Legend holds that Cornelius Vanderbilt had built a massive fortune in the steamboat shipping industry, but then realized the railroads were the way of the future and invested almost his entire net worth into railroads.  The gamble paid off and made Vanderbilt one of the wealthiest entrepreneurs ever.  But risks are inherently…risky.  How do you think about risk and how has it affected your life and career?  Some of our community favorites share their perspective below.

Bryce Oprandi | Tattoo Artist

Risk ‘makes’ everything happen for a reason, in my opinion. Don’t try anything; just do it. If I didn’t take a risk, drop out of college & athletics and forego a scholarship all just to learn how to tattoo…I certainly wouldn’t be where I am today. I’ve been able to travel the world, meet the best people, try the best food, and really experience things I normally wouldn’t do without taking risks. I take risks everyday with my artwork. I draw, paint, and tattoo what I want to. Regardless of what people think, I take the risk to differentiate my work and style from others. That’s really what art is about. Taking the risk to make something not everybody is going to agree with so you can create a conversation. Good or bad, being able to rely on risks is definitely going to define how you are perceived. And if you stand by the risks you take, you will hopefully prosper and flourish. In th 13 years of my professional tattoo career, if risk has taught me anything, its that taking risks makes us all the most vulnerable, and from that you truly learn who you are as a person in one way or another. Read more>>

Xavier Jones | Style Enhancer, Influencer

I believe that taking risks are essential to achieving your goals. Taking risks gives us the opportunity to discover more about ourselves and develop new tools in order to grow. Moving from my hometown in Indiana to New York after college has been one of the biggest risks I’ve taken in my life. It forced to get me out of my comfort zone and break down my many walls and fears I had about pursuing my passion. It gave me the opportunity to discover a path of my own and lay the foundation that I am continually building on today. Once you take that crucial first step you really discover who you are and can more confidently be you. The sky is the limit when you believe in yourself. Read more>>

Bart Mastronardi | Photographer/Director & Teacher

Risk is me being naked on top of a tall cliff, looking down at a river moving quite fast, and knowing I have jump from the cliff into the river of life. Not only is the river moving fast it is cold and I am naked. It’s all a metaphor. We are all vulnerable. We all know we have to take a jump at points in our lives. We all know life can move fast at times. In the end we all have to do it if we choose to. I choose to take the risks. I also know I have train myself to be prepared for the results when I do jump into projects, life matters, and situations I may not understand once I am there. Without taking the risks I have done I would not be answering your questions. I grew up in Queens, NYC to a family of immigrant Italian blue collar workers who worked quite hard for to raise a family. Each day they worked hard my mom and dad to provide for us. I repeated it so much. Read more>>

Max Gold | Film Director

I think about risk by starting with the fact that I am going to be dead in 60-80 years. In the ground, not loving or feeling or tasting or doing. I have this limited amount of time before then, so what do I want to do with it? Who do I want to spend it with? What do I want to build? From that vantage point, there is no risk. There is only a question of ruthlessly going after the few things that are deeply meaningful to me and having the courage to let go of the things that aren’t. The latter has been a challenge; it’s hard to face the social repercussions of letting go of things that most other people find valuable (or think they do.) There is also the ever-present potential for failure, or not meeting my own high expectations. But my experience has been that I learn and move forward most from failures. So I’m working on being less afraid of that. Read more>>

Will Martins | Music Producer

Risk has always been part of my life. I can’t see the person I became today or the person I want to become without taking risks. Actually, if you’re reading this is because I took a risk 4 years ago, and sold all my stuff, left my family and friends behind in my country (Brazil) to pursue my dream in music here in LA. I believe life is a constant decision-making process, and in every decision, there’s a risk. Even if you don’t make a decision, you are already making one. I can see some level of risk in every part of my life. On Elementary School I took the risk of being bullied, just by being myself. On High-School, the risk of not being accepted by the “Cool guys”, because I also liked to hang out with the “nerds”. On College, the risk of saying no to parties, because I had to rehearse with my band, or even on my last job, I took the risk of saying no to a guaranteed promotion to live abroad. Read more>>

