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.

Isabel Mazzolini | Cinematographer and Director

Risk equals opportunity to me. I was born and raised in Italy but I have always dreamed of pursuing an artistic career in the United States. I knew it was not going to be easy but I was ready to work towards that goal. Three years ago I got the opportunity to spend a year in San Francisco as part of an exchange program with my formal hometown University and I decided to take it. I was leaving everything behind: my family and friends, amazing food and strong working connections but I had to take that risk. Read more>>

Junior Mintt | Drag Artist, Founder & CEO of Mintty Makeup, Proud Black Trans Woman

Risk-taking is essential to discover the pieces of yourself you didn’t know were there because there’s no risk in doing what you’re comfortable with or used to doing. Without risk-taking, I would have never left the house in clothes that make me feel affirmed as a Black Trans woman, I wouldn’t have ever gotten on a stage to perform, or started my own makeup line and believed I could make it successful! But it’s important to note that risks are much easier to take when you have a community around you that will catch you if you fall. Read more>>

Evie Smith Hatmaker | Founder and CEO

I have an ever-evolving relationship with the risk. In my life outside of work, I am pretty risk-averse. I’m afraid of heights, I get intimidated by authority figures and I really dislike conflict. At work and in my career I have classicly run on pure instinct. I have a really good gut and learned to just listen to it and not ask too many questions. I would say as my business has matured and scaled it’s harder to take risks in the same way I used to. I miss being able to move fast and not have to explain my thought process or gut feelings. Risk is good and takes you to unknown places. It makes life exciting! Read more>>

Shannon Parayil | Visual Development Artist and Background Designer

With risk taking, I feel that taking risks correlates with doing what I’m afraid of as an artist and what I’ve been avoiding. For me, I really had to push myself to create art that I knew wouldn’t turn out looking beautiful the first time. I only felt confident in my color design sensibilities when I was developing my portfolio after graduating college; so creating characters, layouts, and painting backgrounds felt extremely overwhelming. I knew that if I pushed myself to make these pieces I’d be able to improve and become a designer in the animation industry. Read more>>

Dyve | Professional Rapper

That’s tough to answer. I believe there are two sides to risk taking. The actual risk taking that’s necessary for growth and then the feared socially created version. People view pursuit of a career in creative arts or anything of the sort as a, “risk”. The general population thinks it’s risky because it’s not the normal thing to do. They think starting your own business is risky, not doing what your told is risky, and believe that working for a comfortable job is security; or that’s at least what they are lead to believe. Read more>>

Camden Retzlaff | Dancer and Choreographer

If you had asked me this just a few months ago I would have said I don’t take enough risks, that I’m not a risk-taker. This is true to a point, I have never been a “live life on the edge” personality. But I will say that I evaluate every situation, opportunity, or challenge that presents itself to me and take it on full force, which comes with quite a bit of risk-taking. I went from a homeschooled high schooler living in Texas who only went to dance and work, to an openly queer, professional dancer, graduating college and living in California within 2.5 years. If that’s not a risk I’m not sure what is. Fear of rejection, disappointment, and failure lives within all of us, and sometimes the risks you’re willing to take don’t feel like risks at all, they feel like necessities. Read more>>

DaeSun Cupid | Choreographer and Performer

Taking risks for me feels essential in all aspects of life. I am the type of person that doesn’t thrive in safety. I find the most success in my career and personal life by taking risks intentionally to pull out the side of myself that fights to make it through because I have no other option. Read more>>

Jared Hales | Founder of Hacea Coffee Source

My family and I are all pretty risk-adverse people. To this day I have had minimal injury, no broken bones, no sever accidents, no costly self-inflicted losses. That said, I have also been riding motorcycles (not exactly a risk-adverse activity) for nearly 20 years and have clocked many many miles on long distance trips off the bike as well as some gnarly off-road riding experiences like Barstow to Vegas rides or camping out in Utah to ride loops by day. I think risk should be calculated, understood and approached with a clear head. It is impossible to avoid all risk in life so choosing what risks one takes and why is critical to success in my opinion. Read more>>

Sammi Lappin | Writer & Actor

To me, risk taking means going for it and trying the new thing simply because you want to do the thing, regardless of your level of experience. If no one else is asking you to do the thing you wanna do, do it yourself! Utilize every resource you have, and jump in feet first to spend your time how you want to – you’ll learn and grow a ton in the process. A great example of this is my sitcom webseries “Marnie & Nora” that I create with my good friend, Ann Hurd: we started during quarantine and through my writing and her editing, found ways to act together when isolated apart. Read more>>

Patrick Hilgart | Actor, Singer, & Writer

I have a tumultuous relationship with risk. A big part of me longs for simplicity and control, so I often romanticize what life would look like had I chosen a path with less risk. However, I also recognize that nothing I have achieved in my life or career has been by remaining in my comfort zone. I have always had a desire to learn how and why things work, and so much of my process has been trial and error. I try things out, risk failure, learn what fits, and discard what doesn’t. It is curiosity that pulls me to continue to learn, create, explore, and expand. Read more>>

