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.

Manuel Levy | Director & Producer

The topic of taking risks in life is incredibly fascinating and complex. For me, it’s essential to recognize that each situation where you’re contemplating a risk is unique and should be treated as such. Taking a risk doesn’t automatically guarantee success just because you had the courage to go for it—you also have to be prepared for the possibility of failure. When making that leap, it’s crucial to ask yourself if you can be at peace with the consequences, even if things don’t go as planned. Read more>>

Kristine Bautista | Medical Intuitive & Hairstylist

I see risk as the intersection of opportunity and uncertainty. It’s not just about the potential for loss; it’s about the potential for gain that wouldn’t exist without stepping into the unknown. I think of risk-taking as a calculated move – understanding the stakes, weighing the possible outcomes, and then deciding if the upside justifies the leap. It’s about being bold enough to venture beyond what’s comfortable, while also being strategic enough to ensure that the risk serves a larger purpose. In my view, risk is the fuel that drives innovation and growth; without it, progress stalls. Read more>>

Jonathan Sherer | Graphic Designer & Artist

I believe taking risks is one of the most important aspects of life. Not to take them for the sake of risk, but to take them for the chance of growth. Read more>>

Oliver Williams | Musician & Sound Engineer & Camera Operator

Risk is part of every day life. Whether it be for creative purposes or career. For me risk has allowed me to grow and be outside my comfort zone. Allowing me to explore things that I’ve never experienced before. Read more>>

Karina Marquez | Beauty Influencer

I think taking risks has played a huge role in my life and career path. My best example of this is me moving across the country from Connecticut to LA. It was a huge move and it definitely wasn’t easy. I based this move purely off of just my gut feeling and intuition telling me to go and I was super emotional about leaving my comfort zone and my family but, now that I’m here, so many doors have opened for me and confirmed this was the right move. If I had let my emotions and fear get in the way and stayed in my comfort zone, I never would have known how good it could get. Read more>>

Phil Yeh | Author & Artist

I guess if we think of taking risks as something dangerous, I am not sure that I took a risk when I started my professional career as an artist at the age of 16 in 1970. I had been drawing since I was two. My father gave me computer paper from work with old programs printed on one side. The other side was a blank canvas and was absolutely perfect for making pictures with my pencils and crayons. When I entered elementary school in New Jersey, I was already an accomplished artist, at least according to my first grade teacher, Mrs. North. She believed in my talent and always told me that I would be a famous artist someday. Read more>>

Annie Alden | Design Consultant

Seeing risk as an opportunity for organic evolution invites me to embrace the unpredictable nature of life. I have definitely climbed ladders only to discover that the view isn’t what I hoped for or thought it would feel like. This perspective had encouraged me to swim downstream, allowing the currents of life to guide me rather than resisting them with hyper-vigilance … letting go of the need for control has opened me to SO many unexpected possibilities that have fostered growth and adaptability. I truly believe life is cumulative. Read more>>

Hot Stepmom | Band

Devoting so much of our passion, creativity, and resources towards such an uncertain career path is a huge risk on its own. Pursuing music can sometimes feel so reliant on luck and chance that we’ve just had to learn to accept the risk and keep doing what we love. Read more>>

Solange Nolan | Author, Actor, Model & Branding Guru

I believe risk is essential for growth, both personally and professionally. Without it, we stagnate, and miss the opportunity to unlock our true potential. Throughout my life and career, taking risks has been a driving force. From leaving my home country of South Africa to build a career across three continents, to stepping out of my comfort zone in new fields like publishing and modeling, every leap I’ve made has been worth it. Whether it was telling the stories of former child soldiers, breaking into the entertainment industry or taking a stand on what I believe, I’ve learned that risk leads to profound change. Read more>>

Ari Parker | Professional Dancer & Coach

I actually wouldn’t consider myself much of a risk taker. Choosing dance as my professional career is probably the biggest risk I’ve ever taken in life because it’s not always consistent, and I’m the type of person who needs consistency or structure to stay sane. With that said, as a dancer if you don’t take risks in your craft, you grow at a much slower pace. I had to learn to redirect my fear of “going with the flow” into embracing the endless possibilities that can come out of freestyling, both in life and in dance. Read more>>

Jackie Webb | Actor, Voice Over Actor, & Writer

To me, life is all about risks. And some risks allow for life to change in the most magical ways! Others allow an opportunity to take the next step in one’s career, creative process, romantic life, friendships, etc. Read more>>

Vishnu Sinha | Screenwriter, Director & Educator

Nothing creative has happened for me without risks. For me, risk taking has been the difference between feeling unfulfilled or disengaged and creating work that I would like to talk about in the future. I believe it’s how the most exciting storytelling takes place. Read more>>

Marcus Ellison Jr. | Actor/Director

The entire industry that I’ve been called to (the film industry) is predicated on risk, so I have to at least make a relative peace with the concept of it to proceed. I’ve taken a lot of risks in my career as an actor/director/editor, the biggest of which being uprooting my life back in Maryland 3 years ago and moving to Los Angeles in my 30s at the tail end of the pandemic. As the old adage goes though, nothing worth having comes easy, thus the risk. Read more>>

Milena De Vera | Food Culture Entrepreneur & Business Student

“The risk of riskless living is the greatest risk of all.” I came across this quote in high school while attending a hybrid charter school called iLEAD Exploration. The 7 Habits of Highly Effective People played an influential role in shaping the school’s approach to lifelong learning, and this book—particularly this quote—shifted my entire outlook on life. Read more>>

