In our experience, most folks, including ourselves don’t have enough of an understanding of risk and the role it plays in our lives and careers and so we have made a concerted effort as a team to have conversations about risk with our interviewees. We’ve shared some highlights below.

Isaiah Harmison | Health Coach & Personal Trainer

One of the number one rules I live my life by is; never regret something you didn’t do. The fear of getting to the end of my life regretting the things that I didn’t do or or the dreams I didn’t pursue drives me to take risks. I also believe anything great that was accomplished or created involved an immense amount of risk, courage, and resiliency. I have the desire to become great and do great things, so I’ve adopted risk as a large part of my life. Read more>>

Oren Soffer | Cinematographer

I have a complicated relationship with risk. I am generally risk-averse in my day to day life, avoid confrontation, don’t like spontaneity or surprises, and am generally someone who likes to overly plan. However, I also think that a successful career, especially one in film, requires embracing a certain amount of risk and spontaneity – from accepting jobs last minute that may disrupt major plans but could be career-changing projects or working with an all-new team of people you have never met or worked with before, Read more>>

Yongkai Lin | Production Designer

Being a filmmaker, an artist, and now a production designer, these choices I made were incredibly risky and challenging. We have all heard artists starve, and it’s not an easy route, but just like everyone, the fuel is my creativity and passion. I enjoy the process so much, and I never regret my choice. I still remember the first short film I made in college, with an iPhone, a basic tripod and microphone, and a lens kit. Something just clicked, I never liked schools and learning, but I had the strong urge to learn about filmmaking from that day. Read more>>

Kim Manfredi | Artist

Every day I find a new way to fail flamboyantly. Willingness to experiment through taking risks is what allows me to try new things, build projects beyond my imagination and discover capabilities beyond my belief. There is no way I could have become a full time artist if i wasn’t willing to take a chance on myself. Read more>>

Deborah Shirley | Actress

Choosing to be an actor/actress is a risk. You never know if you’re going to land your next audition. You don’t always know if or when you will be paid. And your loved ones/society will probably mock you (even if it’s lovingly.) Choosing to follow your dreams and passions is never easy. It is always a risk, and it is always scary. But if your goal in life doesn’t scare you then it’s not a big enough goal. I’m not sure who said that, but I heard it once and it stuck with me. Read more>>

Chris Guglielmo | Coffee Roaster

Taking a risk or risks is interesting. The word risk itself has such a negative connotation to it. My business partner and I play in a band called Bayside full time and we have had plenty of experience in the risk taking industry that is music haha. I believe, a lot of times, risk comes with reward depending on your perception. If a risk is taken that could destroy your business than its more of a bad idea than it is a risk. If a risk is taken that can either push you further in the right direction or push you back a step than I think it is a matter of how we view the decision and/or result. Read more>>

Sasha Marie Speer | Artist and Filmmaker

Risk is all about perspective and being really clear on what you value most in life. My father used to always say, “Sash, the only things you ever really have in this life are the memories you create for others.” I do my best to live by this and let this determine the risks I will take in other areas. Read more>>

pearce cucchissi | Mental Freedom Engineer : Former Special Operations Soldier

Taking risk has been a very integral part of my life, much of it has been driven by risk taken. Driven by a curiosity towards fear and what the eventual feeling of overcoming that fear in a positive way would feel like. This manifested even when I was young with sports such as skateboarding and mountain biking, all the way to the sports I played that were more on the rough side such as Rugby, through my military career, the activities I like, and ultimately what I do now. I think human nature is to be curious about what is on the other side. Read more>>

Xiaoqian Zhu | Visual Artist & Stop-Motion Filmmaker

I am sure my opinion does not apply to all the fields. I feel that if you’re willing to take a risk, then it is not really a risk, because you’re willing to take the worst possibility. I think risk is something not only related to our knowledge and experience, but also to our sensitivity and imagination. Risk is what you foresee about the uncertain future. We can always sense risk and to try to avoid them. Read more>>

