By far, the topic that comes up most in our conversations with entrepreneurs and creatives is risk. We’ve had conversations about risks that worked out and risks that did not. We’ve seen eyes light eye sharing about career-trajectory changing risks as well as folks sigh about the risks they wish they had taken. Below, we’ve selected and shared some of those thoughtful conversations.

Bachida Wilson | Makeup Artist & Esthetician

Without risk how do you know where you’ll be in life? How do you know how far you’ll ever go ? I always say the biggest risk is not taking any at all! I truly would not be where I am now in my career if I hadn’t taken a leap of faith . My makeup journey started as just a hobby & while working in the medical field the only other career I knew , I found myself focusing more on my clients. I mean it was all I could think about . I dreamt, ate , breathed Makeup ! & it was at that point when I realized if I just take that risk & make my passion into a full time career I would never work a day in my life . With whatever obstacles that came with It was a risk I was surely willing to take ! And im so glad I did . I learned that when we live in fear we will never know our true potential . Read more>>

Kiana Tate LaRoche | Documentary Wedding Photographer

I have always looked at myself as being in the risk taker category. From an early age, we moved around a lot, switched schools, lived in different states and I think that element of change really stuck with me. I love what being a risk taker has done for my career and perspective on being a photographer. I love to constantly put myself out there, travel for anything, and I’m not afraid to start something new. Looking back at the decision to become a full time photographer and knowing that it was one of the greatest risks I’ve ever taken is what pushes me to better myself for my clients and the work I create. Risks allow me to see and experience new things and that never gets old. I look forward to being able to continue to take on new risks with this career in such an amazing industry. Read more>>

Anthony DePalma | Author, lecturer and journalist

I’ve never gambled at a casino, and a dollar a hand is about the upper limit my friends and I have set on a card game. But I have always embraced risk in my career, especially since striking out on my own. There’s a quote I like from Nelson Mandela that I think pretty much summarizes my approach to risk. He said “May your choices reflect your hopes not your fears.” I wasn’t always aware of that saying but looking back on the decisions I’ve made I think they all strictly followed that advice. When I left what may be the best job in journalism–correspondent for The New York Times–in order to launch my book-writing career, I gambled that what lay ahead would be even more satisfying that what I already had accomplished. Had I focused on the possibility of failing, and losing all that I had already gained, my decision would never have been to leave. That’s what Mandela meant by making your choices reflect your hopes and not your fears. It requires a degree of self-confidence as well as faith in your own abilities. Ultimately, it is a decision that no one else can make for you. It has to rise up from deep inside you. and carry you forward with optimism and hope. Read more>>

Laurinda Hafner | Senior Pastor

It has been said that “if you are not risking your job, you are not doing your job.” This must be true for those in the corporate or business world, just as it is for those in ministry. It may seem strange that the world of pastoral ministry involves risk, but if indeed you are doing your job it comes with the chance of church members not liking a decision you make or a position you take. Over the years, the biggest risks I have taken are around issues of justice and peace. What some people may see as being too political, or not a part of the pastor’s job, I see it as living out the tenets of our faith which is to do justice, love mercy, and to walk humbly. The result of such risk-taking has been the engagement and attraction of folks who do not want to be “pew-sitters” but rather activists for transforming their community and beyond toward equality and justice. This has resulted in church growth, vitality, and the creation of a strong, dedicated congregation. Read more>>

Johanna Chone | International Fashion Model

Risk, to me, is an inherent aspect of growth and progress. In both life and career, taking risks has been pivotal in pushing boundaries, fostering resilience, and discovering new opportunities. As a model navigating uncertainty, embracing risk has allowed me to pursue my passion wholeheartedly, even amidst doubts of success. It’s about embracing the journey, learning from setbacks, and persistently chasing my dreams. Read more>>

Daniel Pedroza | Real Estate Advisor

I view risk as an integral part of personal and professional development. When I arrived in Miami 20 years ago for college, I brought with me a bag full of dreams and a very introverted personality. Taking the risk to step into the unknown was a defining moment. It’s my belief that we have to take risks in order to succeed; otherwise, we’ll never know what could’ve happened. Embracing challenges and stepping out of my comfort zone in pursuit of my aspirations has been transformative. This willingness to take risks not only shaped my academic journey but has been a guiding principle throughout my career. It’s through these risks that I’ve discovered new opportunities, learned valuable lessons, and honed the resilience needed to navigate the twists and turns of life. In essence, taking risks has played a pivotal role in sculpting the person I am today, contributing to both my personal growth and professional success. Read more>>

Lup Cheung | Ice Cream Shop Owner

Coming from a Chinese household where stability is often prized, choosing to open an ice cream shop was a big leap. I view risk as an essential, calculated, part of growth and innovation. In my career, taking risks has involved stepping out of the comfort zone of a traditional path, investing in a business that reflects my personal vision, and constantly experimenting with new ideas to stay relevant in a competitive market. Read more>>

Dorka Jones | Pro Makeup Artist

I’m a big fan of taking calculated risks! As much as I love to have control, know the outcome, have every little thing planned out, I see so much value in taking risks. If you take a chance on what you know could potentially be a stepping stone in the direction of your goals or dreams, then it is so worth it. If it works out, the reward is great. If it doesn’t, you don’t lose anything and you continue to live the way you are right now. It takes more effort but almost always leads to a new opportunity, mindset shift, connection, etc. Staying safe will keep you stagnant. Read more>>

Michael Freiburghouse | Finance Executive & Family Man

Risk is a critical aspect of life; both on the personal and professional front. How one approaches risk, will have a material impact on their long term success. When determining which risks to assume versus avoid, it is important that one be calculated, thoughtful, and understand their end goal throughout the evaluation process. Despite the appropriate level of due diligence being performed, when assuming risk, one must be comfortable with the potential for failure. How one views failure and the undeniable learning opportunities that exist as part of it, will determine whether they grow from such experiences or falter. Read more>>

Damion Fraser | Personal trainer/clothing brand owner

Taking risk as an entrepreneur is literally the best and only way to be a true success in our country America was built on bussiness and infrastructure which is all built on risk taking the rule of the T.R.A.P is to take risk and prosper you are creating opportunities to work in a space where your income is only limited by your ability to work and you can work as much as you want. Your income and future success solely relies on you. Read more>>

Chidiebere Oji | Fine artist and forex trader

We all have one life to live and being alive alone is kind of risking to an extent. My thought process concerning risking is always a win or a lesson to learn from. In life, we all have to take risks. Often times, calculated riskes. Sometimes, based of instincts and courage having it at the back of my mind that I either win or learn from it if it does not turn out well Read more>>