Minnie Ma | Imaginative Executive, Idea Alchemist, Architect of Decisions

Risk has always been a part of my story—and in many ways, it’s a part of all of our stories. From the moment we’re born, we face risks. That very first breath is a risk, a powerful reminder that risk is woven into the fabric of our lives. The question isn’t whether we take risks, but how we face them and manage the uncertainty they bring. Read more>> 

Elizabeth Mateo | Manager

When we think about risk and how it has impacted us as young adults, our minds inevitably turn to the lessons passed down by our late father—lessons that have profoundly shaped who we are today. To him, risk wasn’t merely a gamble; it was a necessary part of life, a challenge to never give up, no matter the outcome. Read more>>

Kay (khloud) Shehata | Kay Shehata | Art director

Risk-taking is a fascinating part of life. It’s all about finding that balance between comfort and growth. Sometimes, stepping out of your comfort zone can lead to amazing experiences, while other times it might not go as planned, but you still learn something valuable. Read more>>

James Austin Kerr | Actor/Filmmaker

Well, for one, it’s made my life way more exciting. I do all sorts of wild hobbies that the majority of people are often fearful of – I’ve never been afraid to jump out of a plane or dive into the depths of the ocean. I love it. Whether it’s career, or hobbies, risk taking is fundamental for growth and only improves your strength as an artist and finding your identity. Read more>>

Sarah Fraser | Podcast Host, TV Host, Entrepreneur

I love taking risks. My entire career, moving to LA, has all been based on risk. I started a pop culture podcast about 8rys ago and it was a huge risk. A major radio station had offered me 195k per year to stay on and be a midday host or take a severance package. I took the package and started a podcast. I knew after 9yrs in radio that radio really was dead. People thought I was nuts and couldn’t believe I would walk away from that kind of money. Read more>>

Jennifer Harkavy | Interior Designer

If you don’t step forward, you’re always in the same place. In 2009, we were living in New York, which is where I spent most of my life. This was at the height of the mortgage crisis, my husband and I didn’t have financial security at that time. On and off we talked about relocating, and so we packed it up and moved out to Los Angeles. I knew that taking a chance could open us up to a fuller life, and the result has been an incredible 15 years raising our children here in Palos Verdes. Read more>>

Carson Christ | Actor & Singer

When we hear the word “risk” we think of words like danger, fear, or threat. It’s natural as humans to be afraid of taking risks in life and as artists. The fear of rejection and the outcomes that come with taking risks is present in everyone including me. But it’s always important to remind myself that from taking risks comes words like opportunity, possibility and prospect. As artists, it’s important to take risks in trying new things and taking whatever opportunity presents itself in front of us no matter how small. I’ve always believed that from a negative outcome can bring great opportunities that can lay a foundation for our future. If we avoid taking those risks or stay in stagnate then we’ll never reach our true potential. Read more>>

Aarushi Menon | Book Cover & Graphic Designer

When I was a kid, one of my favorite things to do would be to take stacks of printer paper from my parents’ study and fold and staple them into makeshift “books.” I’d doodle on the covers and then promptly abandon the otherwise blank sheets in some shadowy drawer for my parents to later fish out and try to salvage (sorry Mom and Dad!). There was never really any doubt for me or my family that I would choose to pursue a creative career, so I didn’t perceive my initial foray into the arts as a risk. I had my parents’ full support. Read more>>

Ashley Knight | Graphic Designer & Fine Artist

Taking risks has directly caused all my biggest successes in my career. I got to design an EP cover for one of my favorite musical artists because I reached out to her and made sure she was aware of my existence. I go for what I want, and I understand that the best things in life take a lot of investment even if you’re not sure if my efforts are worth it at the time. Read more>>

Avi Kabir | Filmmaker, writer & designer

Risk? Yeah, I’ve thought about it, but I don’t obsess over it. Maybe I should sometimes, but then where’s the adventure in playing it safe? For me, risk feels like the horizon—it looks like the edge of everything you know, but really, it’s where the known meets the unknown. And beyond that point is where discovery happens. Read more>>

Moses James Rankine | Professional Dancer

When it comes to risk-taking, it’s something I’ve always embraced as a critical part of my journey as a dancer. I believe that taking risks is necessary to push boundaries, both artistically and personally, and it has played a major role in shaping who I am today. Read more>>

Roman Slappey | Character Designer/Illustrator/2D Animator I go by the alias “Viewtiful Jeau” (Pronounced Viewtiful Joe) on social media as an Artist.

I believe risks are a necessity when it comes to wanting to be successful in any field. Whether they’re a big or small risk varies from person to person. Taking risks has played a large part in my life. I consider myself to be a confident, positive optimististic person. So, whether something has a 1% or 100% chance of success, I’m going to take the risk if it’s something I really want. I’m not too worried about how much work/time it will take. Just need to take that first step, which is the risk most people are afraid of. Read more>>

Elizabeth Moore Kraus | Author & Educator

Risk taking is innate to me. At age 13, I went to a boarding school in Montemorelos, Mexico. Although one of five kids, it was my older, beautiful, popular (must I go on?) sister who I wanted to get as far away from as possible. Another country should do the trick. Oh, sure, I didn’t know Spanish, but I didn’t care because no one would know her at this new school. Read more>>