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.

David King | Restauranteur & Cocktailian

Risk is a funny word; it almost acts as a euphemism for “fear”. If you ask a business owner if they are afraid to take risks they will inevitably say “no”. Yet, if you ask the same business owner what fears they have for their business most will provide a litany of potential catastrophes. Therefore, I’d rather frame the discussion of the role of risk in my life/career with the way I acknowledge and evaluate fear. I think for most small business owners it is extremely hard to accept that your business might fail. We put so much love and work into our businesses that we’d never want to imagine that it might not work out. In reality, there is a large chance we will have to close our business within the first two years of operation. The small business start-up statistics bear this out. So I try to refrain from simply thinking that, “It won’t happen to me. Read more>>

Katelynn Mills | Artist

In the always brilliant words of Dave Hickey, “there are pirates and there are farmers.” I am, unmistakably, a pirate. And even though being classified as a woman-anything (i.e. woman-artist, woman-auto technician) typically pisses me right-the-fuck-off, I cherish and acknowledge the Wild Woman (or lady pirate) archetype I manifest. Taking risks means something different for every one; pirates and farmers don’t think about it the same way. A farmer might make a calculated investment while a pirate may sacrifice a comfortable situation and move to a foreign place with nothing but a backpack and a feeling that she’s doing the right thing. Generally speaking, risk is something women are socialized/ trained to avoid. Personally, I have a lifetime’s worth of examples to point to. When I was thirteen, my parents gave me a “promise ring” and made me promise that I would “remain pure” until I met my husband — and was later demonized for exploring sexuality. Read more>>

Letxia Cordova | Director & Dancer

Risk taking is so important! I think you’ve got to be willing to take risks before, after, and while you succeed. I once drove 14 hours roundtrip from LA to film a dancer I admired. She was from Humboldt County and after dm’ing her on Instagram had agreed to dance for a music video of mine. I was so excited! I loved her work and had spent weeks conceptualizing a music video for her. I drove by myself 7 hours just to find that the roads were closed and would call for an additional 5 hour detour. I was exhausted, and after a lot of texting friends for advice and moral support, I decided to cut my losses and head back to LA. I think any time I’ve decided to pursue my passion has not been in vain, even if it ends up as amusing as that story. I look back on that and treasure the idea that I decided to go for it. Read more>>

Rodrigo Varandas | Multi-faceted Actor, Singer, Dancer, Photographer and Writer

Risk huh?! Well, I don’t think a person can fully achieve their true potential without risk. I am a tad crazy so I took a step further and made risk part of my life. I left my home country at the age of sixteen and never looked back. After that, I was constantly making big moves in order to remain in the US and/or get a better opportunity in the business. Read more>>

Shane Stanley | Filmmaker

I subscribe to coach Bruce Arians’ approach of “no risk it, no biscuit” and always have and believe anything worth doing is worth overdoing. I worked for over 25 years to get to a point in my life where I could do what I wanted to do and have never taken the path of least resistance to achieve that. My goal was to become a gamechanger and in my business, that was about punching way above our weight class and showing Ho-Ho Wood that you don’t need tens of millions of dollars to make a film that feels like you had it. In order to accomplish that, I had to partner with people who believed enough in me to allow us to take the reins and do things our way. Read more>>

Davi Lorenzo | Singer-Songwriter & Professional Dancer

I think risk as everything to do with the way my career has blossomed throughout the years. Without it, I wouldn’t have left my home town in Spain and move to Paris to become a professional dancer and from Paris to Los Angeles to dance for international artists and to start producing and writing my own music. I could have chosen another path, one full of safety and comfortability but, where is the sense of adventure and discovery in that. Read more>>

Ashley Von Helsing | Photographer, Artist, and Designer

I’ve always believed risk is an essential in understanding the push and pull of life and business and my ability to take them has been due to my early life experiences. Not growing up with a lot of opportunity and living in a rural conservative town, I had no choice but to be mentally ready to jump knowing there was a high chance of failure. The thing is though, is that every time I’ve done a giant nose dive into uncertainty, whether it be packing up and moving to a new town, switching professional careers, or even taking new approaches to art, I’ve grown through the decisions good or bad. If you’re afraid to fail, you’ll never know how how satisfying it is to grow from the unknown. Read more>>

