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.

Sofia Leão | Singer-Songwriter & Film Composer

Taking risks has truly defined my journey as a singer-songwriter and media composer. When I was just 18, I made the bold decision to leave behind everything familiar in Rio de Janeiro, Brazil, and head to Boston, USA, to pursue my musical passion at Berklee College of Music.  Read more>>

Jade Fink | Touring Bassist & Artist

As a touring bassist and artist, my entire career often feels like a risk. In order to make genuine art and music, I have to open myself up and put myself in a vulnerable position by sharing something that comes from a place deep in my heart.  Read more>>

Alan “89 the Brainchild” Grant jr | Hip Hop Performer/Host & Production

Sometimes the ppl u dnt kno could care more than the ppl u do. I was goin thru shitty circumstances that alot of 20something dreamers faced. Broke, brokenhearted, unsure how to make rent; nonetheless fund artistic endeavors. A man who I seen bts working visuals randomly invited me to visit a space in pre-production phases. Read more>>

Luis Ángel Mondragón | Actor, Writer & Producer

I believe that my upbringing was deeply rooted in taking little-to-no risks. What I have come to learn from life and art is the importance of finding a healthy relationship with being comfortable taking risks.  Read more>>

Ellen Durkan | Artist & blacksmith

I think as an artist you have to be willing to take risks since there is no straightforward life path. When i started college i was in the Nursing program because i didn’t want to financially struggle.  Read more>>

Eden Dugger | Model & Creative

Everything in life is risk and reward. You just have to decide which risks are worth the reward. Here in my suburban town at 16 I ended up in retail simply wanting to be close to clothing and the newest trends.  Read more>>

Dalia Hayon | Established and well recognized entrepreneur in Retail, Wholesale, Business Management and a Registered Representative

Believing in my ability to adapt and make a difference in people’s lives, led me to strive in a few positions and later successful businesses at a level I could have never imagine possible while raising a beautiful family and having a long successful marriage. Read more>>

Yingu Pan | Urban Designer & Architect

When it comes to risk, I like to think of it as the secret ingredient in the recipe of my career – it’s what turns a good dish into an unforgettable one. In my life and career, taking risks has been like adding a bit of spice to a meal; it can be daunting at first, but it often leads to the most rewarding flavors. Read more>>

DeshPlease | Indie Music Artist & Content Creator

I think taking risks is crucial to growth both personally and professionally in any industry. Being a creative, taking risks has become part of my daily routine. I’m constantly trying to expand my knowledge, learn new skills or push myself to step out of my comfort zone and try something new.  Read more>>

Maxx Wavvy | Post production Audio Engineer & Film Director

Risk is an essential aspect of growth and progress. Personally, I believe that risk-taking is necessary to achieve success and discover new opportunities. Throughout my life and career, I have embraced risks as stepping stones towards personal and professional development. Read more>>

Miguel Canchola | Creative Director, Organizer, Musical Artist

When I think about risk, I think about what I am trying to accomplish and where I want to be. I have never been the type of person to be content with where they are, instead I have always been the kind to take chances whenever they’re presented.  Read more>>

sankalp dubey | Cinematographer

Transitioning from a stable career in engineering to the unpredictable and unconventional world of cinematography was a daunting leap, but one that I embraced wholeheartedly.  Read more>>

Brandon Wisecarver | Art Dealer & Community Organizer

I think you gain very little by not taking any risks. When I moved to NYC in 2008, I came in a GMC short bus that I had bought for $1000 off a Ska band in San Francisco. I had zero friends, family or connections out here.  Read more>>

Aubree Estrella | Photographer / Videographer

I think the entire foundation of my career has been based upon risk – whether calculated or uncalculated and for better or worse. I grew up a very high level athlete and was being recruited to play D1 collegiate soccer from a young age. Read more>>

Andie Desiderio | Artist & Illustrator

Most of my family have conventional lives. So I was encouraged to do the same. After college I got a conventional 9-5 job at a company. It was safe and not risky but I was unhappy with that life. To leave that lifestyle was to accept I was leading a life with greater risk but it felt right. Read more>>

Grace Hansen | Screenwriter

When I was working as a prosecuting attorney for the Shoshone-Bannock Tribes in Fort Hall, Idaho, I watched the consequences of poorly executed risk evaluation every day. I talked to defendants who regretted forging a check, stealing a car, or, quite literally, playing with fire. Read more>>

Carmen Grier | Artist

My paintings come alive when I take risks. When a composition becomes too tight, stiff or just not working, that’s when I need to loosen it up by taking chances with it: smearing paint, scratching away paint, altering shapes and influencing textures in a hopeful return to the looseness the painting had at its earlier stage. Read more>>

Unorganized Home | Professional Organizing

The fun part about our job is that every day is different. Every client, every space, every situation. And when things are different all the time that means we can’t be afraid to try new things. Risk is that possibility that we could fail when we try new things like starting a business but honestly, the idea of not attempting the tetris game at all seems pretty boring. Read more>>

Terra Marotz | Electronic Music Producer, Singer, Songwriter, DJ

I think my entire career path has been a risk, but I wouldn’t change it for anything. I think being the first of my family (that I know of) to try and pursue a music career has been nothing short of insanity, and although I love it, my art itself has never paid the bills. So I figured, what’s second best to making money as an artist?  Read more>>

