By far, the topic that comes up most in our conversations with entrepreneurs and creatives is risk. We’ve had conversations about risks that worked out and risks that did not. We’ve seen eyes light eye sharing about career-trajectory changing risks as well as folks sigh about the risks they wish they had taken. Below, we’ve selected and shared some of those thoughtful conversations.

David SZABO | Singer/Songwriter

Since day one, risk has always been a major factor in my life, especially when it comes to my career. Not being satisfied and having the urge to look for new opportunities was always the engine that pushed me out of my comfort zone. I need to be on the move to prove to myself that I can do more, I can do better. I was born in Budapest, Hungary and in my first 30 years, I achieved a very successful acting/singing career. I became one of the most popular theater actors, I acted in films, released two golden records with my former band, and competed on the X factor. Read more>>

Tina Demirdjian | Poet, Arts Educator, Culture Bearer

“And the day came when the risk to remain closed tight in a bud was greater than the risk to blossom.” That was a quote from Anais Nin that I kept on my bulletin board for six months before I made the decision to leave my 9 to 5 job more than 20 years ago. At the time it also meant that once I made the decision, I needed to move forward. My mother was 60 years old and she had gotten breast cancer and I was her caretaker. How ironic that I now am 60 years old. I remember after one of her chemo treatments, we had lunch together. Read more>>

Zach Sutton | Commercial Photographer

I’ve always been a bit of a risk taker, from being a licensed skydiver to being an active motorcyclist here in Los Angeles. But in terms of my career, the biggest risk (and reward) I’ve taken is to get out of my comfort zone. I’m from Michigan originally and was building my photography business and branding while in college. After college, I felt like I was stagnant – living just a dozen or so miles from where I was born. I was comfortable in how much my photography business was making, but was deeply uncomfortable with the impact it was making. Read more>>

Sruthi Dhulipala | Entertainment PR Manager & Musician

I see risk as a catalyst for growth in both my life and career. I’ve learned that calculated risks often lead to the most significant rewards. For instance, I made a bold move by transitioning from engineering to the world of publicity, and that leap paid off. It involved moving to another continent to pursue my passion for promoting Hollywood titles and advocating for South Asian representation in the industry. It was a gamble, no doubt, but one that I’m incredibly grateful for. Read more>>

Allen Dent | DJ

I believe that taking risks is necessary in life. Risk-taking forces you out of your comfort zone and that’s where personal growth happens. I moved to California 8 years ago from Alpharetta, Georgia. I did not have any family or friends here at that time. The first few months were tough and I was ready to move back home. However I pushed through it and I am very happy that I did. Moving to California was the best thing I have ever done for myself. Getting to reset your life in a new state gave me a new perceptive of everything. Read more>>

Shannon Wild | Wildlife Photographer & Filmmaker

Throughout my career as a wildlife photographer and cinematographer, I’ve always been drawn to taking risks to capture the most breathtaking moments of the natural world. These risks have played a significant role in shaping both my life and my career. One of the most memorable and life-altering experiences was a cheetah mauling incident during one of my assignments. It was a stark reminder of the unpredictability of wildlife and the dangers that come with getting up close and personal with these magnificent creatures. Read more>>

Sammy Spencer | Plant Designer & Entrepreneur

How do I think about risk? Honestly, I don’t; I just tend to take them. Entrepreneurs are innately risk-takers, and it is an obvious component to starting a small business. They are statistically risky, often forcing us into uncharted waters that at times are scary, but mostly exhilarating and exciting. From others’ perspectives, I have been a risk-taker since adolescence. After high school, I traveled across the country to attend college in Philadelphia and went straight to South America after 4 years of undergrad to teach English in Chile in a small mining town in the Atacama Desert. Read more>>

Sonez | Singer & Songwriter

To an outsider’s perspective I’m probably considered a risk taker, but from my point of view, I don’t actually feel like I’ve taken huge risks in my life and career. All I’ve done is follow my gut when it comes to what I feel I’m supposed to do. Whether it be quitting my corporate job to go full time with music, releasing my first solo album without any label or team, or deciding to make the big move to LA – these were all choices that seemed risky to others, but made perfect sense to me. Read more>>

Suzanne Merritt | Visual Artist & Tarot Reader

Risk has and continues to play a huge role in my career as an artist. I have been told more times than I can count that forging a career as an artist is an uphill, near impossible battle. The truth in my life experience is I’ve had little choice in the matter, because my passion, often bordering on obsession, when it comes to creating art has dictated the choices I’ve made. Choices that, I’m certain, to others have been risky and unconventional. Plus, I love a good old fashioned risky challenge and and equally love proving that it is possible to follow my heart and create a life doing what I love. Read more>>

