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.

Jana Landon

I’m very risk averse but I follow the mantra of “Do it scared but prepared.” Preparation makes me feel more comfortable with taking risks. It took me 13 years to make the pivot to being a full-time creative! I left a very comfortable job in tech to follow my dreams but I had been putting in the work to enable this pivot for years. Much of the preparation involved getting more clear on what I wanted to do by doing it. At first, I thought it was acting but after three years of improv performance classes at UCB New York and a two-year, part-time Meisner acting program at the William Esper Studio I knew that acting wasn’t quite it. Read More>>

Sarah Hughes

Risk has absolutely played a pivotal role in my life & where I am today with my career, taking the leap of faith to move out to Los Angeles from Philadelphia being the most obvious. I didn’t have a job set up and all I heard was how hard it is to break into the music business, but I just kept my blinders on and stayed bullish, figuring it eventually had to happen. Read More>>

Heather Jocelyn Blair

Risk taking has been the heart of my journey, a fundamental part of my personal and professional growth. From an early age, my parents instilled in me the drive to challenge myself, work smart, and not be afraid to try something new. I was exposed to pushing boundaries in elite athletics, academics, and creative pursuits. As an adult, when faced with a big leap, I ask myself, “What’s the worst that could happen?” If the answer is clear and there is potential for something great, then I take the leap!  Read More>>

Paulette Victor Lifton

From Runaway to Hollywood Powerhouse: Paulette Victor Lifton’s Bold Leap into the Unknown

I watched my diary pages swirl down the toilet. A year of teenage angst—gone with a single flush. That was my first day of my new adventure. At just 14, I was a runaway in Hollywood, and whatever image just popped into your head is probably right. Read More>>

Damien Curry

I hate to sound like “Captain Positive”, but I generally approach risks with the mindset of – what’s the best that can come from this, rather than the worse. Failure is so easy to calculate and envision. Our minds are powerful and we can create whatever reality we focus on. In my opinion there is no place for being risk-adverse when it comes to innovation. Whatever the medium of innovation is, some sort of risk is required. I would say that literally everything that I’ve been successful at has been wildly terrifying and/or intimidating at first. Read More>>

Bo Bridges

Risk has been a constant companion in my life and career. From shooting the first-ever X Games to filming in the impact zone at Jaws or Teahupo’o, I’ve built my career by getting as close as possible to the action—oftentimes in places where one wrong move could be life-threatening. But to me, risk is where the magic happens.

You don’t get the shot of a lifetime by playing it safe. Whether I’m hanging out of a helicopter, duck diving with a fisheye lens into heavy surf, or launching an immersive film like Big Wave with new technology that’s never been used like this before—risk is always part of the process. Read More>>

Rick & Josh

1. Risk Taking: How do you think about risk, and what role has taking risks played in your life/career?
Josh:
“For me, risk is part of the game especially in today’s fast-paced world where trends shift overnight. Launching The Break Room was about recognizing where culture is headed: people want experiences, not just places to sit and drink. I leaned into social media, local buzz, and creating a vibe that resonated with the community. Sure, there were risks, but I see risk as fuel for innovation. Read More>>

Igor Bardykin

Risk has always been a defining force in my life, both personally and professionally. For me, risk isn’t about reckless leaps or seeking thrills; it’s about making intentional decisions that push me beyond my comfort zone, creating space for growth. It’s about embracing uncertainty, trusting the process, and knowing that discomfort is often a sign of something greater waiting on the other side. Read More>>

Fiorella

I’ve taken risks all my life. Even when I was afraid, fear never paralyzed me, it pushed me forward. I took the risk of studying a master’s degree in Australia without being fluent in English. Read More>>

Ryan McCue

Taking risks is totally necessary and completely terrifying. It’s difficult to put yourself in situations where there’s potential for failure, especially if you’re already an anxious person prepared to slip on a banana peel the moment you step outside. Read More>>

Down Time

Risk is everything! We love risk. Without it there is no challenge. We take risk when we write a song and share it, when we book a show, when we moved to LA to shake things up in 2021. Read More>>

Dali Ma

I think of risk not as something to fear, but as a necessary ingredient for growth. For me, taking risks has never been about being reckless—it’s about being intentional, informed, and bold enough to step into the unknown when something calls to you. Read More>>

Yarden Brikman

I’m pretty naive when it comes to risk, and it always played to my advantage. I never think about the outcome, or what could’ve go worse, but how it excites me. Read More>>

Kim Darren Salas

I see risk as an opportunity because every success comes from taking risks. If you don’t take risks, you won’t achieve success. That doesn’t mean I consider myself successful yet but I believe we need to try more things in life to reach our goals. Read More>>

Sabrina Mccarthy

I think since a very young age I’ve always had the perspective that without risk there is no reward. A of the greatest leaders and successful people in the world have taken huge risks to get to where they are. Read More>>

Kelly Diaz

I ask myself is that risk worth taking? If it wasn’t for the risks that I took my life would look very different from what it is now. Taking a risk is one of the most scariest decisions you make and can be one of the darkest parts of your life.  Read More>>

