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.

Elaine Ryan | Songwriter, Singer & Event Performer

I’ve had kind of a contrarian relationship with risk my whole life. On the one hand I’m a perfectionist and as a kid I was very into doing everything right. Ok, maybe I still am… But at the same time I had a non-conformist streak and refused to go along with trends or ideas just because they were the done thing. As a young adult I was miserable in my office job and in academia and I think I felt that the biggest risk would be to not follow my inner voice, which was yelling pretty loudly that I wanted to be an artist. So I took a chance on not having all the trappings of a secure job and committed to being a musician. It was a pretty privileged position to be able to choose that and I feel lucky that I did get to go to university before I made that choice. Read more>>

Joi Stearns | Co-Founder/Owner

I am not afraid of taking risks—it has been crucial to the success of JOi Cafe. I think some people are so afraid of failure that they never get started. I have hang ups but fear of failure is not one of them. I take a lot of risks, which means I make mistakes and sometimes I fail but, more often than not, I succeed. Even more important is that I am learning along the way. “Failure” is nothing more than an opportunity to learn. My risk taking, successes and failures are teaching me to be a better person & business owner, to be wiser and more discerning. Without the risks I have taken in my life both personally and professionally, I would never have experienced all the success I have now. Without taking risks, I would have stayed small, what a waste that would have been. Read more>>

Whisper Washington | Actress & Comedian

I believe risk is very important in life, especially if you have big dreams.Risk are sometimes the only thing that can push your life forward. Risk has played a very big part of my career every opportunity i have ever had came from taking a big risk. I moved from Maryland to California to pursue my dreams. That was a big risk but so many opportunities and doors have opened up for me in California. Read more>>

Annabel Garcia Torres | Podcaster

Risk taking has been foundational to my current business and my future plans. I think we all get overwhelmed with the potential mistakes we’ll make and we can get bogged down before we get started. I definitely believe in planning, whether it’s publishing your first podcast or starting your business you absolutely have to take the first step. When I started my podcast, it was seemingly a quick decision. I had the concept of sharing Latinx stories but I didn’t know how I would do it. I had just moved to Los Angeles. I only knew a handful of people but I knew I wanted to interview high achieving Latinx. I phoned a friend and asked him if he would let me interview him. Since my friend pool was so small here in Los Angeles I asked him to refer someone. The weekend after our phone call I had recorded two episodes, not my best by the way. I had a big learning curb, from audio style to publishing. It was a little tough at the beginning trying to navigate these new waters. Read more>>

Stacie Vanags | Podcast Host & Surfer

For me, taking risks has been a lifetime of unlearning, and also one of my greatest joys because I’m in a constant state of uncomfortable motion. Fear very clearly stems from my childhood; my mother is a worrywart at heart. She doesn’t know how to swim, for example, so is petrified of the water, a fear many people actually share. She cringes when I travel to mystical places in search of surfing waves and new culture and just waits for me to “get home safe.” I have had to very consciously practice not leading with fear because quite honestly, it’s easy to do between the news / media and things we are taught in childhood. One of the most significant risks I’ve taken in my life was learning to surf at age 32. I thought I was ‘too old’ to learn a sport like surfing, and while it hasn’t been easy, I can’t imagine my life without my connection to the ocean. Read more>>

Yasmin Le Comte | Actress

Choosing a career in acting means taking a lot of risk. Of course, every profession has it’s own risks, but acting is known to be one of the most uncertain jobs out there. When I was 14 and started thinking about acting school I immediately thought about the risky future of actors. So many people told me to not do it. “It’s too uncertain, it doesn’t pay well, you’ll never get a permanent contract, you won’t be able get a mortgage”, etc. I remember I had a talk with my dean in high school, and when I told him I wanted to become an actress and move to LA, he started laughing and said: “I am here to help with the more realistic options”. When I told him I wasn’t joking he said:” Then I guess we are done here”. As a professional actress I try not to worry to much about the risks I’ve taken. If I start worrying about my career choice I get anxious, stressed out and insecure. Read more>>

Vanessa Fitzgerald | Holistic Health Coach & Nutrition Response Testing Practitioner

I find that risk typically has a negative/scary connotation attached to it, however, I wouldn’t be where I am today had I been afraid to take risks. Playing it safe and keeping myself small never served me. It was always through total disruption and reinvention, that I achieved my greatest accomplishments and so I’d like to think of risk as opportunity. For example, I was raised to believe that health and wellness was not a real career and that venturing down said career path would be too “risky.” I began to associate risk with being broke, scarcity, and irresponsibility, so I chose a corporate job that paid very well and made me miserable. I would spend my days researching what I love and holding hope that where there’s passion, there must be purpose. Read more>>