Erin Reynolds | Chief Mollusk | Creative Director, Video Game Studio Founder

I suppose I have certainly taken my fair share of scary risks in my life – from moving to cities where I know no one to starting my own company without any formal business training. Yet, I don’t think I would define myself as a natural risk taker – in fact, I remember one of my college application essays (yes, from way back in the day) started with the line, “They say that on the road of life, there are passengers and drivers. I’m a passenger.” However, over the years I’ve come to realize that one of the most destructive things anyone can do is to simply “stay comfortable.” I think comfort can be the enemy of “fulfilling one’s destiny,” so to speak. And so, I consider making “big scary decisions” less as taking a risk and more as pushing myself beyond my comfort zone – because the “risky” decision is almost always better, albeit often more uncomfortable, than the alternative. Read more>>

Farzad Golpayegani | Musician, Producer & Visual Art Artist

It played an important role. I believe I risked everything I achieved when I moved from my home country about 11 years ago. I lived in multiple countries and eventually states and cities in US. Usually, creatives get the best result where they develop their fan base and eventually build their brand in one location. I already had followers for my art and music when I decided to move, but I risked moving in order to grow and progress in my professional life and career. I face a lot of hardship during the years, and to be honest I am just recently getting a bit settled! But I believe the risk totally worth it. Your readers might wonder how successful I in my career am, and I want to clarify that I believe success is a relative subject. I don’t necessary consider those who make a lot of money or have a lot of followers successful in general. In my case, and in my opinion, I might consider myself successful because I achieved an expert level in what I do, and I try to enhance my skills every day. Read more>>

Sean Costell | Architecture, Interiors and Portrait Photographer

Anyone who chooses to be self-employed is taking a risk. It provides a lot of freedom, but it’s also a lot of work. My photography career has been filled with amazing experiences, all from taking risks. I’ve always believed that taking smart risks can lead to new opportunities, that will potentially open new doors. It’s like an adventure filled with uncertainty and a little fear of the unknown; but without taking risks, we don’t move forward. Read more>>

PHOBIK | Artist

Risks are what life is about. You win some, you lose some. You sometimes make the wrong moves to end up righy where you’re supposed to be. Whatever the circumstance might be i think as long as you give it your all, always bet on yourself. This year in particular can show you that risks are everywhere and it presents itself every second of your life. I’ve had time to reflect and acknowledge how much of those risks we take on the daily. All I can do is try to adapt and hold myself responsible for the outcome. Whether its art related or personal or everyday in general. Read more>>

Sarah Ivey | UX Designer, Content Creator, Coach & Entrepreneur

When I was a young adult, I had always wanted my life to be comfortable, safe, and predictable. I had strived to fit into the narrative of what success was pitched to me as; go to college, be a “good” girl, land a good job, find a rich husband, have kids… blah blah blah. I did some of those things, fell short, and found myself unfulfilled and unhappy. Not because I was doing it wrong, but because it wasn’t me. I also wouldn’t recognize that these “failures” were in fact necessary opportunities to pivot and lessons I’d draw from later in life. If you think about it, we are faced with risk throughout every moment of our lives; a collective of decision making where we have to evaluate the pros and cons of inaction vs action. Risk can be interpreted in a few different ways and I resonate with the idea that risk can be translated into opportunity, growth, and transformation. Read more>>

Katy Zanville | Registered Dietitian Nutritionist & Certified Intuitive Eating Counselor

I decided to take the biggest risk of my life and change my career at 30 years old. I was working at Sprinkles Cupcakes as their General Manager and, while I loved working for that company and spent 10 formative years of my life with them, I wanted to pursue a career that I was more passionate about. At that time, I had a bachelor’s degree in nutrition but did not want to get my credentials as a registered dietitian (RD) because I didn’t feel like I fit in with other RDs. It wasn’t until I started seeing like-minded dietitians in the anti-diet/intuitive eating space that I decided to go back to school, get a master’s degree in nutrition, and start on a new journey as a registered dietitian. When taking a risk, I outweigh the pros and cons. I could have stayed in my food service role, with the security and benefits it provided. Read more>>