Lemond IMAG Brown | Artist, STEAM Activist, Entrepreneur

There is no growth without discomfort. There is no reward without risk. Whether it’s risking rejection by asking someone out, or risking a loss by investing millions into a business, the one who is willing to risk the most usually has the most to lose; and the most gain. My career didnt even exist when I started, I had never met any STEAM educators. After my parents worked to help put me through engineering school at Drexel University, I was leaning toward a different career path, it was the first time we disagreed strongly on my life choices. Read more>>

Sophie Spiers | Standup Comedian & Writer

Risk taking is behind everything I do/have ever done. I live to take risks. I’m not saying I hop into strange vans or participate in Ponzi schemes… but I do follow that rush of energy in my gut that comes when I know it’s time to do something new. I recently said to someone, “There’s nothing sadder than living with fear or fear of embarrassment,” and I stand by that. When I feel afraid, I know it’s because I’ve been confronted with something new, and that it’s most likely an opportunity worth taking. Read more>>

Shy Jones | Creative Director & Photographer

My whole life has been about taking risks. But risk backed up with Faith actually guides me. Moving away from LA was a risk. I had only visited ATL once at the time, but made the drive with NO cross-county experience and definitely NO knowledge of driving in snow. Not to mention not knowing anyone. But I decided to take a leap of Faith, and it worked out. Read more>>

Karen Vizcaino | Business Owner / Photographer

I owe most of my business success to taking risks. I feel your hunger for growth has to outweigh your fear of failure and the sooner you take risks, the less you have to lose making it much easier to bounce back. We are always proud of our achievements but our failures ensure that we learn valuable lessons, whether it is about our personality, our approach or our mindset. With each attempt, we have a chance to cultivate a better plan than the last and increase our chances at accomplishing our goal. I have had moments in my career where I have been extremely confident of my decisions and things didn’t pan out the way I had expected. For instance, Read more>>

Cherokee Jackson | Licensed Esthetician and permanent makeup artist.

I think risk is a huge part of most successful small businesses. I once met with a producer when I was looking into transitioning from a stable office job to freelance and she told me to always take the jump and the universe will catch you. It might not catch you in the way you expected, but it will send you in the direction you are meant to go. I have always set myself the best I can to mitigate risk so that when I do take those chances, either way the chips fall is the right way. I am a firm believer in trying. If you try and fail, at least you know it wasn’t the right direction and you never have that “what if” lingering in your brain. Read more>>

Alana Scott | Founder/CEO of Kinkz Hair Products

Taking risk separates those who have a dream and those who live their dream. Risk will be necessary in every stage of your life, but it’s not something many are willing to do. I’ve been asked many times before, what do you contribute to your success? My answer is, I didn’t stop. Even when I risked emptying my bank account on a new launch that may possibly fail, or moving forward with an idea that may not succeed. I didn’t stop, and I never will. I do not define success as the amount of cars or money you have, success is living out my purpose. Everyone has a dream, but those that live their dream are those willing to take the necessary risk to get there. Read more>>

Omotola | Musical Artist

No risk, no gain. You’ve got to take your chances. One of the biggest risks I’ve taken is the path of following my own intuition and desires and facing the possibility of returning back to square 1 at a “late age”. Traveling this path isn’t easy, but it has lead me towards great feelings of fulfillment. On my deathbed, I wouldn’t feel any regret for it. Read more>>

Ani Akpan | TV/Film Producer

Years ago I saw a quote in the hallway of a company in lower Manhattan that read: “Risk is nothing more than solving for x, where x= uncertainty. The good news is, x is a constant and not a variable.” This quote really slapped things into perspective for me. Everything we do in life involves some level of risk; risk is inherent, it is always present. You get into a car everyday for work, you run the risk of getting into an accident. Read more>>

Ilse Duijn | Abstract artist

Taking risks is inevitable if you are committed to yourself -and your growth process- in life. I believe that humans are meant to grow, to move, to strive forwards. Life is dynamic and we should learn how to sail the winds. To me – life is not about containing. It is about breaking the mold and about finding a way to discover your given talents and monetizing those. Read more>>

Jon Benward | Producer & Artist

I think risk is everything. To put it in the most simplistic way that i can, risk is the reason i’m still living. My background as an artist is a pretty humble one compared to the many that i’ve heard over the years. I did however, like many others, grow up in a home that wasn’t always supportive of my interest in the performing arts. When i was young i heard a lot of talk surrounding the college lifestyle and the benefits that a competitive four year degree could reap for me. Read more>>

