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.

Timo Elliott | Specialty Costume and Prop Fabricator

I have always considered myself risk-averse. I make very, very few decisions without considerable forethought. So from my vantage, all my risk-taking is calculated and within acceptable margins of loss. That being said, I’ve discovered that my opinion towards risks is considered almost cavalier by most people, my family especially. My parents wanted me to be an engineer or a lawyer, you know, nice stable careers. Instead I got a degree in art and moved across the country to pursue contract work in entertainment. Risky? Probably. There is a certain amount of uncertainty inherent in contract work, but I knew going in this would be the case. My mantra is that someone out there is doing what I love and getting paid for it, so why shouldn’t that person be me? In that context, a lot of risks are acceptable, so long as they help achieve my end goal of doing what I love. Read more>>

Casey Kell | Entrepreneur

I enjoy going the non-traditional route. Little risk, little reward doesn’t excite me. Some of the more brash decisions I have made in the last decade have worked out very well from entering the medicinal cannabis industry, inventing a product called Chapfloss, starting a blog, Shopify store, investing in cryptocurrencies, etc. I’m a “swing for the fences” type of guy so whichever way I decide to go, I go 100 mph. Read more>>

Abigail Stone | Journalist, Writer and Founder of Home-Werk

There was a game when I was a kid that posed questions about the future. The one that stands out asked: given a choice, would you chose a steady, comfortable life or one that was filled with highs and lows? I chose the latter because it sounded…well…fun. I was 9 and “fun” was a defining factor of what I wanted my life to look like. Now, although I’m many times 9, not much has changed. I’m still looking to have fun and to be part of the conversation: to be excited by life, to learn things, to discover new places and to meet interesting people. I don’t think of myself as a risk taker but I can see how, looking at the way that my life has been architected, it may appear that way. Viewpoint is a funny thing, isn’t it? From my perspective, it was about being practical and doing what needed to be done. For example, when I moved to Los Angeles on two weeks notice, I wasn’t doing something brave. I went because that’s where the job was (and, okay, the week-long road trip across the country sounded like fun — and it was!). Read more>>

Brittney McCourtney | Photographer- Families, Mirco Weddings & Brands

Taking a risk is one of the most beneficial things you can ever do for yourself and your business. When I first decided to start a photography business the only way I was going to get bookings is by putting myself out there. I would message people left and right about doing shoots and every time I got a no I would tell myself I just need one person to trust me enough to let me photograph them. While doing that I was photographing anything and anyone I could get my eye until it finally happened. I finally booked a maternity shoot and it kinda of took off from there! I booked a couple weddings and families and now I’m shooting for a few brands and setting up style shoots. If I didn’t take the risk of putting myself out there I wouldn’t have built all the amazing relationships I currently have, and I would still be sitting at my computer wondering what it would be like to be a Photographer. Read more>>

Fabiana Fonseca | Experimental Artist and Designer

Risk-taking is one of the most important and impactful things someone can do in their life. It’s one of the best teachers because you can never really know the boundaries and limitations of what’s possible and what you can achieve until you try it. I’ve never been one to shy away from things considered difficult. I mean just pursuing an art career is a risk in itself. And I believe it’s extraordinarily important for someone to take those leaps of faith because if they work out, amazing! Your life is that much richer because of it! And if they don’t, okay no worries! Your life is still that much richer because now you’ve learned something you didn’t know before. There’s no growth without change. There’s no development of character without trial and error. And there’s no layers to life without a variety of experiences. And yeah, of course, it’s going to be scary. I moved to Switzerland when I was 18 and I broke my ankle in a foreign country by myself. Read more>>

