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.

Ashley Chavez

As an up-and-coming Latina artist from Pomona, CA, choosing to pursue this path was a bold risk from the start. Coming from a background where that path wasn’t seen as ‘safe’ or realistic, every step of my creative journey has involved taking risks—whether it was committing to photography, graduating from ArtCenter, or continuing to create even when financial stability was uncertain. Read More>>

Will Sivy

Risk taking is paramount if you’re going to find any form of success on your own. I understand why it may be appealing for some to maintain the security and structure of working for someone. There’s absolutely nothing wrong with that, it’s just a path that never resonated with me personally. I’ve observed time and time again, that there is a clear correlation between risk and reward, not only career wise, but with life in general. More often than not, the greater the risk, the greater the reward. Furthermore, I also believe that our mindset completely shapes our existence, you’re more capable than you realize once you begin taking risks. Read More>> 

Alina Rozwadowska

I view risk as a necessary part of growth, both personally and professionally. Throughout my life, I’ve taken many risks—whether it was pursuing an unconventional path, making a career change, or stepping into the unknown by opening a Pilates studio. While not every risk led to immediate success, each one taught me something valuable and pushed me out of my comfort zone. Read More>>

Hunter Kelly Cahalan

To me, risk is necessary if you want to do anything meaningful. The biggest risks I’ve taken haven’t always been loud or dramatic — sometimes they’ve just been moments of saying “yes” to something that scared me or felt uncertain. Writing from a vulnerable place, releasing songs that reveal parts of myself, trusting my instincts instead of chasing trends — those are risks I take every day. Read More>>

Levi Hadley

For any person wanting to pursue a creative career, risk is an intimidating entity you have to befriend. I suppose I think about risk exactly like that—a being. It appears, often unexpectedly, and asks you to step outside your comfort zone. It feels both threatening and also exciting. Risk asks more from us and gives us a chance to gamble on our own potential. Pursuing any kind of creative career will not be a choice of safety and certainty, as you are not given a well-worn path to walk. For that reason, we must become well-acquainted with risk to have the confidence to bet on ourselves in hopes of building a fruitful creative career, and living a life that feels “on-purpose”. Read More>>