Shoot your shot? Take a chance? Society bombards us with messages, phrases, examples and stories of how taking risk is the key to success, but is anything ever that simple? We asked some of the brightest folks we know to tell us about how they think about risk. We’ve shared their responses below.

Joshua Morey | Insurance Broker

Playing baseball my whole life has taught me that life is a game of failure. In baseball, the best hitters fail 7 out of 10 times. Learning to deal with failure has been one of the most valuable lessons I’ve learned as I approach my life and career. Changing my mindset to accept failure as a part of the process has allowed me to get beyond the fear of what could happen and focus on the lessons learned that build for the future. Even when I lose I win. Read more>>

Rhyan LaMarr | Filmmaker & Music Artist

In my life and career I have taken many risks. Some of them were questionable and that mainly comes from not knowing The Lord when i started my journey. It’s funny how we can be so hopeless without our faith and guidance. I used to take all the wrong risks in my life and therefore my career suffered in the beginning. That was all a part of learning and man did i learn. See there is nothing wrong with taking risks you just have to use the proper discernment. In the world they call it an assessment but it’s all under the same root. When I made the wrong decisions, hung around the wrong people and accumulated the wrong persona, I ended up taking major risks with my life and career. Read more>>

Kevin Mangold | Producer & Stuntman

As a professional stuntman and former Thoroughbred jockey, risk is a large part of my life. As long as the risk does not extend to others, I welcome it. Mostly, I enjoy the challenge of doing what others say can’t be done. Truth be told, risk has always played a leading role in my life. The entertainment industry, or any creative career for that matter, requires an obscene amount of confidence and a willingness to hear friends and family hope for a different (perhaps safer) path for you. For me, the most important thing is to be sure that I’m right where I want to be, doing exactly what I want to be doing and it feels like an acceptable risk knowing that any failure does not stop my movement up the ladder. I’ve always rejected the conventional wisdom that one should start at the bottom and work their way up. Read more>>

Kyle Lupo | Dr. of Chinese Medicine and Acupuncture

I say I’m not a huge risk taker, but that’s a lie. I saved up for a couple years as a teenager working at a record shop to move to LA the moment I graduated high school and did it. Back then it didn’t seem like a risk, but in hindsight, it was a huge one I followed a dream. My risk taking didn’t stop there. After chasing a dream or two and not having the success i desires, I found myself over 30 at a crossroads. Not knowing what I was going to do with my life. I had a knee problem that was causing severe pain for about 9 months. I tried steroid injections to physical therapy and nothing worked. Someone suggested acupuncture. I’ve always been attracted to holistic and alternative health but for some reason was so skeptic of acupuncture. Read more>>

Jane Szabo | Artist & Photographer

Choosing to become an artist is a risky decision. There is no clear path to making a viable living as an artist – and each and every one of us is forced to find a way to pursue our creative dreams, and build a sustainable career. For most artists I know, that means a “day job” above and beyond their art making practice. I was fortunate to have a creatively rewarding career in the film industry with a hands-on job, making props, painting sets, and running scenery construction projects. The job kept food on the table, and a roof over my head – but the bottom line was that what I was making at work wasn’t the same as making my own work. About ten years ago I summed up the courage to take on more risk by significantly reducing the hours at my day job to more fully pursue my artistic career. Read more>>

Ana Osgood | Artist & Designer

When I first sat down to this interview I was posed with a couple different questions to choose from. Immediately I was drawn to the question of why I have chosen an artistic or creative career. That seemed very fitting and an obvious choice for me, being that I have always worked in some sort of creative way. But as I thought about it a little more and reflected on my experiences, I realized that being creative is some how already woven into who I am. It has always been part of my life, from very early on. There has always been a natural curiosity and passion for artistic and creative ways that started from childhood for me. As I thought more about these questions and how they relate to me ,it became clear that what has made my experiences so rewarding is the very fact that I was willing to take risks. Read more>>

Lindsey Wilson | Founder & CEO

I’ve always believed in taking calculated risks. There’s always a chance that things don’t work out as we envision – in fact, they rarely do. Despite this knowing, I trust in listening to my gut and following my heart. When things don’t work out there are lessons to be learned, and when they do, it’s often better than expected.. A little over 8 years ago I quit my job and moved to California. I didn’t have a plan, just a one way ticket and a knowing that this was where I needed to be. Starting OWL felt very much the same- I might fall or I might fly. Every step of the way I’ve taken risks and made sacrifices for the long term vision, and the belief in what I am creating. Less than a year into starting OWL, I gave up my apartment so I could afford to keep producing broth- that was an incredibly vulnerable and pivotal time. Read more>>