Natasha Wilson | Photographer

In 2011, I graduated from photography school feeling pretty lost. I understood that I loved photography and had a passion for it, but I didn’t understand how to jump from student to a high fashion photographer like I thought I wanted to be. I traveled around for a while, immersed myself in different cultures and climates, and eventually moved to Los Angeles in January 2015. My roommate Cole convinced me to start an Instagram account to display my work and cultivate an audience. I started posting images from my portfolio daily and to my surprise, I saw a quick response. I jumped to about 4,000 followers after just a few months. During this time, I was working at a furniture company, daydreaming about being a freelance photographer. In June I decided to take a leap of faith and put my two weeks in to pursue my dream. The last day at the office I had butterflies in my stomach about what the future held for me, and if I was going to be able to “make it” by being my own boss. Read more>>

Zach Meyer | Artist

You never know how good you can be as an artist until you take a risk. It took a risk to start my career. Risk informed my career in ways I would have never expected. I remember I had just finished art school and I was working a job that I hated. I knew at that point to get out of my situation that I really needed to market myself in the art world. This came with an expense. I needed to purchase a client list so that I could find art directors and gallery curators emails. I ended up spending my paycheck on a list of art directors and galleries, not knowing if this risk would pay off. That turned out to be my last paycheck at the job. I was lucky to be able to quit that job shortly after and switch into full-time freelance work. Any move to succeed as an artist involves calculated risk. Many people are scared to take risks in their career, or they get comfortable working a job they don’t enjoy. Some will even turn down work they aren’t confident they can do. Read more>>

Parker Smith | Hat Maker & Musician

Ive been self employed and have made a living off of my creative instincts for as long as I can remember whether it be my music or hatting career. There have absolutely always been ups and downs and that is a risk that you take when you bet on your vision for a career. At this point I feel like taking a risk and going for something I believe in is not even a question of if I should or shouldn’t go for it. There is a drive and motivation you get when you go all in and take a risk on yourself and your talents, whatever they may be. The feeling you get when it works out, in one way or another, is a feeling I’ve not felt elsewhere. Small victories become your driving force and big victories become the cherry on top. Risk is something that I think scares a lot of people, maybe because failure sounds scary, and if you do fail in someway its easy to blame yourself. But I promise you, you didn’t fail in every aspect. Read more>>

Tim Carr | Actor, Film Director, and Activist

Sometimes you just have to get out of your comfort level and just go for it. Risk taking has been such a driving force for me. Career wise, there have been moments where I had left a lot of money on the table for one project in order to do a project that just “felt right”. There are 2 movies I am incredibly proud of called “13th Grade” and “Down With The Boogey”, for both of those movies, I had the option to do those or projects that may have had a larger paycheck attached. Those are never easy decisions to make, the ultimate “take the check or take a project that feels creatively fulfilling?” If faced with that same choice now, I’d do those movies 10 out of 10 times. Neither one broke box office records, but the opportunity to work with such great directors, great scripts, great casts, when those things line up, it can feel very fulfilling career wise, but for movies like this? When all of those things line up AND they become these truly original movies that connect with their audiences? That’s enough to make your soul sing. Without taking risks, you don’t get that soul singing. Read more>>

Anton David Jeftha | Actor

As an Actor, for me its all about taking risks. I had initially studied and completed a degree in Finance, and decided to drop out of my post graduate finance degree to pursue Acting. That was the very first massive risk, as they say its hardest to start..and since then its been a series of risks which have led me to where I am today. However, it is one thing to say Im just going to roll the dice, and another thing to put the work in to make sure the risk pays off. Since becoming an Actor 10 odd years ago, its been a rollercoaster ride of up’s and down’s and throughout Ive had no plan B and the tenacity to stick to the game, assess the amount of effort neccessary to succeed and to keep showing up. I took a major risk 5 years ago, moved to LA barely knowing anyone there and pursued my career out there, now I am fortunate enough to have a presence in both the US and my home country South Africa. Read more>>

