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.

Jalawni Appling | Natural HairStylist

I have always dreamt of entrepreneurship, hoping to one day create my own business. During the beginning of the pandemic, when people began to fear instability in their careers, I came to a realization: we are on borrowed time. I needed to begin using my talents to manifest my dreams. I grew tired of constantly hindering myself from beginning a journey that would not only bring me happiness but also create generational wealth. I kept asking myself questions like “where would I even start?”, instead of just starting. Finally, I took a leap of faith, and now “FauxEver Loc’d” has grown into a truly amazing venture. Read more>>

Lisa Lebofsky | Painter

Risk is part of my practice. My motto: “Be like an iceberg: ride the current, wind up in a beautiful cove, be glorious and inspiring, and slowly melt to your ultimate demise.” I had lived a structured existence. One night, with little warning, my personal world was turned upside down. The confusion set me off on a course of perpetual searching and failed attempts to hold together something that was perhaps never real. This was my calving moment. In that unending psychological free fall, I found control by getting rid of all control. Read more>>

Jordan Walczak | Photographer & Motion Designer

I think that taking risks is necessary in the creative field. You may find a formula that works for a while but then people may loose interest after a while if you continue to repeat. I think you should constantly be trying new things and see what sticks, it could be subtle changes but you want to continue to grow and keep your work from getting stale. Read more>>

Adam Wamsley | Photographer & Director

I feel that taking risks is an integral part of growth, and has been essential to getting me where I am in life and in my career. Most of my advisors in school and in life as a teenager to young adult advised caution, safety, stability and making the choices involving the least amount of risk. Being the restless kid that I was, that didn’t sit too well with me, and I’m extremely thankful for that. The decision to try a new artistic medium, investing my money into a camera setup, and switching majors from the sciences to design were the beginning of a series of risky decisions. I quit my stable paying job in college to pursue art and, with a sink or swim mentality, figured that “if it was worth it to me, I’d find a way to make it work”. Read more>>

Tedd Wakeman | Co-founder/Director – The Sycamore School (Educational Designer and Revolutionary)

How do we define risk? Is it jumping out of a plane or swimming with sharks? Is it public speaking, driving in Hanoi, or dining with a street vendor in Nicaragua? I don’t know, honestly. Evaluating and defining risk feels like a very personal journey and is closely tied to real or perceived consequences. We weigh the rewards against our physical health, our bank accounts, or our reputations. I’ve done all the above and I can tell you that the biggest risk I have taken was developing a set of beliefs about education and then trying to convince people to follow me into the fray. I sell courage to parents, students, and educators on a daily basis. Read more>>

Nick Ramsey | Director of Photography

I’ve definitely always been a bit of a thrill seeker, so I kind of live to take risks. Nothing good is gained easy, so the only way to really get ahead, in life in my opinion, is to take risks. This attitude has definitely shaped my life. I was working a 9-5, shooting video as a contractor in the Army, but it wasn’t providing the creative outlet that I was looking for. I wanted to take my career to the next level. It was a huge risk to quit my job, take out loans, and move my family across the country to go back to school. I have plenty of classmates that aren’t in the industry anymore. It’s not like trying to be a doctor; Read more>>

Vicki Lynn Tippit | Musician and producer

I look at risk as a component of growth, and necessary for reward. Being yourself, or pursuing something you love involves risk. There is always a chance of failure or rejection, but if you don’t put your sense of complacency at risk, you’ll never experience the full magnitude of the love and success you are capable of. Read more>>

Shane Finch | Leader of Alt-Rock/Pop-Punk band Pinstock

As the leader of Pinstock, I try to have a risk it all mentality. When I was just out of high school I did not have this mentality, and I look back at that time with some regret. While everything has worked out for me and. the universe unfolded as it should, I realize most of the risks I’ve taken worked out as well. I moved across the country with less than a thousand dollars to my name and nowhere to stay, and now I have built a great career as well as an incredible band with an incredible following. Now I try to keep this risk taking mentality, as I do not want to look back with any more regrets! Read more>>

Lil Trunk | Rapper & Musical Artist

I think risk is the most important thing to have as a young artist like myself. If you aren’t willing to invest money into your brand/career then you aren’t doing it right. Risk taking is everything. Im constantly taking a risk on myself because I know what the outcome will be when all goes well Read more>>

