Rolling the dice: conversations on risk

Taking Risk is essential, but how much, when and why? Taking risks effectively is as much of an art as it is a science and we’ve asked some of the brightest folks in the community to tell us about how they think about risk taking.

At this point, everything feels like a risk. I’ve worked in my industry for a long time, and now more than ever I feel like everything is upside down. And while I’ve at times felt lost, uncertain, and like really sad, I’m now starting to feel a sense of excitement. No one really knows what’s gong to happen next, and that’s actually sort of thrilling. Read more>>

My entire career has been shaped by taking risks. I’ve always been more afraid of the “what if” than the outcome itself. I’d rather try something and face an unexpected result than spend my life wondering what could have been. I was raised on my dad’s motto, “You already have the ‘no,’ so you might as well fight for the ‘yes”. That mindset has guided me through every difficult decision, and whenever I’m faced with a challenge, I choose to take the risk—because the ‘no’ is always there by default. Read more>>

I joke that when I die, my gravestone should say, “Sure! How hard can it be?” I have always been very risk averse physically, even as a child, but personally and professionally I think my curiosity and trust in my own capabilities (whether merited or not) have always outweighed my more cautious side. I am always game to try new things, and half of how I’ve built my business is to say, “Yes, I can do that!” and then figure it out as I go along. Sure, it’s gone astray a few times, but I’ve always learned something in the process and built on that to create bigger and better things in the long run. So I am a big fan of risk taking and pushing myself to try new things. Read more>>

I have lived and studied in several cities across the world from China to New Zealand and now the US. Each move I’ve made has felt like a deep plunge into the unknown. I see these relocations not just as new beginnings but as radical risks, and moving to New York on my own to study filmmaking has probably been the boldest of these moves. The city’s relentless pace, its sheer scale, and the demands of making a life in the arts were intimidating, yet I was drawn to the creative energy and possibility it holds. Read more>>

I think taking risks is one of the most important things to do in order to succeed in any career. If you’re not pushing yourself outside your comfort zone then growth will be nearly impossible. Anyone who decides to step into a creative occupation is already taking a huge risk – these industries are tough, unpredictable, and take a lot of getting back up before you’ll see success. It’s not for everyone but the rewards are huge. Read more>>

I moved from Pasco Wa 3 yrs ago! I packed whatever fit in my car and left to Los Angeles! I posted on social media a year before and got to be part of a one year partnership with a big business inn 2021-2023! I worked with a lot of top brands in the beauty industry because I moved! Sometimes you got to take risk! And this changed my content creation!! Read more>>

I see risk as a necessary part of growth, both personally and professionally. For me, taking risks often means stepping out of my comfort zone and trying something new, even if there’s uncertainty. For example, when I started sharing my natural curly hair journey, I was unsure how people would react to content but I still put myself out there. I was scared because I didn’t want to be judged. Read more>>

I see risk as an opportunity to learn, innovate, and reach new heights. As a young man and entrepreneur, my mother instilled in us the belief that “you never know if something will succeed unless you try.” I’ve always embraced that mindset, willing to take risks in both life and business. Read more>>

I think there is risk in everything. In my art career, especially this year, I’ve committed in doing art shows full time. Most of the art shows I’ve done so far, I did them for the first time. I remember in the beginning of the year, I’ve already planned out and paid for art shows up to July. It was a huge investment up front not knowing whether it’d be paid off or now. As a traveling artist, a lot of the stuff I do comes with risk. I’ve had some bad art shows where I didn’t make what I expected to be making; there was a time my car broke down while I was driving to a show; the last art show I’ve participated in, there was a strong wind that damaged a lot of artist’s artwork and canopies, I was lucky. Read more>>

Over the past five years, I have wholeheartedly embraced the belief that “the biggest risk is not taking any risk at all.” While this is easier said than done, I would much rather learn and grow from failure than be haunted by the regret of never having tried. Taking risks can be so terrifying, but in the creative field, it is essential to embrace uncertainty and learn to find “comfort in uncomfortable” situations. Read more>>

Everything about being an artist, whether it’s in the music industry or film industry, is taking a risk. There are absolutely no guarantees. But we only have one life to live, so I say take all the risks you can.
Moving to Los Angeles, CA 10 years ago was the biggest risk I’ve taken. I was from a small town in Idaho and Utah. Since a young age, I was taught how to live my life, which career path to take, when to get married and when to have children. But the moment I chose to move to LA, I left everything I knew behind. I was starting fresh with absolutely no guidance, and I did not know a single person down in LA. 10 years later, that was the best risk and decision I ever made. The rest is history. Read more>>

I’m a very risk-averse person, anyone who knows me knows that I think way too much before making any decision. However, for such a risk-allergic person, I sure take some risks. Such as not looking for a stable job, or wanting to be a musician. I believe most of the risks I take to be calculated risks, or at least risks that I can take without losing much in return. However, the risks which I do not take 1000 years in calculating for, seemingly are the ones that pay off the most; which is something I encourage others and myself to keep pursuing. To leave your comfort zone and to fail is the only way you will improve and get better. Read more>>

