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.

Karreno Alexanyan | CEO, Chef, Charcuterie Artist

I started Charqute, a charcuterie and cheese board company, and at a time when all the businesses around me were shutting down. The pandemic did not make it easy for any business owner. As a private chef, my income was dependent on private events and catering. As group gatherings were diminishing, so was my business. This forced me to become the most creative and innovative I’ve ever been. I came up with a product I can safely prepare and deliver that would meet CDC standards as well as local laws and regulations. That’s when Charqute was born! Starting a company from scratch is no easy task, as it involves so many different factors. I really did not know whether or not my products would sell, but it was a risk I was willing to take. Failure was never an option. Read more>>

Tyra Gabrielle Morrison (Tyra The Creative) | Actress & Digital Content Creator

I wouldn’t be who I am now if I didn’t take risks. My entire life has been fueled by risk-taking. Im originally from Louisiana, and I took a risk to move to the East Coast. Now, this may not be big for some, but it was for me. I grew up in a very small tight knit community, so when I decided to move away, I was leaving the comfort of my little “box”. Leaving a world of close-mindedness – that I honestly didn’t know was within me. I think taking risks is one of the most powerful things you can do, because it really shows how much faith you have in God. Any time I’m thinking about doing something wild, crazy, or new.. if it makes my heart drop and I feel fearful, I take a deep breath, and I prepare myself to do it because I know that its something I need to overcome and something that will get me closer to where God wants me to be in life. Read more>>

Shayna Rattler | Founder, The God Shift Movement

Without risk, there is very rarely a reward. This is also a great opportunity to partner with God in co-creating our next level of destiny because what feels like risk to us, is business as usual to Him. Being willing to take risks, even when my steps were laced with uncertainty has allowed me to accomplish goals many have not and make a lot of money doing it. Read more>>

Maxine Dillon | Blue Star Guidance – Energy Healing for Creative Professionals

I believe you can not live a creatively fulfilling life without risk. When you align with what truly feels inspirational inside of you it may feel simultaneously exhilarating and terrifying. I remember this feeling when I decided to leave my career in fashion and start my energy healing practice. It felt like I was jumping off a cliff with only my inner knowing guiding me towards the safety net that would catch me below. Trusting the inspiration to build a new career made the risk feel expansive, like I was pushing up against my creative edge. My mind experienced risk as danger and possible loss but my heart knew the risk would bring reward. Read more>>

Lee How | Music Artist and Dancer

Calculated risk is absolutely necessary for growth. By being afraid of making the wrong choice or having the simple idea of becoming a failure and/or an embarrassment, you only further ensure a bumpier road. We learn life through experience and risk is always a part of the equation. In the same way with car insurance, where we pay for coverage incase we decide to play bumper cars. Yet we don’t obsess about crashing, instead we just drive understanding the risks. Well what if we thought like that for everything? What if success is simply a numbers game and more “try’s” equals more “wins”. One bad game doesn’t end the season (unless it’s the finals of course haha). On the contrary, most will proceed to live to shoot their shot another day. The key is to keep practicing your shot. Read more>>

Matty Carlock | Artist & Record Producer

I have an odd relationship with the concept of risk. As a producer, songwriter, and artist – risk is something you get to know almost instantly. As a kid I left my whole life behind, rolled the dice, and went on tour. I risked my family, my friends, stability, potential future stability, my relationship, and my future, to chase an idea I truly believed in. A better life. The life I wanted. Its easy to be complacent when you achieve accolades – no matter the size. So currently the role a risk plays is a feeling I get when I know something great is on the horizon. If I didnt take risks, I wouldn’t have the life or career I have today. Read more>>

Anna Chi | Film Director/writer/producer

When I think of risk, I think of choices. We face choices in our lives daily, whether it’s as simple as what to wear in the morning to as important as to accept someone’s marriage proposal to you. Regardless of what choice we make, there’s always a risk factor involved. Every choice we make would have its own consequence, and every consequence has its own importance, its own mark, and gravity, etc. In my mind, there’s no wrong choice or right choice. But if we use the word “risk”, it gives our choice a definition of either succussed or failed. Read more>>

