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.

Jacqueline Powers | Retired Math Teacher/ Steel Pan Musician/ Surf Enthusiast/Jimmy Buffett fan

I believe that risk taking is an essential part of life. It helps you to learn about yourself and it helps to increase your confidence. Taking risks creates change in your life, you meet new people, and you develop emotional resilience because when you take on risk you must consider failure as a possible outcome and so you learn and grow. One big risk that I took long ago was accepting a sailing invitation (I had no prior sailing knowledge) to sail the Caribbean islands. The 50′ Gulfstar sloop began it’s voyage in Rhode Island and two of us sailed that vessel south to Florida, through the Bahamas, the Dominican Republic, Puerto Rico on onward through the Virgin Islands, the Leeward and Windward Caribbean islands all the way to Trinidad. Read more>>

Meka Lolita | DJ, Artist, Entrepreneur

I am a BIG risk taker. I have taken some huge risk in my life and I can’t say that I regret any of them. Im a first generation college student and graduate and for me, that was the first huge risk I ever took. Moving away to a new city by myself, not knowing a soul at the age of 17 was the start of my risk taking journey. I hold so much pride in being the first to bring a degree home to my family. And when I succeeded at that risk, that helped me build confidence in myself to be able to take even more risk. Like packing up my car and driving across country to move to LA in the middle of a pandemic. Or like quitting my job in 2022 during the rise of inflation with no savings to fully pursue my DJ career. Now, I do not recommend ALL risk. I am a little insane. lol. Read more>>

Veranice Berry | Author

Newton said “an object at rest remains at rest and an object in motion will continue moving.” I believe risk taking applies along the same lines. If I have a brain full of ideas and goals I want to achieve, I must put them in motion and they will continue on. I will say this a lot during this interview, I am a single mother so my daily decisions are huge risks because it is not just me the outcome will affect. Self publishing is a big risk because my books may never take off, a traditional publisher may not want to rebrand my works, and using my own personal funds to create these goals of mine takes away a lot, BUT it is a risk I am willing to take because if what I want to achieve remains at rest, then I have nothing moving forward. Read more>>

Joa Suorez | Poet, Artist, Visitor Experience Assistant at the Anderson Collection at Stanford

I like when artists take risks. Who knew just what would happen when Agnes Denes decided to grow a field of wheat in downtown Manhattan? Giving up some measure of control—to process, materials, or environment—feels full of possibility. I try to stay open to opportunities to take risks. I enjoy painting en plein air and drawing a live model in figure drawing class in part because of the unpredictability. If what I write or paint starts to feel too automatic or comfortable, it’s time to change my approach. Read more>>