Van Jazmin | Artist & Designer

For an artist, risk is paramount. It’s the difference between fading into the background or putting a spotlight on oneself. I personally take risks on a regular basis, because I am a freelance designer. It’s risky because I can’t guarantee an income every month. However, the payoff is always great in terms of freedom and self-reliance. Outside of my commercial work, I am taking risks as well. Every personal project involves risk because I’m investing in something that may or may not turn out the way I planned. For example, I’ve thrown money into visions where I was the producer, photographer, stylist, and casting director. Even with all that creative control, It’s a hit or miss. Another type of risk I take is the risk of working in new mediums – trying things I’ve never done before. Recently, I published a book. I took a risk by self publishing. I produced 100 copies, not knowing if people would actually buy it. Read more>>

Phil Guthrie | Creative Director + Founder @ Two Fresh Creative

Risk taking, to me is how you start a business. My business thus far has been a series of risks that panned out. I started as one guy in an office in DTLA, and moved slowly to get to the size we are now, moving from DTLA, to Culver City, to Sawtelle area in West LA, and finally now into Santa Monica. Risks are funny, once you take small ones they don’t become risks anymore, they are more of a calculated risk. Then you get used to this and make larger and larger risks, but only adds to the reward. But we don’t take risks without backup safety plans to some degree. Read more>>

Heyltje Bond | Fashion Designer/ Fabricator

I believe risk taking is a must if you are to truly live a life worth living. As an artist it’s a matter of putting yourself out there despite what people think of your work and without regard to whether it is financially successful. I had a painting professor who talked about the stress of making a living through his work and he would say ‘I wouldn’t have it any other way. Read more>>

Ellen Surrey | Illustrator

By choosing an artistic career you’re already taking a big risk. Unlike traditional job choices, you are not guaranteed a salary or even regular pay. You are risking not making a lot of money in order to pursue something you’re passionate about. Growing up, I was lucky to know what I wanted to do. My goal was to make a career doing something I love to do, drawing and painting. I knew that money was going to be an issue, but I was willing to deal with that anxiety if it meant I could be happy drawing and painting. I also knew that with a lot of hard work, persistence, and belief in myself I could one day become a higher paid artist. After working professionally for just over 6 years, I’m being paid to do the thing I love and know I can get by with very little if I have to. Read more>>

Derek Hughes | @StandUpMagician

There’s nothing that feels quite as risky as improvisation. You step out into the stage light with absolutely nothing planned. You trust your scene partner and they trust you and together, guided by audience laughter, you find your way to an impossibly funny, interesting, fulfilling moment. A foundational idea in improvisational performance theory is “yes, and…”. When your scene partner makes a statement. “Nice purple hat.” you never negate “It’s not purple, its orange.” Because negation immediately cuts off the creative flow. Rather you, without hesitation, respond with YES. “Yes it is a purple hat.” Then you add “and..” You build upon the reality being created. “and…my grandmother gave it to me for my birthday.” Now we’re going somewhere. “YES, and…she always gives you a birthday hat.” “YES, and…” and so on. Fresh out of college, studying comedy improv at the Dudley Rigg’s Brave New Workshop I had an epiphany. Read more>>

LEONIE CASTELINO | Contemporary Bojagi Fiber Artist. Textile

I was in Strategic Planning and Business Development in Corporate America. I was one of the early female MBAs, with a hard earned high executive position, when as a young mother, I was unexpectedly caught in the same dilemma as many working moms are today. This lockdown in the Pandemic of 2020 is forcing working mothers to prioritize and make life altering career decisions. Art saved my sanity when I gave up my career, income and identity. Studying the lost textile arts of Japan, over a decade, exposed me to extraordinary artists. The standards were so high. I was in awe. They risked all to their art. I joined professional textile organizations, and was invited to exhibit, but I didn’t dare. I was terrified of rejection and failure. In 2002, I was shocked when a renowned artist challenged me with a solo exhibition. I had a year to create work. It was akin to dancing naked in the village square. Read more>>

