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 up 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.

Athena Brensberger | Science Communicator Specializing in Astrophysics

I think of risk taking as a strategic curiosity. You see, taking a risk is simply driven by curiosity however you can be strategic about it. For example, knowing WHEN to take a risk and allowing for that vulnerability to allow for any outcome and accept it. Risk taking has lead me to come of my greatest breakthroughs and most humbling moments. Sometime sit can lead to denial and learning to cope with denial is a very important trait to gain as a business owner. Risk taking is also fun and adventurous when you give something your all but don’t expect an outcome. Sometimes your greatest outcomes can form through these very moments. Read more>>

Vanessa Canaveral | Photographer

I took the risk of quitting my part time retail job to pursue photography full time. It was very scary, I thought about it many times and backed out many times. I didn’t think it was possible for me to make a living from taking photos, I was scared of not having my steady income, I was scared of the unknown. I wasn’t happy working somewhere I didn’t like, and doing something I wasn’t passionate about. One day I said “I’m done” I couldn’t take it anymore, and took the risk without a plan, but the universe aligned everything for me. I started getting booked constantly and now it’s been two years since I’ve building my business slowly but surely! Read more>>

Eric Welch | Artist & Entrepreneur

Risk taking has played a major role in my life, from business to everyday life. I believe that we all should take risk, but of course be smart and have some calculated thought before jumping. It’s risk that led us into something bigger. I get it though it can be scary jumping in the unknown. For instance if I didn’t take the risk to move from Louisville Kentucky to Los Angeles I may have not made as much forward progress as an artist/entrepreneur. I decided to leave Kentucky with no job lined up in California, no family, and no place to live. Although I did it because I knew I would be able to build something bigger than myself and then share with the world. Read more>>

Adrienne & Brittany Hughes | Mixologist & Skincare Specialist

Life is about taking risk. Some people are afraid of taking risk and rather play it safe, staying in their comfort zone. We both feel that in order to achieve our goal, we had to be willing to pursue our passion while afraid, and in many times of uncertainty. We pushed beyond the unknown to build a brand that is becoming recognized across the country today. Read more>>

Dom Jones | Artist, Musician & Creative Entrepreneur

I proudly wear my culture and heritage on my sleeve, in my aesthetic, in my music, and generally how I navigate life and my career. As a black woman in entertainment (and specifically music), I know (and am constantly told) that this is a risk. It is a risk to be myself. It is a risk to have pride in who I am and where I come from. It is a risk to wear my hair naturally or to use the parlance of the neighborhoods from which I’ve come. Yet, I am asked to be authentic. So, I think about risk like I think about breathing. I don’t get to live without breathing and I don’t get to thrive (in music, career, and life) without taking the risk of being myself, no matter what. Read more>>

Esteban Carvajal | Professional Drummer & Instructor

I believe that the only way to grow in your life and career is to take risks. Getting out of your comfort zone helps you to develop new ideas and have new experiences. You never know what opportunities are going to present themselves if you just take a chance! Read more>>

Brooke Jean | Research Coach & Digital Business Consultant

Taking risks has been the KEY role in my life/career. I took risks as a spoken word artist getting up on stages around the world sharing my innermost feelings. I took risks working a year traveling around the US as a freelance photographer/videographer. I took risks leaving my corporate job making about $4.5k a month to making $1.5k a month getting my consulting and my partner and I’s marketing production businesses off the ground. I’m taking risks as a self-employed business owner in the midst of a global pandemic and growing recession. I would not be where I am right now without taking risks. If you want to reach your level of personal success, you have to get uncomfortable and take risks to see what works for you and the lifestyle you want to live. Read more>>

Malibu Dana | 10-year Breast Cancer Survivor, Fashion Designer, Philanthropist & Butterfly

