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.

Madeleine Beadle | Dancer & Choreographer

For me, I’ve had to work really hard at starting to actually take risks in life….only to realize that I preferred the possibility of getting denied over the fear of never knowing what could have happened in a situation had I not just closed my eyes and jumped into it full force. I’ve learned to trust my instincts even if it seems like the risky thing to do. Read more>>

Hailey Gorski | Registered Dietitian + TikTok Strategist

Risk is the catalyst to success; it opens up closed doors. As a dietetics & entrepreneurship student at UW – Madison, I felt deprived of opportunities that merged my passion of nutrition and social media. Doors weren’t opening for me. My options were to settle or take a risk or pound the door down myself. Read more>>

Jacquie Joy | Film & Multimedia Composer, Sound Designer and Music Producer

I’m definitely comfortable taking risks. I think risk taking is a ‘necessary evil’ in music and in business generally. For example, as in with general business, you often have to back yourself, and spend time and money producing a demo of a ‘product’ in order to gain interest in your services or try and land a special soundtrack gig etc, and that often involves a ‘loss’ of time and money in the short term, but the gains are much greater from going through that process. Read more>>

Margaret Halkin | Artist & Entrepreneur

The word risk gets a bad wrap, it is steeped in fear and defined as exposure to danger. In my mind it is the exact opposite, I do not see risk as a scary thing, for me risk denotes the possibility of creating abundance, following your hearts desire and doing good work. Read more>>

Punk Adams | Music Creative

In this life, especially in entertainment you have to take risks. I went to college for music but I knew a degree in music wouldn’t gaurantee my spot as an artist in the music industry. So I dropped out of school and moved to LA. I’ve never been to LA prior to moving but I felt it was the right move for me. Read more>>

Kristin Moody | Makeup Artist

Risk, to me, is making decisions where the outcome is unknown, but with a belief that the end result will ultimately be more beneficial than not. It has played a huge part in my career, particularly in the last few years. I spent 13 years writing insurance policy language in Missouri before I took the leap in 2019 to follow my dreams in moving to California to learn makeup and work in the film industry. Without taking that risk, my life would look very different right now. Read more>>

Dre Lamonte | Artist & Prophet

Playing it safe gets you nowhere. Risks are necessary I’ve payed attention to my life over the years of journeying and I saw that where there is no risk there is no elevation. Many of us hope and wish we could do something or go somewhere while others of us do it and don’t apologize for it. Risk taking has played a great role in my life because It has opened my eyes to endless possibilities. Read more>>

Glenís Hunter | Actress & Writer

Risk is definitely one of the scariest words that I’ve had to confront in my life. Without it, I KNOW for a fact I wouldn’t be where I’m at today. When I think of this word I think of leaving my comfort zone and seeking situations that will help me grow. With that also comes a lot of discomfort. I think it’s important to analyze what you’re risking and if it’s really worth it. Read more>>

Destini T. Riley | Creative

Taking risks has always been something I never hesitated to do and plays a massive role in my professional and personal journey. I believe that I have to take risks to grow as an individual and as a creative. I have taken risks that took me out of my comfort zone however, each risk has been worth the journey. Read more>>

Nicole Blessing | Actor / Model / Comedian — the standard LA trifecta

Acting is all about taking risks. It’s played a huge part in my life and career. Everything I’ve done has been a measured risk. There are a lot of ups and downs in a career in the arts. Nothing is ever a sure thing. You have to constantly approach risk at multiple levels. Read more>>

Aleari Reed | A Dancer, Choreographer, & Creative

Taking risks in your life is necessary. Having faith in your decisions is essential. My junior year of high school I decided I didn’t want to go to college. I just wanted to dance. I began taking dance classes and training after being self-taught most of my life. Read more>>

Millie Rose Heywood | Director, Writer & Producer

As a filmmaker, risk is an intrinsic characteristic of the job. When I started out, I had no idea whether my projects would be successful or find an audience, I had to believe in myself, back my decisions and have faith in the stories I was telling. I was fortunate that others believed in me too, including investors, producers, cinematographers, cast and crew. I credit much of my success to the incredible collaborations I’ve had with them on my films. Read more>>

Junryl | Singer-Songwriter/Artist and Hairstylist

I’ve always had to tell myself that if something scares me, I should go for it. That is a piece of advice that I’ve lived by for years. For a while, my own fears and insecurities about what my future could be have held me back from really going after what I want. And at some point, I had to take my power back and realize that without risk, there is no reward. Some of these risks have paid off well. Read more>>

Janine Jarman | Celebrity Hairstylist, Self-proclaimed perm queen and Founder of Curl Cult

I am a jump first ask questions later kind of gal and basing my biggest career move to date on the success of a NEW perm concept definitely was a risk from outsiders looking in. Although so many laughed and teased about the idea and overall hatred for perms in general, I knew what clients have been begging for for years: hair freedom and hair that can air dry to perfection. Clients want to look great by doing less and have a look that is created for them. Read more>>