Kyle Waters Geller | Filmmaker & Artist

Risk is everything! As a Director, FIlmmaker, and just a creative individual who enjoys creating for creating sake, I think if you play it safe you might find your self feeling shittier than you would of, if you couldn’t sell the same piece, or get any recognition for it. As an artist through in and through out, the creative struggle is a real bitch. Do they like my work? Then why is it not selling? They said they liked my films and videos, but there are no views… After years and years of beating myself up over questions like this, theres always a voice that sits in the corner of my mind that says, “Cater to everyone else and make something so in the “”Now””, that everyone will jump for it”. Read more>>

Krystle Hartsfield | Artist Manager

I always say take the risk if it’s something you want, otherwise there will always be regret about what could have been. Bet on yourself and let life do what it does. I took a risk when I left a 5+ year position with full benefits, vacation, 401k, etc. in Corporate America to start from the bottom in music. Now my colleague and I run a purpose centered boutique artist management company. Read more>>

Linda Marcus Smith | Comedian/Interviewer

I am a leaper, not a creeper! I have made my mistakes…ask my lovely Daughter, Lisa! But I would not have been able to have done any better at the time! Shakespeare turned all my tragedies into Comedy and that is what I will do for our Veterans as long as God allows me! Read more>>

Stratøs | saxophonist // composer // producer // photographer

I think most creatives are told to “take risks” but it’s never really explained how. Many of us can’t afford to take many financial risks, so taking creative risks can be tricky since the two are often linked. For me, I’ve taken a couple of big risks in my career so far. Going to college for music, becoming a composer, then a producer, and then a photographer. I juggle saxophone, composition, audio production and film photography which means I don’t practice one discipline as much as say, someone who just plays saxophone might. I constantly go in between whatever I’m feeling or whatever needs to be done. It’s a little bit scary because as a jazz musician, not putting in hours on your instrument a day is pretty looked down upon. Read more>>

Nora Jobling | Writer, Director, Producer

I don’t think you can pursue a career in the arts without a healthy amount of risk taking. The very nature of what we do is a risk because there is no guarantee of success. We all go in blindly hoping that the risk will be worth the reward, and personally, I have found that it is. This is an industry of unknowns, and there is always a fear of rejection or failure, but putting yourself out there is the only way to succeed. The exciting part is that anything can happen, and you never know what kind of amazing opportunity might be lurking on the other side of that uncomfortable phone call. The best things in my life and career have come from pushing myself outside my comfort zone and taking big risks. So send the email, make the short film, ask for the coffee meeting. The worst thing anyone can say is no, but what if they say yes? Read more>>

Nico Staub | Supervising Sound Mixer and Business Owner

It’s funny. The way some people see life or their career as a game of Chess or Go, I tend to look at it as a game of Backgammon, where strategy can only get you so far until the fate of the dice has anything to say about it. In order to do risky moves it’s important to consider the odds of success along with the price of failure, and what either of those might mean to us. Risky moves should come with a plan, but also with an expectation for the unexpected and a readiness to turn around any disadvantage. Human nature will always be a variable, and everyone is capable of “not seeing the right move at the right time”. Lastly I remind my self It’s just a “game” and although wining can be fun, we do most of our growth through hard lessons and our will to succeed. With this, I believe the concept of risk becomes secondary and every outcome can be a reward. Read more>>

Efrain Flores | Ar

I think risks are awesome! I think they are necessary to live the ideal life that you want. Without risk there’s no story but I think it works both ways. You see when you take risks it can either succeed or fail. Either way you’re growing from success and failure so risks are necessary to grow into the person you wanna be. I took many risks in my life and they either failed or succeeded but let me tell you; from the ones that did succeed payed off from all the ones that did fail. If it wasn’t for me to take risks, I’ll probably still be working at that Asian Restaurant I so desperately wanted to get out of. I probably still would’ve been shining spoons and forks instead of Acting, Making Music and Film. I’m very happy for the way it all worked out for me and it is still the beginning. Read more>>

Wilner Joseph | Community activist, Mentor, coach and community outreach.