Heidi Santos | Health and Wellness Spiritual Healer

If you don’t step out of your comfort zone you’ll never know what’s on the other side. I’m curious by nature and I know that taking risks is a big part of life. Growing up as an immigrant child I faced many obstacles, so I had to learn to be patient, resourceful, and persistent.  Read more>>

Vishvak Prakkruth | Director and Filmmaker

I honestly believe that risk-taking is an integral part of life. Growing up with undiagnosed ADHD, I found myself constantly seeking new challenges and opportunities, often acting on impulse. This aspect of my personality has profoundly influenced my approach to life and my career as a filmmaker. Read more>>

Bin Youn | artist & poet

Risk is desert, here. Barren land where no milk flows. As a visual artist and poet, I’ve come to understand risk not as a mere concept, but as a visceral experience—a journey into the unknown where the familiar comforts of security are stripped away, leaving behind a landscape of challenges and opportunities. Read more>>

Pamela Peak | Award Winning Inspirational Filmmaker & Artist Coach

Early on, when I first came to Los Angeles, I took acting lessons from the great director Milton Katselas, an Academy Award winning film director. And his motto was: Validate Your Own Passport! So, when I’ve wanted to do something, I’ve always said, “Why not me? Why shouldn’t I do this? I’m willing to take the risk.” And as long as I had the skills to do it, I’ve never let anything stop me. And that meant . . . taking risks! Read more>>

Blake Zirpel | Recording artist

I think calculating risk is a critical factor in any artist or entrepreneur’s success. With that being said I think %95 of people do not take enough risks In life and therefore put themselves in was less opportune positions. I also don’t think that means anyone with a dream should just quit their job and expect success right away. Read more>>

Claire Risoli | Mom, Entrepreneur, Restauranteur

My motto is “Start before you are ready, just START!” It is never the perfect time to take a risk and I am not one to be “getting ready to get ready.” You have to just start with where you are, with what you’ve got. None of us knew what we were doing when we decided to embark on the journey of entrepreneurship.  Read more>>

Kelsey Blackstone | Professional Musician

Choosing a career in the music industry is all about risk. It’s a completely unstable and ever-changing field. But strangely enough that has not been enough to deter me from pursuing my professional music career. I’d rather be happy doing what I love, and doing something that I know makes people feel joy and unity, than doing something safe and being unsatisfied with my life. Read more>>

Ezekiel K. | Musical Artist

including myself fall into the trap where we’re scared to take risk because we’re not sure we’re cable or ready, or we’re afraid of the outcome. Most decisions you make in life, you’re taking a risk, you are risking something to gain a certain outcome, good or bad, big or small.  Read more>>

Chris Jai Alex | miracle worker (producing actor)

Do it now. if youre wrong, be wrong fast so uou can change course. We never know where our next check is coming from so when you’re up, plot a couse to stay up because money has a way of missing you when you need it. Read more>>

Waves | DJ, sound curator, and event producer

I never really thought of myself as a risky person until I stopped recently to look back at what I’ve accomplished in my DJ career. It hit me that risk taking is essential to success (in whatever way you define that), because you have to think outside the box and operate different than the average person in order to really grow.  Read more>>

lindsey glass | Author, Advocate, Subject Matter Expert

I am both a small business owner and a creative professional and I don’t think you can be either without taking risks. The key factor with risk is, what kinds of risks are you taking and are they thought-out strategic risks or are you throwing spaghetti at the wall to see what sticks? Read more>>

Claudia Chakmati | Producer & Development Executive

This is a very good question because, in the entertainment industry, risk assessment pretty much constitutes the bulk of our job, and we can do that in many different ways. Right now, the landscape for film & TV doesn’t look as exciting as it did 7-10 years ago. Read more>> 

Shana Francesca | Scholar of Intentional & Ethical Leadership & Living, Keynote Speaker and Consultant

Taking a risk on myself and starting my business was the scariest choice I have ever made but certainly not the scariest moment of my life. I knew I had no idea what it would require of me, I only knew the first few steps, but I also knew I would never let me down. Read more>>

Jutta Charbonnier | Actress & Model

To be fair, if I didn’t decide to take a big risk I wouldn’t be here! I think it is very important to take risks for your career and your life. Otherwise you don’t go far in anything. And honestly it gets boring! It could either go good or bad but if it goes bad then you just learn from it! Read more>>

Edina Hiser | Costume and Production Designer

Risk taking is a huge part of my career. In order to work in the entertainment industry, I think a certain amount of risk taking is a necessity. Moving across the country to go to school in California (I was born and raised in Maryland) was really the risk that started it all. Read more>>

Deborah Correa | Film Director

This is a really interesting question. That saying, “no risk, no reward,” is true but up to a point. It actually annoys me when people throw it around. There is an important element of internal discernment that must be tapped into before making risky choices.  Read more>>

Jane Holland | Owner of Seventh House Vintage Jewelry

When it came to my vintage jewelry business, Seventh House, I was taking a huge risk. 7H required me to invest in an expensive product (fine jewelry), and invest in myself to properly source and educate myself about the jewelry world. Read more>>