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.

Amber Blaski | Content Creator & Social Media Marketer

We’ve all heard the phrase “No risk, no reward”. As much as I’d like to tell you that sayings are just sayings, I’ve always found this one to reign true. A little over a year ago I was living in Michigan, in a small town, with big dreams. When I made the decision to leave and move across the country, I took a big risk (probably the biggest risk of my life). I was leaving everything I’ve ever known – to chase everything that was unknown. I had no real plan other then to pack up my things and move into an apartment I had signed a year lease to, sight unseen. But I knew that I wanted to reside in the mountains, to embrace nature creatively and to be surrounded by things that set my soul on fire. I yearned to travel, to make my job to create content for outdoor brands, maybe even live on the road.  Read more>>

Jennie Tucker | Professional Live Event Painter

For the past 10 years, I have worked as a professional live event painter, traveling to and painting at some of the most luxurious and beautiful venues across the nation. Along the way, I’ve met incredibly interesting and amazing people. To say I am “living my dream” is an understatement. However, this didn’t happen overnight; it required taking significant risks. In 2012, I served as a corps member with Teach for America in South Carolina. I was placed in a struggling school in a predominantly minority area, where all my students came from challenging family situations. Through that experience, I learned the value of endurance and perseverance in the face of job-related difficulties. Teach for America and the lessons I learned there played a crucial role in propelling me into entrepreneurship. Read more>>

Graham Johnson | Photographer/Artist

Taking risks was foreign idea to me growing up. I often played things safely to avoid the consequences in failure. Failing is uncomfortable. As I have grown older I have realized the importance in failing, being uncomfortable, and putting myself out in the world in a way that is conducive to my ideal future that will get me closer to my career goals. Doing so presents opportunities to learn lessons I otherwise would not have. These lessons expand my abilities and perceptions of myself and world around me. Even taking risks with learning more about myself emotionally has helped me become more vulnerable with the community around me to see how I can help others in their journeys; while also continuing to advance my photography skills.  Read more>>

Nicole Treska | Author of Wonderland: A Tale of Hustling Hard and Breaking Even

I have a tattoo from the poem “A Brief for the Defense” by Jack Gilbert, one of my favorite American poets, the line reads “We must risk delight.” I think that’s one way I’ve considered risk in my life. To me, real risk was pursuing what brought me joy, which was/is writing and experience. I worked in the service industry and as an adjunct instructor to give myself time to write and travel and take long walks to think. And to some, and sometimes to me, I felt like I was failing in being an adult to take long walks. It felt like a giant risk to pursue this idea of writing as a life, terrifying and uncertain, but the thrum of what I wanted was stronger than that fear. And I guess I think that’s what risk means to me. Read more>>

Joe Diaz | Owner & Creative Director

When I started my business in 2020, it was right after I got fired from my second job out of college. I knew I didn’t want to jump into another job that made me hate waking up every day. Plus, I had this golden opportunity—no major obligations, no kids, no mortgage—so I had this rare chance to take a risk without too much on the line. I grew up in a household where my parents ran a business together, so I think that kind of life makes you less scared of the risks other people might see. With that experience, I knew I wanted to start something of my own. After a couple of ‘real jobs,’ I also figured out that I wasn’t exactly a stellar employee. At the time, my only real skills were coming up with marketing strategies and making videos, so I decided to dive in and make it happen! Read more>>

Micah Mitlyng | Owner of Denver Mobile Sauna

I use to work a sales rep for a service that worked with private Amazon sellers. I would do phone calls all day with different sellers, and talked with them about their product, and how they brought it from a concept in their head to an actual product people could buy on amazon. One thing that always stood out to me, was you don’t have to be the brightest, or best, I was often shocked how many people I talked to who in my mind seemed fairly unintelligent, but because they didn’t overthink it, they where able to just go forward, go through the steps and come out the other side with a product they could sell. Read more>>

Lura Caillouet | Business Owner | Charcuterie Artisan

I have a tattoo in French that translates to, “the risk is beautiful,” and it’s a phrase I really live my life by. To me, taking a risk means acknowledging that it may not turn out in your favor but being brave enough to do it anyway. What sets apart a smart risk versus a reckless risk is how calculated it is. I’m a planner, and I almost never jump into something headfirst without thinking it through and understanding both the upside and the consequences. With that said, once my mind is set on something, it’s almost impossible to pull me from it, and I have a tendency to hyper-fixate and problem solve until I have a solution and a plan that works. Read more>>

Laura Anderson | Founder

Risk-taking is an inherent part of entrepreneurship—it can be daunting, but it’s essential for growth and success. Strategic risk-taking means truly understanding your market, knowing the intricacies of your business, and being prepared for unpredictability. This mindset has been crucial in my entrepreneurial journey. Transitioning from a consistent and stable career in the medical field to starting my own aesthetics business was a significant leap, especially as a single mother and the sole provider for my family. With no clients to start, the stakes were high, and failure wasn’t an option. Read more>>

Lee Tripi | Architectural Designer and Artist

I’m a natural born risk-taker. I’ve made many risky moves in my life, some major, many minor. There are varying levels of risk. One major risk I took was at a crossroads in my career and became a re-invention of myself. In 1990, I was tired of my job and after eight years of working in a corporate sales management position, I left. I wanted to fly on my own as an architectural designer and painter. This is where my real interest resided. Not even the lack of prior technical training would discourage me from my dream. With determination, I set out to teach myself everything I thought I needed to know to get started. I kept thinking about the phrase, “Fake it ’till you make it.” I read classic architecture books and writings like, Towards a New Architecture by Le Corbusier and everything I could get my hands on regarding the profession. I also took a few classes. Read more>>

David Rosckowff | Automotive YouTuber

“Failure is only the opportunity to begin again, this time more intelligently.” – Henry Ford. I have tried many different things in life, and most of them have turned out to be valuable learning experiences. Because I refuse to stop trying, I have gradually become wiser. I am definitely a risk-taker and hardheaded, but I believe that, if you learn from failures and incorporate those lessons into the future, you can make great choices that lead to positive outcomes. I apply this approach to everything I do in business. The risks may get bigger, but they are also more informed by my past experiences and accumulated knowledge. Read more>>

Consuelo Sierra | Permanent Makeup & Brow Artist

I think taking risks is essential for growth. I’ve had to take risks that have cost me careers and relationships but have brought me so much knowledge, and deeper relationships with loved ones and myself. It has pushed me to have the courage to see so many beautiful places worldwide. Taking the risk to start a business has given me a deeper trust of that feeling in your heart that there is something for you that can bring you joy and that you look forward to doing every day. Risks can be scary, but exploring that fear and doing it anyway can lead you to the most incredible places inside yourself that reflect outwardly in your life. Read more>>