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.

Mike Murfitt | Traction Coffee Co-founder // Marketing // BMX Rider

The importance of risk taking is something I’ve been tuned into for the better part of my life now & I owe that to a bicycle. I grew up riding BMX (still ride) & learned early on that if you don’t take the risks you’ll never grow or learn new things. In BMX when you take risks you end up on the ground bloody & broken from time to time which is never fun but it teaches you what NOT to do & I believe there’s a massive lesson to be learned there. From a young age of becoming accustomed to taking risks & knowing that they’re either going to pay off or have repercussions as I started to transition into business I realized taking risks on my bike was very synonymous with business except for one major difference; one didn’t lead to broken bones & concussions. There’s also various levels of risk that can be taken, for example I wouldn’t jump on my bike & try a backflip if I haven’t done my homework – that same rule applies to how I approach risk in business. Read more>>

Amy Yetman | Director & Co-Founder, Horseshoe Market

By nature, I think I may seem like a safe, non-risk taker type, but I’m known to upend things with gnawing dreams that I can’t ignore. When it comes to business and and being an entrepreneur, taking risks is just part of the deal. When we started our Horseshoe Markets in 2010, there was a recession and we literally had no income. With that came a sense of desperation but also a sense of–there’s nothing to lose so taking risks was the only way to go. We started our markets in a funeral home parking lot. I had no idea how to run a market and I didn’t have any ‘in’ with the maker community. But I had wished there was a flea market in our neighborhood so with my husband’s, Doug, encouragement and entrepreneurial push, I started walking the Berkeley neighborhood and introducing myself to the businesses saying we were going to be bringing a flea market to the neighborhood and would they like to collaborate/partner. Read more>>

Kristie Latimore | Tattooer And Fine Artist

I have always been a risk-taker. I’ve never been one to shy away from a good challenge or push myself harder when facing adversity. I believe that life’s most precious lessons are learned through hardship and perseverance. In 2009, when I began to pursue a career in tattooing, it was a different world for women trying to break into the industry. I experienced my share of discrimination, sexual harassment, misogyny, and degradation while looking for an apprenticeship. Thankfully, this experience drove me to work twice as hard and take the necessary risks to be successful and become a mentor to other young women with the same aspirations. I am thankful for the experience, as it made me the strong woman I am today. Read more>>

Becky Miller | Founder

With regards to risk taking, generally if something nags me on a constant basis, I know it’s time to take a leap of faith. Opening a retail store scores high in that category, but it is something that I was hell-bent on trying and I also knew that I was looking for something creative to satisfy my soul at this time in my life. Read more>>

P.O.M.E. Product Of My Environment | Owners Of P.O.M.E. | Product Of My Environment (Earth-Conscious Apparel Company)

Taking risks and getting out of your comfort zone are necessary, especially in the world of entrepreneurship and being a creative. The need to stand out as a brand is crucial these days and that is best done by thinking outside the box which can be a risk within itself. With the industry being so competitive and being a small business on the rise if we don’t take risks we won’t be able to make an impact through our brand. Stepping away from the societal norm of working for a large corporation and blazing the trail on your own really pushes you to hold yourself and your business partners accountable. There is of course no actual “boss” there to hold your hand. Not all risks work out for the positive but you can’t let that discourage you from taking the next risk that presents itself. As the old adage goes, no risk, no reward. Read more>>

Stan Yan | Graphic Novelist, Caricature Artist, And Instructor

The funny thing is I never looked at myself as much of a risk taker. But, it’s undeniable that starting my own business is fraught with risks. Despite this, I never felt like any decision I’ve made as an entrepreneur was a risk. When I started, unless my spouse had been already earning a steady and reliable income and able to add me to her health insurance, I don’t know if I would have tried starting my own business. Prior to starting to do my artwork full time, I had already started self publishing my own comic books and traveling to comic book conventions to promote them, so by the time I got laid off from my financial business career twice in 3 years, I already had some momentum in my art career and experience promoting my artwork. So, this gave me data to work with and helped me decide to add caricature commissions (zombie, to be specific) to my mix to help me generate more revenue and make these events reliably profitable. This was definitely a risk/reward analysis. Read more>>

Tara Kelley-Cruz | Artist

The principle of risk is one that I practice regularly in my art making process. When I am stuck, when my art practice is feeling stagnant, or when I don’t absolutely love what I’ve created, I force myself to take a big risk. Risk in this setting can take the form of painting over areas that I love, sanding back into areas that I thought were finished, or sometimes just adding a bold swath of a contrasting color to the painting. This gives me something to react to. It enlivens my practice and my art. I have learned that if I have risked nothing in a work of art, it shows. It feels “safe”, and a bit boring. I am learning to take the principle of risk from my art practice into my life. A life where nothing is risked feels “safe” and a bit boring as well. Read more>>