Baker Chase Powell | Actor & Filmmaker

I think that in order to grow, not only as an artist, but as a human being, we have to take risks that force us to step outside of our comfort zone. I think risk-taking is actually ingrained in the art of acting. It’s necessary for any character or story to have something at risk or at stake, otherwise the story would be quite boring. Even with auditioning- if you’re only reciting the lines and giving them the performance that you think they want, then you’re not bringing anything unique to the role. In order to stand out, you need to be vulnerable and bring yourself into the role, which in itself, is taking a risk. Read more>>

Amelia Burns | Photographer and Multidisciplinary Artist

Art is a risk. From asking people to take their photo, or sharing my art with the world, I am always risking something. I think being an artist, or being a fully self-expressed human, involves risk at every level. For me to create work, I have to risk it being bad. I have to risk when I get up in the morning, that I may put out my best and still fall short of what I intend. I think in order for me to be successful, I need to risk something. The more scary it is, the more important for me to risk facing that fear. The more risks I take, the further I discover who I am and who I can be as an artist. I am always pushing myself. In full disclosure, I don’t feel I take enough risks in my career and work, and I am changing that. Read more>>

Brian Cavallaro | Producer + Director

Every time you commit to a project it’s a risk. If it’s a personal project you’re taking a financial risk as well as an emotional one — but even work-for-hire jobs run the risk of not panning out or turning into something you’re not particularly excited to work on. Read more>>

Eric Jordan | Designer

Life is a risk. However, I feel, most people view this in reverse. Often the big endeavor is looked at as a risk. I think, it is risky to diminish success before even attempting. In other words, not going for it is what should be looked at as a risk. In my life risk has yielded both failure and beauty. Having children is a risk. Their life is the reward. Working for myself is a risk, freedom and significance is the reward. Without working through the risk, it is difficult to know what wonders await you on the other side. Read more>>

Dino H Carter | The Brand Whisperer | a Brand Strategist & Marketing Consultant

I believe that risk-taking is crucial for success. Risk is subjective, and it changes from one person to the other just as the definition of success is subjective. I think the biggest risk one can take is to believe in oneself. Taking a chance on yourself and go for it. I took a huge risk by moving to Los Angeles from Israel at the age of 37. It meant “closing” a grown man’s life, get rid of everything, your friends, family, position, and go into the unknown. It’s hard to take risks when you feel like you have something to lose, but if you want to grow and be more successful it’s a must. This is something I constantly need to remind myself on my journey of growth, but if you think about it, what do you really got to lose. Read more>>

Leslie Alejandro | Director/Photographer/Writer/Producer

I think taking risks is essential for anyone who wants to pursue their dreams – Especially when it comes to creatives. There is no guarantee of financial success or acknowledgment when it comes to being a creative in any industry. I take pride in the risks I take. I took a risk being a career musician for the better park of my teen years and into my early 30s. Then I had a family and had to switch careers in my mid-30s when I went into beauty doing hair and makeup, which transformed me into being a creative director and editor for a fashion/celebrity magazine when I was in my late 30’s. Then at 40, I found photography. Once again, I took a risk by finally realizing that my love for photography would lead me into pursuing it full time as a professional. And most recently, I took a risk by wanting to use my love for story telling through still imagery, and applying it into filmmaking. Then at 42, I took directing courses at UCLA and finally ended up directed my first film at the age of 43 years old. Read more>>

Alessandro Gentile | Film Festival Artist Director / Cinematographer

Sometimes in life you need to take big risks that can potentially impact the trajectory of your life. I the case of 2020 it seems like everything is a risk. As the artistic director and co-founder of the Highland Park Independent Film Festival we were faced with a big challenge since the movie theaters were closed due to the pandemic. We had many discussions and knew that we didn’t want to do what everyone else was doing (The Virtual Film Festival). We wanted to do something interactive but safe. That’s when we can up with the idea of producing the first drive-in film festival in Northeast, Los Angeles. “If you jump off the cliff the net will always appear.” Read more>>