Kai Tsao | Artist & Audio Engineer

Lately, risk-taking has been more about challenging the conventions and trends of pop music – I spent a few years trying to fit the mold in terms of formatting my music, which for me meant making my songs shorter to adapt to shorter attention spans and implementing generic rhythms and progressions to make my music feel more “accessible”. Setting out to make something that was true to my own artistic impulses meant that I had to reason with myself and come to terms with the prospect of putting myself through more while gaining less attention and exposure for my work. Read more>>

Eleanor Yang | Graphic Designer

To me, risk is synonymous with opportunity. I’ve always been drawn to a life that isn’t entirely predictable or safe. Risk represents not just a chance for a better life, but also a means to refine my skills and abilities. Rather than viewing risk as a reckless gamble with potential loss, I see it as the unwavering pursuit of my passions in the face of uncertainty. Before my foray into graphic design, my creative inclinations were rooted purely in the realm of fine art. Read more>>

Hyun woo Lee | Producer

I would typically describe myself as a very calm person who is accustomed to making reliable and comfortable choices. For instance, I tend to consistently order the same items from the menu. However, when it comes to my career, I’ve come to realize that I have consistently embraced decisions that involve a significant degree of risk-taking. Upon entering Yonsei University, I joined a club to pursue my love for musical theater and dedicated my summer and winter breaks to directing musical productions. Read more>>

Ermia Hamidzadeh | Fashion Designer

I think every day life is a risk. Leaving your house is a risk, getting in your car is a risk, so why not take risks to live the life you dream of? I’m a huge risk taker, maybe even a risk junkie because I get a high from it. I can’t live a normal mellow life, believe me I’ve tried and I feel dead inside when I do. Read more>>

Chance Davis | Costume Designer / Stylist

Risk taking has been key to my career. Throughout my professional journey, I’ve embraced opportunities that required stepping outside my comfort zone and venturing into uncharted territory. Whether it was pursuing ambitious projects, making strategic pivots, or seeking out new challenges, I’ve learned that calculated risks often yield the most significant rewards. While not every risk I’ve taken has led to immediate success, each one has contributed to my growth and development, equipping me with valuable lessons and experiences that have propelled my career forward. Read more>>

Kara Snethlage | Mixing & Recording Engineer | Guitarist

As humans it’s in our DNA to explore, to discover and to grow as individuals and as part of a larger community. This is how we have managed to became who and what we are today, and at the root of it all is the courage to take risks and carve out a path into the unknown. It is this sentiment that leads me to believe very strongly that anything that has the potential for greatness involves a certain degree of risk, and when that risk is handled with intention and deep consideration it pays off more often than not. Read more>>

Morgan Canty | Actor & Singer Songwriter

My life has felt like one big risk. To dare to be myself unapologetically. Risk taking to me It can be scary. Many times for me its been met with great trepidation. But more often than not I’ve found that pushing past the boundaries of that fear that on the other side of that risk there is something beautiful. Growing up being a performer an artist was not encouraged on most levels in my environment.It was sports and school and dont divert. And if you diverted from those two it was a shortcut to being made fun of in school. Read more>>

Federico Yniguez | Graphic Designer

I believe that risk taking is necessary to elevate not just a creative person’s career but any person in life. While that’s easy to say, I know that it’s hard to put yourself out there, especially in a world so oversaturated with talented and amazing people. For years, I was known as the timid and shy kid in my classes; the kid that often didn’t say anything in class because they feared being wrong. Once I started designing and honing in on my craft, I gained the confidence to take risks. Sometimes it just takes research, knowledge, and practice to gain the confidence to take risks and make hard decisions. Read more>>

Xinran Wang | Motion designer & Animator

Risks have always been an integral part of my life and career journey, and I view them as opportunities for growth and transformation. The decision to leave my hometown in Jinan, China, and move to the United States was one of the biggest risks I’ve ever taken. It was a leap into the unknown, with uncertainties about culture, language, and education. However, I saw it as a chance to pursue my passion for art and design in a new environment. Read more>>

Eloise Harpas | Professional Dancer & Artist

Risk is the reason i am where i am today. I believe to be the best version of yourself and to live to your fullest capacity, risks need to be taken. Yes, sometimes its hard to make the choice but ultimately risks are the reason to get out of your comfort zone. While being in your comfort zone can be good, i find that staying there for too long will slow down or stump my growth in life. As a professional dancer, i have to take risks nearly everyday. Both mentally and physically and its not always smooth sailing but in the end i’m always grateful for what i have learned and where that knowledge can take me next. Read more>>

Brooke Eliot | Comedian and Performance Artist

Risk is always exciting because it immediately makes a connection to fear. What will happen if I try this new thing out? Will I fail in front of everyone and become cringe or will it be iconic? I would say that creatively, I actively pursue risk. I constantly want to break free from the status quo of “safety” that keeps my self-expression small. I’ve been told my performance style is considered “risky” as it doesn’t always elicit the audience response one would typically want as a performer (adoration, acceptance, love ect.) but that is what keeps things interesting. Read more>>