Yanz Zeng | Artist, Illustrator, Visual Designer

Risk-taking has been a big part of my life in the past 10 years. I moved from China to New York City. I transited from being a food engineer to a visual designer and illustrator. I have been jumping around different creative channels and fields. From exhibition design and experience design to healthcare technology design. From marketing design to print design, illustration, and product design. My business partner has been away from the business we created for a while and came back in the last few years. From working with my business soulmate from the same time zone to 12 hours away. Every step has been unexpected but this ride so far is very exciting and rewarding. Read more>>

Janelle Gatchalian | Screenwriter

Risk for me is all about baring your insides, and making yourself vulnerable to exposure. That’s scary! I grew up in Manila, Philippines and was creative as a child. I created books with stories out of the paper my dad brought home from his job at the printing press. Yet I didn’t imagine I could carve a career as a writer. For the first 25 years of my life, I was afraid to take risks and make myself vulnerable. Read more>>

Rachael Gillette | founder

I think Nelson Mandela truly said it best-“there is no passion to be found playing small and settling for a life that is less than the one you are capable living.” Taking a risk and venturing into the unknown can be quite intimidating; there is often a fear of failure. But without risk, I believe there is no reward. As I have gotten older I have realized that the chances I haven’t taken, are the ones that I have regretted most. And have learned that not all failed risks are negative. Sometimes they can provide the most valuable lesson one can learn; and those lessons can be truly beautiful. Read more>>

Athena Garcia | Actress & Dancer

As an Actress and Dancer, every decision I make is another risk I’m taking that reflects how I live my life. I’m an over thinker which can hold me back from a lot of opportunities but once I get that leap of faith to take the risk and go the extra mile, in the end, I never regret it. I think, without the passion and drive that I have to achieve my goals, I wouldn’t be able to motivate myself to take risks. I like to think of risks as a way of overcoming my fears and being able to experience things that I’ve never experienced before. Read more>>

Katrina Darby | Visual Development Artist

I believe risk is something everyone should take to a certain degree. Without it, life would be a pretty mundane path to go through. I would say risks in my life have played a major role, in which it has led me down certain opportunities that I would have never expected. Risks have also played another role in helping me seek adventures in places far and beyond! Due to more travel in recent years, my perspective as an artist has expanded immensely due to the world being my own set of inspiration. Read more>>

Shira Myrow | Psychotherapist and Relationship Expert

When it comes to risk, I actually think of myself as quite risk-averse, and yet when I look back on my personal life and career, I realize that I still managed to take risks in big ways and small ways that deeply impacted the trajectory of my life. Risk has to do (in part) with your relationship to uncertainty, agency and failure. And you can’t really know where you are with these aspects of life until you live the questions to some degree. Read more>>

Nicole Mallari | VINTNOIR Founder

To be honest I feel like I’ve played it safe most of my life. From high school to graduate school , and into my public service career. I told myself that I had to check off certain boxes and that would lead to a fulfilling life and career. I’m proud of what I’ve accomplished but I don’t feel that I took any risks until now. During the pandemic I had this wake up call. I felt like I was on a hamster wheel. There was an overwhelming desire to make a change or be left with regret. I decided to take a risk and pursue something that I’m excited about, and that’s celebrating Black winemakers, merchants and negociants. Read more>>

Alexis Toney | DJ/Producer & Analyst

If you want to be on top, then you gotta take a risk – point blank. I think there are levels that come with risks as well. Everything doesn’t need to be some drastic thing – a risk can be something small like reaching out to someone for help when you usually tend to do things on your own. That’s something that’s been key for me – realizing that it’s essential to take risks for growth but also understanding that as long as I’m attempting something to make me uncomfortable or doing something I wouldn’t normally do – that’s a risk in and of itself. Read more>>

Gretchen Voelcker | Winemaker & Winery Owner

Taking risks has been my guide to where I am today, and I have always viewed risk as intimidating, yet great opportunity in my life. Even at a younger age, I had a very adventurous spirit that encouraged me to take the risks presented to me. In high school, I had worked hard to be at the top of my class and get accepted into a national drumcore, which took countless hours of practice and perseverance, but when presented with the opportunity to move to Brussels with my parents for my mother’s job, Read more>>