I have never been one to dip my toes casually into the water. I have always had a tendency to act first, think later, and just go for it… laughing my head off and diving in headfirst. My Mom started calling me “Dana the Brave” when I was a little girl… I was always climbing up trees, breaking every bone imaginable- and I was active in gymnastics for over a decade… I was fearless. I’ve been independent, impulsive, and headstrong since day one… but those traits combined with a passion for life and oftentimes relentless drive … have served me well on this wild roller coaster ride we call life. They define my spirit, informing every choice I’ve made and helped me with every crossroad I’ve faced. Read more>>

Rachel Berkowitz | Artist (Painter & Photographer)

Prior to the COVID-19 pandemic, my work was all about taking risks (see the series “Illusions of Risk” on my website). I am constantly finding myself in situations where I am forced to take risks, whether it be in art-centered business decisions, personal relationship choices or constant financial, risk-taking opportunities. I believe strongly that, in order to truly succeed as a creative, one must always be willing to take risks, big or small. I realized during this intensely contemplative time of the global lockdown, that there’s a mental gamble in every choice we make as humans. It’s our own mentality that determines our ultimate fate. During this pandemic, just going outside is suddenly a health risk. Read more>>

Angela Paul | Writer, Life Coach & Model

As far back as I can remember I’ve always been a risk taker. It’s part of my DNA. When I moved to Tokyo from Yorkshire alone at age seventeen some in my family worried that it would be a dangerous move for a young girl alone. Fortunately my parents were very supportive, especially my mum who wanted me to have a better life than the hard, working class life she had.growing up. So after winning Miss Teen UK at sixteen I got the opportunity to live and work in Tokyo as a model I couldn’t wait to get on the airplane and start a new adventure. Entering the contest itself had been a risk and potential failure. And even though a voice in my head whispered you’ll never win, the louder, braver voice urged me forward. Read more>>

Susan Leonhard | Artist

My nature is to be a bit of a risk taker. I have never been one to analyze a decision for any length of time. Sometimes it has paid off and other times, it has been a disaster. I believe taking risks is a trait most artists share because we are dreamers! Stepping out of my comfort zone is something I did back in 2014 when I came up with my series of paintings “Underwater & Beyond.” Having painted landscapes for almost 40 years, I was yearning for something new and creative. While snorkeling off the coast of Kauai, I visualized a series of underwater paintings, where the focal point was not the marine life but the water itself. Read more>>

Eileen Cowin | Multimedia Artist

As an artist, I want the work to be recognizable as mine. And yet…I always want the viewer to be surprised and challenged; I want to derail their expectations. I also want to be surprised and challenged as I am making the work. When a friend’s wife died, his mother advised him to “accept all invitations”. I also make myself say yes to opportunities that make me nervous- that cause insomnia and stomach aches. It can be a 400 ft public art project or a multi screen video piece. With each piece I think: what would happen if… and then I hope I can go right up to the edge of the cliff without falling off. But right now, in this world, the word “risk” has taken on a whole new meaning and using it to describe my artistic process feels misplaced. Read more>>

Jimmy Luna | Artist & Founder

You gotta fly. You gotta turn all the other voices of fear off in your head and mindlessly pursue what you’re after. Most people are afraid to chase what they’re after because of X Y and Z and never find their wings because of that. My whole life has been predicated on taking risks and doing what I love to do and even when things get rough I’ll know I’ve made the right decisions because I trust myself. I remember back when I first left my mom’s home to be in the world on my own with nothing but the idea of being creative and among other things like bein’ broke and homeless and overall lonely, I had a choice to make. I could let all of that stuff hold me back or could I just take a chance on myself and let the world know I exist in my own way. Read more>>

Donato Ricci | Hospitality Management Professional & Chef

Risks are an integral part of anybodies life, any choice comes with the possibility of risks. When I chose to make hospitality my career I didn’t calculate that I would have to go thru a pandemic where my field would be one of the that got effected the most. However, myself and so many others are in the same position which makes the risk a more universal issue that everybody needs to deal with. I personally am utilizing this time of being left without a job to sharpen up my skills to be ready when things will start back up. We have a saying back in Italy that translates as “who doesn’t nibble doesn’t chew” meaning that you got to take risk to get somewhere, otherwise you are not going nowhere. Read more>>

