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.

Gina Onativia | Course Consultant & Digital Strategist

Risk taking: how do you think about risk, what role has taking risks played in your life/career? Early on in my business I had mentors tell me: Be unreasonable. In other words: don’t be satisfied by the status quo. Don’t be afraid to go against the grain. And have the confidence to do something that others will say: That will never work. Five years ago I took a risk in my business when I decided to double down on course creation. Up until then I was doing all sorts of tasks to cobble together a business as the behind-the-scenes girl. Need a script for your virtual event intro video? I got you. Ten-post blog series? I am your girl. Produce a livestream? Let’s go. Read more>>

Jeff Rossman | executive chef-owner, Terra American Bistro, Terra Catering and Bunz gourmet burgers

I was a newly mined UCSD grad with an economics degree and no clear direction beyond that. My parents were longtime local restaurateurs and I’d helped them at their diner, Pam Pam — now Bunz gourmet burgers — over the years, quickly realizing the hazards of late night partying when I had a 7 a.m. shift at the restaurant the next day. I instated my own curfew. In the late ’90s, I’d gone back to work at Pam Pam, toying with recipes and developing menu items during the day and managing the front of house at night. Soon, I’d created a supplemental menu that helped us double revenue in one year. It was 1998 — and time to take a risk. Read more>>

Sigrid Qian | Painter/ Fine Artist

My life is full of risk, to be honest. I am a painter and mixed media artist, to be living as an artist with a traditional Chinese background is a full package of risks I had to take. My parents wanted me to be a scientist. To be fair, none of them was good at mathematics, so they were expecting me to be the game-changer in our family. That didn’t work out because my gene told me so. So I had to fight with my parents to be able to study any type of arts when I was 14 years old. So they’ve discovered I was sort of good at negotiating, that was how I got into a business college later when I hit 19, or they won’t pay any of my living expenses or tuition. Read more>>

Amy Forsythe | Author and Military veteran

“Risking is always better than regretting” is a quote that has fueled my passion for global travel, pushing my creative limits and challenging the status quo. When we reflect on crossroads in our lives, sometimes people regrets about the things they would have, should have or could have done to achieve a different outcome. I’ve always tried to make decisions based on the fear of regretting to take risks with my career and relationships. Read more>>

AMANDA HENNESSEY | Public Speaking Coach, Author & Acting Teacher

I really like adventures. In my mind, adventure is made up of possibility plus uncertainty plus beauty plus risk. Taking calculated risks helps me feel awake and excited. Do I love jumping out of airplanes into shark-invested waters? No. I’m not usually craving physical risks. I’m drawn to creative risks, intellectual risks, and business risks. I feel confined by too much of a predictable routine. Read more>>

Chef Robee | Private Chef/Proprietor

I have always been a risk taker, as it has always been a part of my personality. As a child I loved to travel. My parents exposed me to traveling, fine dining and the arts at a young age. By the time I was 6 years old, I had traveled from California to NYC alone to visit my best friend and her family. I have always been a dreamer, a reader, and a thinker. By the time I graduated high school at 16 years old, I moved into my own apartment in San Francisco to attend the California Culinary Academy (now the Cordon Bleu School of Culinary Arts). I’ve always bet on my own talent, my drive and my ambition. Read more>>

Ashton Wilson | Adventure Enthusiast & Travel Vlogger

I spent many of years not risking anything; not my words, my actions and a lot of times not even my thoughts. It felt dangerous-which is the literal definition of risk. Then my world flipped on a dime and I had nothing to lose. So risking became almost a challenge for me. What CAN I do that might seem dangerous to some but will bring me ultimate joy? To me that was traveling the world. Most of my traveling is done solo-mainly because thats just where I’m at in this stage of life. Solo travel is wild and crazy and terrifying but also crazy rewarding and entertaining. It forces you to submerge yourself in the culture and be one with the world the around you and be as fully in the moment as possible. Read more>>

Heena Jain | Photographer

Risk taking is all about risk management. Life is all about risks and the saying “No Risk, No Reward” summarizes this aptly. Every choice we make or every decision we take in life has some sort of risk. I firmly believe that when you have a maniacal focus on your passion and have strong conviction in whatever you do, you learn from your failures and keep moving towards your goal. In the process of doing so, you learn how to take calculated risks and manage outcomes. It wouldn’t be an understatement to say that I have gotten this far because of the risks I have taken and the lessons I have learned. Read more>>

John Howler | Visual Artist

Risk is big. Risk is huge! I believe that the amount of risk taken has to have an equal or bigger amount of commitment to back it up. In my life, taking the risk to pursue a creative career in lieu of a “stable” job has to be one of the biggest commitments because I am the only one holding myself accountable to create and find work. Some days it’s easy and other days there’s no motivation, but in the long run I know that just showing up (at my desk) and doing my best to put in a little work will help reinforce a healthy habit so that when the muse does happen my way, I am more than prepared to take on the challenge. Read more>>

Nadim Zoghbi | Photographer & Content Creator

I was born and raised in Lebanon, which has been under turmoil and hardships for as long as I remember. My parents had planned to move my sister and I to the US to give us the opportunity for a more prosperous life and better future. We ended up moving to Tampa, Florida in 2006, which is where my journey began in the US. My entire life, I was guided to follow the traditional path of success – study hard, do well in school, get a college degree at a reputable university, get a good job with solid benefits, climb up the corporate ladder and save enough money for retirement. That was my idea of happiness and success in life. Read more>>

Kerye Maull | Owner of KARE by Kerye Mone skincare brand

Risk taking is absolutely essential to growth ! Facing your fears head on will help to build character and self confidence. I knew establishing my skincare brand KARE by Kerye Mone which is truly my bainchild was a risk that I never fathomed would come into fruition,simply due to overthinking… but once i took the RISK the outpour of support was gratifying! I say that to say face risks with confidence and the abundance in all forms will be sure to follow you ! Read more>>

Tiana Lee | Lifestyle/Beauty Blogger

I think Risk taking is like the opening a door that leads you to an unknown. We don’t know if that unknown place will be good or bad. When taking Risks there’s always an option for failure and it allows others to scrutinize and judge. But at the same time there is a chance that you might strike gold and be really successful. As the saying goes, “If you never try, you’ll never know”. I’d rather take a stab at something and have a bad outcome; instead of always thinking what would’ve happened. Life is about risks as well as rewards. At the end of the day you have to be content with your own decisions and not others’ preconceptions and judgements. Read more>>