Emma Kopkowski | Freelance Director and Unscripted Producer

I’ve always considered myself a type-A, stability craving person when it comes to my career, so the decision to freelance felt like a massive risk to me. When I graduated college, I was considering two routes: a corporate job within the unscripted industry or freelancing as an unscripted producer. The latter felt like a massive risk, but it also felt like the way to scratch my creative itch and get to learn the industry in a hands-on way. A mentor of mine told me it would be a mistake to start in the safe role, and that early in my career is the time to take risks and throw myself into what scares me. Read more>>

Taline Postajian | Public Relations & Social Media Manager

One of my favorite finance professors would always say “No guts, no glory” and the older I get the more I realize how true this is, not just in finance but in everything we do. It takes guts to go after what you want. To pursue something you came up with in your head and turn it into reality, not knowing what the outcome will be. To start that business, or new job. You have to take risks or be okay with staying stuck where you are. This doesn’t mean take unnecessary risks or to invest in risky projects. It means dare to succeed. Read more>>

Elle Vernee’ | Actor, Writer, Producer, Theater Director

In my opinion risks are necessary if you believe that your life has a unique purpose. While I do believe taking risks is important, I am a bit of a procrastinator in carrying them out. The thought of being 80 years old and looking back over my life wondering “what if” is frightening and seems like mental torture. It’s this fear that eventually inspires me to act on any risk that I need to take. Whatever happens at least I won’t be wondering “what if”.  Read more>>

Timmy Ong | Actor & theatrical artist

Talks and questions about risks and risk-taking hold a special place in me, because I used to work a corporate job–in the Risk Management department–before I transitioned to be a full-time actor. In the nine years that I have worked as an actor, I still think about the lessons and tools that I learned from that time, and how I can apply them. Read more>>

Jenie Gao | Artist, Creative Director, Consultant on Equity and Ethics

I have built a successful business as a full-time artist, as a woman of color, second generation Taiwanese-Chinese American, and daughter of working class immigrants, in an arts industry that is structurally designed to rely on unpaid and underpaid labor. I am the outlier statistic. There are two big risks that I regularly contend with. The first is that I am a primary breadwinner in my household, in a field that is notoriously difficult to succeed in. The second is that I am outspoken about issues facing marginalized artists and exploitations of the arts industry, while enduring the harms of the current system myself. Read more>>

Alexandria Corn | Nashville Musician & songwriter

I think taking a risk scares a lot of us. We are typically used to our normal routine that goes well for us, and we get scared of the thought that something can interrupt that and go “wrong.” For me, it took one risk I took for everything to go right. So from now on, I believe taking risks can be the key to success. And if you fail, you can always try again. Being in music, I’ve been told “no” for years. When I started taking risks and doing things differently or “my way,” I was starting to be a massive change in how people perceived me. Read more>>

Steven Vargas | Hip Hop Artist

Risks shows how much a person is willing to dedicate their time, energy & money to a goal and/or dream even knowing that the odds may not work in their favor. At this moment in my life I am taking a bigger risk with pursuing my music career. I stopped working a full time job and transitioned to working a part time job so that I can have more time to invest in my career but it does have it’s downfalls. Certain struggles that I deal with on a daily basis is the fact that I have way less income, which means I have to cut back on my spending and budget my money correctly to be able to pay my bills and get groceries for me and my girlfriend. Read more>>

Neiko Neal | Actor & Entreprenuer

Risk for me is essential to growth, in my opinion. I have a hard time settling for the same old thing because of fear. If you are on the road and not moving because you are afraid to pull into the Fastlane, your never going to make it to your desired location. Don’t be that car on the side of the road, constantly missing out on opportunities because you’re too afraid to put yourself out there. You have to take a ‘risk’ to grow. Read more>>

Desmond Sam | Event Producer, Model Agent, Publicist & Entrepreneur

Risk is inevitable if you’re trying to be successful. The number one lesson I’ve learned is that I am my most productive when I am uncomfortable within a space. The times I doubt myself and have to fight through that doubt by breaking out of my comfort zone is when I personally feel like I’ve leveled up mentally and physically. Through my life and career I’ve been know to switch paths a lot. Read more>>

