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.

Jaya Madray | Model, Creator & Pageant Competitor

I think that risk taking is a major part of life. In order to achieve any goal, it starts with taking some sort of risk- whether that risk be big or small. Within my own life, while it may not have been easy, taking risks has attributed to some of my most valuable accomplishments. For example, there hasn’t been much Indo-Caribbean representation in certain industries, so it was challenging for me to make certain decisions without having a specific example to look up to. Competing in pageants was one of those decisions. However, I persisted and took that risk- even with the scarcity of other competitors that looked like me. Little did I know that that risk would lead me to some of the best moments of my life. Read more>>

Travis Raab | Guitarist and Content Creator

Leaving the safety of my hometown, then my safe teaching gig, then my safe cover band gigs have all lead to better things for me. I left a group that had a recording contract when I was about 23 which was a good choice. It’s all a risk. If you’re going into the arts I guess it’s better to shoot big you can always quit and do something else. That way you’ll never worry you didn’t take a chance. Read more>>

Troy Ambroff | Re-Record Mixer for Film and TV

Risk / Reward can Make or Break your career. Knowing when to risk it all, and when to fold is something you can only learn by doing. Shortly before my first day in the post production world, I risked it all to get to the top. I was working as an usher at the Wiltern Theater, on New Years Eve, dressed to the 9’s. That night was a Joe Rogan comedy show, and a shift that I badly needed in order to pay my rent. Unfortunately, instead of being inside (and being paid to watch the show), I was assigned to oversee parking… Alone, underground, on New Year’s Eve, in a suit, and miserable. They may have put me there because I had already been reprimanded for talking to the sound team on my breaks. Read more>>

Brendan Merrill | Filmmaker, Producer & Editor

I’d like to say that I’ve taken lots of big risks as a filmmaker, even though I haven’t really. Risk-taking sounds romantic, and at the same time a little desperate. It’s easy to love somebody willing to put everything on the line, win or lose. It’s also easier to watch them if they fail. But part of taking HUGE risks as a filmmaker… for me… was knowing which ones to take, and which ones not to. Granted, if you didn’t know me and looked at some of the decisions I’ve made while working in and around entertainment for the last decade… I bet you might say I allowed myself to take certain large risks. Read more>>

Maclaine Diemer | Composer

I think being comfortable with risk taking is essential for anyone in a creative line of work, whether it’s trying to get out of your artistic comfort zone on a day to day basis or making moves that will grow your career. Taking risks is scary, but with some faith in yourself, it can open doors for you that otherwise may have remained closed forever. When I first broke into the game industry, it was as a sound designer, a job I did for four years across two different studios. I had spent most of my 20s in a failed effort to make a living with music playing in bands and hoping to make it big. I switched gears and became a sound designer because I felt there was enough crossover with what I was already good at and it would provide enough challenges that would scratch my creative itches. Plus, I could make a living wage doing it. Read more>>

Antonina Fedorova | “Anybe” Founder & CEO

I stand by the belief that life is a game, and risk-taking is one of its essential rules. Thankfully, it makes life more breathtaking and striking, allowing you to grow faster and in a more intensive way. In my opinion, there are two ways of your life/career development: evolutionary and revolutionary. If you choose evolution, that’s the minimal risk. You should put affairs in order, add new tools, join a supportive community, create external motivation, observe the discipline. And you will grow X2 sustainably. Read more>>

Goar Hovhannisyan | Realtor & Business Owner

As someone who was once afraid of coloring outside the lines, taking risks was never an option. Nevertheless, I began coloring outside the lines and stepping out of my comfort zone, and I can confidently say that I am never going back. Taking risks open up doors and allow you to discover the answers to those what-if questions. You may not always like the outcome, but at least you have a definite answer rather than always wondering what could have been by making up scenarios in your head. Growing up, I was always taught to go for the sure thing, like going to college to get a degree and be a salaried employee with benefits. Read more>>

Jason Tiger | Change Agent

Fast and repetitive calculated large to small risk is a necessary function towards success. Pulling the trigger fast and pivoting quick when a mistake is made is a necessary formula to reach your goals. Not making a decision fast enough can be far more negative in most situations. Risk becomes more and more prevalent as you become a change agent and innovate. Calculated risks allows you to learn faster to succeed. I learned this early in my career. I left everything behind at age 24, including friends and family to move to Hong Kong where I did not know anyone to pursue an opportunity at the world’s largest bubble solution and bubble toy company. Read more>>

