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.

Chef Raquel Oderbert-Hemphill | Traveling Personal Chef

Taking risks has been the forefront of my entire career. I’m from a small town called Daleville, Al. Most people from there don’t even try to move out of state for college but I did. I took the risk of moving to a new state with no friends or family near to purse my career as a personal chef and attended Johnson & Wales University in North Miami. I took an even bigger risk in 2020 during the pandemic. I lose my job and only had $200 in the bank account and decided to just go for it and start Chef RockieBree Luxury Personal Chef Dining Experiences, which was the best risk making move I could have ever done for myself. Read more>>

Henna Pryor | Workplace Performance Expert + 2x TEDx and Global Keynote Speaker

My relationship with risk-taking is what evolved to become the entire basis for my new book – Good Awkward: How to Embrace the Embarrassing and Celebrate the Cringe to Become the Bravest you. All of the career success I’ve had so far, including two total career pivots, has been because of the willingness to place small bets and take small, strategic risks. I can count so many times when I felt I wasn’t ready, or didn’t have the qualifications, or wasn’t sure if this *thing* I wanted to try would be well-received, but early on I developed a mantra: Do it awkward, but do it anyway. Read more>>

Krystal Maynor | Commercial Mural Artist

There is a lot of trouble in the world that we live in. I also have been in a situation where I felt like I had lost everything. Its moments like that when you think more about what is most important and what truly matters. Most people are fed the idea that the secret to a successful life is going to college and working hard in their chosen career. I have been taken down that path too. Now I realize that I would rather not live at all than live a life without the time to understand why we are here or without the time to be there for my family and to help other people. Some risks are worth everything even if it feels like you are leaving important things behind. Read more>>

Maroxby | Mixed Reality Artist & Creative Engineer

Risk has been such a critical piece of going on this creative journey. Every new opportunity for me as a creative has come from my willingness to put myself out there. That’s not to imply that there hasn’t been failure or fear paired with those risks – tbh fear of risk held me back for a long time – but as you venture out and surround yourself with folks who have walked to the road you want to travel, you quickly realize that there is no reward without the risk. Read more>>

Michelle O’Kennard | Branding, Communications, & Marketing Specialist

If it were not for the outcomes of the risks I’ve taken over the years, I wouldn’t be standing here today. I believe taking calculated risks can make a positive impact on the quality of your life and professional career quickly. In my professional journey, I have taken risks that have resulted in both lessons and success. Learning about myself in the process is the true gift taking risks brings, and for that, I am grateful. Read more>>

Jashua Sa-Ra | Communications Artist & Spirit Bender

The simplest of things involve risk. If you stand up, you risk falling. If you eat, you risk choking. We learn to use our bodies in a way that reduces risk so that we can do anything in life. I think that you can acknowledge risk but you can’t fully prepare for it, no matter how much data you compile. If you are willing to do what needs to be done, then failure is just an accepted part of the possibilities. But to focus too much on that possibilities of failure is to take away from focusing on the execution of success. Risk is what makes the process alive and exciting. If there was only the possibility of winning, then I think the human spirit gets bored with that and relishes a challenge that brings out our best abilities. Read more>>

Telesee Tootle | Teleseemonae, Fashion Model

Hi , My name is Teleseemonae, I am a wife and a mother of a 3 year old. I just start pursing fashion modeling. I would say taking risk has played a huge role in my current way of living. From working longer hours to being away from home more than expected. I’m learning that risk taking requires a lot of sacrifices that I know I have to make, in order to achieve my goals. I’m a mother and also a wife, so taking this leap of faith is to pursue a career path that I enjoy while also making a better living for my family. I spend a fair amount of time networking and these events are starting to pay off. Read more>>

Nick Kane | Artist & Performer

I feel like you have to take risks in order to succeed. As an artist every step you take is a thrilling risk. I’ve been risking for years and honestly if i hadn’t i wouldn’t be where i am nor accomplished half of the things i have today . Read more>>

Jarrel Hanna | Serial Entrepreneur, Studio Owner, Retreat Host

As a woman who usually goes against the grain. Risk can be necessary to achieve your end goal. We may not always have a clear path in the direction we’d like to go in so taking that risk is your only means to getting there. For me that has been the story of my entrepreneur career. Continuous rush to complete the vision be it opening a trending nail studio in a small town, leading yoga classes in a community that didn’t see it as a true resource or hosting wellness retreats with no guide , just vision and execution. Risk are sometimes necessary and often times rewarding when met with pure intentions.. Read more>>

Michael Cooke | Director

There’s an attractiveness and allure to risk. In a lot of ways I seek it out. From a young age I was taking photographs, documenting family events and drawing. I had an affinity for filmmaking and visual arts. I started making films at 13 and I went to college for Television Production at SCAD. Very early on I carried with me a beginner’s mind when it came to my creativity. I just wanted to try to make the things I saw and I was passionate about figuring it out. By the time I realized what risks were associated with my chosen career (entrepreneurship, financial instability) I was already fully invested in film making. Read more>>