How do you think about risk? Risk is apart of everyday life. Without taking risk, I wouldn’t be where I am today. Risk requires hope, faith, sacrifice, and believing in yourself. When you believe in yourself nothing can’t stand in your way. Taking risk has lead me to where I am today. It’s important to understand that in order to make your dreams a reality, taking risk is going to be part of everyday battle. When I say battle, it depends what risk your taking. Ensuring that every risk is a calculated risk. Not a risk that will jeopardize everything that you’ve worked hard for. Taking your time to sit with your thoughts, writing down what works and what doesn’t. Understanding what certain risk can mean for you is so important. Read more>>

Robert Slocum | Actor, Writer, and Director

Choosing to be come a filmmaker is a risk within itself. 9 times out of 10 a filmmakers parents or close confidants, has advised them to get a traditional job or to have a Plan B, I’m against both, so it’s a risk. I’m a firm believer in “High risk, great rewards” but take calculated risk. Risk is essential in innovation. Read more>>

Julie Phan | Filmmaker, Creative, & Writer

Risk is not only a necessity for success, but for me, it’s the exhilaration of life. Being a woman of color in the entertainment industry is entirely built on risk-taking. My identity itself can be seen as “controversial.” Every move forward I take can be considered a risk. It takes a lot of courage and confidence, for me especially, to step into spaces that have never been walked by people like me. The thought of just making myself comfortable in spaces not meant to include me can be scary. A huge risk I took was stepping into the entertainment industry at all. I strive to be authentic and true to myself, which can be very difficult and carry large consequences. This industry lives off the backs of marginalized folks but will never allow for their flowers to bloom. So in short, my entire career was a leap of faith, but I wouldn’t be here without the support of my close ones and the blessings of my ancestors. Read more>>

b r e s m i t h | abstract artist

Risk often has a negative connotation, but when I view risk as a challenge, it becomes exciting and stimulating. Sometimes given opportunities to take risks, I fear people will not like what I create, but that fear itself reminds me to be more concerned with expressing how I feel. I really should be the one who likes my art. Risks compel me to double-down and choose to be confident in my art, in spite of the unknowns. Read more>>

Michael Faers | Concept Artist for Games, Film and Animation

I think by simply existing, we’re naturally prone to positions of risking something regardless of personal choice, be it in our relationships, career choices, financial choices, hobbies, so on and so forth. To me, every moment in our waking lives is another risk taken, whether we are self aware or not. We live in a sublime state of reality filled with complexities beyond our understanding, most of the time. Obligations and events we are not prepared for happen when we least expect them to, and the scenarios we’ve prepared for rarely come to fruition. I guess what I’m trying to say is, we’ve already taken on the biggest risk by simply existing, and the absolute worst thing that can happen to us, will. The inevitable end. That’s what drives me to take risks for the things that I’m truly passionate about. Without risk, we fail to grow. Read more>>

Calvin Chen | Leadership and Executive Coach

I don’t take risk for risks’ sake, but what I want and enjoy most is usually on the other side of risk-taking — from the thrill of pushing my limits in snowboarding, competing in Tae Kwon Do, swing-trading the markets, or committing career suicide to be where I am now. But what’s the difference between bravery, and stupidity? I pondered that a lot growing up. Eventually I figured that if it worked out, I’d look brave. And if it didn’t, I’d look stupid. Read more>>

Jillian Colin | Fashion Designer & Vintage Dealer

Risk is a super important factor in life changing decisions. Where there is risk,  there is value. In my life and in my work I have risked financial, personal, and honestly emotional stability for the sake of following decisions that I have believed in. Notably, moving across the country in a pandemic with my company to pursue something new. And it’s paid off in more ways than one. Read more>>

Kristina Gauer | Illustrator

Risk-taking has never felt like a natural thing to me, mostly because I didn’t grow up in an environment that embraced risk. My family had a small business for a number of years and our motto was “slow and steady wins the race.” Let’s just say I would never make it as a world-class poker player or an Adventure Capitalist. Being wary of taking risks in my early life was not a smart approach because it led to me becoming paralyzed when I would have to make more important decisions and actually face risk head on. I found that when I did take a risk and committed to the outcome, no matter what it was, I gained a sense of inner confidence and determination previously never felt. Read more>>

Alexandria Cheng | Co-founder, Shen Generation

Taking risks is uncomfortable, we are creatures of habit and change removes us out of our comfort zone. When it comes to taking a risk, I try to understand the situation from all perspectives by questioning everything and everyone. Personally, I tend to be more calculated and prefer to play things on the safe side. However, I know how crucial it is to disrupt patterns and to make those bold leaps in the beginning of any endeavor in order to create something different. Read more>>