Grant Gulesserian | Drone Pilot & Camera Operator

Risk is the basis to all growth. Without taking risks, I wouldn’t be where I am today. When I first started Flyby Imagery, I had to pull out a loan and go into debt to start my company. Things were a challenge at first, but with the belief that I would overcome the risks involved in this endeavor I kept growing my company and eventually paid back all my loans. I met some amazing people and role models along the way. They helped me get to where I am. As I am writing this, I am working in Washington State on a TV show for Discovery. Without the initial risk of starting my company, there is no way I would be here. In my opinion. risk is essential in any new venture and it has played a huge role in my life and career. Read more>>

Heather Tucker | Graphic Designer & Business Owner

I knew that starting my own business would be one the greatest risks of my life. One of the things I’ve learned is it’s better to take a risk than live with regret. I have found that since I started taking risks I’ve succeeded more times than failed. Just recently I started my second business, To the Altar, specializing in custom wedding invitations. It’s a risk because it’s not an ideal time to start a business in the wedding industry during a pandemic, but this allows me to take my time to create and build my branding, marketing and audience. Read more>>

Paul Pescador | Artist & Filmmaker

I don’t think of myself as a risk taker, but do find myself making decisions constantly about changing things whether it be how I live or work and how to improve them. I try to allow myself to be vulnerable and I think that in itself is a risk.  This past year and a half I began transition my gender to trans non-binary, which has been a daunting and exciting experience. The process of changing how one moves through the world and how they are perceived is both exhausting and scary, but has really allowed me to open myself up to the world and myself in ways I hadn’t imagined previously. Read more>>

Cynthia Catania | Singer-Songwriter & Producer

I keep discovering that the more willing I am to risk – the better the results. Staying within my comfort zone creates what I already know, what I’ve already experienced. I spend A LOT of time outside my comfort zone. I just finished a project with a group of collaborators (several new personalities in the mix) that was ALL about being outside typical parameters. It was during the entire process, from start to near finish. It is an epic music video filmed in the Sequoias. The entire team (a total group of 6) was outside its comfort zone from preliminary conversations to shoot days to post-production. I’m hoping it turns out as beautiful and interesting as its potential! Read more>>

Kodjovi Olympio | Artist

Living is like being on top of an empty building. The center is the safest place to be, but if you can manage to live on the edge with out falling down, you would be able to see not just what is on top of that building, but also what is at the bottom of it, only then you can truly get a sense of what is going on around you. Yes I believe in taking risks, taking ricks has led me to experiences that thought me about myself and the rest of the world. But I also believe taking ricks is not something you choose or should choose, it is something you feel, it has to be who are. Read more>>

Brenda Salamone | Fine Artist, Writer, Book Illustrator & Maker

To be honest, risk terrifies me, and I’ve let it paralyze me in the past. However, in the last five years I’ve embraced it and in doing so, I’ve opened up my life to some amazing things. It started with quitting a steady job to pursue art full time, a risk that is only beginning to pay off! In late November, 2020, I took a huge leap of faith and leased a semi-permanent vendor space in Carlsbad, inside the Adore Boutique in Carlsbad Village. I set up a shop called Loft & Lair. Eclectic Essentials for Unique Lifestyles, Loft & Lair presents my rescued and revitalized furniture, Salamone Fine Art paintings, fun vintage items I’ve discovered, and my handcrafted papier-mâché bowls and small decor pretties for your Loft or Lair. Read more>>

Natalie Imrisek | Physical Therapist & Pilates and Gyrotonic Instructor

Taking risks is something I learned from my parents. They both worked and had high expectations of me and my siblings. So, I grew up believing risk taking was an important part of growth, life and success. If something makes me a little uncomfortable then it is an opportunity to learn. My life and career have been about seeking new challenges and opportunities. I love taking risks and exploring new places and opportunities. Never settling in one area to long I have lived in many places, such as Chicago, Reno, Lake Tahoe, Newport Beach, San Francisco, New York and now Los Angeles. I’m not sure if Los Angeles is my forever place, but for now I am enjoying all it has to offer. In addition, to experiencing a variety of lifestyles and cultures I have had varied interests. Read more>>

Margaret Burton | Sustainable Streetwear Designer

Taking risks has definitely shaped my life and career. I have lived with open hands and a readiness to go where life wants to lead me. I remember at a very young age I said something like “I will never live there or do that” and an adult scolded me very seriously and said something along of the lines of, “Do not close yourself off to things because you might loose out on where you are meant to be!” It was a very impressionable moment I never forgot. I lived in Ohio my entire life and was awful in high-school so the only option for me was art school. When I was there my confidence grew tremendously. I was into my second year and dating someone who lived in NYC. He said if you are going to be in artist you have to live in NYC. So I visited and realized how many more possibilities there were in life. Read more>>