Sean Danson | Poet, Musician, Artist

I think that the larger risk is moving in the unpopular direction when it resonates with your gut to do so. You may not have a clear view of what the outcome will be. Modern gurus will tell you your gut doesn’t matter—but aim to follow the crowd to fulfill your dreams I think that is an incomplete view. Crowds are insane and they shift focus very quickly. Not a good plan for building longevity. Every example we have of successful heroes tells a story of those who went in their own direction. Sometimes it took forever (or they died before the world caught up to them) but in the meantime, they were living as true to themselves as they could. When you live that way, everything you touch holds that value. Read more>>

David Puskas | Actor

Risk is essential. It keeps us sharp, keeps life exciting and full of wonder. The highest rewards of life can only be reaped after taking the highest risks. For me it’s always important to introduce, or look for the element of risk because as humans, our brains are masters of efficiency. Even the most complex of tasks become facile after enough repetition. Once you’ve repeated something enough times it becomes habit, have enough of these in muscle memory and you are running half of your day on autopilot. I try to counteract that any way I can. Read more>>

Mick Lower | Business Owner, Photographer, Self-Care advocate & future investor

By definition risk is exposure to loss. I believe that setting goals and having the courage to go through the process to achieve those goals is a risk within itself. I truly believe that life’s risk involves love, growth, and experience. On the other hand risk in business, in my belief, are investing time and money. Anything you have to sacrifice for in life or in business is a risk. Life will provide opportunities for growth, love and experience but it is up to us to take that leap of faith. Within those opportunities you will have to lose, “cut-off”, some old habits by doing so you may LOSE out on friends & even family. Read more>>

Jacob Pacheco | Creator and Speaker

Risk to me is about managing expectations. “You are entitled to action, but not the fruit of that action.” That is a quote from the Bhagavad Gita, a book about personal growth and spirituality written thousands of years ago. It is my reminder to value effort and process over results. A key I use to unlock the fear of success or failure is: accepting the best and worst scenarios then aligning those with my values and purpose. It keeps me focused on moving forward when I want to settle, or worse give up. Read more>>

Izzy Marcil | Singer Songwriter

I think for me, taking a risk had to start with me deciding to believe in myself. And it wasn’t like, I woke up after that and didn’t ever struggle with fear or insecurity, it was, I’m going to decide to do this thing even though it feels scary, even though I feel unworthy. I guess taking risk for me was like that saying, being brave isn’t the absence of fear, it’s doing the thing even when you’re scared. I think taking risk for me is also being less results focused and more process focused. Like, I might get this wrong, but if I do, God is going to catch me and it’s going to be ok. Remembering this helps me to make a decision, and pride myself in making the best decision that I could at the time with the knowledge and resources I had. Read more>>

Trevon Sailor | Business Owner – Sailor’s Brew Coffee

Risk is the common denominator in terms of achieving success. I have yet to achieve my personal goals without taking risks, nor have I met a successful person that has not taken risks to get where they are at. I wholeheartedly believe that everything is constantly in motion, thus you are either moving forward or backwards. Many people do not realize that risks are innate and are apart of your daily life whether you acknowledge them or not. I choose to be proactive in my risk taking and by doing so, I stack the odds in my favor. Read more>>

Grace McCarthy | Film Director

Actually, I am a person who has a hard time making decisions. I’m a Libra. However, if you asked someone who knows me on a professional level, they’d tell you I’m an extremely adventurous person who is always taking risks. When an opportunity comes my way, I almost always say ‘Yes!’. You can’t learn or grow without adventuring out of your comfort zone. Just deciding to pursue art is a huge risk in itself. There is a low success rate, lots of competition, and you can never guarantee how your work will be received. I live under the philosophy that you should always try and make your dreams a reality because you can always regret not trying but you won’t regret believing in yourself, even if it doesn’t work. out the way you planned. Read more>>

Nicolas Neidhardt | Music composer and producer

Risk taking has played a major role in my career. I think that (calculated) risk taking is essential in order to evolve, be it personally or professionally. Innovative thinking in business comes with risk as one explores unknown territory and somehow pushes existing boundaries. Risk taking has helped me to become more creative, involved and aware of my industry. Read more>>

Hassan Ali | Actor & Entrepreneur

Risk taking for me is going against the odds. Get out of your comfort zone. I don’t like being comfortable for too long and always looking for new challenges. I am an actor and have had a good career working in tech prior. I was comfortable and took risks to get into acting and go through the grind. In the end it’s a good feeling because I have been able to make progress. Read more>>

Elza Burkart | Artist & Curator

I believe Risk is vital, but I like to think of it more as a CHOICE, rather than a risk, because you really cannot predict an outcome. Every success has come from making a choice, and also from the choices made when enduring a difficult time or challenge. I’m naturally anxious and have a habit of picturing every single possible outcome before doing something, which is a quick way to get overwhelmed and psych yourself out. I’ve had to remind myself that I’m not psychic and to dive in anyway. You aren’t in control of anything OTHER than your presence, your life and career (one and the same) aren’t going to flourish if you stay in stagnant waters. Read more>>