Christine Martin | Interior Designer

Career-wise, I played it safe for a long time. As an international educator for over 15 years, I stayed in my role knowing that it paid the bills and afforded the lifestyle I enjoyed. Still, since the beginning, I knew it was not what made my soul sing. It took me a long time to transition into interior design. I could jump all in until I had some experience under my belt, momentum on my brand, and positive response from clients. Up until about a month ago, I still had my foot in the teaching door. I was offered a more secure position even. In pandemic times, having job offers is golden. But, my intuition…the knowing in my gut whispered to me to pass it up. Filling my time like that would inhibit me from cultivating my business further. Saying no to this offer and others has been scary; I wont’ lie. But, I felt the time right to take a chance on myself, to give all of my creativity, effort, and stamina to the business I created. Read more>>

Lizzeth & Kevin Bastierrez | Architectural Designers

We believe, that there is no life without risk. We think in life as an adventure, and like any other adventure there is always risk. If we don’t go out of our comfort zone, we don’t really live! If you don’t take risk, there is no chance to win, probably many times it feels like we are losing, but the true is that we are learning, and getting stronger. Maybe it sounds a cliché, but is true: You need to fell many times, to stand up. Our life and journey as entrepreneurs are full of risk taking. We took a risk when we leave our country and move here to the US, we took a risk when we leave our steady jobs, we took a risk every day, be on a path without any secure, sometimes is overwhelming, but it is part of life, part of the adventure, of the passion. Many of the hard moments that we have, probably wouldn’t have it, on a steady job, but also we wouldn’t have the excitement and the adrenalin. Risk is part of the life of any entrepreneur and we are proud to take it and handle it, because, you know, we only live once. Read more>>

Douglas Hill | Architectural and Fine Art Photographer

I fully admit to generally speaking being risk averse, extremely so at times. I’ve operated on the erroneous assumption that the objective of life is to get through it experiencing as little pain and disappointment as possible. This is of course not only futile but completely counter-productive, because in order to avoid pain and disappointment it’s necessary to limit one’s experiences to those where all outcomes are foreseeable and desirable. Obeying fear keeps me safe, or so it seems. The thing is, so far as work is concerned at least, I’m my most productive, my most creative, when I don’t know what’s coming next. Fortunately, the fear that comes up is in anticipation of what may happen in any given day, and I’ve now had enough experience on the street with a camera in my hand to know that the most interesting and exciting things the world has to offer are around the next metaphorical corner. Read more>>

Nick Brown | Artist, Educator

Taking risks is vitally important. It’s best if there is foreknowledge of the subject of risk, it’s history and present function etc. This obviously creates an informed risk with a desired outcome. Naturally, with any risk the outcome is uncertain and part of it’s allure and challenge. The risk opens up possibilities, new outcomes, immediate and future challenges. This really is growth. For me, I see making artwork as exploring. In order to explore one must find new territory. This new territory is within myself and then expressed through the work. Read more>>

Vanda Asapahu | Michelin Bib Gourmand Chef + Restaurateur

Risk taking is in my blood. My dad’s father migrated from China on a Danish Cargo ship headed for Singapore in the early 1900s. Bad weather made him settle in Thailand on the banks of the Chao Phraya river in Bangkok. Like most immigrants, he took the risk of leaving the familiar motherland with only the clothes on his back, all his worldly possessions in a small sack, and in pursuit of new opportunities. My dad’s mom was second generation Thai-Chinese. She was a talented chef and an avid gambler. She went into labor with my father in a card house across the river. My grandmother ran a curry shop out of her home during the day and by nightfall—a dozen pairs of shoes lined the front door, shoes of patrons of her home-turned-illegal card house. She hustled to provide opportunities for all 8 children. My parents relocated our family of four from Bangkok to Los Angeles when my brother and I were both under the age of 6. Read more>>

Doug Woolverton | Professional Musician (Trumpet/Bass)

I believe taking risks are a huge part of being a successful entrepreneur. Taking risks for me personally have definitely advanced my career and credibility in my business. When I was in college I would practice 8 to 12 hours a day as well as taking a full credit class schedule knowing what work I put into being a musician I would definitely get out of it. After I graduated I immediately placed myself in environment where I could network network network! I took a lot of risks. Asking people that I respected that may not have known who I was at the time, to sit in with their band. I met a lot of amazing musicians this way and continued to become a far better musician than when I graduated college. And then created a website, create a logo, and started my own band. I invested a lot of money putting this all together which one would say is also a risk. I believe the music industry has a lot of risk. Read more>>

