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.

Scott Goldsmith | Arcade Fanatic | Dream Builder

Risk is a scary thought for a lot of people, including me. For the majority of my life I played the normal game, get a job, try to find something I enjoyed and worked hard to be the best I could at it. It worked fine for a while but there was always something missing and that was working for myself and having all the effort, long hours, blood sweat and tears go towards my business/goals vs someone else’s. The only way to finally make that happen was to take a huge risk and start my own business, leave the corporate world and go for it. Read more>>

Sarah Kay Love | Creative Agency | Marketing Consultant | Brand Strategist

Taking risks is undeniably one of the scariest and bravest endeavors one can embark on, regardless of its magnitude. As someone who finds solace in familiarity, order, and a well-devised plan, it has always been challenging for me. However, there are certain moments in life when I feel stagnant and unfulfilled, repeating the same patterns with no change in sight. It is during these instances that I realize the need for a leap of faith, a daring change that beckons me to take the plunge. Read more>>

Evan La Ruffa | Founder & Executive Director @ IPaintMyMind | Consultant, Artist, & Curator | Fine Art, Experiential, Brand & Community

Most times the option we initially think is the riskiest is actually the safest. We often associate safety with less action, but in fact I find that taking action produces more data, which is way more actionable than our internal dialogue, and so we get vital info on what to do next. Read more>>

Amanda Fennell | The Art Nanny

Risk – entering the unknown can be discouraging, but a risk not taken is an opportunity or stepping stone to the next lost. Every part of my career was a risk. When I was in college and enrolled into graphic design, I had no ideas what I was entering – only that I had a live of art. Once I was able to learn the skill to communicate visually with graphic design, it set me up for continued use of all that I do. Having the knowledge to perform most of everything I send out into the world, doing my own marketing, set up, implication of The Art Nanny – lessened the risk. I had to count solely on myself, I knew what I wanted to communicate and didn’t have to depend on an outside source to convey for me. I built the brand – from there the public fueled me to continue. It was more like the general public became the energy that took risk out of the equation. If you are doing what you love, the risk seems less intimidating. Read more>>

Armando Guarnera | Soccer Coach and Trainer

I have been playing professional soccer all across Europe since I was 17 years old. I was raised in Staten Island, New York. I am now back home giving back to my hometown by being a coach and trainer. I took a risk not going to college and leaving my family right after high school. I took risk after risk and it has paid off tremendously. I have traveled the world, honed my skills, and made a successful career out of doing what I love. While the path I chose was unconventional, I am grateful for the opportunities it has brought me and the chance to inspire others in my community. Taking risks has not only shaped my professional career, but has also taught me important life lessons that I am now passing on to the next generation of athletes. I am now scheduling individual one on one soccer training sessions to help support and mentor aspiring athletes in reaching their full potential. Utilizing my experience and knowledge gained from playing at a professional level, I am dedicated to providing personalized instruction and guidance to help players improve their skills and achieve their goals on the field. Whether it’s refining technique, building strength and agility, or developing a winning mindset, I am committed to empowering each player to excel in the sport they love. Read more>>

Deanna Radulescu | Founder & Host of Label Free Podcast, Speaker, Executive Contributor

Life is truly lived when it’s accompanied by a dash of risk. I firmly believe that without a bit of daring, one is not fully experiencing the richness that life has to offer. Personally, I have navigated a plethora of risks, from gracing the stage in a bodybuilding competition to free-falling from an airplane, and from establishing a fashion label to now hosting a globally recognized podcast. In each daring venture, I discovered not only growth but also invaluable lessons and wisdom. Read more>>