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.

Amber Harper-Young | Comedian/Writer/Actor/

I have a healthier relationship with risk now that I’m older and more confident. In October I went full-time comedy which is very tricky within the Canadian Comedy scene. And I’ll soon be co-producing a monthly Stand-Up Show called, “Cool Fun” on Feb 16th, as hopefully a stream of income that I can somewhat control. Bigger leaps are still something I’m pushing for artistically. Read more>>

Lauren Elizabeth Harris | Actor, Producer, Podcast Host, MFA Candidate

In my opinion, risk taking is integral to success. Of course, I mean this in the sense of risks that aren’t dangerous to your well being, but risks that make you nervous and could offer great value to your career path, I think are very important. Anyone who pursues a career in entertainment is inherently taking a risk as it’s not a path that often offers stability or a sense of security when starting out. Read more>>

Yishan Hao | Actor

I used to be a very risk-averse person. I’d always go for the safe choice. I can go to a coffee shop for ten times and always order the same drink. Gradually I found out going for the safe choice doesn’t bring me the things I want. Instead, I missed a lot of opportunities. Read more>>

Jon Primo | Film Director

Risk-taking is like a thrilling adventure for me, both as an artist and as a person. It’s like diving into the unknown, with the potential for both triumph and failure. But for me, the reward of growth and self-discovery is worth the risk. Every time I take a risk, I feel my confidence soar, and it opens up doors to new and exciting opportunities. Read more>>

Kenna Monrroy | Professional Spray Tan Artist

Taking risks is what life is all about. Often people are so afraid to step out of their comfort zone and it holds them back from doing things they’ve wanted to do. When I first started my mobile business, Got to Glow, I was working full-time at a gym. I chose the 5am shift schedule in order to be able to go to school after work. I was enrolled at Cal State LA full-time and arranged my course schedule to make time for school as well as the things that were important to me. Read more>>

Erica Anenberg | General Contractor & Master Manifester

I thrive in risk taking. I believe the only way to succeed in life and business is to be willing to take risks. I don’t think of risks like other people. I believe that most people view risks as a potential of possible failure. To me taking risks is about learning and growing. Read more>>

Alisha Collins | Brand Manager, Art Director

Being a risk taker is literally my driving force. I’ve never been afraid to try new things or change my mindset. I spent years focusing on the same industries when it came to my creative talent, then one day I just decided to go a different direction. Entering a new territory, unsure of the outcome and just taking a leap of faith. Big risks, big vision. Read more>>

Moldazor | Artist

I’m from a very small town of around 1000 folks, in the Appalachian foot hills of Kentucky. I’ve seen people spend their entire lives in a place where they couldn’t possibly follow their dreams. I think about them a lot. It’s easy, safe, and familiar there to most who have chosen to stay, hunkered in the hills they call home. Read more>>

Nygel Robinson | Artist

I feel like your career can’t begin until you understand that you’re going to have to take some extraordinary risks. You have to realize that nothing is in your control. You’re at the mercy of the universe or God or whatever you want to call it. Releasing the control over yourself, in my opinion, is the first step and possibly the biggest risk of them all. I was working at a theatre in New York called New World Stages. Read more>>

Adilene Rodriguez | Real Estate Agent & Entrepreneur

I’ve never been one to follow the beaten path. Seeing my friends start careers and families earlier than me felt scary and discouraging at times. Instead, I dropped out of college, traveled the world, and chased adventure instead of a steady paycheck. This resulted in a more profound understanding of myself and my passions. It gave me a clearer picture of who I was and most importantly who I no longer wanted to be. Read more>>

Tami Farrell Wyrick | Winemaker

I think so often in life we get in a mind set of worrying about what can go wrong that we don’t allow ourselves to imagine what it will be like if things go right. Risk taking is important in life and business. You need to take chances on yourself and your ideas. There are really only two outcomes, you will succeed or you will learn. Life and business aren’t alway black and white. Read more>>

Gabriel Anker | Violinist

I believe creative audacity is a powerful force, inherent to the artistic process. While the risk evident in open-heart surgery is absent from performance, for the artist, the act of taking the stage, to reveal innermost expressions, implies a risk of existential proportions. Some formative violin lessons echo in the recital hall of my memory with clarity: Read more>>

Gilde Flores | Music Composer/Producer

For me, a risk is the thin line that separates dreams and reality. I’ve taken any and every risk my entire career if the desired outcome lines up with my vision. It always starts with an understanding that fear and doubt will almost always try and either create a comfort zone, or try and derail any thoughts before it becomes an action. Read more>>

Thomas Clark | Performance, Environmental, Graphic & Commissioned Artist

I think we need to define what “risk” is as an artist since the whole nature of what you do should be defined by that word–instead of it being something to strive to conquer. It should occupy your very nature. But what we risk in our studio isn’t often consistent with the marketplace. Read more>>

Hajja Barnes | CSO and Founder of Moore Color Shop

I’ve always loved the idea of taking a calculated risk. The way I see it, as long as the reward out weighs the risk then the risk is worth taking. I believe that fortune favors the bold and I am so grateful to take the is leap of faith in starting my own company. Taking the risk of starting a beauty brand is such a highly demanded industry has been a constant motivation. I have always loved a challenge and this is the greatest challenge thus far. Read more>>