Stephanie Winarto | Designer

For me taking risks is like letting go of control for a little bit—and this can make see from a new perspective and reevaluate my goals. After graduating from RISD(Rhode Island School of Design),I had quite the tunnel vision. I thought the only way to succeed as a designer was to find a job in NYC and stay there. As an international student, this meant spending a lot of time and money navigating visas, immigration, and lawyers to get to stay in the US. In 2020, during the beginning of the global pandemic and when things got bad in NYC, Read more>>

Ruston Ropac | Soprano & Composer

Sometimes putting yourself out there is terrifying. I’ve definitely gotten nervous before when reaching out with cold e-mails, or introducing myself and pitching projects to potential collaborators or artists whose work I admire. Sometimes I am afraid of being seen as overly forward. However, I would rather have tried than done nothing at all. The worst that can happen is nothing, or that I hear back “no.” Read more>>

Rory D’Lasnow | Singer-Songwriter

Risk taking is so important. My musical journey has been somewhat circuitous because so much of it was hindered by self-doubt and procrastination. Pursuing a life in music is a risk in and of itself and so it’s easy to become overwhelmed with the logistics of it and stick to something safer. But once I really committed to pursuing what I love with reckless abandon, I found an entire community of artists and music lovers that embraced and inspired me. Sometimes it feels easier to only take precisely measured steps, but the best thing I ever did was just jump in and not look back. Read more>>

Desiree Harrison-Brown | Wine Educator & Founder of The Wino Shop

In the last quarter of 2021, I decided to leave my full-time corporate role in the wine industry to pursue my entrepreneurial endeavors. It was a huge risk to leave my salaried position after having been in Los Angeles for four short months, but I knew that with more time and freedom, I would be able to focus more on running The Wino Shop and collaborating with brands. I also had enough saved to give me some peace of mind financially. I believe in taking calculated risks. I have a strong work ethic, so I’ll bet on myself every time. Read more>>

Tara Mascara | Make-up Artist

I think that risk taking is crucial in leveling up in your career. If you stay stagnant and not take risk, then you will not grow. It’s so important to push yourself to achieve your goals even when it’s scary. If you’re not scared to do it, then you’re in your comfort zone and you won’t move up while you’re in your comfort zone. Over the course of my 13 year career, I have continued to challenge myself and take risks so I can push myself to the next level. I am constantly creating new goals and trying things that I’m not good at so I can be better. Read more>>

Matt Adame-Valencia | Creative Director & Video Editor

For me risk has been an essential part in my journey and making me who I am. I was on a whole different career path when I was younger. I graduated with my Associates degree in fire science and had just graduated as fire academy, while working as an EMT. I for sure thought that’s what I was going to do for the rest of my life. In the process while I was applying for different fire departments I decided to transfer to University and pursue my bachelor’s as a backup option. At the timeI was in love with concerts and making videos with my friends and picked up my camera again after years. Read more>>

Sabrina Sentoso | Concept & Character Artist

Coming from a more conservative upbringing and community in my childhood, my whole career choice was often seen by others as a risk in itself. I didn’t even consider that being an artist was a real, viable profession until my high school years! When I made that leap into pursuing art, everyone was skeptical, including me. I remember being so afraid and anxious, I was that one weirdo going to art school while all my relatives and classmates went for academics– I didn’t really have anyone who could give me advice either, since being an artist was such a rarity. Read more>>

William Schinsky | Artist/ Founder & Executive Director Coachella Valley Art Center

Risk, professional and creative, is an essential. Ignoring risk will result in mediocrity. I do not participate in physical risk. While on active duty in Viet Nam in 1968-69, I promised myself that if I returned alive, I would pursue a professional career that made me happy. Subsequent to Viet Nam, I returned to college as a US History major. Taking the required Intro to Art class envigorated me so much I changed my major to Art. Once I found myself in the real world, I have always said “Yes” to employment, projects or other professional involvements that promised something new and exciting. I continue to produce programs and Art that do not follow the current local trends. Read more>>

Cierra Swingle | Fashion Stylist

To many, the thought of taking risks may feel scary and intimidating. The unknown, the what if’s, and the different variables that need to happen in order to ensure it’s been calculated and managed well. Life is all about perspective. I view risks as an opportunity to advance and to see God move in a supernatural way. As a believer in Christ, risk or what we call “taking steps of faith” is a part of exercising the foundation of our belief. Faith, in biblical definition, “Is the assurance of things hoped for, the conviction of things not seen.” Hebrews 11:1. Read more>>

Jovanna Vidal | Actor, Author & Voiceover

I believe risk-taking is an ESSENTIAL part of life for growth and fulfillment!! I believe that without risk we do not challenge ourselves therefore we do not experience the GREATEST aspects of our life INTO living our TRUEST and most authentic selves!! Taking, for me, “calculated” risks is one of the BIGGEST contributors to the GREATEST joys I am SO blessed to be experiencing right now in my life!! THEY ALL have led me to THIS place of inner strength and inner contentment and most of all inner appreciation for my journey and all THE BEAUTIFUL people along the way!! Read more>>

