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.

Elyse Perron-Evans | Floral Designer & Generally Crafty

I’m actually right at a decision point of a big risk for Poppy & Pomegranate so this question feels very relevant at the moment. For the last three years I’ve been working full-time alongside kick starting my floral design studio. After my busiest wedding season this past summer I’ve decided that in order to bring Poppy & Pomegranate to its full potential as well as offer the level of client service I’d like to, I will need to dive feet first into working solely for myself for the first time. Read more>>

Kyler Jakubowski | Musician/Songwriter

It seems like the fear of taking a risk only prevents the actualization of your goals. Many things make me nervous, but overcoming that often leads to a greater outcome. It took strong criticism from my peers to get me to play in front of people, a live audience, but once I overcame it I was offered greater opportunities to learn and to perform music. Read more>>

Teddy (Jacques Cousteau) Brown | Electronic DJ & Producer

I know risk taking very well. You could say my middle name is risk. When I was a child, I lived at the top of a big hill and I always saw a big metal structure off to the distance. I lived up the street from WKIP, a local radio station, and I grew up wondering what the big antenna looked like up close. So when I was about 5, I walked down the street and wandered into the WKIP building. I wanted to meet the person talking on the radio and I wanted to get on the radio. My wish was to have my parents hear me announce the songs.. Read more>>

Anne Hodgins | Brand Content Manager + Film Photographer

I used to be absolutely terrified of risk. I was the smart kid in class who was always recommended for the AP classes, but turned them down because I was too scared I would fail. I liked being comfortable. But comfort isn’t where the success (or money) is. Before I started my business, I was super stuck. I was working a job I no longer enjoyed, and living out of my savings because I wasn’t making enough to afford living in California. I had thought about starting my own business, but it was always in a far off, “maybe some day…” kind of way. Read more>>

Natalie Morales | Licensed Esthetician & Owner of Beluminous Skin Studio

When I think about risk, I think reward. I’ve lived by the saying, “jump and the net will appear.” Growing up I wasn’t afraid to jump into doing different things. Sports, dance, music, and different jobs in retail, food and beverage, events, sales, and beauty. It excited me to try different things. Before opening Beluminous Skin Studio, I worked for 10 years at various positions for Marriott International. There, I was given many opportunities to grow and practice taking risks. Read more>>

Nicholas D. Monteilh | Actor. Writer. Director

The biggest risk for me is to not take one because despite all of the fears and doubts and anxieties that come with them, the only risks I have regretted are the ones I never took in the first place. If you learn something from every experience, if you can make any outcome an opportunity, if you’re always growing, then failure only happens when you never try at all. It also comes down to my own sense self-worth because by taking a risk, I’m also saying I’m worth taking a risk for…that my dreams are worthy of it. “Proving the concept” to myself, in a way. Read more>>

Anna Maecie Collard | Artist

Risk demands result, no matter the result. Risk ushers in a discomfort that only gives you the one choice; to grow. As an artist, risk is essential and in my creative process, a non negotiable. I can often feel comfort creeping in and upon discovering it, it then gives me what I call the “ick”. The “ick” for me is the moment where I realize I have settled for the current circumstances and the hunger for growth subsides. Read more>>