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.

Craig Ambrosio | Professional Photographer

I think every successful individual has taken risks or done something outside of their comfort. I’ve been a successful portrait photographer working for 20 years. I recently pitched as a concept to a well-known brand doing something I have never done before. Read more>>

Javen Campbell | Recording Artist, Author, Speaker, and Leader

I like to call it steps of “faith” more than I would say risk. But I think without real risk and without taking a chance no one gets ahead. As an independent artist for many years it was up to me to come up with the budget for all my recordings. Read more>>

Barry wolfryd | Visual Artist

It’s an awkward tight rope to wake. Taking risks more than ever seems to be part of ones daily life. With the virus just going out onto the street is now a challenge. As an artist risk is just part and parcel of the carrier and life style. Risk is a double-edged sword. Read more>>

David Camargo Pablo Zepeda | Founders of Dade Plant Co.

Risk is natural and encompasses every aspect of life, aside from business. We take risks every day, and sometimes some risks can be serendipitous or lead to a straight disaster. Risks can mount over time, and/or change. Interestingly, the weight of risk is always subjective and affects everyone differently. Read more>>

Lauren Fannon | Realtor Associate | Fashion Executive | Global Traveler | Yogi | Dreamer

Throughout my life I’ve taken many risks, oftentimes jumping into something and figuring it out along the way.  I decided on New Years Day 2006 that I should move to Miami. I had just taken the GMATs, felt unfulfilled working in corporate finance, and knew there had to be more to life than updating spreadsheets and PowerPoints. Read more>>

Abiola Akanni | Yoga Practitioner | Founder of Iya

Risk taking has played a large role in my business but not on purpose. When I left my corporate job as a fashion marketing copywriter in 2014 to be a full time entrepreneur I had no idea I was taking a risk. Similarly when I decided to pivot from one business to another or create a new business model in the midst of a pandemic. Read more>>

Kaytee Papusza | Artist, Clothing Designer and Writer

Risk taking has definitely played a key role in how I’ve developed as an artist. When I was a young designer and finding myself as an artist a lot of the work that I did and choices that I made where centered around experimentation and exploration. Read more>>

Justin Mesteller | Graphic Designer

Being in the large format graphics industry, risk is a very integral part of our business. Often times we take on certain jobs that other companies pass on or that we have never attempted due to scale or difficulty ourselves. When you commit to take on these kind of jobs they tend to push you out of your comfort zone. Read more>>

Marianela Perez | I am a Visual Contemporary Artist from Venezuela, Base in Miami FL

Some time in life you have to take risks. ” I like to take risks in the use of color, in drawing lines, and in composition”. I was living in Venezuela throughout the period of the anti-government protests in 2017. The rough political and social situation there led me to decide to leave my homeland and to look for a better place to develop my art. Read more>>

Gina Torkos | Collage Artist

I often take risks in my art. However, I don’t really think of it as taking a risk, but as answering the question “I wonder what will happen if I try this….” I believe that the moment you touch upon a new creative idea, you owe it to yourself to follow through in some way. Read more>>

Jose Li | Entrepreneur & Dad

I consider myself a calculated risk taker. I believe the higher the risk, the higher the reward, and vice versa. There are some things that are worth risking for, and others, because life is too short, are not. Leaving a nice Corporate America job to start 71lbs has been a huge risk decision for me. Read more>>

Kyoung eun Kang | Artist

As an artist, taking risks has always played an important role in my life and my practice. One of the biggest risks I’ve ever taken was studying and living abroad, away from my family in Korea. I was eager to experience different cultures and explore broader art scenes, so I stepped out of my comfort zone and decided to live in New York City. Read more>>

Nayla Atallah Cross | Founder and Creative Director of NAYLA

I think that risk is fundamental to growth! Nothing worthwhile comes without a little risk, right? I launched my brand of luxury sustainable footwear during a pandemic and it was one of the riskiest things I have ever done. Read more>>

Hazel Griffiths | Artist

One could say that embarking on a creative career is taking on a huge amount of risk in and of itself. But I actually think I’d risk losing a lot more if I didn’t. If creativity is an option, you risk not becoming yourself if you don’t take that path. Read more>>

Samuel Diaz | Video Producer

I deeply feel that risk is a necessary and essential part of an artist’s lifestyle. Without risk we can never ultimately never achieve our rewards. I think what draws people away from risk taking is the high possibility of failing but failure has to be a part of the equation because from our failures we learn where to succeed. Read more>>

Michael Hugue | Graphic Design & Visual Artist

Risk-taking is a major key in my career honestly, it’s like the fear before you jump into a pool knowing you could swim or drown. The thoughts before you jump are rushing at 100mph to your brain then you just jump, and in the moment of being in the air for 10 seconds, it feels like the time slowed down before you going to hit the water. Read more>>

Niki By | By Niki | Leading Photographer and Owner of By Niki Photography Team

Without taking risks I would not be where I am today especially when it comes to creating By Niki Photography Team. I hired all Photographers through the internet, we did not have a chance to meet in person, in both towns Houston and in Miami. Read more>>

Ethan Punal | Digital Artist

I think anyone who gets up everyday and follows their dreams is taking a risk. By pursuing what makes you happy, you are essentially taking a gamble on yourself despite the odds. In my artistic career, I have snuck into record labels just for the slight chance I would have the opportunity to get some of my artwork to anyone who works there. Read more>>

Steffi Hibbard | Visual Artist

I’ve thought about risk the same way anyone else does. I could see it and I feel it. I had an urge to avoid it and stay closer to what I knew and what I could rely on. I did this for years, through college and graduating and through finding a career and working full time. Read more>>

Marsha Tessler | Marsha Tessler & Karen Rogowski /Directors – My Safe Harbor

TAKING RISKS -What role has taking risks played in your life & career Marsha’s Story I Spent many years living in an exceedingly difficult situation. I was not a risk taker and did not have the courage to make a change. I stayed stuck in a situation out of fear. Read more>>