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.

Shakira Shenee’ & Rumana Sultana

At Sultana Collective, we see risk as something not to fear, but a necessary ingredient for growth. Risk has been the throughline in our careers for both of us, especially when the traditional paths didn’t quite fit. Taking risks has meant betting on ourselves, our vision, and on building something that didn’t yet exist in the way we dreamed it could. Read More>>

Pico DaGuy

Taking risks is an integral part of my passion and career. Every song I release is a risk of acceptance and approval. Although I release my music in my own comfort, the vulnerability that I put into my lyrics puts me at risk of judgement. I’ve learned to accept this as a part of the creative process. Read More>>

Amber Chisholm

Growing up, I was a timid girl who would do whatever it took to stay comfortable. I would always shrink myself small and feel like the next person deserved the spotlight, other than me. Risk was something I would constantly run away from. It wasn’t until I entered my adulthood and embarked on a personal healing journey that I noticed the effects of avoiding any risk or discomfort. I was limiting the opportunities to allow my true light to show, build my character, and honestly bet on myself. Read More>>

Patrick Cheng

Let me tell you something—big rewards come from bold moves. I’ve seen too many smart people stuck in “play it safe” mode. They save every penny, avoid risk, and never take the leap. And guess what? They never win big. In Asian culture, we’re taught to save, be frugal, and only spend when absolutely necessary. But that mindset held me back. I used to resist buying new software, hiring professionals, or investing in tools that could scale my business. Once I shifted that thinking—once I embraced risk—I started taking out loans to invest in growth. And the results? Tremendous. Those investments paid off far more than I put in. Read More>>

Ashley Rouse

I absolutely love this question, because taking risks is something that my mother ingrained in me since I was young. She would say, “nothing beats a try but a failure,” emphasizing that attempting something, even if it ends in failure, is better than not trying at all. She encouraged taking risks and pursuing goals, as the experience and potential for growth always outweighs the fear of failure. I’ve taken some big risks in my career, from turning down big promotions to protect my peace, to leaving a cushy job at Conde Nast in the World Trade Center to explore entrepreneurship full-time, to shutting down a company that I had run for a decade in order to refind happiness. Read More>>

Yulissa Ayala-Valles

Risk is a seed that grows resilience, perceptiveness, and confidence. Pursuing my career and life with risk led to many open doors. I believe humans need to embrace necessary risks to grow in wisdom. Ignoring this spark leads to stagnation and comfort. I once cared too much about others’ perceptions of my “failures.” But a failure to them may not be one to you—it’s often just a projection. I want those newer to the field to know there are always people ready to support you. You’re never alone when facing a needed risk within trusted community. Read More>>