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.

Marly Knapp | Marly’s Everyday Solutions

Risk taking is a scary thing for most people. At the beginning of the year, I read Shonda Rhimes book, The Year of Yes!, and it has really made an impact on me. The book is about saying yes to the things that scare you and also to the small things. One thing I remind myself often is something the co- founder of Norwex, Debbie Bolton, says, “If your dreams don’t scare you, they aren’t big enough!” Read more>>

Corbin Doyle | Filmmaking teacher at Greenhill School for 25 years & Maker & Partner & Father

Following your gut is real advice. That was a skill that took a while for me to trust. I don’t think I had a real thought of my own in my head until about my third year of college. I just did what I was told or what I perceived was right. I had done well in school. I felt good about being a good student. So people said you have to do something smart like being a doctor. Read more>>

Emefa Boamah | Women’s Life & Business Coach with focus on Healing and Leading through Embodiment

I have come to see risk-taking as an integral part of life and career. Through my own experiences, I have learned to approach risk with a blend of courage, adaptability, and resilience. The pivotal moments in my life, such as moving to a new country and battling COVID-19, have shown me the transformative power of taking risks. Read more>>

Terica Wright | Nurse Injector, BSN RN

I always try my best to assess the risk to any situation realistically. I try to understand and accept what I’m willing to lose before doing anything. But, I have the mindset that “if they did it I can do it too”. I think that helps me be okay with making more risky decisions. I do feel like i can accomplish anything i set my mind too. Read more>>

Bailey Chambers | Tattoo Artist

I took a risk in my career and refused to ever let failure be an option. I was going to tattoo, no plan B. Failure doesn’t exist, only a lesson I had to learn to get to the next level. Every time I fucked up, every time I got told no, I took it as a personal challenge. To prove that I could do it, and no one could stop me but myself. Nothing just doesn’t work out if you are passionate enough, and strive to improve yourself and your art at every step. You either overcome or you quit. Read more>>

Andrea Monecia De La Rosa | Co-Owner of Texas Taxes & Insurance

I truly believe you need to take risks when it comes to business. There is no way to know if you will succeed if you do not even try. Texas Taxes & Insurance was definitely a risk and through the ups and downs the risk was definitely worth it. That one risk that we took changed not only our lives but even those around us. Read more>>

Jaydyn Barral | Artist

I’m taking all risk, every outcome is a lesson win or loss. I used risk to show myself you gotta do it to know the answers and unlock other doors Read more>>

Mary Speranza | Marketing Director at Patrick Jones Gallery

Risk-taking has played a significant role in both my life and career journey. At 19 years old, I took the risk of moving from my small hometown in Northern Italy to Belfast, Northern Ireland, without really knowing what to do or where I was about to move to. I just knew that following the safe path of high school and straight to college felt very limiting at the time.  Read more>>