Kai Leo | Music Artist

Everything about my career is a risk. There are no guarantees in music, but I still bet on myself knowing that all of the hardships and shortcomings in the music game might lead to my ultimate dream. Risk-taking has become an essential part of my life, I don’t want my life to be a reminiscent loop of what could’ve been. Read more>>

Carolina Massote | Screenwriter, translator, journalist & author

I grew up in a household where people truly believe in stability. My mom is a dentist and, besides her private practice, she would also work for the city, and she had tenure in that job. Dad is an agricultural engineer and also had tenure working for the State of Rio de Janeiro. Read more>>

Lauren Partch | Actor, Producer, Writer

Taking risks in my life and career has been the key behind my success today. I think about risks as the key that leads to the reward on the other side of fear. Risk to me is also fully trusting yourself and standing behind the decisions you make. It can be especially daunting if you grew up not taking risks or being judged for going down a path that is different than the norm. Read more>>

Anuschka Van Lent | Actress & content creator

I moved from Germany all the way to the US to pursue my acting career, leaving your family and your hometown behind can be really scary but sometimes you have to step out of your comfort zone in order to achieve better things and grow as an individual. I didn’t know if it’s gonna work out but I have the willpower to take the risk and go for it! Read more>>

Andrew Olszewski | Founder of Good x Studios

One quote that I love, that took me a while to fully grasp is “you don’t grow inside your comfort zone”. I think we have the ability to become really solid in our comfort zone, however the real growth comes from outside of it. Everyone has the ability to take risks. Everybody, every single day, has an opportunity to make their entire lives change with a simple risk. Whether that be quitting a job that doesn’t fuel the soul, to moving, to simply work on forming a new healthy habit. Read more>>

Jenna Glassock | Trusts and Estates Attorney

I think about risk a lot as I am a generally risk averse person who chose a relatively risky career path of starting my own law firm. Coming out of college, I picked the path that felt most familiar to me and chose to go to law school. My mom and step-dad were both lawyers, and I liked being in school, so the choice felt obvious. Upon graduating from law school, I picked the career path that law schools tend to nudge you toward: I went to a big law firm. Read more>>

Chaniyia Davis | Los Angeles, California

Being an entrepreneur is a risk within itself; especially in the beauty and hair industry because so many people are in the field. A few risk that I took into consideration were relying on cash flow, not having a steady pay check, the market demand for my service, completion risk, balancing life and work as well as my health. Read more>>

Georgia Van Cuylenburg | Actor & Youth advocate

I believe anything worth doing has an element of risk involved! I think we often see risk as just being a physical thing but every day we are always taking emotional risks; hard conversations, doing something you don’t know the result of, asking for something you want… it is all risk. Read more>>

Colin Stauber | Artist

Risk is what life is about. It’s allowed my music to be distributed to a massive audience across the world including multimedia agencies providing music for TV and Film. I recently partnered with multiple music tech companies which wouldn’t have happened without taking risks. When you want something in life, you just got to reach out and grab it. I’m really inspired by people that do that. Read more>>

Risto Miettinen (Risto R Muzik) | Composer

“It’s better to regret something you did than something you didn’t do” might be cliche, but in my life I’ve found it to be true. I think we all have these fork in the road moments, getting in touch w someone who could offer you a gig, asking a girl out, moving to a new city or country, etc. if you’re actively thinking about making that choice, it’s probably a sign you want to do it. Read more>>

Chevy Laurent | Los Angeles Fitness Trainer – Cycling, Boxing, Yoga, & Strength

I think it’s important to take risks and be willing to “bet on yourself.” I’ve built my career on the principle of stepping out on faith rather than letting fear hold me back. I took one of the biggest risks of my professional life when I quit my decade-long full-time corporate marketing and sales career to move to New York, to train with the hope of joining a major fitness brand and becoming a fitness instructor. Read more>>

Dash Jo | Writer/Director & Production Designer

I think we often like to play it safe for the sake of keeping a steady course that will keep us afloat. We fear that if we take a big leap then we might destroy the safe bubble we’ve built for ourselves and that makes us uncomfortable. For me, I was not willing to leave my job and life in Boston to pursue filmmaking in LA. Read more>>

Matthew Kaner | Consultant | Sommelier | Producer | Host

It wasn’t until recently that I finally started to understand how I felt about risk. Early in my career, risk was not a consideration AT ALL. When my first business partner Dustin Lancaster and I opened Bar Covell together in 2010, risk was not part of the discussion. We were blind to it. Our youth allowed us to brush off the gravity of opening a business and instead we put our faith in the communities we had help build and be a part of! The only option was getting open. Read more>>

Soha Panah | CEO of Dryp By Soha & Holistic Lifestyle Coach

I think risks are the biggest opportunity for growth. From a spiritual, mental, and physical level taking risks can lead you for bigger expansion in almost every area of your life. I would say that I recently (the last 3 years) have been more open to taking risks and have been more comfortable in the uncomfortable. Read more>>