Angela White | Film & Television Producer

I am an entrepreneur, and I have a quote that I like to cite, “To be a “true” entrepreneur, you have to be ready to jump off the ledge and not know where you’re going to fall.” The meaning of this quote is that as an entrepreneur, I have to be ready to take risks and just go for it without a safety net. Risk-taking has always been apart of my business as if I was going to play it safe; then, I might as well just work within a confined corporate structure system and not have any worries. When I started my company, Silver Lining Entertainment, years ago, I knew then that I was going to have conduct business in a way that involved not only taking chances but having faith in my ability to succeed in the unknown. Read more>>

Justin Galindo | Director, Entrepreneur, Writer & Producer

Risk is everything. I’ve taken many risks in my life. As cliche as it sounds, life is all about taking risks and stepping out of your comfort zone. The start of my entire career was the day I left my home in Ohio at 19 to drive to Los Angeles with nothing, but a suitcase and my car. I have taken many risks in my life including creating multiple films, investments, and companies JIG Reel Studios and Warehouse 1 Productions. My most recent film includes the feature film, LOCO. This was a huge risk because I was willing to throw down my own personal money and pass on other projects to get this made. This pushed to help get us investors that helped produce this film then help us get distribution for the Fall of 2020. Read more>>

Christina Kai- Marks | Personal Trainer & Coach

There’s a quote “ if you are not willing to risk the unusual, you will have to settle for the ordinary.” This quote sets true and deep for me. I never wanted to settle for “ ordinary“ So I always push myself to overcome fear/ failure for not succeeding and taking multiple risk In my life. From becoming a professional MMA fighter and starting that journey 2 weeks after having my son. To letting go and moving away from a stable and good financial job of a financial aid director of a school to pursuing and diving in headfirst into becoming a personal trainer/coach and devoting more of my time to my practice of an MMA fighter. Which led me a job with the ufc gym as well as being on the ultimate fighter season 26 show. Read more>>

Taylor Gallion | Cartoonist

Be brave and take the risk if you are really passionate and talented! There were plenty other alternatives that could be making me more money but I chose to pursue art as a career which brought me to Los Angeles from Kansas. That alone was worth the risk and living in a new amazing city with tons of opportunity. It can be very challenging and not every risk pays off. Risk in dating are a hit or miss, I took a risk on opening a business only to watch it suffer from the Covid 19 pandemic, but it could have gone very well. There’s just so many unknown factors but you’ll have fewer regrets and know the truth for yourself. Don’t miss an opportunity to experience something amazing. Read more>>

Monica Edwards | Artist & Painter

I have a strong belief about taking risks. I’m a person that feels very strong about saying YES to life. I find it very difficult to be around people that are limited by fears. The fear of survival is good, I don’t advocate doing obvious life threatening things (although some of my decisions can be questionable), but plain old fear is a bore, annoying and just old. Some of my best experiences, both personal and professional have been from saying YES, even if everything inside of me was trembling with self doubt, apprehension, the fear of the unknown. . .but the risk is (almost) always worth it. Every career move I’ve had was by taking a risk, saying yes before I thought I was ready. Read more>>

Samantha Williams | Co-Founder

Everything in life is a risk, to making any decision. But not making a decision is a risk, too. There have been periods of my life where all of my decision-making was based on managing risk–falling in line with the status quo, or the path of least resistance. I’ve done that more than once, and each time I’ve ended up in a situation where I was feeling suffocated. For me, having my whole future planned out took all of the mystery and excitement out of life. But whenever that happened, I would throw myself into the deep end and lean in to the unknown. And it was scary, but totally worth it. I moved to LA at 27 from Denver, I didn’t know anyone or have a job and it was one of the best decisions I’ve ever made. Read more>>