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.

Jessica Sanchez | Adventure Travel & Lifestyle Photographer

I feel risk taking is essential in any business or career. You never know what will happen if you “apply for this job” or “pitch to your dream client”. I can personally say it’s been scary to take risks in my own life, but what I can tell you is that, anytime I have, I’ve created some incredible experiences for myself. Some I thought would never happen and others where I brought up important topics I felt needed to be discussed and I was connected with the right people to share that conversation with. Read more>>

Briana Borten | Founder of Dragontree Sanctuary and Energy Worker

Taking risks is essential for achieving success in business. You have to be willing to do what others won’t and follow through relentlessly. Risk-taking has profoundly shaped my life. The rewards are incredible, and the lessons are invaluable. No matter the outcome, I always feel like I’m winning because I’m growing—and that’s my true purpose. Read more>>

Colter Hinchliffe | Professional skier

As a professional skier taking risks is a huge part of my career and my life. Managing those risks is what has provided longevity and success in my career, and again my life! A huge part of my career revolves around being in ski movies which is where we gain exposure as athletes which his what is valuable to brands who support us. Read more>>

Rubye Moore | Drag Queen

I’m actually not much of a risk taker naturally. But I know it’s essential to the growth of a creative businessperson. I’m a little timid about taking risks but when I know it’s the right move for my career, I almost disassociate and have an out-of-body experience, watching myself make certain moves. But once I take the risk and get through whatever I’m working toward, the payoff is always completely worth it. Read more>>

Colleen Hunter | Photographer

In my journey as the owner of Colleens Captures, taking risks has been a key part of my personal and professional growth. Starting my business during COVID was a challenge, but I believe that beginning with risk has made it easier for me to face any challenges my small business might encounter in the future. Read more>>

Koko Arenas | Mother | Photographer | Unreasonably Passionate

As an individual, a mother, a wife, a business owner, risk taking has played a major roll in the outcomes and ultimately the experiences I’ve had in my life and career. I had a rough upbringing as a child, resulting in having to grow up before my time and take on responsibilities that I wasn’t ready for. As I grew, I began to shy away from having to make the big ‘scary’ decisions, not wanting to create conflict or continue to ‘let people down’, and as a result I landed being stagnant in my life, feeling unhappy and unfulfilled. Read more>>

Jessy Tierney | Boutique Bakery Owner

Risk…or should I say, taking a chance on risk – now that’s quite a concept! The journey to Rollin In Daisies was certainly a path paved with risk. A few moths ago, nestled in the stability of my corporate job, the word ‘risk’ seemed like a scary concept. Read more>>