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.

Kelly Wilkniss | Interior and Garden Designer, Podcaster, Blogger, Author & YouTuber

How do I think about risk? Well, I really don’t think about “risk” per se. If you think about the risk involved in every move you make, you’d never get out of bed! That being said, taking action in your business or personal life that would be generally considered risky is imperative. With risk comes empowerment, growth and often success. Even if the so called risk doesn’t pay off right away do not consider it, or yourself, a failure. It is a step, perhaps a faltering one, but a step nevertheless, toward your ultimate success. Thinking about risk and what role it has played in my career/life, led me to consider – what is risk? The definition of risk is: the possibility of something bad happening. Yes, I have made many a move in my career and life that would be considered “risky.” However in doing so, I never thought that something bad would happen. So were those moves risks? You tell me… As in most everything in life, it is all in the way you look at it. Do you see risk or do you see opportunity? My advice, choose the latter. Read more>>

Glennellen Anderson | Music Artist, Actress & CEO

Risk is everything. My career, my successes, would not operate without risk. If I had ever played it safe, I would likely still be living in my little beach hometown, participating in local theatre now and then with a decent job that paid well. Is that a shameful outcome? Of course not. But it would be doing myself + my gifts the greatest disservice. In that reality, the creative in me would be drowning in my thoughts of what could have been…if I had only taken a risk. We can plan, structure and proceed with caution all day long. But at the end of that day, we must take risks. I’ve found that society has associated the word “RISK” with the word “RECKLESS.” It’s why many people I have met fear taking a majority of risks. Financial risks, career risks, lifestyle risks… All of which can be acted on with a level-headed approach. To risk, means to go after something without relying on guarantee. Read more>>

Anna Livermore | Fashion & Business Coach

Risk has been a huge factor in owning V.Mora and starting a company. In the beginning I would take a small risk and see if I would live through it. Then take a larger risks to see if I would live though that. While owning a company for the last 12 years I now know if I’m not taking risks, if I’m not uncomfortable, then I’m not growing. Risk is a part of the game I always try to wager my risk/ reward to make sure the risk is actually worth the reward. There’s the balance of taking risks all the time that aren’t smart. I do try to evaluate that and make sure the risk/ reward pays off. Read more>>

Dianne Galindo | Business Owner

I started my business when I designed assisted and saw a gap within the design and production end. I found it natural to walk between the sewing floor that I grew up in, and help give the designer’s just what they are looking for. Now my business is built on helping designers bring their visions into reality. When I think of risk, I can honestly say my body tenses up. The thought of going into something without knowing what the outcome is going to be is one of the MOST frightening things. With risk comes loss, and the thought of losing for most (including myself) is frightening. I can say I have lost more times than I have won, and have had to start over from 0 more than once. Risks are taken in many forms. 1. Partnerships- sometimes you will find partnerships that start off great, and I do believe there are great dynamics within some partnerships. Understanding each other’s goals is important. You can lose a lot more in not being transparent with the situation from the start. Read more>>

Meaghan Maples | Songwriter & Vocalist

As a kid growing up in the nineties, the conventional path was spelled out; finish high school with flying colors, go to university, get a great job, meet a great guy, have some kids, keep your credit better than terrible… maybe toss in the quintessential soul search abroad during the quarter-life crisis portion. Any path outside of those very practical life choices felt like a risk to me. The course of a woman’s life can be easily guided by society and family and cultural influences, and those paths are beautiful and organic for some, and for others of us, there’s a tether to stray from the implied norm and carve an alternative adventure. I’m 35 years old and have learned a lot by just being a woman of color in a challenging and oversaturated industry. Taking over a decade to get my degree, choosing not to settle down right away, growing to love my curvy body, and working hard to live whole and well and full of joy… Read more>>

Lala Ziemski | Food TV Personality & Hotel and Restaurant Owner

When starting a biz and moving to a new country there is a huge element of risk involved, a lot of unknown, a lot of learning as you go. I guess I have always assumed the risk is worth the reward. What’s the worst that could happen? If I fail, I just start again, perhaps approach it differently, gain knowledge and try again. Taking the risk has left me with such an amazing sense of accomplishment and pride. It really is the best feeling and always worth the risk. Read more>>

