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.

Theresa Tumminia | Director of Development and Programming

Risk plays a significant role in both the workplace and the journey of being a successful social entrepreneur, regardless of gender. However, for women, navigating these spaces may present additional challenges due to societal expectations, biases, and historical gender roles. Risk has shaped my success and set the stage for comeback through failure. While risk is inherent in both the workplace and social entrepreneurship, the unique challenges faced by women necessitate a nuanced approach. Overcoming gender biases, building resilience, and strategically navigating risks are crucial elements in the journey of successful women in these fields all equate to one defining factor of RISK. Read more>>

Armando Fitz Jr | Sales Associate & Entrepreneur

Risk Taking is important because it allows you to get out of your comfort zone. It has created space for self development and growth within my personal environment and in my career. I have been able to gain experience in things I never imagined myself doing before. Taking risks has also taught me to trust in the process of failure and perseverance, to keep chasing after my dreams/goals without getting discouraged. Read more>>

Jason Whitbeck | Director / DP / Founder of Yes Go Productions and Co-Founder McSWiF

This question resonates deeply with me, as I find myself embarking on a new entrepreneurial journey for the second time in my life, alongside a couple of like-minded individuals, to launch a new business (McSWiF) and initiate some exciting projects (Spirits Hunters, Bat Friendly, and The Vinyl Word). Read more>>

Oliver White | Musician/songwriter

I think it’s important for artists to take risks. Risk is a main ingredient in a work of art. If we don’t push boundaries or try to do something out of the ordinary we’ll become become ordinary and push products. Read more>>

Godwin David | Dropshipper, Digital Marketer And A Speaker.

Well, I see risk as an opportunity for growth in my life and career, so I approach it with the right knowledge and that helps me to be better at what I do. Taking a well calculated risk has helped me attain heights in my career that I never thought could come in such a short time. I feel so fulfilled whenever I see myself doing what I once doubted I’d do, and the best part is that the more I get excited doing it the more better I become at it. Read more>>

Wendy Michelle Davis | Painter in Acrylics

I’m learning more and more that risk taking is an important and necessary part of life, and especially in my art business. It starts at the core of what I do. I am an artist. When I paint I need to open myself up to failure, because taking risks is about putting myself in situations that can be daunting, scary sometimes and have unforeseen outcomes. Read more>>

Abby Alley | Founder and Designer at Abby Alley

Risk taking is something I’ve thought a lot about over the course of my life. I’ve never considered myself to be a big risk-taker as I’ve always been somewhat calculated in the decisions I make, careful not to come too close to failure. That said, from a young age, I knew I’d have to fight against my natural tendency if I wanted to accomplish anything truly great or experience all life has to offer. Over the course of my adolescence, high school, and college, I credit playing sports (I played lacrosse at Northwestern University) for teaching me how to fail…and therefore how to take risks. In sports, someone is always coming for you, whether it’s another team or perhaps a teammate trying to take your spot, and it’s in these moments you have to rise to the occasion to put everything you have out there, not knowing the outcome. You might experience the elation of victory, but you might suffer the devastation of defeat. And to me, that’s the definition of risk. Putting yourself out there, hoping to achieve something big, knowing full well the world may see you fall on your face. I got used to this kind of risk taking playing sports and experienced both the highs and lows that come with attempting to achieve greatness. And although the mountain top moments were worth every minute of the blood, sweat, and tears, it was the valley moments that gave me the confidence to keep taking risks and laid the groundwork for being an entrepreneur. It may sound counterintuitive, but to be an entrepreneur, you have to have get really comfortable with failing, hearing no, and people doubting your ideas. The failures I had playing sports taught me I can come back from anything. They showed me I can survive the worst of times and figure out a way to get through it. They taught be to be creative, trust myself, and how to adjust in the midst of adversity. When it comes to taking risks in my life, I try to live “in the arena” as Teddy Roosevelt said, because I fully believe there is no victory without defeat. Read more>>