Mary Christopoulos | Actor

Risk taking has played a HUGE role in my life. I knew that pursuing acting was taking a big risk, but I told myself that if I didn’t try, I would look back and wonder “what if?” I made it a priority to take risks in life becuase I think that if you do, you will be surprised about how many wonderful things can happen. Read more>>

Emily Wilson | Writer & Director

I find risk taking quite exciting and do believe in the old saying, “fortune favors the bold.” When it comes to artistic pursuits, there is always a certain level of risk and I think that’s why artistic accomplishments are so emotional and profound. In terms of my own personal risk taking, I spent all of my money (and then some) to make my latest short film, Danny’s Girl. Creatively, I had to do it because I was pretty down on myself for not utilizing my passion for filmmaking more. The film went on to premiere at Sundance, 2020, which was a lifelong dream come true and 1000% worth the risk. Read more>>

Isaac Estrada | Wine Specialist & Creator of “Decant It” Wine Podcast

Risks are one of my favorite parts of life. The only way you truly know if you desire something is if you are willing to take a risk. It is a healthy mindset that can teach you so much about yourself,. There are negative and positive outcomes that shape the person you become. In my case, one of the biggest risks I probably have ever taken was dropping out of college. Popular to contrary belief, It opened up more doors for. I soon became a wine specialist and a passion quickly grew. Once that passion was strong I decided to start my own wine podcast, and that was another risk in itself. Risks have played a pivotal role for me, it is how I got to be where I am now. Read more>>

Mercedez Higgins | Art Department for film and media

In life if you don’t take risks you don’t know where you could go or the potential you could have if you don’t just go for it and for me taking risks have been a huge part of my life and my career. For example, I’ve moved many times specifically to further my education and my career in the film industry and if I didn’t take those risks to move out of the city that I was comfortable in then I wouldn’t have made it as far as I am now. I think that the worst thing that can happen if you don’t take a risk is the endless possibilities of not being as successful if you were to take the risk and people telling you no or simply ignoring you. Which for me I would rather jump for the opportunity and be a risk taker then not take that risk and feel as if I didn’t shoot my shot. Read more>>

Skyler Lawson | Film Director, Writer, Producer

Overcommit and deliver. I live by those words. Risk is present in every component in my work, I almost see it as a collaborator. I feel the real work happens once you’re outside the comfort zone. I like pushing everyone I work with to let go of expectations and let the work speak. That allows an atmosphere to create something fresh, and the audience deserves that. When you get out into the unknown, you have no choice but to trust what the film/story wants to be. Accepting that leads to authenticity which is of top importance in filmmaking. I always tell my cast and crew “If the needle lands in the middle then we made nothing.” Taking risks is the key to making something fresh. Read more>>

Jacqualynn Harris | Business Owner & Network Producer

From leaving home and everything I knew behind to pursue dreams to having my daughter and going above and beyond to break generational curses, taking risks has been vital in my life, career and success. Leaps of faith have been a recurring theme on my journey. Without taking those chances, my dreams wouldn’t be manifesting the way that they are. The bigger the risks, the more substantial the opportunities and blessings from each of those risks. Each time I step out on faith, I remember something my grandmother always used to tell me, “You will Always have Everything you Need in this World.” When you believe those words, it takes the fear away because when you know the universe is working on your behalf, it makes taking that leap effortless. After all, the reward is already yours! Read more>>

Lotara James | Certified BodyTalk Practitioner

Everything I’ve accomplished in my life involved some amount of risk to achieve. Taking risks can bring up feelings of vulnerability, insecurity as well as the exhilaration of feeling like I’m on the right path; I have a clear vision of my goal even if I don’t know exactly how I’ll get there, and I can anticipate and hold that vision with joy. In my experience, if I’m drawn in a particular direction there is usually something valuable to learn on that path. Ideally the goal, once achieved, still resonates with what drew me to it in the first place. If it doesn’t, I can usually see the value of what I learned along the way. I think we are trained to believe achieving a specific goal is the important part, but often the real reward is how much I grow in the process of working towards a specific goal. Read more>>

Anthony Montes | Actor & Writer

I am an actor, so by definition, it means taking risks. My life has always been about, what are you willing to give up, to have the life you want. For me, it meant a life without possessions, vacations, a nice car, being unsure of employment, if I could pay my bills, have a family, a home… When I moved to LA from NY, I thought I would be the next Pacino. I had no idea how difficult it would be. I thought if you worked harder than anyone else, studied, were passionate, and were good at your craft, you would work. I didn’t know how much luck would be needed and I didn’t seem to have any. Tired of going up for, “Truck Driver #1”, I decided to start my own theatre group and I called it, The Artist Theatre Group. Read more>>

