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.

Kevin Crenshaw | Love/Relationship Coach

Anything you want is on the other side of risk… and what gets in the way of this for most people is trying to feel certain about the outcome of a situation, which is near impossible. I let go of trying to control or have certainty in anything quite a while ago. That’s why making a $35,000 investment, traveling the world from my backpack during 2020 pandemic, or falling madly in love again after having my heart shattered so many times… is worth it. The ONLY thing we can be certain in is death, taxes, and that your psyche will follow your identity/beliefs about yourself. So, I focus on myself and realize the rest is out of my control anyway. Risk is the price to pay for fulfillment and achievement in life. The higher the risk, the higher the reward. If no risk is taken, you may feel safe, but you give away dangerous freedom or certain safety. Realize that your mind just want certainty to be safe. Consciously remind yourself you’re safe, and take the risk anyway. What’s the worst that can happen? You break your heart? “you’ve got to break your heart until it opens” – Rumi You lose money? You can make more You get injured? Your body heals. Read more>>

Stephanie Mercado | Artist

When I was in college one of our art professors lectured us on the difficulty of becoming an artist and said “Out of a 100 of you, 10% will continue making art when you graduate, of that 10%, 1% might have a career in the arts.” Life is a series of decisions, some of them yield positive results and others are learning experiences and opportunities for growth. I take many soft-risks. I have made some life-changing decisions that have had a positive impact on my work and have connected me with wonderful people across the globe. I have applied for exhibitions abroad and artist residencies for which I have received some awards and many rejections. Rejection is part of the experience. Other risks have included working a job with a swing shift from 5 pm – 2 am so that I could make art from 8 am – 4 pm. I printed and painted in my bedroom before I had a proper studio space, sniffing ink, and squeezing between my etching press and my bed to prove my commitment to the work. Read more>>

Wendell Phipps | Musician, Roller Skater, and Software Developer

Risk is an absolutely necessary part of the human experience. Somehow we unlearn the fearlessness of infancy as we age. We get hurt too many times, we fail, we experience loss…all of which are also valuable, but none of those things should make us risk-averse. When we’re babies, we fail hundreds of times taking the ‘risk’ of learning how to walk. As a roller skater, whenever people tell me that they’re afraid to fall, I say “how do you think we learned to walk?” The reality is that we’re GOING to fall. It’s going to happen. It’s probably going to happen a lot. But at the other end of falling is learning. To me, the pricelessness of learning is far worth a reasonable amount of risk. There’s definitely a balance that needs to be struck, because I don’t think that ALL risk is worth taking. But in the pursuit of happiness, success, whatever your goals are…risk shouldn’t be what stops you. You gotta risk falling in order to walk, to run, or to fly. I want to soar, and because of that, I’m willing, almost eager to take risks. Read more>>

Mary Trunk | Filmmaker, Choreographer and Multi-Media Artist

When I first think about risk I imagine myself bungee jumping and I panic. But that kind of risk only lasts a short time and it doesn’t really build on anything even though it takes more guts than I could ever muster. For me risk is about starting somewhere that has no end. As if you’re looking at a fog bank and you know you need to get through it and there’s not much to guide you. It is making the decision to move in a direction that could lead anywhere and having the courage to keep going. It is trusting that you will come out the other end with a new understanding and a new way of looking at the world – despite how difficult the path may seem. And just when you think you understand where you’re headed, the rug gets pulled out from under you, another fog bank appears and you have to keep searching and moving. Read more>>

David Phan | Founder

As a first-generation Asian-American, my parents took the risk for me and left everything to fled a war for a better, promising, and certain future. I was conditioned that the risk they took was worth it for the true American dream — stability. While I finally reached that level of stability, it was at the cost of my endearing parents’ hardships. Despite a comfortable lifestyle that took a whole generation to build, I had the opportunity to do more. This means quitting my corporate job to fully commit, starting all over, and building my dream — a business I can call my own. The risk of not quitting that job to chase my dream of building a company for social good was much greater than not taking the opportunity. Although startups are tough and I am now working more than I have ever had, it is fulfilling to know I have the full support of my friends & family. It is also a privilege to have the opportunity to take risks. Read more>>