Allegra Richdale | Founder of Tessa James

I am a huge proponent of risk. I came from a highly academic background, but my childhood dream was to become an actor. I took the leap right after college, and launched a ten-year career that led me from New York to Los Angeles. Exhilarating times, and indelible experiences, but ultimately, not the road I wanted to pursue as I entered my thirties. So, I “pivoted”—to use the buzz word of the day-and made another leap to law school, and an ensuing career as a litigator. Though I relished a return to academia, the law proved to be too far from the creative sphere for me. I thought long and hard about the next step, and then there was an answer. Tessa James is the perfect marriage between engaging, challenging work and artistic expression. I have finally found the shoe that fits. And I have risk to thank for it. Read more>>

Donna de Soto | Designer and Ceramic Artist

Risk has played a significant role throughout my life and career. Evaluating risk vs. reward is something humans do using quantitative data, historical experience and intuition – both science and art. And while every risk I have has not necessarily led directly to a “success,” each one had been a learning process that has ultimately broadened my horizons and knowledge base. Read more>>

Summer Jordan | Health Food Business Owner & Fitness Instructor

As someone who is usually risk-averse, I have come to learn and appreciate the value that can come from trusting your gut and just going for it. Taking risks can feel like a trust fall with yourself in a way — everything is on you. However, there can be great lessons learned from whatever the outcome may be. Read more>>

Shanna Forrestall | Storyteller, Advocate, Animal Lover, Human

I believe intelligent risk-taking is one of the primary ingredients in experiencing success in any area of our lives. When I look back at the things I am most grateful for or most proud of – they would NEVER have happened without some risk. As a creative, it’s typically in taking a “risk” that I find my best work. The “problem” with risk-taking is that we fail sometimes and we believe for some odd reason that that is strange or unacceptable, when it’s failure that is often the BEST catalyst to success. As a human, I know that my greatest loves were often the greatest perceived risks, because they came after many failures and I knew what I could lose. As a humanitarian, without the risk of stepping outside my comfort zone to help others, and by risking my time, money, talent and/or emotions I would not have the amazing memories I have or have been able to help so many after devastating losses caused by natural disasters. Did it hurt my heart… yes… was it often emotionally painful, physically uncomfortable, ego challenging and/or financially straining … yes… but was it worth it …? ABSOLUTELY. Read more>>

Priscilla Woolworth | Online Retailer, Writer and Environmental Advocate

I’ve taken so many risks in my life that I have lost count! The risks I have taken have happened when an unexpected opportunity presented itself, one that seemed promising and of course with no guarantee what the outcome would be. Some risks have been worth it and others, perhaps not as successful but still worth it for the life lessons learned which have in turn helped me in other situations down the road. Taking a risk, as long as your life or someone else’s isn’t in harm’s way, is so important to living your life to the fullest by not being afraid to try something new and different. Risks do have to be weighed for their worthiness but they shouldn’t be avoided because they may disrupt your life. Disrupt your life! Live it as fully as you can, and when an amazing opportunity presents itself to start a new career, travel or meet someone for the first time, do it. Most risks will definitely take you out of your comfort zone, and this is a good thing. One of the biggest risks I took was starting an eco friendly e-commerce store without having experience in running a store. Read more>>

katrien van der Schueren | Artist and Founder of voila! Creative Studio

Without risk there is really no business when it comes to creative businesses. Innovation is key to success in our type of work. Every step of the way, each decision, each push for change or for something new means taking a risk in some way. There is no creative new idea without taking the risk to fail at executing it. Sometimes you ll try something and it won’t work. Better to have spent time trying, then spent time thinking about to do it or not. If you see something doesn’t work after all, you can always change route and you ll have learned from it. Not taking the risk of doing it, will slow everything down in stead. If you stay stuck in certain ways and don’t embrace some challenges, I don’t think you can evolve profoundly enough to stay relevant in this industry. Read more>>