Alvin Makori | Singer, Songwriter

To me, risk is anything in life that requires faith. With risk, there are always unknowns that remind us we cannot control the outcome of the situation. This can lead to a fear of failure, which we have all felt before. In moments like these, it is important to remember that everything we strive to achieve is on the other side of risk. Without risk, there is no progress, no lessons learned. Taking myself seriously as an artist was one of the biggest risks I’ve ever taken, but doing so has given me so many blessings in return; meeting other creatives, stretching my creative boundaries, and seeing the joy that my music gives people. Read more>>

Katina Karl | Owner, Kefi Marketing

I believe as a business owner and in life it is important to take risks! I have never shied away from taking risks that were going to change my life or my career. I’ve lives in multiple states from Long Island, NY to South Florida and now living in Central New York. If I didn’t take the risks I did, I would never be in the place that I am. I was able to start my business, meet my fiancé and the great people who live here. Not to say there weren’t scary times of wondering if I would fail or if I could do this on my own. But, I always made sure to push myself and work hard to make the life and career I’ve always wanted. Sometimes we can hold ourselves back from trying something new, moving to a new place etc. because we are scared of failing, being alone or having to start over. Success and happiness is on the other side of fear. Read more>>

Kenneth Ruddy | Visual Artist & Writer

Risk is an absolutely essential part of life, especially if that life is to involve a creative pursuit. Without risk and the desire to push yourself, life can be complacent and unmotivated. It was that fear of complacency that led me to take some of the larger risks in my life, whether it be moving to California after college or pursuing a freelance photography career. That fear was opposed by a natural fear of failure, the biggest bridge to cross when taking risks. Overpowering my fear of failure has allowed me to not only explore art in more meaningful ways but to also discover a truer sense of myself as an individual. I’m so thankful to myself for taking the risks necessary to get here and look forward to where my future ones will lead me. Read more>>

Christy Hayek | Political Lobbyist by day & Artist Manager by night

I’ve never been afraid to meet a challenge head on. I think the biggest risk I took in my life was switching career paths from politics to music/art. I went from a stable job in Washington, DC with benefits to taking a leap of faith to see if I could start my own management company in music since I had always been super interested in that scene. The bell curve there was extremely difficult in the beginning, I went from having 6+ years experience in policy to knowing next to nothing and moving to LA with $500 in my pocket. But I took it one day at a time and learned as many new skill sets as I could in order to ensure I did it properly. I tried to learn it all by myself and quickly, from the nitty gritty of composition contracts to setting up an LLC, it was a thrilling and very scary experience, but I am really grateful with my life in LA and that I get to pursue my passion here. I am excited to see where the next 5 years in this industry take me. Read more>>

Bruno Seros-Ulloa | TV Executive and Clothing Designer

I think about risk in terms of potential. A lot of people equate risk with fear, and that can be a slippery slope. In my experience, maintaining confidence and a clear vision is everything. If you believe in your idea, and that idea is clear cut and well thought out…make that idea happen. At LATV Network, taking risks is what has given us an edge against our competitors. We create content that other Latin networks are not creating despite its absolute necessity in the market. We know how to listen to our audience, because we ARE our audience – and we deliver. Another risk that really propelled me forward personally was starting my own clothing brand. Read more>>

Melissa Tillman | Founder & CEO of Nonprofit Growth Advisors

I believe the greatest risk in life is not taking any risks! I’ve taken several risks in my life, including relocating back to California in my early 20s after growing up in South Florida. I left the comforts and familiarity of home and although I had some friends and family in California, I truly had to start over to build my personal and professional networks, and it was one of the best risks I’ve ever taken. Read more>>

Nicklaus Gray | MC, Illustrator, Music Producer, Pop Vocalist, Mixing Engineer, Uniform Designer and Animator. Allegedly.

Phew, to be frank, risk taking is how i’ve been able to make any significant progress towards my dreams, even when I wasn’t sure what those dreams were. Many of the opportunities i’ve been afforded have been because I said something like “f**k it, let’s just try it”. For example, I hit a hard mental block in early 2019 working a 9-5 selling denim to (alleged) Karens and Kens. It was the most financially stable position I had acquired in years but I was hilariously unhappy working there. I ended up quitting, moving out of my grandma’s and essentially Airbnb hopped from Los Angeles to the Inland Empire for 3 months working solely on illustration and production. One of the toughest times i’ve had in life, but the foundation and mentality I gleaned from it has stuck with me ever since and made me much better as a human… overall. Haha. Gotta risk it to get the Popeye’s biscuit. Read more>>