Zeina Baltagi | Artist and Educator

Life is a series of decisions. Some may seem more risky than others. There is this myth, saying graphic design is a safer route than fine arts. The reality is far less concrete, yet far more personalized to the one involved: anything you do takes handwork and dedication. I believe we all have a purpose in this world – it is a natural human instinct to want to be of service to the collective whole; if we do what we feel we excel at it cuz it is our jam; whether it be in the humanities; in tech, biology, graphic design, animation or law… I have taken quite a few risks in my career. One was quitting my jobs in plural teaching art and being an artists around Los Angeles which I full enjoyed. This was in pursuit of an illusive Masters in Fine Arts degree that may or may not put me in a better position in my art and teaching practice. I just graduated in 2020 from the University of California, Davis so I will see how it goes. Read more>>

Elif Sanem Karakoc | Fine Art Photographer

Years ago, right after I graduated art school, I told one of my teachers that I was soon moving to Los Angeles to pursue my fine art photography career. He looked at me and said: ‘Why choosing to drown in an ocean while you can peacefully swim in your own waters?’ While expecting to get some support and encouragement from him, I received such an insincere comment, and immediately said to myself, “well, this sentence —also that mindset— is exactly the reason why I decide to leave my home country that I was renowned for my photography since I was 14 years old. The idea of leaving everything behind, starting from zero must have scared them and I don’t think that comment was out for a good cause. It was their lack of confidence, imagination and inspiration, and that idea bored me so immensely, for years, that I wanted to just leave.  Then I did, almost 4 years ago.  The stressful process of meeting new people, not knowing a single person from the industry, and speaking a language other than your mother tongue is not something everybody would want. Read more>>

Tari Segal | Director of Photography

Taking risks takes me out of my comfort zone but it is probably one of the most important attributes that has shaped my life and career. I’m always trying to push myself to take chances with my work. It’s what sets you apart from others. You don’t always get the results you want but you learn and develop your talents that way. I keep a list of all the things I was afraid of doing but did anyway to remind me that it’s been worth it. Read more>>

Curt Merlo | Illustrator

I am learning that risk is on a spectrum of low-risk/low-reward on one side and high-risk/high-reward on the other. In art, as in life, You cannot gain anything without taking on some risk. Otherwise, everyone would do that easy thing. I continuously have to ask myself how much risk am I willing to take, everyone has to. Often, the answer is “none” because I am naturally a fraidy cat but every once in a while I put it all out there. Those are typically the images I am most proud of even if they weren’t well received. Failing is hard but the regret of not trying is harder. Read more>>

Nick Cavalier | Director/Filmmaker

Risk taking is a crucial part of being a filmmaker/director. Any good creative pioneer will take risks and break rules. But like Picasso had a blue period where he stuck with traditional anatomical proportions, you need to understand the technical and visual language of film to be able to create a new approach to that language. Be masterful first, then take your creative risk. There is a reason some things are done they way they are. Calculated risk is really what the entertainment field is built on, so I’m all for taking on a financial or a time investment that will benefit your growth as a creative. But proceed with caution; there are predators in the wild ready to exploit young talent. Have conviction in your own risk taking, as long as it benefits you and your team, and not just someone else looking for free labor from a person with a talented future. Read more>>

Tasha Prothro | Chef/Owner of Cali Gold Blends

Life is full of risk! In order to see whats on the other side you have to take risks to conquer fears. On the other side of fear is success. Read more>>

Preston Landers | Event Producer & Community Builder

I love risk! I think of it as a positive feeling and use the fear that comes with risk to my advantage, it makes you feel alive inside, risk gives you edge, lets you know you are pushing your limits out of your comfort zone and awakens that energy and creativity that is locked away, and that is when magic happens for me. In event planning, production, and curation I am always playing a high risk game, “will this event be a flop? Will people even like this? Will too many people show up!? Will the artist get exposure? Do we have enough alcohol!” Leaning into risk always makes me triple check my lists, keeps me on my toes and pushes me to keep setting the bar with whatever I do. Read more>>

