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.

AJ Ramos | Music Executive, Content Creator and Multimedia Public Figure

In a world that is changing so quickly. Life is all about taking risks. If you never take a risk, you will never achieve your dreams. The biggest risk is not taking a risk. You learn to live and live to learn. Taking risks has played an important role in my life and career. One of the biggest risks I took is dropping out of the Rutgers University Pharmacy program. I entered the program with a full scholarship for Pharmacy and graduated with a Bachelors in Criminal Justice and Minor in Journalism and Media Studies. Read more>>

Jas & Ty | Barber Owner/Lash Technician

Ty: “ I look at taking risk as everyday life! Waking up walking out your door is taking a risk because you just never know what will happen after you open that door. We can’t be afraid to explore doors in life because you will never find out whats on the other side until you open it! Risk taking has taught me life lessons as well as brought me big blessings. I took a leap and quit my job almost 7yrs ago to be a barber thinking to myself Read more>>

Dameka Davis | Attorney & Candidate for Broward County Commissioner-Dist 7

When representing people, you have to fight against isolation, doubt, and exhaustion. As a Tribe, we all know that the real work begins with ourselves. Each and every day and with the love of myself and what I represent, I have found the same to be true not only in practicing law, but also in running for office. Running for office has introduced me to the weakest part of myself: it introduced me to my self-doubt and risk-taking. The part of myself that says you are not qualified. You cannot do it. The part of myself that whispers in my ear, you can’t do this, you will lose. Read more>>

Juliet Meskers | Co-Founder and CEO of Mental Health Global Network

Risk has played a monumental role in the trajectory of my lifestyle and career. Prior to Co-Founding Mental Health Global Network I was studying fashion design and working as a freelance fashion journalist throughout each NYFW season. My senior year of college I was interviewing with a high end fashion agency who after several interviews, gave me a tentative start date for the job. They told me I was a must hire and that they were excited to get to know me in the office. One week after graduation they told me that they had decided to go in a different direction. Read more>>

Stephanie Ahr | President & Founder of Frankie’s Runway

The biggest risk I ever took ultimately lead to the creation of my company, Frankie’s Runway. After only knowing my now-husband for SIX MONTHS, I agreed to marry him and move my life to DC where he resided (insane, I know!). This also meant leaving NYC and my career in communications at Estée Lauder Companies. A few years later I had my daughter, Frankie, and landed my dream job, full-time Mama! Read more>>

Ruben Campbell | Luxury Real Estate Agent

Risk is essential to personal growth as it does require to test the best of our abilities facing the unknown and always brings a lesson to learn after you have gone through the experience. When I was 22 years old, after my business degree, I had to do my military service as it was still mandatory in Spain. Most of the times, you spend the 9 months in your city, but after the initial 3 months of instruction, the Captain saw something in me and suggested to participate in a 3 days tests to join the NATO forces in Bosnia for the remaining of my military service. Read more>>

Willis Brown | Seagreen Founder, Surfer and Skier

I think about risk in a sense of my current standing in any particular situation. It’s about assessing the risk vs reward. One of two things can happen, I either don’t take the risk and there’s a likelihood that nothing changes and everything remains the same or I take the risk, accomplish what I was either nervous or afraid of, and experience the growth and satisfaction from believing in myself or my team. Risks have played a huge role in my life everywhere from decisions as an athlete in multiple sports growing up to the adventures eventually leading to Seagreen. Read more>>

Christian Lora | Professional Photographer

I think risk is absolutely necessary. At some point in your life you just have to go for it. One of my biggest fears is laying in my death bed, looking back at my life with that feeling of “what if?” I refuse to let that happen with anything in my life, not just my career. Read more>>

Brooke Hall | CCO of

I believe most adults are born with their risk values – how they prioritize safety and consistency versus big risks for big rewards. I myself, am a risk taker, and I don’t think it’s a choice. I simply live for today’s decisions in what feels right and will live with the repercussions when they come. That doesn’t mean I fly by the seat of my pants… I’m a planner and I weigh out decisions. But when something feels like it’s going to work for me, I roll with it and will have to face failure if it comes. Read more>>

Adaliz Calderon | Somatic Sex Women Empowerment Coach/Mentor

For me taking risks is key both in my personal and professional life. I associate risk-taking with getting out of your comfort zone. And as they say, “great things await you on the other side of your comfort zone” This is something that I have been able to live throughout my life, from ending toxic relationships, moving from my land to seeking a better quality of life and job opportunity. Doing interviews in a language that is not my native language, saying yes to opportunities without knowing how I was going to achieve them. Read more>>

