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.

Barbara Rogers | Visual Artist, Painter

My entire career as a visual artist is one big opportunity for the taking of risks by painting whatever I want and not worrying about what will sell or appeal to museum curators To feel comfortable in using this approach to making my paintings I had to admit that I knew next to nothing about wise investing, the stock market or when to buy bonds. Read more>>

Varol Ozkaner | Digital Design Artist

What I think about taking risks is that you should not stick with whatever you are introduced to for the sake of standing out from the crowd regardless of who and where you are. This can only be enabled by following a path that is likely to lead you to a state of mind where you get to encounter new possibilities and have the privilege of experiencing new things that, by the end of the day, you will benefit from. Read more>>

Mathew George | Co-Host of SheRatesDogs the Podcast

Before switching from a life that was going towards medicine to a life in entertainment there were a lot of questions going through my mind. Some questions included was it worth it? Am I sure this is what I really wanted? Could I really do this and still make enough money to support a family one day. Read more>>

Miguel Angel Monzón | Interdisciplinary Artist and Curator

Risk is necessary for growth. I believe it’s been front and center for the majority of my life. Confronting your fears is a giant part of being an artist for me. I’ve always felt that if I got too comfortable doing any one thing it is time to try something different. Keeping things challenging is a way for me to stay creative and invested in a project. Read more>>

Lara Ruggles | (Sharkk Heartt) | Singer-Songwriter & Rialto Theater Communications Coordinator

I think that my perception of what’s risky is actually kind of skewed after years of going on tour and finding ways to scrape through in tricky situations when things have gone off the rails, although when I look back at some of the tours I’ve been on now, it seems kind of unbelievable to me that I went on some of them at all. Read more>>

Chantel Pitts | Photographer, Style Blogger & Brand Designer

Taking risks have always played a huge role within my day-to-day life and career. From attending college out-of-state and pursuing a career where there often isn’t a straight and narrow path, to going full-time with my business and moving to a state I had never been to before, just about every major aspect of my life has been a result of taking a risk. Read more>>

Kristen Lundberg | Comedic Actress & Stand Up

loved taking risks since I was a kid because it was an exciting way to break up the mundane Ohio life. Taking risks pulls you into the present. When I attended iO in Chicago, I learned my favorite Del Close quote “follow the fear”. I followed the fear of “making it in comedy” all the way out to California and now I live a vibrant life that I’m proud of and that is authentic. Read more>>

Ernest Tsosie | Actor, Comedian and Motivational Presenter

In the past few years and all the up to the out break of the pandemic, I’ve used my business platform as an actor, comedian and public presenter to share a message of being drug free, alcohol free, commercial tobacco and vaping free. My message is for all but I’ve been privileged to focus on and go into schools, K-12 and focus on speaking and performing to our awesome and precious youth. Read more>>

Jesse Perry | Southwest Pop Artist

Risk is on par with passion. The more passionate you are about the things you love in life, the more willing you are to take risks to achieve your dream. I consider myself to be a passionate person and I have taken a great amount of risk in my life and my career, yielding both failures and successes, but all of my experiences have made me who I am. Read more>>