Hayley Kassel | Makeup Artist and Beauty Photographer

I personally think life is all about taking risks. My dad always told me through out my childhood, “The things you regret the most, are the things you DIDN’T do.” I’ve taken that saying and applied it to my life/career the best I could. Moving 5 years ago from Chicago to LA without having any connections, or friends, or family, or anything waiting for me there was a huge risk, but I knew I had to do it. I knew that is where I was supposed to be. Low and behold, it worked out for me! But once I got to LA to try and start my makeup career, it was again all about taking risks. I was told by numbers people how I should run my business, what kind of makeup I should be doing, how I should go about running my social media, and I listened to one of them. Lol! I did it my way, risks and all. I’m a firm believer in following your dreams, and in doing so, make sure you are doing exactly YOU want to be doing in that dream! Any person who chooses to follow their own beat’n path knows how risky it is, but the pay off is amazing. Read more>>

Shelly Mosman | Commission Portrait Artist.

I believe risk taking is apart of growth and without it creativity is stunted. I enjoy a feeling of healthy fear, in turn fear brings humility, in turn brings gratitude and finally the overall state of happiness and contemnet we all long for. So it’s always worth walking into the darkness because the rewards on the other side are what allows us growth and change. Then we do it all again and again. Risk is apart of my creative process. I’m quit the procrastinator, therefor allowing things to just happen and fall into place has worked well creatively. There’s a very fine balance between organizing and letting go and I have found to be a sweet spot. Offering clients something unique can always be a risk, but always worth the journey. Read more>>

Lisa Liu | Violinist, Entertainer & Entrepreneur

Risk means growth and expansion. If I don’t feel at least a little risk in jumping into a new opportunity, then I don’t think I’m making any progress. I’m obsessed with progress, and when I’m doing one thing for so long that it becomes routine, I know that it’s time to break free. Risk has rewarded me by making connections to people I’d never dream of meeting. It’s pushed me to new levels of learning and existing. That feeling you get when you’ve broken through a personal boundary or fear is something that gets me excited to wake up each morning. Keep taking enough risks until it becomes an addiction. Read more>>

Cristina Vane | Musician & Performer

The fact that I am a musician, which is an especially nebulous career in some ways, delayed my fully committing to it. I guess it’s a personal decision when you weigh those risks, but, for example, I wanted to drop out of college to start my music career earlier. That was a risk I didn’t feel comfortable taking at the time. I got better at taking them, though. When I did my first 5 month tour around the country, I was alone, and relying on the kindness of fans mostly from the internet. I took many risks that summer, and they all enhanced my experience. Every time I went out to the Venice boardwalk to busk, I was taking a smaller risk, but a risk nonetheless. In fact, every gig was somewhat of a risk, especially when I hadn’t fully developed my sound, my band, or my vision. As those things have gotten honed in, I feel like it’s a matter of minimizing the risks during a live show so that you can take other ones (wardrobe risks, dancing around on stage, whatever dialogue happens between songs). Read more>>

Dexter Story | Musician, Songwriter, Producer, Student

I owe my existence to the risk my parents took to raise a family in 1960s America. My life has been a constant push and pull with risk taking. And I’ve certainly failed many more times than I’ve succeeded. I’ve also avoided risk to my own disappointment and, perhaps, detriment. I think that the nature of human being is a survival dance, or a constant attempt at preserving or protecting oneself. Risk taking goes against all of that. It is a choice that demands letting go, dealing with the unknown, with uncertainty, having faith in the unseen. I remember taking an 8mm movie camera class in my adolescence in East Hollywood and, although the experience was enlightening, I played it very safe. I didn’t want to go outside of my comfort zone around those other kids. I have many stories like that, like being afraid to ask an attractive girl out, being afraid to raise my hand and or speak out about something, or being afraid to simply excel. Read more>>