David Phillips | Professional Visual Artist & Musician

My entire career and life is a risk. I took a risk and showed my first painting professionally at age 12. I played my first rock show at age 14. Music and art have completely controlled my whole life. I have failed so many times that I got good at failure. I became a survivor. I’m from absolutely nothing. The middle of America. Raised dirt poor by a single mother of three. I figured I had nothing to begin with…so why not aim high? Fuck it, I had nothing to lose. I knew being a full-time artist was an extreme risk because it takes you out of the system. You have to write your own rules. Do your own taxes. Pay your own health care. Be your own boss. You have to work six times as hard. You can never retire. What “works” or what “sticks” comes to you through persistence and experience. Read more>>

Samantha Black | Interior Designer, Space Translator & Artisan

I now think of risk generally by Brené Brown’s description of ‘Daring Greatly’. There is a magical sweetness to the vulnerability and bravery needed to jump off the cliff toward the unknown. Through challenge after challenge I began to formulate my authentic design voice. My father a few years ago told me, citing a Psychology Today article, that, ‘resilience is my superpower’. And this to me is what daring greatly entails. I dared to change everything, I gave up all stability and ventured out into the world as a newly divorced single-parent almost 4 years ago, and I was reentering the workforce 10 years behind my peer group. Have there been challenges? Absolutely, too many to count, just ask any parent about homeschooling this year. Read more>>

Greg Harada | Entrepreneur & Go-Giver

I think that being willing to take risks is a necessary characteristic to achieve anything great in life or business. If you don’t take risks, you won’t give yourself the opportunity to really stretch to your full potential nor put yourself in any position to make quantum leaps in your accomplishments. The mind is wired for survival and there will always be those negative thoughts that creep in, sharing ‘perfectly justified’ reasoning for why you shouldn’t do something or take action. The what ifs and negative self-talk will keep most from listening to what their soul really wants. If you are unwilling to take risks, you will live a life settling and wondering… what if? One of my favorite quotes from Earl Nightingale is this: “Most people tiptoe their way through life, hoping they make it safely to death.” Make ‘taking risks, then taking action’ a habit and you will open yourself up to a life of greatness. This is how I strive to live my life. Read more>>

Catherine Ruane | Visual Artist

There are no guarantees in life so why not jump into the deep end of the pool and take the ride into the unknown. I’ve approached much of my life with this attitude and so far I have ended up in places I never imagined I would go. Both awful and terrific. Being a visual artist is somewhat an unpredictable profession but if I wasn’t pursuing that I would be part of the “walking dead”. Risk is simply part of the equation and I have learned to live with the insecurity. There have been times when the path has gotten rough but it would have been even more rough if I had to be working in a cubical with the same daily job description. I had that sort of a job at one point and quit within a week. Taking chances often involves rebuilding things when I fall flat but even then I get a step closer to my goal so I can see a reason for the madness. Read more>>

Dave Tweedie | Composer, Producer & Multi Instrumentalist

I think if your not taking risks then your denying yourself the opportunity to grow and to move forward with your life /career. I’ve historically always pushed myself and put myself in situations where I’ve had to rise to the occasion. I haven’t always succeeded but my failures have taught me how to move forward without fear. There’s always a risk when attempting new things , even more if you’re an autodidact like me but I’ve always found the reward far out weighs the potential failures. The only thing on the other side of fear is yourself looking back at the fear thinking “ is that all it was “. Read more>>

Made of Hagop | Artist & Muralist

The element of Risk is a huge factor in my life. It is the ultimate trust in the unknown, a choice that has proven its benefit to me time and time again. Every journey is personal, but there are so many unforeseen opportunities that come with risk taking. For me, it has been about internal growth and learning about the strength in the core of who I am by building confidence and establishing a deep trust in the Universe which has in turn, shown me a world of new possibilities. I have to be willing to risk everything in order for me to reach my full potential. The road less traveled is not always smooth, but it is definitely rewarding. Read more>>

Lori Sitterding | Photographer

I think taking risks in your life and career is imperative. If you’re always comfortable you’ll never grow. You won’t evolve as a person. I bought a camera that I couldn’t afford at the time, in hopes that it would someday pay for itself with my patrons. I knew dipping my toes into an already oversaturated industry was and always would be a risk. I guess the comforting part to me is that everybody sees things differently and hopefully the way I capture it will make somebody happy along the way. Read more>>