Nate Rodriguez | Aktiveight DJ/Producer

One thing that I have learned in my 10 years in music is that taking risks is very crucial to develop yourself as an artist. Many artists have fallen and have picked themselves back up and they were able to succeed much better than they were before. When I first started I never wanted to take risks because I was afraid of failure. And guess what, I failed a lot, even without taking those risks. There is so much work to do when you are in music and taking that one risk could be the defining moment in your career that’ll make you the best. Read more>>

Jay Combs | Comedian, Actor, Writer, Creator

“you cannot just exist in this life… you have to jump” – Steve Harvey I started my response with this quote from my favorite comedians of all time because it truly defines me and my way of thinking about risks and life in general. Being a kid from a small town in Lousiana, shout out Shreveport, you realize early that in life you have to create your own opportunities or you’ll end up stuck, letting life pass you by. And for me, I realized at an early age that this was just not an option for me. I wasn’t gonna get stuck in small-town America, counting the days until I die. The world is bigger and greater and it’s yours for the taking, you just have to “jump”. Read more>>

andrea rueda | Bilingual TV Host / Digital Creator

I love this question!!! Risk is EVERYTHING, I remember I read somewhere or someone told me “The universe loves risk” and I live by it. Of course, I’m not gonna pretend that I don’t sh** my pants sometimes at the thought of speaking in front of hundreds of people, but people think that risk involves people who are not scared, but ‘au contraire,’ people who take risks are usually very scared, but they do it anyway, and learn to navigate thru those emotions. Read more>>

Ama Rose | Artistic Healer

The biggest risk is to allow fear to keep you from taking chances. I love risk, and it’s the reason behind many of my choices. When I was very young, I sat and listened to my elders talk about all the things they wish that they’d done, and it became obvious that so much regret was weighing on them, so I made a pact: to have lived a life that I can look back on at 50 without regret. I’ve taken a lot of risks in life, dropping out of college, moving states alone, traveling foreign land alone, and every opportunity has reinforced and reminded me of who I am, and what I’m capable of. There have been times where I wasn’t sure how I would manage, or even survive, which created several of my businesses. Read more>>

Kyla Skinner | Optician

Fear of risk has handicapped me most of my life. Fear of debt, fear of failure, fear of change, fear of unknowns. I stayed with what was comfortable, what was safe, what was predictable, what other people expected of me. 2020 was climactic. Out of all the things I’ve worried about in my life, a global pandemic was never on my radar! Combined with the traumatic loss of my biological mother and religious confusion, anxiety and depression literally stopped me in my tracks. Read more>>

Cyrus Soliman | Actor, Snack Enthusiast, World Champion

I’m all about the risks baby. I think that you have to give to receive, for some people that’s money, other’s it’s time, and for me that’s safety. Being born and raised in the Bay Area it seemed like I was on the fast track to have a career in Silicon Valley, but big tech couldn’t be any less appealing to me. I needed to do something that pretty much everyone told me not to do, which was pursue acting. After years of hearing it wasn’t stable or safe, I’d decided I had enough of everyone killing my vibe and I peaced out to acting school. Shoutout to NYU Tisch. Read more>>

Scarlet Parke | Artist, Songwriter, Entrepreneur, Vocal Expert

I’m a big believer that comfort is the death of innovation, so anytime I start to feel complacent, I like to think of new ways to collaborate, create, and pivot. Every risk is terrifying, especially as the stakes get higher, but there’s something special about trusting yourself and eventually, you crave the adrenaline. I think greatness comes from fearless risk-taking. Read more>>

Kevin Zulueta | Senior Operations Manager & Upcoming Music Artist

Risk taking has played a significant role in my overall journey throughout life. The field of music alone is a very risky career path that always intrigued me due to the passion I have for music. I attended a unconventional high school that allowed me to study music technology and sound engineering. This was a difficult decision to make especially watching all my peers attend traditional high school with football games and pep rallies. After high school I took another risk and decided not to go to college and took on an internship with Florida native Grammy Nominated producers Cool & Dre. Read more>>

Kat Chaos | Visual Artist, Event Producer, Business Owner

Risk taking, just saying it gives me anxiety; it is not for everyone but if it is truly what is meant for you, the end result will be so rewarding. It was 2008 and I had just graduated from high school with Honors, I knew exactly what I wanted to do because I knew what made me genuinely happy. What I did not know was my self-worth and had absolutely no confidence in my craft, much less any confidence to succeed in this Industry full of nothing but competition. I was fresh out of high school and I was scared of failing, I decided that I would make a decision that would be financially stable and that would make my family proud; I decided that I was going to join the military, the United States Air Force. Read more>>