Risk has been the thing in my life that has propelled me forward. I moved to LA with only a carry on of clothing and no plan, 10 years later I would still take that risk over and over again. My husband and I self financed two indie features in two years… HIGHLY risky! But we have been rewarded more than two fold for that risk. To put it simply, over the last 10 years, the times I have played it safe, I haven’t gotten anywhere fast. The times I have been bold, I have reaped the greatest rewards. Book the flight, send the thousands of emails, take the class, make the movie… Just jump. You may not always land where you hoped you might, but you’ll always land on your feet. Read more>>

I see risk as a necessary step toward growth and self-discovery. Taking risks means stepping out of your comfort zone to chase something greater—whether it’s an opportunity, a dream, or the chance to grow. For me, risk is not about being reckless but about having the courage to embrace uncertainty and trust in my ability to adapt and learn along the way. Read more>>

Without risk, there is no growth. However, I understand that with risks comes an inevitably high probability of failure. That’s inherently scary—acknowledging that not every risk taken ultimately leads to a handsome reward. It’s not like the movies, where you put yourself out there and automatically get a happily-ever-after. Instead, you can end up with heartache. However, there’s also a flip side to this: sometimes risks do amount to a gratifying reward that can be life-changing and fulfilling. Read more>>

Risk taking is essential to success and to grow in life. Playing it safe will only keep you at the same place. I believe the essence of my work as a director involves taking risks, experimenting, and challenging myself both technically and creatively in order to achieve new results. Read more>>

I think taking a risk is a sign that you’re doing something right. I think every person that’s accomplished something great had a life full of risks, big or small. I took a risk when moving to New York. I had a choice between berklee college of music and the American Musical Dramatic Academy. at first the choice was clear. Berklee. I wanted to make music, it was a safer choice, one clear path following something I was good at. But for some reason I couldn’t get New York out if my head, so I plunged into a school teaching a world I didn’t know. Read more>>

In my understanding, risk represents encountering unfamiliar situations that have not been tried before. (This does not refer to risks arising from a lack of preparation or planning.)
In a new project, the absence of risk might suggest a lack of conceptual refinement. Filmmaking, compared to other art forms, demands strong teamwork and coordination. At the same time, it requires finding opportunities to innovate and challenge within meticulous planning—a balance that relies heavily on synergy. This is also one of the aspects I enjoy the most. Read more>>

Risks can be your best life teacher or a downfall. It all comes down to how you perceive them. Risks are a powerful tool, in my opinion. They are like a combination of lessons and challenges to me. Because when we master the lessons and overcome challenges, a beautiful thing happens – we grow as a person and are ready to step into the subsequent unknown with more knowledge. The most significant risk I took was when I quit my 9-5 office job and traveled across the sea to pursue a profession that doesn’t have a linear journey. Success may show up right away, or it can take years. Read more>>

I believe that taking risks is a necessary part of building the life you want. Although I know I’m still early on in life and career, I’d say this is an ideology I’ve really come to live by especially after the events of these past two years. I graduated from college in the spring of 2023, and although I received my degrees in Sociology and Chicana/o Studies, there wasn’t a career path I felt passionate about pursuing. I’m passionate about both major’s and their real-life applications, but I was having difficulty finding a job that didn’t require me being over-worked and under-paid. All I knew was that I needed a job, and the one I had at the time had let me go right before I was set to graduate. Read more>>

I think of risk as giving yourself the chance to go after something that feels true and real, even when the way ahead is unclear. Coming from Panama, I embraced the prospect of leaving everything I knew and felt comfortable with to relocate to the United States to immerse myself in what were already risky waters – the creative field. I made it all the way to New York City relatively unscathed but with no stable plans for the future of my graphic design career, a classic girl with a suitcase and a dream situation. As I was treading these waters, the people in my life suggested I shift my focus to more commercially viable work, but it felt out of sync with who I am. Read more>>

Risk-taking is a given when pursuing a career as a musician – even going all in doesn’t guarantee success. At first, this was a discouraging thought for me until I realized: this really just applies to life in general. Success isn’t guaranteed outside of music either, so why not spend my time doing something I’m passionate about? If I failed, at least I’d have spent my time creating something meaningful, rather than at a job I was eager to get home from every day. Read more>>

For me, taking risks means embracing the courage to make and grow from mistakes. It’s human nature to wait for the “perfect time” to launch a business, start a project, or pursue a dream. But the truth is, there will always be challenges, and life rarely goes as planned. The secret is to start anyway and let your ambition serve as your GPS, guiding you toward your goals. Read more>>

You know what, this is a great question with usually, a cliché answer: the more risk, the more gain. Funny enough, in my case that is true. I balanced the risk of migration, leaving a “comfortable” life behind to pursue my dreams and a better life. I was born in Santiago de Chile, a great city where I spent most of my school days playing guitar without knowing much about my future. Fast forward to my college years, where I ended up studying Sound Engineering, at the University of Chile (an important fact for later). A career that I didn’t know existed or what it even meant to be a sound engineer, I simply found it because it was a “proper” college degree that involved music, in a country where if you aren’t a professional, you can’t find jobs or actually survive. Read more>>