Vivian Capulong | Illustrator & UX Designer

I have probably said. “I don’t know, I’ve never done this before” more times than I care to admit. Whether it be experimenting with a new art technique or moving to a new city, I’ve always been down to try new things. For me, risk has exposed skills and capabilities I didn’t know I had. It gave me more confidence to branch out of my comfort zone and discover new limits that I’ll eventually overcome. While I’m all for taking chances, I also have a more cautious and calculated approach. Weighing pros and cons sheds light on different perspectives of a situation, and that usually factors into my decision making. However, after all the careful and thorough research, I just let my intuition guide me through uncharted territory. If it feels right, then it’s typically right. If not, then I’m in for a valuable life lesson. Read more>>

Caitlin Whelan | Interior Designer

If I never stepped out of my comfort zone and learned to take risks, my job would be a lot less thrilling. It is so important to take risks when you’re a creative professional, and as designers we are constantly working on new projects with different objectives, so each new project means pushing yourself to come up with something fresh and creative. It’s important to us that we are always aiming to reinvent the wheel rather than use a formulaic approach or simply reuse the same ideas. Although risk-taking can be terrifying, it’s one fundamental component of my creative drive, and it’s also part of how I value myself as a type of artist. It is essential in moving me forward and keeping me on my toes. The challenge to be truly innovative and original is a welcome one. I’ve become a huge advocate of taking risks and ever since I started my career in interior design, I’ve been rewarded by the risks I’ve taken. Sure, sometimes it doesn’t turn out, but we have to be willing to take risks and to persuade our clients to be bold, too – that’s what allows us to truly transform their living spaces. Read more>>

Amir Whitaker | Human Rights Lawyer, Artist, & Educator

I owe much of the success that I have to risk-taking. I’ve embarked on lots of projects and ideas where the outcome was unknown and success was not probable. If you’re doing something that has never been done before, or trying to create something never seen, the associated risk is likely part of the reason why. Most people have a healthy fear of failure and embarrassment, and this prevents them from taking risks. I’m not as concerned with fear or the embarrassment that might come from failing. This is part of why I’m known as “Dr. Knucklehead.” While studying human motivation in graduate school, I remember a professor sharing an impactful example of how adults could benefit from aspects of the mindset they had as toddlers. The Professor talked about how toddlers trying to learn to walk afraid of falling down and are not concerned with people laughing at them. Each time the baby falls down, they slowly get back up until they eventually walk. The walking eventually evolves into running and jumping. Read more>>

Gregory Price | Visual Artist

The experimental nature of my studio practice has taught me to reevaluate what risk means, and its relationship to what is personally defined as failure. Those difficult moments can offer monumental shifts in perception as opposed to simply reveling in the success of an expected outcome. Naturally the successes are important, but it’s that mental space energized and informed by the inherent risk of potential failure which drives innovation within my approach to a material. What is initially perceived as a misstep often leaves clues to something unexpectedly interesting, providing inspiration for future directions. Read more>>

Shante Threatt | Maker of Scented Goods

Taking risk is something I used to be of. Risk taking is probably one of the biggest challenges in life and as an entrepreneur, I think it will alway be. In life I usually like to play it safe but I had to learn to take some risk in order to elevate. Risk taking allows you to figure out what works for you and what doesn’t . It’s very uncomfortable to go into any situation that you don’t know will work out in your favor. When taking the big step to start a business you are thinking about the risk of investing into something that you don’t know will work out the way you envisioned. Risk taking teaches you to explore and be brave. And just because you might feel a little uneasy with taking the risk doesn’t mean you don’t take it anyway. It’s apart of the process, it’s been a huge battle for me but I’ve learned to do it scared and have faith that whatever it is will work out in your favor. Read more>>

