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.

Melissa Walling | Artist, Designer & Creative Entrepreneur

I think taking risks may come naturally to some but taking calculated risks is a skill anyone can develop with time and a certain level of confidence. Society often paints risky behavior in a negative light, but there are many achievements in life that can only be reached by stepping outside one’s comfort zones. At the beginning of my business journey, the prospect of putting myself out there and facing potential rejection felt incredibly overwhelming, particularly in the subjective realm of art. This fear led to a fair amount of feet dragging on my part. Getting past these initial challenges (and social media anxiety) marked a turning point in my mindset, and each step that followed has become easier. I feel more prepared and confident about tackling the next risk to reach where I aspire to be. Read more>>

Kathleen Haley | Educator, Instructional Coach, Mentor

I’ve experienced a significant shift in my approach to risk-taking over time. Initially, I tended to avoid change and stick with what was comfortable. However, as I’ve encountered various life and career choices, I’ve come to realize that taking risks often leads to personal growth and unexpected opportunities. Fear used to hold me back, especially the fear of potential failure and worrying about others’ perceptions. Now, I see the value in productive struggle and the beauty of overcoming challenges I didn’t think were possible. This shift has empowered me to follow my passions, become a more resilient leader, and make decisions that align with my own values and aspirations, free from concern about others’ opinions. Embracing risk has truly been instrumental in shaping both my personal and professional development. Read more>>

Anna Leathery | Tarot Reader, Reiki Instructor, Spiritual Life Coach

Risk is everything. Think about it! I can wake up in the morning and decide to pack all my little crystals into my favorite basket bag, put on a cute outfit that I feel good in, go find somewhere to pop up readings and put myself out there in front of the world. Or I can decide to just day dream about it. If I don’t take the risk…I’ll never ever know what’s out there for me. Life truly begins outside of your comfort zone. I get a lot of comfort in knowing that everyone is uncomfortable on some level- Being a human is super awkward after all. That gives me strength and courage to be different and bold. Read more>>

Luciano Ruscitto | Owner & President

In my opinion, risk-taking is a very subjective and complex aspect of decision-making, and its role in one’s life or career can vary depending on personal beliefs, values, goals, the nature of the industry that they work in, etc. It’s all about understanding your own risk tolerance. Some individuals thrive on high-risk situations, while others may prefer a more conservative approach. Knowing yourself and your comfort level with uncertainty can guide your decision-making process. The fear of failure can be a significant barrier to taking risks for some, however, trying new things, whether it’s taking on challenging projects or entering unfamiliar territories, can lead to valuable learning experiences. Read more>>

Jess Kellar | Owner of The Heart Baker

I think that anything you do includes some level of risk, right? When I had an IT job, for example, I had some level of risk. I could be fired. As AI increases my job could have become obsolete. Then there are more of the risks that aren’t calculable like what is my likelihood of happiness if I stay where I am? Those are the types of questions that led me to leave what others may have considered a ‘less risky’ job and start my own business. Its very personal- what level of risk am I willing to accept? For me, my risk of unhappiness outweighed my risk of failure in starting a business, so I took the leap! In 2021 I began taking baby steps into starting my own business and now 2024 and I can look back on all the progress I have made. Read more>>

Lisa Mort | Breathwork Facilitator and Trainer

I fully understand the battle between fear and risk: a long standing challenge that kept me hostage within my comfort zone for most of my life. Despite having a successful career as a hair stylist, the fear of potential failure and the uncertainty of stepping into the unknown consistently held me back. It led to a self imposed inertia, where the idea of moving forward was overshadowed by a ton of excuses. I became quite fluent in excuse making. This fear, coupled with bouts of self doubt, eventually led me down a path of depression. The turning point came during a wellness retreat in Costa Rica. Returning to the States amid a Covid induced lockdown provided me with the opportunity to reflect deeply on my desires and aspirations. Read more>>

Courtney Godsey | Actress & Entrepreneur

Taking risk for me overall means bravery. The role taking risks has played in my life and career is nothing short of phenomenal. I’ve been in rooms that i have envisioned myself being in, I’ve inspired, I’ve took losses, had massive wins, Learned so much information. and gained a lot of faith taking risks. Read more>>