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.

Charles Miles-Frost

I think about risk as a balance between a challenge and opportunity. Risk taking comes with a level of belief in yourself that everything will work out and while also being prepared for things to go wrong. Read more>>

Lindsey Riel

I’ve learned that risk is really just another word for growth. Five years ago, I sold my business right before Covid hit – I took some time off, and then had to start completely over from scratch. That could have been terrifying, but I’ve always believed that reinvention is part of the entrepreneurial journey. Read more>>

Briana

For me, risk-taking has never been about being reckless—it’s been about trusting myself even when the outcome isn’t guaranteed. One of the biggest risks I took was leaving a traditional job in the medical field to pursue dance full time. That decision meant walking away from financial stability and the security of a conventional career, all while raising my child as a single parent.  Read More>>

Kelly Thomas

I come from a rodeoing family and a family of entrepreneurs, so the action of taking risk comes naturally to me. I moved out at 18, I let go of people and places that no longer served me, I traveled solo across the western United States, and I went independent as a stylist just two years ago Read More>>

Andrea Alvarez

As an optimistic human, I tend to view “risks” as opportunities. Often, my naturally competitive spirit transforms these opportunities into challenges. This mentality has been beneficial, exposing me to diverse circumstances that have significantly influenced both my personal and professional growth.  Read More>>