nicole O’Neal

I’m a big advocate for experimenting and not being afraid if things don’t work out the way you planned. Because when I look back at my life, usually the biggest moments of growth happened after I “failed” at something.

The first time I pitched an editor as a then hopeful freelance writer, I spent hours coming up with a story tailored to this outlet, and I remember feeling dejected that never heard back from them. However, that editor, unbeknownst to be, forwarded my email to an old colleague who ended up loving the story—and that’s how I became a writer for SUCCESS Magazine. Read More>>

Cinnamon Gray

Risk? I don’t think about it—I dance with it in stilettos, blindfolded, on a tightrope over a pit of my past failures, and still manage to flip my hair on the way across.

Taking risks didn’t just play a role in my life—it was the lead actor, the director, and the entire damn production crew. While other people were waiting for a sign, I was out here making neon ones and stapling them to the universe. Read More>>

 Jenell Kelly

Risk has always had a different meaning for me. Growing up with social anxiety, what others saw as everyday decisions—raising a hand in class, joining a sports team, auditioning for a play—felt like monumental acts of courage. These weren’t just decisions, they were emotional leaps. Every moment that required me to be seen, to speak up, or to engage felt like I was standing at the edge of something unknown. But I learned early on that if I wanted a life beyond fear, I’d have to take risks others didn’t even notice. Read More>>

Melissa Velasco

As a choreographer, stage manager, and author, my career in the Arts has largely been risky. I believe all artists must face the fear of risk, both monetarily and psychologically. I’ve never experienced professional risk quite like I do as an author, though. I strategically chose the self-publishing route when I started my book series, The Hollywood High Chronicles. As I faced the realization that I was producing a sixteen-book series, I initially ran the math. Read More>>