Olivia Bellafontaine | Producer

Risk is inevitable in the arts. When I curated the first House of Red Velvet show, I had no idea what we were making. I was very afraid of it not being good enough, or not translating to whoever would come. I rewatched Santa Sangre by Alejandro Jodorowsky and I was inspired and pushed in the right direction. A good friend of mine also listened and gave me the right encouragement to do it. There is a lyric I like in Pink Floyd’s The Wall album. “The bleeding hearts and artists make their stand. And when they’ve given you their all, some stagger and fall, after all it’s not easy. Banging your heart against some mad bugger’s wall.” That is literally what we are doing. Cutting ourselves open for the audiences. Audiences who come in with their own thoughts on the world. Each show feels like a risk. I have found it exciting though. Even if it makes me feel crazy at times. I think if you are a creator, you secretly love this part. Read more>>

Leslie Kenehan | Prints, Trends & Creative Direction

I truly believe that every decision we make is a risk one way or another. The decision to start your own business, forge a new career or carve out your own path in life is no less risky in my mind than taking that full time 9-5 with benefits and wondering what could have been. We are all built differently, and we all need different things to feel safe. I guess for me, making that choice or taking that risk gives me the opportunity to build something, to create a life with time freedom. These things all mitigate that initial ‘risk’. Read more>>

Matt McManus | Host, Comedian, Rapper & Published Writer

Risks. We are told to avoid them as children. We hear, “That’s too risky, don’t do it.” It persists into adulthood, “I don’t know. The Stock Market is risky right now,” or “IDK, moving across the country is risky.” But I say screw it. Except if you’re about to eat a Bat. That’s risky. Don’t do that. Don’t get me wrong. I look both ways. I moisturize. In regards to my art? I GO ALL THE WAY IN. In regards to opening my mouth to eat something new, or challenge who I was and what The World thinks? I’m all about that shit. I’m from Long Island. I’m in LA. I’m nearly 40. I’m a dad. I’ve always had wild dreams and an abundance of bravery. How I got this way? I took risks. Let me tell you a story. There was once an obese little boy with crossed eyes and a heart full of questions, who’s best friends were the stuffed animals in his room that would watch him put on elaborate shows. Read more>>

Stephanie Greco | Yoga Teacher

If you ask anyone who knows me, they would without a doubt say that I am the least likely person they know to do something risky. I am very much a look before you cross, weigh the all options, make a pros and cons list kind of gal. However, that’s not to say that I have never taken a risk in my life. In fact, when I was 21 I left the comfort of my family in Florida and moved all the way across the country to Los Angeles to pursue a career in film. At the time, this didn’t seem risky to me. I knew that’s what I wanted to do and so I did it. I think the way we define risk has a lot to do with our perception of it. Something that is risky to one person, can seem very tame to another. Probably the second biggest risk I’ve ever taken was when I made the decision seven years ago to shift careers and teach yoga full time. Starting over can be very challenging and scary. But I knew in my heart that my purpose had changed and I felt called to teach. Read more>>

Pia Brannen | Artist & Creative

I think of assessing risk as the ability to discern which of life’s many ultimatums will best preserve my health and happiness. Taking a risk forces me to get honest about what I want to happen and how resilient I’d actually be if things don’t work out. The better I understand the ways an opportunity could help or harm me, the more confident I am betting against obvious odds. I’ve had my fair share of impulsive moments. Those are necessary. They teach you valuable lessons that you won’t learn by remaining patient. But when it comes to taking risks in life’s most sacred spaces, my pleasure or profession for example, I take my time. I slow down to do the emotional, spiritual and literal math. Discernment, perseverance and resilience are all skills involved in healthy risk taking that can and should be developed. And if you’re ever faced with a difficult decision and aren’t sure if the risk is with the reward, remember: anything that costs you your peace is way too expensive. Read more>>

Marci Klein | Emmy Winning Video Director & CEO

I don’t think I really noticed what a risk taker I was until about six years ago when I took what I think was the scariest risk…I became a sports pilot. Sure, I have scuba dived, jumped out of airplanes, been in a hot air ballon, snow boarded, traveled alone, hitch-hiked, shot rapids in a class 5 river, surfed tons of pretty big waves, became a tv director, then quit tv after 20 years and opened up my own video production studio, but none of those risks really measured up to becoming a sports pilot. To me flying is terrifying, and yet somehow, I managed to put my fear aside and make the impossible possible- and risk it all. It still blows my mind to think that I flew in a plane – it looks like a hang-glider with a motorized trike – in one of the most complicated air spaces in the United States, from Hawthorne California to Bracket Field in Riverside. Read more>>

