We asked some of the most interesting folks in the community to open up about how they think about taking chances and the role risk has played in their lives and careers. Risk is by far the topic folks talk to us most about and we hope the responses below will help shed light on many different perspectives.

Casey Immel-Brown | Fashion Designer

In one sense risk is the entire basis of my career as a designer. I left a long, stable IT career in my late-30s to go back to school for a fashion design degree. And then after graduating, instead of taking a job in mass market retail or creating commercially accessible ready-to-wear, I’ve focused on the laborious process of hand crafting luxury pieces that tend toward one aesthetic extreme or another. At the same time, I think often when we label something as “risk” it’s a result of mistakenly equating stasis with safety. I left my previous career because I was completely miserable for the majority of my waking hours. The choice really came down to either staying in place, in which case the outcome was guaranteed to be a life I wasn’t ok with, or to make a massive change which at least had some chance of allowing me to wake up in the morning feeling genuinely excited about where I am and what I’m doing. In a way, the latter option was actually a lot less risky. The same principle applies to the work I produce. Trying to force myself to create the kind of clothing everyone else is also trying to create, especially when it’s not organic to who i am or how I work, seems like a pretty guaranteed way to wind up spinning my wheels. On the other hand, as someone who has taken a rather unusual path in life (and never really started out particularly “normal” to begin with), if I lean into what comes naturally to me then there’s a decent chance I will produce things that there aren’t a ton of other people out there already making. So when some aspect of my work does resonate with someone it becomes worthwhile for them to actually invest in purchasing something. Because it’s doing something for them they can’t get otherwise. There’s a quote from Brian Eno I think about constantly, “People in the arts often want to aim for the biggest, most obvious target, and hit it smack in the bull’s eye. Of course with everybody else aiming there as well that makes it very hard and expensive to hit. I prefer to shoot the arrow, then paint the target around it. You make the niches in which you finally reside.” So from that perspective a lot of the “risks” we take aren’t nearly as risky in comparison to the alternative. They’re the only paths that will actually get us where we want to go. Read more>>

Turich Benjy | Recording Artist & Creative Director

I view risk taking as a faith based process. You have to be some sort of a high believer in whatever it is you’re risking something or someone for. You also have to accept that it doesn’t have to land in your favor, as you envisioned it. You also have to be delusional enough to work towards the feeling of taking a leap of faith. Sacrificing and risking doesn’t always have a negative connotation either. You can sacrifice watching tv just to encourage other, better habits to reach your goal. I’ve learned risk taking was just disciplining myself sometimes. But if you love someone or something seriously, you will eventually walk that spiritual battle. Read more>>

Jailyn Sherell Harris | Choreographer, Dancer, and Teacher

At a certain point, I had to ask myself what was I afraid of. And I also had to reframe my perception of failure. If something doesnt work out, it’s not the end of the world; it either gives me an opportunity to regroup, a new perspective or maybe even a whole new opportunity all together. I found that once I started taking risks and “betting on me” my career actually began to take shape and feel the way I had always imagined. I say feel and not look because I think when you become married to specific version of how something should feel it restricts you. When I reflected on how I wanted my career to feel, I realized I wanted to feel challenged, connected, creatively inspired and secure and now I feel all those things and more. Read more>>