Rochelle Botello | Sculptor

As a sculptor, risk is always about pushing the work in new directions whether in materiality or process. I make objects. I love to use every day materials in unexpected ways. I like to be engaged in an intuitive impulse. A huge part of risk taking is embracing the unknown. I’m often asked if I work from sketches. The answer is no. I prefer to begin by taking one action that informs the next action. I’m always open to seeing what forms start to develop. I have to trust the process. Risk for me is always associated with being open to the process of discovery, wonder and curiosity. I’m interested in using materials as a way to mark these curiosities. I’m fascinated by the bend of a leaf, knee bone of a dog or the anatomy of a grasshopper. I’ve even fallen in love with the fold of a potato chip bag. My observations of the world around me have sustained me as an artist and it is what compels me. Read more>>

Tess Israelson | Sculptor/Artist/Adventurer

Anything worth having requires some kind of risk. You can plan all you want, but at the end of the day, everything you’ve worked hard to accomplish might fall apart. So you might as well take a chance. For some people, choosing what’s easy or safe, over what’s uncertain is just too much of a risk. Creating the life you want is scary. It involves courage, innovation, motivation and risk. All of my major life choices have been risky. Choosing to move far away from everything I knew was a risk, choosing to follow my dreams was a risk, choosing to be honest and true to myself is a risk. But it’s the only way I know how to live authentically. When people say I must be brave, I tell them that I am not brave. In fact I get anxiety every time I travel, I feel uneasy every time I’m about to show my work and as an introvert, I sometimes find it very challenging to interact with people. But guess what? I do it anyways. Read more>>

Jethro Astle | A Teacher and Part Time Rock and Roller in Boa Constrictors.

I was thinking about how in school and parents always talk about how life decisions are risky. They say you should make smart decisions or try to be smart about things. But that isn’t true at all. Everything is a risk if you accept the game that is played by the banks or system. If you want to be successful in that system, you have to play by the rules like at Chuck E. Cheese. You want prizes, buy the coins and get their tickets. But why not just leave and make your own? This probably sounds like ranting and raving but maybe it will make sense in your head. The only real end to everything is death. Don’t risk your life with rock climbing and sky diving (which I see way too often on Tinder). Start a business, start a band, make money, get dumb jobs, go to school, paint, make movies, be a doctor; life is daily risk. I’ll steal a Steve Jobs quote (paraphrased) even though he is an asshole: The only time you actually win big is when you risk it all. Read more>>

Dereck De Mesa | Audio Engineer & Content Creator

I believe risks are very important in a persons life. If you take risks and put yourself out on the line, you create a whole set of opportunities for the future. You can generate many possibilities, whether it’s achieving what you originally set out to do or unlocking a door you hadn’t even considered yet. Even if you fail, it’s beneficial because you gain valuable insight and experience from failure. Essentially if i had not taken certain risks, I wouldn’t be where I am today. In fact it was 5 years ago (2015) where I decided to quit my job and attend SAE Institute of Technology. Within 3 years I was able graduate from the Audio Engineering program and immediately started working as an intern at multiple recording studios in the greater Los Angeles area. Now I am building a network of clientele and working with various artists in different creative industries from all over. Read more>>

Laura Viapiano | Abstract Oil Painter

I feel strange about calling myself a risk taker, because I’m definitely no daredevil of life. That said, I’ve never been one to strive to fit in or do what everyone else is doing or expects. I don’t mind being uncomfortable for a while if it means I am staying true to myself, and the end result is happiness and alignment for me. I did really well academically, but chose pretty uncertain careers to pursue; TV writing and production and abstract painting. When I was 24, I moved to Los Angeles from Buffalo, NY with no job and very limited funds. I think a lot of people who knew me at the time saw that as a risk, but when I got to LA, I was surrounded by tons of people who had done just that. I think risk is about perspective. I’ve always been very intuitive in my decision-making. I try to do what seems to align with my personality and my inherent purpose. Read more>>