Megan Raney Aarons | Writer / Director / Executive Producer

If I look back at my career to date, my favorite projects & endeavors have involved varying degrees of risk, or some equivalent leap of faith. Whether it was the risk of leaving my rural life in England to take a year out before Uni to go live in Toronto, then Los Angeles to try acting. Or deciding to step behind the camera as a cinematographer / director, despite how few female directors had managed to break through at that time. Read more>>

Tiffany Usavage | Strength & Conditioning Coach & Business Owner

How do I think about risk and how does it affect my life and business? I think risk taking is crucial in one’s life to succeed. Growing up, I was super shy and was always afraid to do things that were new and risky. Fast forward to my junior year in college, I studied abroad in Australia and I forced myself to go outside of my comfort zone and take risks. Read more>>

Emily Pokora | Attorney turned SAG-AFTRA Actress

Risk taking has played a huge role in my life and made pursuing my passion for acting possible. After earning two business undergraduate degrees, an M.B.A., law degree, practicing law as a trial lawyer and serving on the bench as a judge pro tem, I left it all behind to pursue my dream of being a professional actor in Los Angeles and never looked back. Read more>>

Drew Cole | Singer-Songwriter & Recording Artist

Well, first off, I see risk as an opportunity to make an impact on people. In my music, risk is what separates me from the masses and helps me stand out. Being bold and intentional, both on stage and in songwriting, is a fun way to engage my audience and makes me more memorable. You gotta risk it for the biscuit. Right? Read more>>

Piotr Niemczewski | Cinematographer

I think that risk taking is essential for personal growth. For me, it’s an inherent element of catching opportunities in life. If you live without risking anything, opportunities will just fly over your head. Especially when you’re young and don’t have much to lose yet, I think that taking a risk in your career is a win-win situation. If you’re successful – great, if you fail, you learn from it and gain valuable experience. Read more>>

Hannah Sward | Author Strip: A Memoir

Writing Strip: A Memoir. Sitting down, pen to paper, being vulnerable, writing about things I never thought I’d share with anyone – what will people think, my family, my friends, romantic partner – choosing to write it all down anyway. I think that anytime someone is being vulnerable, that is taking a risk. Read more>>

Luiza Melikyan | DJ & Graphic Designer

When thinking about how I have taken risks the first thing that comes to mind is the biggest risk I have taken, which is beginning my career. Becoming a DJ is not a dream that most young girls have or are even considered for. However, this was mine. The risk that I took in pursuing my passion connects to many different layers. A major risk being breaking out of the norm and society’s standards to become an Armenian female DJ. Read more>>

Chelaé Cummings | CEO | Creative | Storyteller | Poet

I’m an open explorer and adventurous person, so the word risk doesn’t mean danger to me. It means the opportunity to do something I’ve not yet done and learn a new lesson. My friends will tell you I’m what we’ve coined as a “Jumper and Leaper,” they are two different types of energy and movement; I do both well. As a jumper, I don’t question my ability. I don’t consult with people for approval to do what is best for me, nor do I concern myself with who will go with me to make a bold move. Read more>>

Rubén Navarro | Writer/Director & Editor

I think risk is the beginning of something new. Without that risk and everything that comes with it such as fear or doubts, there’s no opportunity of growing. For me I took a huge risk leaving my home country Spain to move to Los Angeles, I had never visited the USA, barely spoke English and I took a leap of faith to follow my dreams and the new experiences and adventures that were ahead of me. Read more>>

Francesca Quintano | Artist

As meretricious as the phrase seems, “no risk, no reward” is a golden standard to live by when pursuing a creative career. I like to look at a career in art making as my muscle. In order to grow muscle, the body must damage it first. Risk is the damage inflicted on the muscle, which causes it to grow stronger. Read more>>

Yoo Lee | Writer, Director, Animator

I try to avoid having big regrets in life and don’t let fear dictate my decisions. Nothing worthwhile is without risk or sacrifice, especially in life/ career. After having had my fashion brand for 20 years, I fell in love with stop motion animation while entertaining my daughter in my mid 40’s. I didn’t want it to be just an expensive and time-consuming hobby so I took a chance, applied to the USC MFA program majoring in animation, and somehow got my foot through the door and walked away from the fashion industry. Read more>>

Manely Gilardi | Founder & CEO

I’m definitely a risktaker and I feel comfortable taking risks. I live by this quote I heard, which is hilarious by the way, “You gotta risk it to get the biscuit”. And it’s literally the truest words! If you never try, you’ll never know how great you can be! I think early on in my life, as a teenager I realized that its necessary to take risks if you want to be great. I come from immigrant parents, and they risked everything to come to America and start over. So if they could do it, what’s the worst that could happen for me? I would fail? Read more>>

Steve Stewart | CEO & Co-Founder at Vezt & SongHub, Co-Founder at Futureworlds

I believe risk is relative. Some think it’s risky to fly on an airplane. Others fly thousands of miles a month, without giving it a second thought. I’m more concerned about the risk of NOT doing something – the opportunity cost – than about the potential for failure. I’ve met many people who have big dreams, but won’t pursue them because they believe the risk outweighs the reward. If everyone had that mindset, we’d have very little progress. Read more>>