Alison Tavel | Filmmaker

I have taken risks my whole life, but I should say I have had the privilege to take risks my whole life. I switched high schools between sophomore and junior year so that I could attend a music festival that landed on my old school’s first week back from summer. I dropped out of college (with one year left) to move across the country and work as a PA for a music supervisor. I quit a 7 year run of touring to finish producing a documentary film on my own. The risks I have taken have always turned out well for me. I think that risks are necessary because had I been too afraid to do some of these things, I wouldn’t be where I am today. That being said, I have lived a very privileged life that has allowed me the opportunities to take risks – so while I think risk-taking is good practice, it’s more realistic for some people than others. I knew that if I failed, or made a mistake I could always come back home to my parents, I could always find other work, I could always find another way. Read more>>

Scott Yeskel | Artist & Art Instructor

When I was much younger and in College, I didn’t rationalize risk. I just wanted to learn and experience the most I could. I loved living in San Francisco- the city helped me be consistently immersed in the arts. Ultimately, after transferring to an Art School, I kept very busy trying to get good at painting- it was a passion but I seldom realized any risk associated with studying art. Ultimately, after 7 great years in San Francisco, I decided to move to LA. That felt risky. I had part time jobs- but I always continued to paint. The biggest risk in my life occurred in my early 30’s- I was newly married, soon to be a father and a home owner. I had to bet on myself – The world doesn’t need another so and so, it needs artists! I devote everyday of my life to my work- It’s the commitment and constant challenge that rewards the ultimate risk of doing this full time. Read more>>

Joanna Wallfisch | Singer-Songwriter, Author & Adventurer

I always wish I was more fearless. I am one of those people who sees risk taking as an essential part of life, just because I take risks, doesn’t mean I am not wary, or even utterly terrified of taking those leaps. Yet, I do leap because I can choose to embrace that fear, and so far it has always worked out in my favour. Whether it is running into a freezing ocean, or sending an email to a record label I long to represent me, to introducing myself at a party full of strangers, my mantra is, if you don’t try you will never know. I am a professional musician – a jazz musician, in fact. One of the key aspects of jazz music is improvisation, a form of music making that requires deep listening and risk taking. You can prepare for your solo a thousand times over, but when the music opens up for your turn to sing you are diving into the abyss, free falling through the music, hoping that all your preparation and synchronisation with the band add up to a soft landing. Read more>>

Quitting Whitney | Alt-Rock Duo

We think about risk as a necessity in creating anything worth value. For us, that’s creating music. Every artist that we gravitate towards has a story to tell, whether its Tame Impala and isolation, Twenty-One Pilots and mental-health, or Kid Cudi: loneliness and substance abuse moving toward strength. We try to recognize that what makes art so valuable IS the human element; the best artists are relatable because they experience the same success and failure as everyone else. In other words, they take a lot of risks. As songwriters, we really try to communicate our personal stories through our passionate instrumental songwriting as well as our lyrics. Our lyrics reflect not only our frustration with the slow-progress of our world, but also they communicate our personalities pretty well, whether it be our angst, sarcasm, or passion for anything that we work on. Read more>>

Estefania Ochoa | Founder

It’s funny you ask about risk, as I have recently learned to be more critical and risk-averse. Let me tell you why: growing up, I was always very free-spirited, and a bit rebellious, so risk came naturally for me. I have a personal mantra that reads, “We can be safe, or we can change everything”. My mindset has pretty much always been if an idea emerges, then I would see it through. I have moved cross country, traveled solo through Europe with no itinerary, said goodbye to jobs, and said yes to things just for the experience. These risks allowed me to gain skills and lessons, but more recently, my mindset has shifted to be a little more conservative in my decision-making process, and it started… A few years back, I quit a job, which I thought was my dream job. I did so because, after a year into living in NYC, I discovered Art and wanted to pursue starting a creative magazine, known as SOYYOmag.com today. Read more>>

Robbie Kaye | Artist

Risk has been essential all my life. Every achievement, artistic endeavor and every time I grow as a person, is connected to risk. Whether it’s risking by trying something new, making that call, putting myself in front of people or taking the time to dive into my mind and soul, risk always produces the opportunity for me to learn, expand and course correct if need be. When I was younger, I didn’t even know I was risking things and still, there’s a part of me that doesn’t see the risk sometimes, which in some weird way has protected me. The lack of fear sometimes was the very thing that got me through a potentially uncomfortable situation because I didn’t play into that fear. Some people might see me as irresponsible or impetuous because of the risks I’ve taken, but I don’t regret taking any of them. In fact, in a way, I wish I was as spontaneous and courageous now as I have been in the past….and perhaps I will be again, soon! Read more>>