Danielle Wu | Ecommerce Entrepreneur

Isn’t it always surprising when you hear what others may think of you? People often tell me that I was “Brave” to start my own company (Especially in an area that I had no experience in!) or to pack a bag and move to New York City with no job or place to live. Hearing this always comes as a shock to me because I certainly have never viewed myself as a risk taker but rather the opposite. At these two key points in my life I didn’t feel like I was taking a risk but looking back, I was. Somewhere along my journey to adulthood I developed a way to de-risk situations through planning that I’ll share with you. First of all, I have to recognize that I am lucky and grew up around 2 entrepreneurial parents who showed me that working hard and trying new things is fun! Growing up I’ve seen them try many different ventures, some with success and others that generated fun memories. Working late or on the weekends was a given but the life they were able to build together is remarkable and worth it. Read more>>

Hallie “Hal” Chavis | Jewelry Designer

I definitely believe in taking calculated risks. I wouldn’t be where I am today without taking the risk of leaving my steady corporate job to move back to San Diego, and I wouldn’t be working full time on my brand had I not taken the huge jump to leave my clients and pursue jewelry as my full time gig. Getting older has definitely given me more of an ‘if not now, when?’ mentality. The perfect time to start was yesterday, and the next best time is right now. After looking for guidance from my super business savvy aunt, she helped me realize that there is no “perfect time” to take the leap, and that all of the checkboxes that I wanted to hit before I left my job were going to keep adding up. After that conversation with her, I realized that if I wanted to ever pursue Shop Cholla full time, I had to take the risk and bet on myself to be successful. Since being employed solely by Shop Cholla, I’ve started making jewelry for myself, and people like me, instead of making jewelry I think would sell, and it’s been working really well for me. Read more>>

John Weil | Founder Sand Straw

Risk is what brings passion to the forefront of your business. It is the risk that creates a sense of being backed up against a wall, creating an environment where the passion and fire in your belly drives you forward. For Sand Straw, the risk of losing my $5,000 savings when I was 24, inspired me to work till the late hours and again in the early morning. I am a firm believer that when you put everything on the line, you can only go up from there. Read more>>

Lucila Terrazas | Founder of MommyCo, LLC.

Risk has been a part of my life since before I was born. My mom and dad were hardworking immigrants who took many risks to offer my sisters and I a better life and a life full of opportunities. If it wasn’t for the risks that they took many years ago my life and career would look very different. I realized at an early age that it was time to honor my parents’ sacrifices. The first life-changing risk I took was right before I started 10th grade. One day I asked my mom to sign me up in school in the United States. I knew that this change would be difficult because it meant leaving my comfort zone and everything that I was accustomed to. I began my journey by ignoring my insecurities and language barrier in order to create my own wonderful story. After a few years, once the cultural shock had passed and life began to feel comfortable again, I promised myself to never be afraid of trading the good for the great. Despite the insecurities and self-doubt I learned that taking risks would help mold my life and future career. Read more>>

Rachelle Hali | Makeup and Hair Artist

I think it would surprise some that there ARE different risks that we, as makeup and hair artists, take over the time of our career. My first big risk was quitting my day job to become a full time freelance makeup artist. I did not have my guaranteed job security, I did not always know when the next job would be, and I did not always know if it would work out. However, I KNEW I needed to take that risk so I would take my job as a makeup artist seriously and consider myself to be “all in”. Some of the next risks through out my career came in the form of working for no pay in order to “put in my time” and learn as much as I could, or trying different fashion or beauty looks and watch them either fail or thrive. All these risks led me to become a better artist, have more confidence, and step out of my comfort zone once in a while which is all so important to grow in your craft and become a better version of yourself. Read more>>

Ricky Lee Gordon | Artist

I have always been confident or maybe just foolish enough to take risks, Though to take risks is to seek a truth to keep moving through the things that you dont want in pursuit of what is your truth.So important to not settle , to not compromise and to push through on your path The fool is not foolish ,he is a seeker, with an inherent wisdom that pulls him to jump off the cliff not knowing what is there but knowing there is a truth that awaits discovery. The fool is a wise seeker. Read more>>

Joseph Eves | Certified Arborist

I’m all about risk, I think most entrepreneurs are. I will always do my due diligence and research but the one thing that I truly rely on is my gut instinct- that visceral feeling deep inside that tells you that this is the one, this is without a doubt the right decision, the right investment or simply the right move. Every time I have trusted this feeling and acted on it, I have never let myself down. Read more>>