Wolfe Erikson | Designer, Developer, and Artist

I haven’t sought out investors or put out huge capital with the risk of losing everything. But, I show up for opportunities when they are presented, and refuse to turn down the terms I set for myself; which results in a life that may seem risky to many. I’ve been a freelance designer, front-end developer, and consultant for four of the last five years, with a year-long stint at an agency in Los Angeles. While at that creative agency I felt moored down in a way that felt very destabilizing to who I was and what I wanted to do. This was especially obvious after spending the previous year as a digital nomad, working while traveling through Eastern and Central Europe and Southeast Asia. After experiencing agency life, I concretely knew that a typical 9-5 was not in the cards for me, which felt incredibly threatening because of the murkiness of that decision. The beginning was challenging, and a lot of times I did not know where my next client was going to come from, but now I have the mobility and freedom to choose where I want to be, whenever I want to be there; it’s a beautiful thing. Read more>>

John Kippen | Motivational Speaker. Being Different is Your Superpower

I have always been a creative problem solver. My first career was as an Independent IT consultant. I started JDK consulting when I was in college. I was fortunate to grow up with computers and they never intimidated me. As I was self taught, taking risks was part of the job. It is what made me successful. Looking back, I don’t really think I thought of it as taking risks, I just had a job to do and found solutions. If one didn’t work, then I would try another until one fixed the issue at hand. I had self confidence and that served me well. Clients saw this confidence and they hired me as they somehow knew that they were in capable hands. In July 2002, everything changed. I was diagnosed with a 4cm brain tumor called an acoustic neuorma. This tumor was killing me by displacing my brain stem. It had to come out, or else I would die. Although they successfully removed the tumor, in the process they damaged my left facial nerve leaving my face permanently paralyzed. Read more>>

Ok Pebbs | World’s Okayest Photographer

Without risk, I don’t think I’d be anywhere close to where I am today. I owe much of the progress I’ve made in my career and life in general to uncalculated [stupid] risks I’ve taken. I grew up in a small town, where everyone went to college, got married, or worked at a factory. It was actually the area Trent Reznor came from. The bars opened at 0700 (7:00 AM) to cater to Reznor HVAC overnight workers. And while cooking professionally was more the career that chose me vs. the career I chose, I used it as my escape mechanism, literally and figuratively. I was able to work and interview at places that I couldn’t imagine affording to eat at. So, logically: I spent my twenties sleeping on floors and couches, straining relationships with my parents, relatives, and friends, and drinking myself to sleep. Every step outside the nest, the comfort zone has been a risk. With that, though, I can at least say I’ve “been places.” I’m going to refrain from doing the millennial thing of mentioning where I’ve lived/worked. Read more>>

Justin Klosky | CEO of the O.C.D. Experience

Risk-taking is vital in building any kind of business, but you can’t test your risk-taking gauge until you actually start taking risks! There were numerous times growing my business where I had to take financial risks in order to see a product or an idea through. I’ve been grateful that these risks paid off for the most part, but there’ve been times where fear, confusion, doubt, insecurity, and loss of financial independence creep up on you. Risk-taking is also vital in building character, as you never know what you’re made of until you’re in a position where risk could make or break you, just for that moment. Read more>>

Kris Black | Producer, Writer, Director, Abstract Artist

I think attempting to make a living in the arts and entertainment world is a huge risk. But every achievement and accomplishment big or small had someone making the decision that the risk was worth it. I encourage everyone to take risks, whether it succeeds or fails you’ll have learned something about yourself. Read more>>

Keren Ashri | Actor / Dancer

Risk has a leading role in my life play so far. I was born and raised in Israel. I started dancing when I was 4 years old. Ballet, modern and jazz. When I was sixteen I discovered the Latin dance World. At the age of 17 I was already teaching salsa classes in Tel Aviv. After my service at the Israeli Air Force I was still teaching and performing in Israel wherever I could, however there wasn’t a lot of opportunities to make it a career back then. After a little of pressure from family I decided to quit dancing and register to a university. 4 month before school the year started, I performed for what I thought would be the last time at the Israeli Salsa Congress. A very talented dancer and choreographer by the name of Frankie Martinez offered me the opportunity of a life time – to join his Afro Latin Dance Company called ABAKUA based in NYC. I felt like Cinderella. I’ve never been to the US before and I didn’t know anyone or spoke English fluently. Read more>>