Alessandro Bordoni | Director & Cinematographer

Risk-Taking Takes Practice. I’ve always been a little risk taker but like everything else that you want to be good at, risk-taking takes practice. I wasn’t super comfortable at first. We think the creative people we admire have it all figured out and that we’re not like them. In reality, the world’s most successful creatives still carry self-doubt with them throughout their careers, no matter how much they succeed. I forced myself to put my ideas out there over and over again, and eventually, it felt like a regular everyday activity. This applies both to our creativity and business approach. I wouldn’t be here today if I hadn’t jumped off the cliff and learned to fly on the spot. Read more>>

Diana Mausser | Ceramic Tile Artist/Designer & Founder

I think risks are tied to your vision of where you see your business evolving or growing. I always imagined or dreamed that I would own the building where my business resided. I imagined/visualized my business in a house with a detached garage with property around it where we could function as an indoor/outdoor studio. This set up is ideal for tile making and healthy as well. I wanted a garden and a few cats to create a comfortable homey environment. I was forced to move from my first studio location because they were turning the property into a parking lot. After an emotional and tedious search, I found my dream property and it was for sale. The big problem was that I had no money to buy it. I had to take a big financial risk to take this step. Everyone thought I was being foolish. I listened to myself, believed in my strong work ethic and went for it. Read more>>

Stephanie Kutty | Actress & Writer

I think it’s great to take risks! Sometimes you’ve just got to take the leap and see where you end up. As they say “when a door closes, a window opens”. But on the other-hand..if you don’t like where you end up…you can always go back through the door you came from. The biggest risk I took so far is moving to LA. In July 2016, I found out I had the opportunity to get a Work & Travel Visa (J1) for a year. The catch was that I had to leave within 12 months of graduating Tertiary Studies; which at the time happened to be an Advanced Diploma of Screen & Media (Acting for Film). I had finished this Degree November 2015…which means I had till November 2016 to 1: apply for the visa; 2: get accepted; 3. move to LA – all of this in 4 months! Or I would miss out. So…I did it! With no real plans for LA but the golden ticket of the Approved Visa, I moved to LA on November 2nd 2016. Read more>>

Jakob Freudendahl | Composer Film, TV & Video Games

We’ve all heard the phrase “High Risk, High Reward”. Usually people bring that up in relation to investing money. But I think the phrase fits better in relation to how we choose to invest our time. Time is finite, and not on our terms. It’s neither good nor bad. It’s just how life is. I’m currently a Composer for Film and TV in Los Angeles. But the first true big risk I took, was the decision to move from Denmark to Boston to pursue my dream to work, and make money, in the music industry. My first step was attending Berklee College of Music. The risk I took, was that I bet on myself to have the musical skills as well as the social skills not just to adapt to a new country, but to compete with the best of the best. I knew that if I managed to succeed I was likely to have a career full of unique challenges and great people around me. Read more>>

Jacqueline Valenzuela | Artist

Risk has played a major role in my life and career choices. I’m a first-gen Mexican-American. Having parents who are immigrants has always been intimidating. I say this because I know many children of immigrants feel the pressure to succeed in every single aspect of their life. It boils down to, my parents not having many choices during their childhood and young adult life. This in turn meant that they sacrificed a lot and immigrated here in order to live a better life. They were able to provide me and my siblings with endless options and opportunities that they didn’t have the luxury of experiencing. One of these major options was pursing a higher education. Possibly the biggest risk I have taken life and career wise has been pursing art. I saw this as a risk because as said before my parents didn’t have the luxury of taking a huge leap of faith like me. Read more>>

Eganie González Zaga | Actor & All-Ologist

As you already know I am a Mexican/Spanyard “Chica” that has lived in more than 22 houses, 10 cities, 5 countries, 2 continents. Without being a traveller. I have established in all of these places I ´ve lived in. From little huts in the jungle, to fancy apartments in London to Houses in Mexican cities to Penthouses in Rome. I have changed around 10 times of school, have studied 3 different degrees and have changed professions radically every time I´ve wanted. From Marketing, to Fashion Design, to entrepreneur, to Yoga & Meditator Instructor to Actor. Life has just given me the path and knowledge to discover that human race needs constant change, in order to evolve. Evolution = Change, we are dynamic, we shall not get stocked. And what is constant change? RISK! Read more>>

Trang Vo | Actress, Singer & Entrepreneur

“Risk; The Possibility or chance of loss, danger, or injury.” Every year we get older we attain more experience, more wisdom, more memories. And from these things we learn to be more cautious but ultimately more fearful. When we were a kid, getting hit with a ball in the face or falling off our bikes didn’t keep us from getting up and playing again. I Remember my first heartbreak, oh man it was rough, felt like the end of the world at 16. My mom warned me the risks of being around boys and relationships but I did it anyway. He was my best friend, first kiss , first love , and an abrupt end. I put myself at risk of loss for a chance of happiness. I remember joining wrestling senior year of high school, among kids who’ve been doing it since they were 5, I got scared and wanted to quit after the first day of training. I persisted. I endured with the help of my teammates and coaches. Read more>>