Michelle Majors | Singer/Songwriter/Actress

I think by a lot of people, sometimes risk can be seen as something that may not be good. The truth is that risk is crucial to growth and success. Yes sometimes risk can be tricky, but most times risk is the thing that gets you where you want. For example, I lived in Philadelphia my whole life and when I ran out of resources for my music career, I made the decision to move across the country to LA. Now this is risky because it’s basically like starting a new life, across the country, by yourself with no family or friends. It can be scary. I knew though that if I really want to succeed that my next step was taking this risk and moving to start the new phase of my life. Been here for almost 3 years and I never looked back. Read more>>

Glenn Simmons | Professional DJ

Taking a risk is how i was able to be apart of major events like B.e.t and even played an extra on creed 2 . Taking a risk help pushed my dj career foward a lot . The worst thing anyone can tell you is no and thats not even the worst thing . Read more>>

Nazar | Dancer/Choreographer/Model

When we use the word ‘risk’ we think about a situation involving exposure to danger but in an artistic career it’s different. It is more about changing all your plans and what society expecting from you. Being a dancer/choreographer is risky for People who get a ‘normal job’ because it’s not considered as a serious job in our society. Taking risks played a big role in my life. I had a cancer so I decided to take a risk to live thanks to my passion. It was risky because I was just graduated with a master’s degree and I didn’t planned to be a dancer especially in my culture (Middle east), Read more>>

Roshni Lulla | PhD Student & COO of Recordless

Risk has played a big role in my life. It started out by hitting every roller coaster as a kid, even going as far as wearing heels under my jeans to make the height limit. This risky spirit followed me to college and throughout my career. As a junior at NYU I was given the opportunity to graduate a full year early and get a head start on my career. I had the option of staying in school and adding on a major, getting a job at NYU and staying in New York, or moving across the country and starting a job at a brand new lab at Stanford University. Read more>>

Talia Shipman Englander | Artist & Founder, Social Hummus

I see risk and growth as intertwined. A lot of people think it’s brave to risk failure, but to me, it’s not about failure and mistakes, it’s about learning and growing. It’s taken A LOT of risks to get where I am, but none of it feels like I’m a martyr (even though times often felt hard)…it’s just my path. Some paths are more linear, and some are a bit more…zig-zaggy. I’m a curious person, so I like to look behind every door. As I learn to grow my trust-muscle, I can now intuitively feel into what risks feel good (even if a bit scary) vs. the ones I used to take just to get a rush. Read more>>

Lakita Jones | Entrepreneur & Caterer

When it comes to risk taking, it can be a scary and uncomfortable thing. Even in the uneasiness it has pushed me out of my comfort zone, and exposed me to so many more business opportunities and connections that I never thought I could reach. Not knowing how my very first dinner sale would turn out, I risked finances out my own pocket and home to get Soulful Plates started. Had I not took that initial risk to start my own catering business, I would still be leaning 100% on working for someone else. Read more>>

Elizabeth West | Photographer & Visual Artist

I’ve come to realize that I’m quite a risk-taker and that risks are a necessary part of life, despite the fact that they by nature are terrifying and uncomfortable. One of the first risks I took was not going to college right after high school. I somehow felt as though I wouldn’t fit in and wanted to take some time working and living in a new place, on my own, without the confines of a school environment. There are many times when I’ve regretted taking that path, but I do think it led me to the artistic place that I am in now, and of course, I’ve learned from many experiences I had in the “real world” at that time. Read more>>

Stefanie Garcia Turner | Founder of TUYYO Foods

I’d say I was raised as a pragmatic risk-taker which sounds like an oxymoron. But I view risk as a given in life and the only difference in the risk level is how far people are willing to step into the unknown. For me, I’ve looked at opportunities that have arisen in my life and career and have firmly picked the path that I wanted to pursue the most. But I’ve had to go into it thinking, ‘well if this doesn’t work out, I always have X’. It’s kind of a mind trick that has helped me be brave enough to make these decisions and take the risks that otherwise I may have shied away from. Read more>>