Sheridan Ward | Celebrity Hairstylist / Actor / Drag Artist

From teaching myself to swim at 19yrs old and landing a job as a lifeguard (almost drowned in the process?!) then becoming an accomplished swimmer, turned swim teacher to having my own swim club.. To moving to Tokyo for a year (even though I couldn’t speak the language) on my 30th birthday to re-assess my life.. Which is where I had my first and only epithony of my life.. A literal light bulb moment. That I wanted to work in fashion and with Celebrities.. Returned home to London retrained as a Hairstylist and fell into fashion week a few years later, assisting the legendary Sam McKnight (I didn’t know who he was at the time.. Lol) and 7yrs later after a successful fashion career in London, and doing so many amazing fashion week shows in new York, London, Milan and Paris, working on such shows as fendi, balmain and Chanel, ended up taking another risk and relocated to LA to work with A-List stars on the red carpet and events, and have worked with some of my favourite actors from Nicole Kidman and Steven Yeun to Thandie Newton, and I have recently started pursuing and acting career myself (which is the most terrifying thing ever) but, so worth it, another risk, let’s see where this one takes me. Read more>>

Wendy Alane Wright | Leading Acting Career Coach and Inspirational Speaker

I make a decision about what I want to accomplish and I am convinced that I’m going to make that happen. No other option exists for me. I have a clear intention inside that is completely manifested already. I strategize to figure it out what it is I need to do to accomplish the goals and I work like a workaholic every single day to make it happen. I don’t make excuses, I don’t listen to negativity, I ignore naysayers, and I stay focused on what needs to be done and the reason why I want to achieve something. Often when people set goals for themselves they spend time thinking about how they could fail, or why they won’t be able to achieve their desired outcome. That’s wasted energy and it can lead to quitting. Quitting is a sure fire way of not achieving your goals. You have to spend your time building yourself up mentally and emotionally, surrounding yourself with positive thinking and stories of other people achieving success. I create a vision board and I write positive affirmations to myself all over my workspace. Read more>>

Lani Shipman | Co-Owner, YADA – Youth Academy of Dramatic Arts

I once heard some advice given when I was still in High School. This was in a performing arts class and we were picking out songs we were to sing and work on in class. The teacher said “if there is a song that you think of and your first thought is ‘oh I couldn’t possibly do that song’ then you should probably pick that song”. It has stuck with me throughout my own personal and professional life. If something is so scary to you, then there is probably something in there that you should face or walk through. It hasn’t steered me wrong once. Read more>>

Kaleemah Morse | Visual Artist

Me and risk taking have a love hate relationship lol. When I was younger I took risk after risk and every single time i ended up in places I’d never thought i’d be. Not too long ago I used to impulsively move states, travel, network, and take creative risks with my art projects. While doing so I’ve obtained wonderful friends, multiple skills, opportunities, and experiences I will never forget. Ever since I was young, I’d watch my parents take risks all the time. This made it easy to try new things and venture out of my bubble. In all my year of risk taking (and more to come), I had to learn that no matter the outcome when taking that risk, there is always something to learn from it which you can take with you and apply to the next stage in your life. I think that not only creatives but everyone should take risks that benefit them, their lives, and careers. You learn from every mistake and it’s always worth it. Read more>>

Sandra Espinet | Interior Designer

We take a chance every time we drive ( everyone has a near miss or accident story), we trust our hearts in love ( everyone has a broken heart tale ), history is filled with risk takers in play ( America was created by rebels taking risks). And likewise, business is the art of educated guesses entrepreneurs take to create commerce. Just as any other business owner, we interior designers take daily risks and gambles. Starting with the basic decisions of hiring staff. Will they represent my brand professionally, will they perform efficiently, will they be trustworthy? We take a risk every time we hire a vendor. Will they perform, will they deliver on time? Will their quality be what we demand for our clients? And ultimately we take a chance on the clients we choose to work with. Are they trustworthy? will they pay their invoices on time? Are they of good character? Do they match your work style? But risk taking is not easy and not for everyone. Read more>>