Savea Kagan | Dancer/Choreographer

Though it’s as beautiful as it is terrifying, risk is an indispensable part of creating the most pivotal changes in life. Change is inevitable, and I’ve particularly learned during these uncertain times that it’s how we choose to react to change that determines our futures. Risk has played a huge role in my life from a young age. Amidst a global pandemic, I received the Holland scholarship and moved to the Netherlands the day after my 18th birthday to study dance at Codarts Rotterdam University of The Arts. I knew this was the perfect fit for me to further my artistic development and goals to use dance and choreography to create social change. Moving to a foreign country alone as the only American in the program full of students from all over the globe was daunting and exhilarating, I was “nevouscited” as my little sister would say. I quickly overcame any doubts once I met my incredible CODARTS peers and faculty. Read more>>

Tier | Dance Fitness Instructor

I think it’s important to take risks in life. No matter the outcome, there’s always growth in the end. For me as an entrepreneur, taking risks made me become more resilient. Before branching out and starting my business brand full time in 2013 I was just a participant in class. One week the studio needed a sub for their cardio dance class and because I was always front row the other students and faculty voted that I subbed for the night—who knew this would be the start of my dance fitness career. Read more>>

Rachael Kemp | Co-Founder, Creative Drector, & Wearer of Many Hats.

Without risk-taking, most things in my life would not exist. In general, I am a person of curiosity & bold adventure. I’ve always sought out the individualistic & free-spirited routes life offered, instead of opting for the status quo, or what would make me most ‘comfortable.’ I’d rather get lost in a foreign city than take a cruise to the Keys, if you know what I mean. My curious nature drives a lot of my decision-making. As a teenager, that didn’t always serve me well; but I’ve learned to posture myself and build a healthy risk thermometer over time. Funny story, one time in 2006, I wore a silky royal blue, v-neck romper to school, this was when rompers weren’t really a thing yet, & a friend of mine at the time told me, “that’s so risky.” And I’ve never forgotten that moment. One of the biggest risks I’ve taken in my life was to start my business, wayre, at the age of 24. It started with a dream (as all good things do) and has grown exponentially this year in the midst of a global pandemic. Read more>>

Michael Ryu | Wedding & Portrait Photographer

Risk has been a constant theme my whole life. From coming to America at a young age to starting my career as a photographer, I always believed that taking risks requires courage. Courage to face the fear of uncertainty and hoping to achieve a goal. For me, it was definitely worth taking a risk because I am doing what I love, and I can also call it my job. Read more>>



Bonita Helmer | Fine Artist/Painter

RISK TAKING I have always loved the risk of adventure through travel and exploring different countries and parts of nature. However, when I was studying art at Otis College many years ago, I decided to take one of the major risks of my career. I decided to stop taking classes at Otis and I began to study on my own. So much of art at that time was going toward conceptualism and performance art (“painting is dead”) and I had always wanted to be a painter. A short time later I found an ad for classes through USC Idyllwild and I began studying with Francoise Gilot My studies with Gilot proved to be what I was looking for; a strong foundation in technique as well as an historical way to look at painting. I was also pleased to find a strong woman icon to follow. It is a risk to remove oneself from the “trend of the moment” and go off on one’s own to find personal meaning. It is also a risk each and every time an artist approaches a canvas to see where the new adventure takes him/her. Read more>>

Charles Wolf | Fine Art Dealer, The Wolf Fine Art -Los Angeles

I love risk and I hate risk, just like everyone else. In a way, confidence comes from failing. So if it’s not going to ruin anyones life, you have to break it down from there, to get to what the real consequences of risk are. Failing will let you know a few things, but one is that you can recover from failure. So risk of “failure” is really not a consequence to be all that concerned with. Not surprisingly though it prevents most from taking the risk at all. We have all heard the old saying, “If it was easy everyone would be doing it.” To me that degree of difficulty coupled with the degree of risk determines what kind of competition you are going to have and how early. It also determines what multiplier of success you may have. Safe bets pay small returns. Longshots pay big. Somewhere on that continuum you have your safe government workers retiring from their first job with a good pension. On the other are entrepreneurs who are going to make it or break it on their own. Read more>>