Yaroslav Golovkin

Speaking about myself has never come naturally, let alone my work — but I found this question about risk surprisingly welcome. I often hear people describe me as a risk-taker nowadays, and I read that as a compliment. Read More>>

Christine Lee

Honestly, taking risks has always been scary for me. But over time, I’ve realized that fear usually means growth is on the other side. I’ve been actively pushing myself—both in my career and my music—to lean into those uncomfortable moments. Read More>>

Justin Page

Risks, especially in comedy is the reason I love it and also hate it sometimes. If I’m not taking risks at all, things will get stale even though it feels familiar snd comfortable. Read More>>

Nabeeh Shamieh

Risk is something that is essential when it comes to this line work as I live by the phrase “If I won’t, who will”. In order for me to succeed in the areas that I would like to I need to bite the bullet and try something that I’ve never done before. Read More>>

Kyndra McCrary

I have been a risk taker my whole life. There is a common saying that’s “no risk, no reward”. I truly believe this statement. Anyone who is successful took a risk. Read More>>

Tristen Sosa

Albert Einstein said it best ” A person who never made a mistake never tried anything new “. You can take this quote in many different directions, but for me it is a strong value of taking risks. Thru out my whole life I have lived by taking countless of risks. Read More>>

James Byous

I think risk taking is at the heart of great artistry. I’ve always felt like the stories worth telling were the ones in which there was something at stake. If you don’t stand to lose anything, there are no stakes and the story is a long stream of pointless musings where nothing matters. There’s no conflict.  Read More>>

Jamie-Lee Dimes

I feel like I’m constantly living in the ‘risk zone’ of my life. Every time I’ve made the biggest sacrifices or taken the riskiest leaps, ones that could potentially end a career, that’s when my writing, stories, and experiences have truly resonated. Read More>>

Nora Hill

Consider your definition. Merriam-Webster defines it as the possibility of loss or peril. The word likely conjures images of the stock market, Mount Everest, and surgery. Read More>>

Jay Aka Jayfreed Reed

The word “risk” is often met with resistance or thought about in a way that always seems to insure or guarantee danger. While in reality or if the individual chooses to see it, risk is actually just taking a chance. Read More>>

Tracy Yun

I believe that risk-taking is a crucial aspect of running a business. Without taking risks, we can never truly know whether our ideas will succeed or fail unless we try. Throughout my career and personal life, I have made many decisions that involved risk. Read More>>

Luis Sanchez

Risk is just part of the deal when you’re an entrepreneur—especially in the restaurant world. There’s no way around it. But what you can do is prepare, anticipate, and hope it swings in your favor. For me, taking risks has been a constant, whether it was opening my own place, trying out new flavors, or reworking the menu. Read More>>

Sumire Kudo

I firmly believe that taking risks is essential. Before transitioning into fine art, I worked as a designer in my home country, leading a life surrounded by a stable job, reliable income, and close friends. Had I continued down that path, I likely would have climbed the career ladder, started a family, and by now, I might have been living a comfortable, secure life. Read More>>

Joshua Stein

I believe those with conviction take the most risk. I suppose it’s much easier to take risk when the vision of the outcome you want is clearer than the reality of potential dangers. Obviously this is a bit simplifying, but unless the risk involves some sort of bodily harm like say J-walking, or eating strange take-out from the back of the refrigerator, take a shot. What’s the worst that could happen? Read More>>

Jazzmyne Jay

It’s kind of wild, but actually very Libra of me, but on a day-to-day level I am trying to be RISK FREE! I want the easiest daily experience I could ever have. When it comes to career though, I realize that I am out here really taking risks and betting on myself. Read More>>

Jackson Tiller

Taking risks has been the most common theme in my life when it comes to my career. I originally went to college to be a nurse. While at school I took the risk from moving out of the medical field to taking on an arts career. Read More>>

Yeji SHIN

I believe that risk is something we must inevitably face in both life and work—especially in our careers. For instance, I recently transitioned from working at a museum residency to setting up my own personal studio. Read More>>

Courtney Randolph

Taking risks has played a major role in every chapter of my career. Going on reality TV was a risk—it meant putting myself out there, unfiltered, in front of millions of people. But I did it knowing I had a bigger vision. Read More>>

Ingeborg Kolstad

I believe taking risks is essential if you want to unlock the next level of being a creator. Creating entails venturing into the unknown, and for me, that has meant both personal and artistic leaps. Read More>>

Noga Kedem

For me personally every moment of my career was a risk. Nothing was promised, if not even – was assumed to fail by many people among the way. I had a weird and even unsuspected path, slowly covering my voice and earning my skills. Read More>>

Katrina DiMiele

Risk has been the heartbeat of my journey. I was a teen mom and a high school dropout—I wasn’t supposed to “make it.” But I’ve built a life and a business by choosing faith over fear, again and again. Read More>>

Joskie Noble

Choosing to live my life authentically is a risk. Choosing to post myself looking the way I do and doing the things I do, is a risk. I run the risk of people not liking me. Not accepting me. Ridiculing me. I run the risk of being ostracized. Read More>>