Lilliana Villines | Musician

When you decide at a young age to dedicate most of your energy to music, risk is something you get lectured about a lot. I’m lucky that I was born into a creative family; my mom paints and writes poetry, my father was an astrologer who wrote esoteric science fiction novellas, and my grandmother has been a singer, actress, and a birthday clown. So music as a choice never felt like the real risk and financial worries seemed inevitable no matter what I chose to do. I decided a long time ago that I would work odd jobs as long as I need to, even if it’s for the rest of my life, to support my music. However, risk is something I like to think about when writing. Read more>>

Sarah Dashew | Singer-Songwriter Story-teller

The funny thing about risk-taking is that I just feel like it’s the tug o’ war between your gut and your head. When your gut is telling you to do something that your head tells you is illogical or dangerous, the space between those two is where the risk lies. For me, in my whole life, whenever my gut has been telling me to do something that made my heart pound and my head was yelling uh-oh, like when I moved to Austin Texas without knowing anyone to start my music career, it’s ended up being the best move in my life. It’s led me exactly where I need to go. Read more>>

Alán Ramiro Manning | Travel Artist, Designer & Teacher

Risk taking requires faith. The fear associated to taking a risk is the friction required to create a fire. If faith then is the answer to fear, therein lies the key to expanding a purpose driven life. Risk taking has played a major role in my creative and personal development. I call them, ‘missions’. When life routines become comfortable, I plan a mission that has risk involved. The result is a gift! Read more>>

Solange Comer | Founder and owner of CULTURED SLiCE cheese shop

Risk. This word is defined by all negative connotation, yet when risk is taken, positive and amazing things can happen! Sure, taking a risk is scary, and vulnerable. But I think about risk in the sence that if I am not putting myself out there, showing my vulnerablity and taking a chance on something unseen and scary, then I am not growing. I decided years ago to take chances and risk everything in my personal life to change and grow. It was the best decision I have ever made. If we are not living for oursleves, than who are we living for? Doesn’t matter if you have a spouce, or a child, you need to be the best you and that will make for a stronger partner and parent!
Leaving a 22 year career in teaching to start a business was extreamly scary and risky. Read more>>

Senda Bonnet | Cinematographer

Most of people’s life, specially in the western world is filled with fears. Fear of meeting new persons, Fear of trying something n ew, Fear of succeeding, Fear of the future. But that’s when we let fears lead our lives, paralyze us that we cannot achieve anything, that we cannot grow. I am anxious and scared of a lot of things like everyone. But I noticed in my own life that if I put my energy in overcoming it than than in Thinking about it, I get rewarded. So taking risk is important, even essential. There is a beautiful poem of Jane Hirshfield that says “There is no knowledge won without sacrifice. To gain anything you must first lose everything.” Read more>>

Zachary Sitrin | Painter

As a painter, risk is an integral part of my art making practice. Painting is a venue where I can be intuitive and improvisational. Since I do not plan or make sketches before beginning a new painting, each work requires me to be fully present and trusting of the process. Along with this approach comes risk. I aim for my paintings to live on a fine line between fantasy and reality. Occupying this slippery space means that the work holds the tension of falling too far into either realm at any moment. Being suspended between coherence and incoherence is risky; to be in one or the other offers the assurance of certainty, but my paintings are more concerned with uncertainty. Read more>>

Nicolette Acosta | Actor & Filmmaker

To be in the entertainment industry at all – to be in any type of business where you are your own boss and brand manager you have to be at least a certain percentage of a risktaker, right? You have to bet on yourself. When I was younger I defined risks as impulsive choices and actions and I wouldn’t have described myself as a particularly risky person. But looking back I realize I actually took a lot of risks – I told my parents I wanted to audition for adult shows instead of just doing children’s theatre, for college, I was dead set on moving across the country to NYU Tisch despite not knowing anyone in that part of the country and I did it. Read more>>