Omar Zaki | Video Creator, Stuntman & Parkour Athlete

I doubt there was ever anyone in the history of this world that achieved something truly great without risk. Risk is a necessary part of survival, growth, and success. Now it all depends on what you want out of life. For me, I know that I am not here to live a mediocre life. I am not here to live a life of routine and predictability. That’s not what I want out of this experience. And if a person doesn’t actively work against a life a routine then that’s exactly what they will be given because that is the societal formula at the current moment. Read more>>

Letitia Blacksher | Certified Personal Trainer and Nutritionist

It took me years to resign from my corporate job. Deep down I knew I had another purpose, however, I was afraid of quitting a job that guaranteed a steady paycheck, benefits, sick hours, etc. Rather than embark on a risky decision, I fell into a depression that lasted for about a year. I cried to God. I asked for answers. Deep down I knew what I wanted, however I hoped the answer would be given to me. Life doesn’t work like that. You have to go after what you want. You have to trust your intuition and trust that the universe will guide you, while also being comfortable with the possibility of a situation not working out in your favor. I had to take a step back and be honest with myself. Read more>>

Janaya Hampton | Designer/Stylist

I feel like my whole life has been centered around taking risks. I’ve always been willing to do what others wouldn’t in order to reach a goal. Risk taking is an essential part of growth and success in your life. If you don’t take the risk, how will you know if your idea will work or if the gut feeling you had was right? When I decided I’d play volleyball in college in an unfamiliar city, I was taking a risk. Read more>>

Akori | Entrepreneur, Singer, & Creative Director

Risk is scary but worth it. Sometimes you fear the unknown but after getting over that hurdle you’re just happy you pushed yourself no matter the outcome. At a few points of my life I went completely broke, like literally no money to my name just because I was trying to take a leap of faith for my dreams. I feel like it built my character and has helped me to understand risking everything is sometimes worth it if you push through. Read more>>

Roman Styles IV | Chef & Entrepreneur

I wouldn’t be where I am today if it wasn’t for taking risk. In order to get something you’ve never had you have to do things you don’t normally do. I had a vision of where I wanted to be and I took a leap of faith by leaving my good paying job to pursue my own endeavors. Not knowing how my bills were going to be paid, just had my son I mean the list goes on, but I trusted my intuition and my skills and went for it. Went from selling plates & meal preps thru social media to running my own meal prep company ( and opening my first food truck (MacDaddyz) this summer. Risk are necessary. They open up new doors & they help you grow Read more>>

Fallon Webb | Artist, Actress, & Model

In this stage of my life, risk taking happens to be an imperative aspect, and it shall continue to stay that way for as long as I live. I strongly believe that taking risks on yourself enables you to get out of your comfort zone, which ultimately serves no purpose other than keeping you stagnant in life…and who wants that ? Not me. Now, taking risks has never been an easy process, it requires pure courage and confidence, which we all can obtain of course…once you learn how to step into your power…that’s a whole other conversation though. Read more>>

Crystal Carpenter | Hairstylist & Entrepreneur

I think risk taking is probably one of the determining factors to if your business takes off or not. Scared money doesn’t make money is more truth than cliche. You can’t be scared or shaky about your own business because it’ll just make everybody else scared & shaky about you. If I was afraid to take risks I wouldn’t have a suite or a product line. No risk no reward. Read more>>

Saxon Logan | Film. maker

Risk can so easily be equated with recklessness by those outside of film making but I am sure most singular non careerist film makers agree, it equates to courage. I think my whole vocation has been built on taking risks – some came out good, some not so – you live with this because it was your decision, your responsibility. To give an experience of risk, I was the first film maker to tackle the dreadful poaching of Black Rhino in Southern Africa, then taking place in the Zambezi valley, Zimbabwe. Read more>>

Ally Hustings | Recording Engineer

Taking risks is a foundational and necessary pillar of growth for me, it’s just a part of who I am. Every time I’ve advanced the quality of my life it’s because I saw the gap between where I was and where I wanted to be, took a deep breath, and took the plunge to put myself out there. Risks come in all shapes and sizes, and while I can’t find the source of this quote, I read somewhere that courage isn’t the absence of fear, it’s choosing to advance through it and I remind myself of that often. Read more>>

Tyrone Van Tatenhove | Actor and Delivery driver extraordinaire

Risk taking. We’ll, at a very early age I feel as though I was conditioned for a life of risk taking. My twin brother and I were born into a very difficult situation as children. We lived with foster parents, babysitters, landlords, etc..until we were takin in by an immigrant family who had immigrated from Germany after WWII. The family unfortunately suffered a huge tragedy when the father had passed away soon afer our arrival. This struggles my brother and I had to endure were ,at times, overwhelming and even at the age of 6 I knew that life was going to be a daunting task. However, these experiences,I feel, gave me the tools I needed to survive. Read more>>