Mei-Ling Mirow | Artist & Graphic Designer

Ever since I was little I feel like I have always been the one to test out the waters, some could call it break the rules, but I saw it as taking thought out risks! Fear is something that holds back a lot of people from really discovering all the potential they have and I use to let fear control what I did and didn’t do. Over the years of trying new things and not always succeeding I learned that failing at something doesn’t mean you yourself are a failure. In fact I see myself as someone who never gave up on myself and really trying to be comfortable with being uncomfortable. There are so many things that I have accomplished and so many moments where I grew as a person because I took a risk weather that was me saying yes to something that was unfamiliar or me saying no because I knew that there was too much on my plate already. Read more>>

Alecsa Geaga | IT Analyst and Small Business Owner

Just thinking about risks always gives me an uneasy feeling. Typically I like to plan and have a structured schedule and an organized list of tasks both short term and long term. However, I think this past year has definitely pushed me to come outside my comfort zone to take risks and have faith in believing that whatever is meant for me will happen. At the beginning of the year, I was an anxious senior in college scared of what was next. Now, I graduated, obtained a steady job, and own a small business! Being in quarantine has pushed a lot of people to come outside their comfort zones and start to pursue things they are passionate about. After witnessing a lot of people, especially my peers, start to work on things they are passionate about, it made me want to work just as hard, take a risk, and start a business on top of my full-time job. Starting Shop With Grace, a resale shop, gave me the opportunity to share my love for fashion with others. Read more>>

Nathan Cuevas | DJ | Producer

Tomorrow is never promised. Yup cliche I know. But if you were on your deathbed right now would you be content with your life? Stop thinking “it’s too late” or I’m not ” talented enough.” The common denominator of your favorite athlete, musician, streamer, etc. is that they took the first step. Just do it. Risks aren’t a bad thing. I used to paint them in that way for a long time but you shouldn’t avoid them (within reason of course). Risks are what makes life interesting. You’ll get a million no’s for a yes. Your parents will question you. Your friends might abandon you. Your significant other might resent you for it. You might even get hurt (emotionally or physically) taking risks. A quote by Jim Carey at a graduation speech I pretty much live by goes something like this: “You could fail at something you don’t want, so you might as well take a chance on what you do love.” Not just exclusively in music. Anything in life. Just do what puts a smile on your face. That’s it. Everything else will fall into place. Read more>>

Christen Kugener | Owner of Le Caramel and The Basket Corner

I consider risk to be an integral part of being an entrepreneur. I began a career in finance, which was stable, but not very exciting I always figured that I could fall back on my first career choice if the adventure of owing Le Caramel, the business I co-own with my husband Vincent, never experienced success. I felt I may lose a few years in the process, but I was young and knew I could recover from the small loss of income and time. In fact, I imagined the worst possible scenario as losing a couple of years working for somebody else. And I can’t honestly say that I think of that as a loss. However, as I grow older, I find myself becoming more “reasonable.” I am always open to new ventures—in fact we bought a second small local business, The Basket Corner, two years ago—but I proceed with a bit more caution. I have kids and employees, and they all come into consideration when making the next move. Change is a good thing for me. Looking back, the risk was well worth it. Read more>>

Natal1e | Artist

My motto this year is “take every risk.” This is the first year I feel like I can truly do anything I want to do musically and I feel the best I’ve ever felt. We all get so trapped in what society will think of us or how people will perceive us. I think all creators can agree that we all go through these cycles where we get lost in trying to figure out exactly what people want. When we do that, we lose a piece of our unique self and what we want. I challenge everyone to take the risk in betting on yourself. Stop caring about what other people are doing or want. Go after what you want. Reach out to people you want to work with. The universe will respond. Work hard and consistently, take the risk. Read more>>