Tiffany Broadway | Designer

Risks are necessary. Taking risks has always been a keystone in my life. When I look over all the collective experiences; I’ve taken some big ones. When I am able to enjoy the benefits, I almost forget, almost forget how hard it was. I always look back and think wow that was huge. It gives me crazy energy to keep going and doing 5, 10 harder things, scary things. I am amazed that I had no fear of going through it. Others around me not rocking the boat, playing it safe, and going slow. I realize I am not that person. I believe in self-actualization, quicker. and along the way, you find grace and might just surprise yourself and make a few new friends. Read more>>

Yvette Gellis | Artist & Professor of Art

It is evident looking back to even the beginning of my life that the best choices I made were the risky ones. There was always someone telling me not to do something I dreamed of doing… I never listened, I always followed my intuition. I listened to that inner voice and that always came with big risks. Even today, my work is about breaking boundaries – finding new ways of experiencing painting. If I don’t have that feeling that I might be failing then I haven’t push the work far enough. The work that is the most risky is always the best received. I am willing to fail, and fail over and over again. Read more>>

Ari Gold | Filmmaker

As a filmmaker, every creative project feels like a huge risk. You set aside several years to sail towards a shore that you’re not sure even exists. There is the illusion that you might die, and I’ve managed to actually injure myself on the sets of both of my feature films – once by breaking my arm, showing off a stunt to make the crew laugh in “Adventures of Power”; another time nearly drowning while filming a scene from “The Song of Sway Lake” underwater. More importantly, there’s always the question of creative risk. I’ve taken risks with tone in comedy and drama that meant my films are deeply beloved by smaller audiences, though sometimes attacked by mainstream audiences. The attacks can make the more punk side of my personality feel stronger in my beliefs, but since I want to have an influence on the culture, I want to change the kinds of risks I’m taking. Read more>>

Nathalie Gonthier | Pilates Teacher

Taking risks, jumping into the unknown has played and still plays a huge part of my life and my decision making in life and career. From a young age as a student in high school, I was dreaming about traveling and discovering the world. Starting from moving out of my home town in the south of France, to go live in three different cities ending up in Paris. From Paris I moved to Los Angeles not knowing what to expect. I stayed in Los Angeles and build a career starting from scratch in the Visual Effect world. After over 20 years in post production I decided to change career and became a Pilates teacher. That’s the short story. Along the way, the changes and the unknown have always been a booster for me. There is both fear and excitement in the fact to start something or someplace new. Read more>>

Jake O’Flaherty | Actor, Theatre Producer & Acting Coach

In the Entertainment business, the risk is part of the job. I left a full-time job in Cincinnati, Ohio after college and drove out to LA to start my career as an actor in 1992, not knowing anyone or anything, but I had the passion and the commitment to make it happen. I knew from the beginning that nothing was guaranteed and no one owed me anything, but I started from scratch, taking classes, doing workshops, and got an agent. From there it was my responsibility to book the jobs-commercials, voiceovers, TV shows, plays, and films. I never allowed myself a plan B, and I was ok with the fact that the life of an actor would be a process in which I would develop my skills and get better as I continued with each booking. Read more>>

Silas Ruesler | Artist

My experience as an artist has always included risk. I look at risk as something inevitable and beautiful. That’s the whole thing as an artist, especially a performance artist, you never know if what you’re doing will work out or be perceived in the way you want it to. Specifically with performance art, you have no control over your audience or your environment a lot of time. And it’s up to you as the artist to adapt and stay true to your work no matter what gets thrown at you. Because most of my performance work involves the queer, gender non-conforming, and afab (assigned female at birth) experience, I’m constantly being physically and emotionally vulnerable with my audience. I want to spark critical conversations about gender, bodies, and intimacy, and that often means performing in public spaces. Read more>>

De Camille | Artist & Curator

When you are an artist you know that you can never give up at your passion. The concept of this being a risk is interesting because while on one hand it is indeed a huge risk, until you realize down to your core, that you could never be happy doing anything else. It is then that you know that the only risk is dissatisfaction; working to make money and not living your life’s purpose. As challenging as it has been, I would not change it for anything. Read more>>

Mark Givens | Publisher

My artistic life is grounded in the folk revival, marinated in pop art and seasoned by punk rock, with a healthy DIY ethic running through it all. These elements combine nicely, in a way that encourages me to encourage others to try new things and take chances in their creative lives. Publishing books that fall just outside the mainstream and take those same kinds of artistic risks is what keeps the gears turning and the creative juices flowing. I believe that pushing boundaries and having fun experimenting with form and craft is an important part of any artistic endeavor. Read more>>