Hunter Wells | Artist & Print and Frame Specialist

Risk has actually played a huge role in my life and career! I was a high school senior in 2012, trying to decide what I wanted to do next. I knew college was the next step, but I had no idea what I wanted to study. The one thing I did know was that I was obsessed with Hawaii, and it was my dream to live there. I began to research college options in Hawaii, and I was actually invited to participate in an early application program for Hawaii Pacific University. I jumped on that opportunity! Luckily, it paid off because that was the only college I applied for! For a lot of people, that was a huge risk. Most of my peers toured and applied to multiple schools, but I put it all on the line for one university. I was accepted to Hawaii Pacific University, and was even accepted into the marine biology program. Read more>>

Brandy Sebastian | Photographic Artist & Creator

When I think about the word ‘risk’ it’s reflected in what we all do everyday, every breath, it’s not a stranger to any of us. Some risks are small and may feel insignificant in the grand scheme of things, while others are life altering. Risk is something that can hold an enormous amount of fear behind it and can prevent anyone from moving forward or can have the big pay off. My business, as a professional photographer, has been like the tide with ebbs and flows often times quite turbulent. I’ve had business partners that have come and gone, sometimes one assistant and other times a group of people working towards my vision, or a 10 hour wedding that I shot by myself. Read more>>

Erin K Flood

I am not risk-averse though I have learned to take the more calculated kind these days than the “jump right in, feet first” kind of my younger days. That carefree or thoughtless (depending on perspective) kind of risk taking was born out of being simultaneously trauma impacted and a natural disposition towards exhilaration. Years later, having dug out of the consequences of many ill-advised risks, bolstered by that unextinguished joy seeking and an analytical mind, I am today, a person who takes thoughtful, informed chances. Risk taking is an important agent of change. Change is necessary in order to move forward, whether in life or career. Risk cannot be avoided. One has to put themselves out there in order to reap reward. Read more>>

Niccola DeVereaux | Visual Artist

Risk is a moving target, different for ever individual. Their is a risk in choosing to be an artist in the US and in running one’s own business however I also see risk in doing something common. The risk of inaction or the risk or making too many risk assessments has always been a constant fear of mine. Their is always a horrible possibility and an ideal situation in every moment and the chips will fall whether the dice are thrown or not. Although I embrace the risk of going for goal I practice a great deal of risk mitigation. I have always had insurance, license, and anything else that might be required to carry out my work. I set up a demo in my studio before I show my work and make sure I have what I need. The only real risk is what I make. Luckily the risk of what to make work about is for me very engaging. Read more>>

Sandy Delgado | Toothpick Artist & Painter

Risk for me has always led to two things; ending up with some sort of take away from not accomplishing what I wanted to, or it working out completely in my favor and it opening doors for me. The unknown of not going for something and living with all those negative “What if…” questions is more terrifying than going through all the emotions you do taking whatever risk itself. I would rather know rejection or failure than live wondering what could have happened if I had just gone for it. We are allowed to fail, we are allowed to learn, we are allowed to try again. I always think of life as something I’m here to experience with everything it has to offer, the good the bad and the ugly. I am here for all of it. Read more>>

Suzanne O’Connor

Risk, it’s part of business. I often look at risk with the “what if I don’t take the risk” question. What do I lose by not moving ahead. I think risk is easier to do if you don’t have that much to lose. It’s harder when what you’re risking is nearly everything. When in doubt, I council myself with, “You only live once.” and “Great reward usually involves great risk”. Do I jump out of airplanes… heck NO! But I do know that you need to jump on opportunities when they show up. I’d rather be brave than boring. Read more>>

Lindsey White | Florist, Artist & Designer

Risk taking…oh boy! I’d say, owning a business is a risk in itself. I’ve always dove head first into everything I do, so starting a business was no different. I was newly engaged in 2015 and really overwhelmed with wedding planning. I knew that I didn’t have the budget for a florist, and figured doing my own wedding flowers was gonna be “sooooo easy” (WRONG, we will get there later). Anyhoo, it all started with a mish mash of artistic floral Pinterest photos, frequent trips to the flower market and a couple free workshops here and there that I had found on Instagram. What happened was, I FELL in love with the flowers. I couldn’t wait to try out new flower recipes, methods, techniques, etc. It just clicked for me. I was in my millionth year of college at Cal State LA (turns out you’re not supposed to do community college for 9 years…who knew!), and I was miserable there. Read more>>