Bria Williams | Actress & Entrepreneur

Risk sometimes isn’t the most popular thing to do, but to me it has always been the most rewarding. I found that in my life the greatest risks I’ve taken have changed my life the most. The scariest part about risk taking is not knowing the outcome, I think if more people knew what was on the otherside of the risk they are afraid to take, they would take a risk more often. I am a woman of faith, and I walk by faith daily. I believe I’ve been placed in every situation for a purpose that is greater than my own knowledge. I rarely know what’s on the other side of my decisions but I’m a true believer that its always leading me on my own unique, happy, successful path. Dare to risk, I believe it’s better than to wonder “what if”. Read more>>

Aye Mack | Music Artist

I would have to say building up my confidence to face failure has played a huge role in my risk taking abilities. I now understand how the person in the mirror can be held back by personal doubts. The greater the risk the bigger the reward. Being willing and even able is only the beginning musically. Presenting what you have to offer to the masses and remaining self aware needs structure. You are risking layers of skin to be tested by who knows how many people. Only to give a broad point of view and prospective of what you think or feel. That’s a big enough risk to crush a driven man right into a wall of discouragement. It gotta be in you not on you! Read more>>

Caine Whitmore | ThaWe$t Clothing Founder & CEO

I believe taking risks are a necessary part of life whether you are just living your everyday life or if you trying to start a business. You have to take a risk otherwise you can get stuck in that what could of been state of mind. You have to take a risk because it can be the best move you ever made or a lesson learned. ( it ain’t no L it’s a lesson ) I took a risk in my life by putting my work paychecks into creating and starting up my brand not knowing what the outcome was going to be but for some reason God kept telling me I’m going to make it. Read more>>

Monica Challingsworth | Co-founder and President at Eustress and Demeter / Exclusive US Distributer for V10 Plus USA, Japanese Skincare

Successful entrepreneurs are known to be pretty risk-averse, but what makes them different from the rest of us? What type of crazy gene do they have that others don’t? Some people dream of leaving their corporate 9-5 (which we know is never really 9-5) to follow their dreams of being a business owner, tech pioneer, social media star, world-traveling foodie, or an array of amazing opportunities that are out there. However, many do not take the leap because we believe having a “job” or “corporate career” gives us some kind of job security. Ask anyone who has been laid off, right before retirement, after 40 years of uncompromised dedication, or someone who has unexpectantly lost their jobs if they believe in “job security.” Read more>>

Gigi Fields | Stone sculptor/ oil painter with vintage foreign newsprint collages in/ photographer/ therapist

Risk is at the base core of my entire life I’ve lived all over Europe and was honored with 5 artists residencies and Scholarships in ;
Italy ( Tuscany, Rome and Puglia) , Spain ( Barcelona) and Germany (Berlin ) and NYC.
I risked everything I had to go on these and advance my passion ,creativity and career by giving up jobs, homes and relationships…
I started as a stone sculptor. Well , actually I was a therapist for teens in LA. I had a summer off and took a stone sculpture class and my professor flipped out when he saw my 1st piece appearing in the stone. He shouted “ Its a Brancusi “ Who? “ You must go to Italy and study.” Read more>>

Cait Medearis | Actor

I think for many of us, when we begin really following our passion and what we’re meant to do with this life, we’re usually taking a major risk. I know that was the case for me–I had settled into a career in which I was more linearly heading toward success and potential accolades. I had even begun studying for a career in broadcast journalism at the age of 18 and never veered from the path until I was two years into working as a newscaster, at my second news station, and miserable. When I finally made the leap to leave the industry and begin studying acting, things opened up for me. Even though the path hasn’t been as linear or clear, I’m so much happier. Read more>>

Meg Buzza | Quirky. Curious. & a lil’ Kinky.

Risk is a basic requirement of being a producing artist. It’s always mildly terrifying to take my creative brain babies and put them in the hands of the social media monster. I used to feel paralyzed in the face of execution, but once I finally accepted that risk-taking was an inherent part of the art-making process, I stopped strategizing how to avoid the discomfort, and started seeking it out. In my experience, when doubt and anxiety inevitably comes up, it’s actually the “green light” to keep moving. I now have a daily practice that has flipped my fear-based view of risk on its head. It’s a simple formula: when I am fearful, I am focusing on myself and what I am hoping to gain; but when I focus on what I can give, fear is replaced with determination. Read more>>