Quintin Williams | Co-Founder/Chief Global Designer of Q4SPORTS

Taking risks is a major decision to follow through on when finally deciding to become an entrepreneur. It will consist of many days and nights of uncertainty, frustrations, and problem solving. Ultimately, how I evaluate risk-taking is a simple breakdown of the following: passion, network, and market analysis. If you don’t have enough passion for this risky endeavor, you most definitely will burn out during the process of growing your business. This is not for the faint of hearts. Read more>>

Magdala Charles | Fine Art, Artist

Every risk comes with a sacrifice. Every risk also comes with fear. That’s why people are afraid to take them. When I took the risk to discontinue my law school entry process, I knew that I was taking a big risk. I relied on faith, which I still do. If i did not take the risk to accept my talent as a way to live for the rest of my life I would not have been a thriving artist I am today. Risk has given me the opportunity to step out of my comfort zone, it has given me the drive to find my true passion , it has also given me the blessing of finding my true self. Today I encourage everyone to do the same, take risks, challenge yourself to see and do better. Read more>>

Murray Swanby | Reality Tv, Social Media, Non-Profit Founder

Looking back on my life.. the best decisions were also the biggest risks. But in the end, it will either teach you something about yourself, give you life experience, or be the best decision you ever made. Dont live your life comfortable, on the couch.. go chase your dreams full force, move to a big city, take the acting class, take the vocal lessons.. you will love the person that is sitting deep inside you waiting to be let out 🙂 Read more>>

Marina Eliza Holland | vocalist & lyricist

Risk taking has played a huge role in my life and career. I chose to move out to LA during the peak pandemic, after being kicked out of my college dorm. I decided despite the pandemic I knew moving to LA was the right decision for me and my music. In the past year that I have spent living here has taught me that risks are essential to prosperity. Putting yourself out into the world and music industry is taking a risk. Putting your music on streaming services is taking a risk, you’re creating a version of yourself for anyone on the internet to see, which can be a scary feeling. But if you don’t take a risk on yourself, you won’t see the rewards that will come. Read more>>

Eevin Hartsough | Writer, Producer, Actor

I grew up reading a lot of fiction and especially fantasy, and I absorbed a lot of the idealism that’s typical in that genre around bravery and risk taking. Heroes take risks! But as much as I believed in taking risks and daring greatly (and still do), I think it’s easy to misunderstand what that looks like in real life. As a younger person, I took a bunch of stupid risks – risks for risk’s sake; big gestures to get attention rather than to move towards a goal. Those kinds of risks advanced neither my career nor my artistry; at best they were ineffective and at worst they made life harder. Read more>>

Trent Buxton | Actor, Writer, Veteran

I’m an intense, all in type of person and rarely do I find others who are willing and capable of understanding that which can result in fear. There’s nothing I love more than when I’ve been lucky enough to have found a risk I’m so passionate about that I going all in on is a rush and I don’t have another option. The stakes make it easier and authenticity is the biproduct. Read more>>

Joshua Boone | Content Creator

Risk taking to me is nothing more than a strategic plan. Nothing in life is guaranteed but we can increase our chances of being successful when we understand a few key factors. Taking risks for myself wasn’t easy at first until I changed my perspective and realized just how much risk I was taking. I was taking a risk unknowingly depending on a job that could disappear at any given moment. So I decided to take better risk for myself and my life in becoming an entrepreneur. By far it was the greatest decision I made. Being able to live your life on your own terms is the most beautiful feeling. I’ve been able to travel around the world doing what I love because of the risk I took. Read more>>


If you stand a chance at being great or successful, you must take risks. As it relates to our careers, in the past we both have moved on from well-paid jobs to lesser paying ones for the opportunity to develop a new skill set. Making those decisions certainly came with sacrifices, but the risks were worth the rewards, and the experiences, relationships, and skills acquired transcended beyond those roles. Read more>>

Michael Vincent Waller | Composer & Producer

Taking a risk, is often something you hear about, but often don’t know what it actually means. I feel a lot artists might express that sentiment: “This project was all about taking risks…” but, in reality they are exploring a predicable variation within their own comfort zone, or established ‘voice’. I think that concept of one’s voice is the biggest risk that one can take. But once taken, formulated, and even branded, it can become a ‘standard’ or what is expected. Although, important to note, that despite these growing expectations, when one’s art is naturally expressed — it often seems to come from within, organic to one’s own inner experiences and perspective. This is a genesis for great art. Read more>>