Natalie Leton | Professional Marketing Creative & Photographer

I believe that everything worth it, needs to have a little risk. Almost everything I have done in my life had a glimpse of risk, you need to be able to take the situation and weigh the options of either outcome. If the outcome to take the risk outweighs the safe zone, it’s best to jump head first. I took a big risk in moving out to Seattle and starting all over. Going to a new city not knowing anyone except my roommate made me grow as a person, my professional career, and my photography business. It was because of my move I had the opportunity to be a part of a creative showcase where I displayed my photography for the first time, as well as displaying my work at a local cafe for two months. I was able to concentrate on my photos during my free time which lead me to find my niche in photography. The move was also a great outcome for my professional career, I was able to take a step back and focus on life goals and accomplished those goals in the short time living in Seattle. Risk is a scary word, but sometimes it’s all we need to take to get to our desired paths. Read more>>

Kayla DeLaura | Photographer & Creator

Taking risks was probably my number one fear growing up. I would always admire anyone around me who would take these daring actions. Whether it was applying to their dream school, deciding to just go on a spontaneous vacation, or just simply the ones who jumped in their car to go and get a tattoo. The risk takers who scared me the most were the ones who reached out to their dream jobs. How was that even possible to have enough courage to just drop all of the “what if” moments and actually do something about it. I think I didn’t realize the meaning of taking a true risk until I applied myself to Live Nation. The fear and the doubt I had once I reached out asking if they had any photographer positions for me was a decision that got in my head too quickly. With all the whys and the what ifs floating around in my head, I had come to realize that if I had just sat at home and dreamed about being a music photographer I would get nowhere. Read more>>

Carla Olson | Photographer

Life is a risk. Every day we take a chance with every aspect of our lives. For example, Do we work for ourselves or someone else? Do we enroll in college? Do we have children? Do we marry? The list goes on and on. Every day we are faced with making decisions taking risks to see how life’ decisions play out. Risk taking is not always easy as it takes some reflection first and foremost and then action. Some risks pay off and others do not. But, without risking, one will never know how how life’s events unfold. How do we know how life’s opportunities will work if we do not take risks? In my opinion, taking risks is healthy. But, we must be cautious about the types of risks we undertake. We must try to make smart decisions and always keeping safety in mind. Some risks have a dangerous consequence attached. Every individual must make the best choice for their life that they feel will enhance their quality of life. Each one of us is unique about what risks we choose to pursue. Read more>>

Maria Dominguez | Nursing Influencer

I believe if you don’t take risks you will never challenge yourself, you will always wonder what your life would have been if you had decided to take risks. I say this from experience and apply it to school I was always afraid of the risks. What if I take this risk and won’t be able to afford school? What if I leave my job and risk not being happy for taking this step? What if I take the risk and fail? What if.. what if.. what if… I then learned to change my mentality! What if I take the risk and succeed!! What if I left this job and went after my passion and I am successful! I have learned to take risks because I no longer want to waste time or wonder about what if’s. Because I took a risk by leaving my job and went to school full-time, I am happy to say that I have recently graduated with two degrees! My dream was to go to school and become a registered nurse and I achieved my goal. Read more>>

Cynthia Quinonez | Hospital Administration & Content Creater/Blogger

Risk is not only a gamble, but also a decision swiftly made while carefully considering your fear, and your vulnerability, and if it is worth the return or outcome. I say swiftly, as impulsivity is one of my symptoms of my ADHD. While I most likely already researched and analyzed the probabilities, it has been my lack of impulse control that is what makes me pull the trigger. I can’t say that my impulsiveness has always paid off, but it’s definitely led me on the road otherwise not taken, and not wondering, “what if?” I used to allow fear from keeping me from taking any risks, and maybe that’s why I feel that I hit a plateau for so long. I can say with absolute certainty that when I started taking risks, and letting my guard down, my life changed for the better. Risk has helped me find my community, my calling in life, and helped me take leaps with brand collaborations and meeting wonderful people that had I not done so, I would be much further behind in my goals, if I would have even decided to even go down this road. Read more>>