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.

Vanya Allen | Artist: Scenic Design, Fiber Arts, Vocal Music, Acting, Arts Administration.

I regard risk as an assessment of the failures, dangers, disappointments, and unpredictability involved in an endeavor. I weigh the risks or “count the costs” as the old heads say. Then I can juxtapose the risks with the rewards and proceed accordingly. Once safety is established for myself and my team, risk-taking becomes an integral component in the adventure of creating. Because I don’t approach my life or my art from a place of perfection, I’m inclined towards risk-taking. An immediate failure often paves the way for noteworthy improvements in performance that would otherwise be unattainable. You cannot enchant without taking risks. Audiences sense risk-taking and respond to it authentically. Without risk, there are fewer opportunities to find escape inside of the art. Will it make you vulnerable and land you flat on your ass at times? Yes. Yes, it most certainly will. The reward for it, if you can properly self-reflect and recover from disappointment, is a level of bravery and assurance never allotted to the cowardly. Read more>>

Monica Toomey Lila Lazarus | Journalizer, Entrepreneur, Journalizer, Keynote Speaker

Risk is the heartbeat of entrepreneurship; it’s the adrenaline rush that fuels innovation and propels us forward into uncharted territories. As entrepreneurs, our relationship with risk is about embracing opportunities, walking towards what we’re afraid of, not walking away. Journaling helps you work through that. If you want your life or business to be what it’s always been, avoid risk. Read more>>

Lucila Anderson | Founder & Creative Director | Allula Design Group

Risk-taking has always been an important part of my journey, both personally and professionally. The decision to leave everything I was familiar with in Argentina and start a new chapter in Miami was without a doubt one of the most significant risks I’ve taken in my career. It entailed entering an entirely new market, creating a client base from scratch, and establishing my brand in a competitive environment. Read more>>

Maria Morales-Prieto | Artists, Realtor, Yoga Instructor, Tour Guide and Murder Mystery Novelist

I am a natural born risk taker. Life is short so I say “Yes” to everything. Conformity bores me so I always yearn for more and more challenges. Read more>>

Stefan Avram | Tech Entrepreneur

When it comes to risk, the riskiest thing you can actually do is not take any risk. Growing up, I was fortunate to be raised by two immigrants who migrated to the United States from Serbia and understood risk. They took a risk by winning a green card lottery and moving to the United States with $1000 and not knowing a single word of English. Read more>>

Patricia Ligia | Bass player, composer, educator & entrepreneur

I always try to listen to my intuition. I do practice a lot to be in touch with it so that when I make an important decision or take a risk I have the certainty that it’s the right thing to do at that moment. Taking risks has played a huge role in my life and career! I have always pushed the limits of my confort and moved forward expanding that confort zone and very aware of what I was doing. Read more>>

George Pagan III | Personal Trainer & Fitness Industry Consultant

I think about risk all the time. Throughout my career, I have had to get more comfortable taking risks because it’s the only way to challenge yourself to grow. Getting more comfortable taking risks has allowed me to place “risks” in my decision-making model, think about the future, and be more calculated when pulling the proverbial trigger on doing something. After many years of building my business, I recently took an enormous but calculated risk. I became more independent and opened my headquarters for FITLETE. It was an undertaking, but with the right help from Caldera Law, my friend and real estate advisors Romain Liberman, Mirna Zarate, and Lisa Rosen, I was able to find the space in Miami to support this risky decision best. While it will always be scary, I encourage creative professionals to take risks when possible because it keeps your eyes focused on the future. Read more>>

Dasha Saied | Fitness Trainer

Every day, decision-making presents itself as a fundamental aspect of our lives. I firmly believe in the importance of taking risks for personal and professional growth, but with a strategic approach in mind. While embracing the potential for failure, I advocate for calculated risks, which involves planning and tracing clear objectives. Read more>>

Joe Goldstein | Cybersecurity Expert and Entrepreneur

In discussions with fellow business owners, I often emphasize the importance of risk-taking as a cornerstone of entrepreneurial success. I believe that success is unattainable without the willingness to embrace risks. However, embracing risk does not imply reckless endangerment of resources without understanding the facets of the risk involved. Nor does it mean pursuing risks merely for the thrill of it. Effective risk-taking is a calculated process of assessing the situation, quantifying the risk, weighing the potential returns, and comprehensively understanding the advantages and disadvantages before making a well-informed decision. Read more>>

Felicia Zwebner | Designer

I think risk taking is essential to change and growth. The idea is to not do anything impulsive, harsh or sudden, but rather take a thoughtful contemplative risk approach. That can be a challenge in and of itself: I would call that process Managed Risk. Read more>>

Dr. Christina Monford-McNish | Cosmetic Dentist

While risk taking can be very dangerous in some instances, I took a risk in leaving my first career as a high school teacher with Duval County Public Schools in Jacksonville, Florida with a one year old and going back to school to take the required courses to apply to dental school. The coursework set out for me would have been best conquered going back to Tallahassee, Florida where I obtained my bachelor of science degree in Mathematical Sciences from Florida Agricultural & Mechanical University(FAMU). During that two year period, I worked two jobs while also being a non traditional full time student; I worked as an Adjunct math professor at Tallahassee Community College and as a part time math tutor at FAMU. I prepared to take the Dental Admissions Test and applied to thirteen dental programs. I got accepted by my first choice, University of Florida College of Dentistry where I received my Doctorate of Dental Medicine. By that time I had completed a total of ten years of school, had acquired over $350,000 worth of student loan debt and my son was seven years old so I decided to go straight to work. I had interviewed with both private practices and with Dental Service Organizations (DSO); I decided to go with Heartland Dental a DSO. So taking the risk of leaving a career with benefits with an infant was definitely scary to say the least but it has been such a GREAT reward in my life and for my career. Read more>>