Aurange | Editorial Photographer & Filmmaker

I think the more up-and-coming artists should try and take more risk, not just with their art but with themselves. Taking a risk doesn’t mean quitting your job to do this full time, it means trying new things, going out of your comfort zone, or proving to yourself that you can do this! Taking a risk plays a huge part in my life, my mother always told me “it’s okay to take risks in life, if you fail, learn from it and try again” and I live by that my whole life. It plays a big role not just with my life but with my career as well, I’ve made a lot of risks and I’ve failed but I always got back up and tried again! Read more>>

Noel Veloz | Designer

Taking risk is necessary to grow. If you stay comfortable in the same spot you will not grow and settle. It’s important to calculate the risk and write down what’s the worst can happen and what’s the best can happen. Your heart and intuition will tell you when it’s ready to jump and take that risk ! Everyone who is really successful took big risk! Read more>>

Lisbeth Coiman | Bilingual author and educator

I’ve been a risk taker all my life, only I didn’t have the words or time to think about risk in those terms. What I have learned as an adult is that preparing for risk does not mean underestimating the impact of setbacks.. Risk taking should translate in sound preparation for the minimum loss possible. At 17, I ran away from home for the first time. The third time around, I already had a child, and was starting my adult life with an uncertain future for both of us. I risked my education to create a healthy, non abusive home for my son. Years later, I married into another culture, risking my sense of identity for a the occasional joy and the sense of security of a bad marriage. Read more>>

Faithima Wright | Costumer | Costume Designer

“Life begins at the end of your comfort zone” is a phrase I live by. I’ve learned to embrace challenges. I appreciate the lessons I learn good and bad. I feel once you understand that failure is sometimes necessary it makes taking risks less scary. Taking risks and allowing myself to be vulnerable has opened many doors for me. Read more>>

Natasha Luna | Actress

I think of risk as a challenge, it is better for me to see every difficult situation as a challenge that puts my mind on a different path, it is a positive way of thinking that puts me in action with a mindset of finding a way to do it. Rachel on “What We Find in the Night” was a big risk I took as an artist, Rachel had a miscarriage that put her in a very deep and hard emotional world, for me it was a risk taken as I had never done something similar before. I’m glad I took it, it was emotionally draining and absolutely satisfying as an artist. Read more>>

Johany Torres-Maya | Cake artist

Risk taking has played a major part of my success. I truly believe in if you do the hard things in life everything else you do will be easier. Stepping out of my comfort zone and doing the things I never thought I would do, have been the things I do now the most and have helped me tremendously. Think of that one thing you can do in your career that can take you to the next level but your terrified of doing, and just do it. Read more>>

Katayoun Moini | Professor, PA, Dietitian, Hockey Player & Mountain Biker

When it comes to risk taking, the first thing that comes to mind is one of my favorite quotes: “If you’re not messing up every now and then at practice, you’re not doing anything above your ability to progress” ~ Crazy Legs You have to take risks to progress and evolve. However, you also need to know when the risk is careless and a poor decision. I often use my experience in sports to motivate and guide my business decisions. If you are never willing to risk failure then you will never improve or become successful. Read more>>

Monet Dyson | State Worker & Entrepreneur

Life without risk means you’re not truly living from big risks to small risks. Taking risks has played a huge role in my life from my first interview for a job at 16 I decided to wear my hair in its natural state because I wanted to prove to my parents, I can get a job without straightening my hair. I know now they just wanted the best for me and were going off the era they were raised in, but I didn’t want to be anywhere that wouldn’t accept me for who I am. I ended up getting the job. Thats when I slowly began learning to lead with my gut and sometimes that required taking risks. Read more>>

Stephen Robert Johns | Fine Art Painter

Risk taking, yeah, that goes with starting your own business-I imagine any business. And, along with the risk taking are the insecurities that go with it. As an artist, the risks are many, from creating a body of work, taking that first step to present your art to a gallery, then to present it to the public in an exhibition. It’s a super difficult process, since most galleries already represent many artists, and really don’t have the time or need to look at a new artist’s work. Of course gallery directors review new artists’ work, but for an artist, understanding how and when, is nearly impossible. I began painting in my studio in 1972. That’s (50) years of introducing my art to galleries, and, (50) years of rejection letters. But, along with the rejections there were acceptance letters, sales, reproductions of my art for limited editions, fabric patterns, and exhibitions. Read more>>