Mica Adesso | Psychologist and Yoga Teacher

For me, risk taking starts with inviting a courageous conversation within myself. It’s hearing that bare and revealing inner dialogue that I must first call my own. It’s finding the place within my body where my voice resides. It’s paying attention to how/when/where/why the fire of that voice gets dampened by fear and self-doubt. It’s understanding this process in which fear and doubt collapse my chest, constrict my lungs, tighten my airway and shrink my self. It’s learning how to inhabit my full body. It’s discovering the stuck places within my body where griefs and traumas have created a blockage. It’s tending to those wounds. It’s the choice to stand by these wounded parts, even if it burns my present identity to the ground. It’s knowing that my inner world is my home, the grounded place for my belonging no matter the outward change in circumstances. It’s turning towards those parts of my body, my soul that I had disowned, claiming them as my own again. Read more>>

Thomas Harvey | Owner, Earthwood Design. Creator Of Beautiful Wood Objects

I’ve never considered risk as an independent factor or issue. Risk taking in and of itself is not important. What matters is purpose and priority, what is the thing that you want to accomplish, and more importantly-why? Risk is just a simple assessment on the path to success or failure, its just part of life. I have taken many risks, and failed often. But more importantly, I knew what my purpose was and kept working at it. Success is just getting up one more time than you get knocked down. Read more>>

Jennifer Steck | Artist

Motivation and passion have played big roles in many areas of my life and that requires taking risks at different points on the journey. I love new challenges that keep me a bit uncomfortable. I try to walk through the open doors, even when I have doubts and usually, it pays off with new opportunities. Five years ago, I left a 30+ year career in law enforcement and set out to follow my passions. One of those passions was art and creativity. Here I am today, a working artist who not only sells my work, but also teaches classes to fellow artists. I never would have thought I’d be where I am today. Taking those chances has paid off in amazing ways. One open door leads to many more opportunities that wouldn’t be there without taking some risks. Read more>>

Dan McVey | Video Producer & Social Media Marketer

Taking risks at this point in my career is the only thing that has allowed me to live the life that I want. I had barely enough savings to justify quitting my full-time job two years ago, but I took a risk because I didn’t like working there, and I left. Two years later, I’m still working for myself. I’m taking a risk every day simply pursuing my career path, because it’s currently not predictable or financially stable. But in the end, I am more fulfilled because I get to do it the way that I want. Risk taking is not comfortable, but when we’re comfortable, we’re not growing. I’ve grown quite a bit. Read more>>

Elizabeth Boulos | The Ingredient Insider

When we take risks, regardless of size, we’re preparing ourselves for growth. No matter how big or small the risk is, we experience emotions that teach us about ourselves. In my life, I’ve discovered the most about my strengths, weaknesses, and areas for growth by taking risks. This has applied to taking small risks, like taking on projects outside my level of expertise where I needed to learn on-the-fly, to large risks, like leaving a corporate job that no longer served me. If not for taking risks, I wouldn’t have had the opportunity to live and work abroad in Serbia, live in Colorado, or be the entrepreneur that I am today. Through taking risks, I’ve gained confidence and humility, learned to be vulnerable and open, and learned what things are most important to me. I firmly believe taking risks is how we go from good to great. Read more>>

Jeanne Oliver | Creativity is Calling | Become The Artist You Have Dreamed To Be | Online and Live Art + Business Workshops Artist. Author. Coach

I think what we learn about risk only becomes clear as we have to walk it out again and again when we run a business. How I thought about risk 13 years ago and how I think about it now are two different things, but that is also because I am now a different person too. Walking out dreams, using your gifts, collaborating, trying new things, letting things go and taking risk on a regular basis changes you. Risk early on can bring up thoughts of possible failure, public humiliation, loss, mistakes or even the idea of “who do I think I am?”. As the years have gone by I have come to trust my intuition/my gut like never before in my life. I will have lots of wins and lots of so-called failures when I take risk but what I have learned is that by following what is inspiring me, exciting me, keeps me up at night because I can’t stop thinking about new possibilities…these are the things that will always be wins no matter what. I will offer something new and it may not be a huge success or maybe it is complete failure in every way BUT by learning to follow my loves, beautiful collaborations, creating for me…all of these things really lead to wins in the long run. Read more>>

Deborah (Debbie) Jacobson | Past Life Regression Practitioner, Soul Based Psychology, Evolutionary Astrology, Tarot Reader, Dream Interpretation, Akashic Records Reader, Psycho-Spiritual Breathwork

It was a huge risk thirty years ago to start my Psycho-Spiritual practice, in the middle of the midwest no less, where no one had ever heard of anything like that! But, I had invested money in my education and music equipment and we renovated our house to accommodate my business. I was projected on quite a bit, a lot of people thought I was crazy, but I knew that this was my life’s work and my passion, so I kept going because I knew that I could really help people. I ended up having a fairly large clientele, before moving to Colorado six years ago. It was a struggle to start over, because my business was primarily word of mouth, social media wasn’t ever that beneficial for me, mainly because the work I did was mostly known on the coasts and in Europe. But, I have established myself and over the last six years have developed more skills, which are more understandable to the mainstream public now. Read more>>

Sarah Grondin | Esthetician

My life has always been about taking risks. I have never followed the conventional roads in work or my personal journey of life. I like thinking outside the box and I always want to challenge myself. Read more>>