Hunnie B | Musician

My motto in life has always been no risk equals no reward. With that being said, the role risk plays in my life is a role of calculated risks. Calculated risks allow me to break free with my creativity, they also allow for an adrenaline rush without fear. Everything I’ve accomplished and achieved in my life and in my career was a direct result of having taken a risk not knowing if I would be able to achieve a goal. I aim high with my goals and encourage others to never be afraid to take that risk! Read more>>

Ricki London | Educational Specialist

Risk taking is an important part of entrepreneurism, as it is what propels people towards being creative and innovative. If I was not willing to take a risk, I would not own my own business. I would have stayed working in a large corporation with a very steady paycheck and guaranteed hours. Instead, I left that cushion of certainty and took a leap of faith to open my own office with no backing and no guarantees. I looked around and realized the most successful people were those who took risks, failed and saw those failures as steppingstones to their successes. Read more>>

Susie Green | Audio/Visual Artist, Composer, Music Tech Research/Development & Owner of Studio 7 Productions

Risk has been the common denominator in most anything that I would consider the most interesting opportunities or adventures in my life. Think about a time where you have envisioned something different for your path in life: big or small, personal or communal. Whatever it was, it existed in your life only as an inking, a thought. This was the seed of something new. Once the seed of an idea is planted in the right conditions, it germinates, usually in the dark, imagining its future fruitful state. In order for this seed to grow to its full potential it must endure several stages of risk: Read more>>

Akel Issa | Digital Artist & Speed Demon

Taking risk is a scary thing and that’s why most people don’t take a lot of them, they choose a more comfortable route not only because they are scared but also because that is what they have been thought from a young age. Most parents would want their children to have a comfortable life so they tell them to take a career that’s common and often times it might not be something they like, but because its safe they tend to do it. Read more>>

Tae Henry | Singer/Songwriter

When I think about risk. I think about the outcome, if it’s beneficial to me to even want to take that risk. I think me having that “go getter” mind it allowed me to get where I am today In my music career. One day I woke up and said “I really need to stop playing and take my career more seriously, I have the talent, use it” me overcoming that fear and just taking a “risk” has allowed me to grace some of the most epic stages So risk may not always be bad but again it is a risk and I’m grateful that I did take some of the ones I did. Read more>>

Montana Globerman | Founder, The Montana Method

Tap into what you really love and what moves you. That’s where your authenticity comes from and will make whatever you choose to do be successful, because it’s the real you. Try not to get caught up in what you think you “should be” based on what your peers are doing or what anyone may have wanted for you. After college, when it seemed like everyone else was getting an MBA, I got my Pilates certification, and started developing my love for teaching and movement. Read more>>

Tati Jenee | Artist, Entrepreneur, Foodie, Techie

I think risks are a necessary part of life. It is always sad to see how life turned out for people who never pushed for more. It’s like seeing potential in someone that they do not see themselves. However, risk is very scary – especially when you’ve fallen from those risks. It’s like how do I get up again?….Getting up again is what’s scary, and sometimes that requires therapy. Taking risks is actually one of my main drives in life. There’s no greater fear than getting old and seeing what you could have been, where you could have gone, or what you could have done… Read more>>

Kesh Green | Performing Artist, Visual Artist & Writer

I have a secret to admit, I have always had an affinity for numbers – I was that one kid who enjoyed algebra a little too much. For me, numbers represented clarity, certainty and control. As long as one follows the steps and does the work, the correct answer is expected. So naturally in college, I fell in love with Economics and Statistics; their formulas gave clear thought and reason to decision making. In Economics, there is a principle called opportunity cost – it helps one analyze trade-offs between possible choices. Now hear me out, opportunity cost is used for products so one may know how to allocate their resources accordingly. Read more>>

Breanne Pendleton | Your Luxury Self Care Concierge | International Pageant Queen | Author

When you first see the word risk, most people think of something dangerous or see an opportunity to pause and be alot more cautious. I must admit that I was definitely one of these people about a year before I started my business. I avoided any type of risk! I wanted to be in complete control of every single avenue of my life. I did not want the stress or burden of having to deal with the consequences of making a “bad ” decision. Interestingly enough, all that control I thought I needed went right out the window with one decision. I joined a pageant! Read more>>

Daniela Romay | Mindset expert

When I started my career was in times of profound crisis. My son died, my daughter was dealing with her fiscal health and my husband and I with our emotional health plus the financial crisis that was pushing us to the edge. I needed to find the strength to just move forward a little to start momentum at least but all this different factor were against me plus the fact that even if I could have find a job we had no one to leave my kids with (Sofia 2yo and sick all the time, and Lore 4 months). Read more>>