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.

Joel Coen | Managing Partner

There have been a lot of different circumstances in my life where I have had to take risks. The biggest risk that I have ever taken was related to moving to Arizona. When we made the decision, we had built up a huge network in Colorado and we had done what we could to build the connections that have proven to last a lifetime. But the pull to AZ was too strong. My kids were here and we wanted to be better parents. We knew absolutely no one but it didn’t take us long to build up a business and eventually win multiple business of the year awards on the path to building up TruNorth Advisors. Read more>>

Jennifer Dunbar | Reduction Woodblock Printmaker

Over a decade ago, I noticed that I was a person whose first instinct was to answer “no” to most unexpected asks. At that time I determined as a New Year’s resolution to start saying, “yes” and to think of unexpected asks as opportunities. Leaning into those risky situations lead me to change careers, to embrace teaching printmaking, and to joining a printmaking non-profit. Read more>>

Dan Spencer | USMC Veteran/Retired Police Officer/ Owner of Filthy Pirate Coffee

I have taken many big risks personally and professionally. I could have chosen an easier path then becoming a Marine or a police officer but why not go all in for what I considered the top tier career choices. The coffee business and podcast we run were huge unknown risks and something that was completely our of my element but it was so worth it. Risk taking is a MUST in business but only with a clear vision of the goals and future. The negatives of risk taking can be loss of time and or money but rewards can be substantial. I have learned that patience and constant attention to our mission and operations has been huge for us in the business. I am not done taking more risks either. Status Quo is not my style or speed. Read more>>

Sandra Grattarola | Fashion Photographer

One of the things that make me risk it all was not thinking that there was a risk. If we don’t take risks life would be so boring, I think that living in a city like New York implicates taking many risks and I think that’s one of the things that I enjoy the most. Read more>>

Bianca Lessard | Lawyer and Co-founder of 0x Society – Crypto art gallery

Risks are a necessary part of life for success. They may even be the secret to success in my opinion. Of course, it’s easier to sit down in your daily routine and do the same thing everyday – it’s comfortable. But that’s not where happiness is, and that’s certainly not where you’re going to learn. However, those risks need to be calculated, and you need to be ready for failure. Over time, I think you learn to appreciate that failing is a learning opportunity. If you do nothing, there’s a 100% chance that you will fail. But if you do something and take a risk, there’s now a 50% chance that you will succeed. Read more>>

Marie Feutrier | Headshot and Portrait Photographer

Taking risks is part of my creative process. For example, I regularly ask myself: “Did I fall at something this week?”. If the answer is no, it means that I didn’t get out of my comfort zone. Trying something new is the only way to keep my photography current and grow as an artist. However, I’m very cautious with my business’s administrative and financial parts. That’s also why I’m asking for help in areas I don’t think I’m competent. I would choose to spend money on a service and keep peace of mind rather than doing the job myself. Read more>>

Marlon Richardson | Hip Hop Artist, Producer and Educator

I think risk is important for anyone’s personal or professional development. Taking risk, naturally, can make anyone uncomfortable but it is within that discomfort where we often find our biggest growth. Even further, we find new things we didn’t believe or know we were capable of. With that said, I think the risk you decide to take, whether in your career or otherwise, relies a lot on knowing yourself, truly and honestly. Trusting in yourself and constantly testing your abilities are important, because it is that confidence that informs how much risk you’re willing to accept In my life, as well as my career, every time I bet on myself, I won, one way or the other. Read more>>

Devin O’Dell | Buslifer, Skoolie Builder, Influencer and YouTuber

Risks are definitely one of the key things that I think about in a different way to that of my peers. I like risks, because the idea of risks that is generally taught and accepted in our society seems backwards to me. When we first decided to really dive head first in to buslife, and in to building buses for clients, acting, or whatever jobs came at us, Breanna was initially terrified at giving up our comfortable jobs and taking this “risk”. Read more>>

Marion Sealy | Luxury Travel Advisor

Taking risks means trying something new with the possibility of failure. You may fall down, pull yourself up by the proverbial bootstraps, and have to try something else, but you’ll never know what might work out if you don’t try. I think of risk as an experience where I’m making myself vulnerable, and by doing so I’m opening myself up to the opportunity to achieve something greater. Many of us have been raised to believe that being vulnerable is being weak, but comfort never leads to growth. Read more>>

Tara Kukla | Licensed Massage Therapist

I quit my very secure, high paying job and opened my own massage business in the middle of a pandemic in 2020. I spent thousands of dollars on a business coach, the best in the country. I put myself out there and called many other business owners knowing full well I struggle deeply with social anxiety, to connect and build with others who also want to help the community. I left the comfort of my anti-social bubble, my cozy job that I could perform without even thinking about it, and put my trust in expensive coaching. Read more>>

Alejandra Isola | Aesthetician – Corrective Skin Care Specialist

Taking risk has never been much of a problem for me. I love the spontaneous adventure it takes you on. However, if it intertwines with financial decisions that’s when anxiety is at an all-time high for me. When money is involved that’s when the negative thoughts all come rushing in, the doubts, the panic, and the fear of whether or not I would be able to provide for my four kids. As a mom you’re constantly questioning every move you make, hoping the decision that I make every time is the right one. That’s where I begin to second guess myself…… Am I worth the risk? Read more>>

Natali Zollinger | River Guide. SUP Athlete. Podcast Host. Restaurant Owner.

Risk is my north star. It is the guiding light that helps me stay on track. It’s scary to put yourself out there, to choose something new and to pursue the unknown. But that’s the beauty of risk, it forces you to come in and out of your comfort zone. To challenge the norm. To fuel your inner fire. To defy even your own odds. Risk is why I am who I am. Strong, passionate, and fearless when it comes to my dreams. I know that I haven’t always done things right, but at least i’ve done them. I fail, but I always fail forward. Helping me optimize myself in becoming the best version of me. Read more>>

Melotika | Electropop Singer-Songwriter

I feel like my entire life has been a risk. I say that because I come from a safe background growing up in the suburbs with opportunities to go to school, University, and to ‘get a real job.’ I did all of that for a while but it was not providing me happiness. I dropped out of University in 2014 to enroll myself in a trade to learn recording arts and production. After I completely the program, I literally just moved out of Montreal to re-discover myself in Toronto where I invented Melotika. A lot of friends and family thought I was crazy and did not support this but I was happy with my decision. Being uncertain everyday where my music will take me is what keeps me on my toes writing more and more songs. Read more>>

Chris Perkins | Musician/Producer

Risk taking is the foundation I’ve built my life and career on. It takes a lot of risk to be on stage and it takes a BIGGER risk to be singing and playing your own music and not know if people will enjoy or hate it. I pride myself on constantly undertaking risks especially with the decisions involving my music career. I could easily play it safe and pigeonhole myself into one genre by making the songs that sound the same but I decided it would be better to risk exploring new genres and continue expanding my musicality through all the instruments I learn how to play and the different styles I’ve taught myself how to produce. Read more>>

Brendan Byrne | Photographer

Risk is an interesting word. To me it can describe behavior that is incredibly stupid, cleverly calculated, or somewhere in between. Personally I have always found the best things in life are hard to come by without some level of risk. The skill is understanding what the potential consequences are of failing or succeeding in any particular endeavor. I am a creative individual, and I have long known that creativity would have to factor in heavily with whatever career and life path I chose. This is quite a risky way to live. Read more>>