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.

Brooks Whitney | Business Owner & Environmental Educator

I view risk as a necessary framework for life. Without putting ourselves out there we have nothing to lose, but we also have nothing to gain. Healthy risks allow us to challenge ourselves and put ourselves to the test. With the kiddos I work with, I encourage them to take healthy risks such as climbing a tree to gain confidence and learn new skills. Read more>>

Lex Poulakos | Couples + Family Photographer

Honestly I would generally categorize myself as a pretty non-risky person, but my business was truly founded on one big risk. I was working at a company that didn’t value me and had just kind of had enough. One day, without any real plan, I quit. As soon as the decision had been blurted from my mouth to my boss I knew that the only option I was going to give myself was to make my business successful. I couldn’t be more thankful that one of my biggest risks turned into something so fantastic. Read more>>

Nick Chung | Filmmaker & Photographer

For me, risk taking has made a huge impact on my life/career. Ever since I graduated high school, I skipped university to validate myself that I am capable of doing unique things that would build the difference between me and others. I have been making a difficult decision whether or not if I need to attend to a university. Decision making started during the sophomore year of high school, so I had a lot of time to decide. Read more>>

Krystell Pujol | Co-Founder of AP Consultores Legales

My name is Krystell Pujol and since I was 8 years old, I had dreamed of being a lawyer. When I nailed my first internship, I remember I would fall asleep on my desk reading endless documents that sometimes I wouldn’t understand. Even though sometimes I felt completely clueless, I tried my best to learn from the managers, to make myself useful, and to become a reference point within the Law Firm. With time, I developed skills and human tools that helped me survive in this hard world of law and advocacy. Read more>>

Raymond L. Haywood | Fine Art Painter, Artisan Builder and Educator

I am risk adverse I ride a motorcycle, I am a builder and Artist, all of these activities necessitate a highly agile ability to engage solutions that can have risk. As a professional fine artist, Artisan Builder and now Construction Technology Instructor at Freedom High School in Oakley CA all of these professions involve strategized risk taking and problem solving on the move. If there is no risk, then I feel there is no potential learning opportunity in undertaking the challenge or the journey. Risk and chance are what define my aesthetic and ethos. Read more>>

Sam Dean | Hairstylist & soon to be Business Owner.

I think there are two ways you can look at risk and two timelines for risks. First, what is the upfront risk vs the long-term risk? After that you have to look at the risk of doing it and the risk of not doing it. I think most people look at the upfront risk and the risk of doing it. I try to look at the long-term risk and the risk of not doing it. When I was a kid, I grew up competing in high level Scottish tenor drumming competitions and became a professional at 12. Read more>>

Mim Na Chiangmai | Entrepreneur

Risk taking: how do you think about risk, what role has taking risks played in your life/career? My definition of risk is the “unknown.” It is normal to have fears around the unknown because you have never been there before. It’s your ego that wants to keep you safe, because the ego has evidence that you’ve been doing pretty “okay.” You are still “alive” by doing the exact same thing you have been doing, so having fears around risk is a good thing. It’s the first actualization to step into the unknown which is infinite possibilities. Read more>>

Ellory Gilliland King | Owner and Operator of The Mellow Baker LLC

Risk taking has been a large part of my success over time; a conglomeration of bold decisions propelled me to be a full time business owner of The Mellow Baker LLC at just 24 years old. I think about risks in a very positive way, risks are actually opportunities hidden behind anxiety. I approach risks with optimism and confidence, if I take the wrong risk, I know a new risk will present itself later, probably an even better one. Let me tell you a little bit about how I got here. I grew up in rural, Eastern Washington, and experienced a small town, community-oriented upbringing. Read more>>

Joanna Faivre | Makeup Artist

I think life is meant to be lived. So risk is part of the process. When I started doing makeup I was a waitress, going back to school at 25 to be an artist in an overcrowded industry was a risk, but I thought : worst case scenario, I will be a waitress again and I ll be fine. I was blessed to work at a good rhythm in Paris when I moved to America. It was a risk, because I had built a steady clientele in France, and like I said, it’s an overcrowded industry. But I thought again, worst case scenario in the US, I book a flight and I go home. I am someone that takes decisions based solely on my intuition, not logically, so risk is part of my everyday life. I think we have a short term on this planet, so just like a kid I want to play in the meantime! Read more>>

Andrew Hobbs | Entrepreneur

I always advocate to take risks! I’ve personally always done them to a smaller scale, but within the last 3 years I’ve somehow managed to double down when taking risks. I think without taking risks you risk thinking “what if I did that” rather than man I’m glad I did or didn’t do that. You also run the possibility of having a stagnant life, I would hate to just plateau and sit idle and not any type of growth in my life. I have a fear of living in regret I don’t want to leave any stone unturned, however my love for pushing the envelope has landed me big and has landed me on ass, just know it takes 100 loses for one win. Read more>>

Dre Carrera | Frontman & Guitarist of Jagged Lines/ Bassist of Falling Doves

Interview Mitigating risk has been ingrained in my mind as a responsibility of mine since I was a financial advisor years and years ago. Because of that job, I learned that risk needs to become something you seek and eagerly mitigate, not fear and avoid. I went to school for psychology and worked in finance on a bet, but I wasn’t happy with any of it because I needed to create and make music. That last sentence alone contains a lot of risk mitigation, but giving up everything I’d worked for my whole life for music couldn’t have happened if I didn’t have a strong stomach for risk. I hadn’t even written that many songs when I decided to leave the New York area for Southern California to make music with a friend. Read more>>

Chanel Bagheri | Mortgage Loan Officer

Taking risks has defined my young adult life. I would not be where I am today if I hadn’t taken any risks. How I got here was not an easy path, but it was one that required taking risks. I was in banking for quite some time pursuing management, and I took the biggest risk by quitting. Knowing I was about to lose my salary paid job, to jump to a job which was commission only is a risk in itself. Read more>>

Nicia Trice | Owner & Co-Founder of Dope Ass Meals

I am a true believer of taking risks and have done so consistently in life and with my careers. From a very young age, I have always had a great sense of adventure and love trying new things. I never have or will live life with the regret of could of, would have, should of. I am not fearful of taking risks and when I decide to do something, I jump right in. I believe taking risks are some of the best ways to learn as the outcomes can be very rewarding while others may not be as successful. I think society has conditioned most to think of failures as a bad rather than good. Read more>>

Shagwhelin Shaggy” Bullock | Cannabis Educator”

I’m a big proponent that we are the only ones in control of our own happiness and the only one who can change things to become happy. So the first area to start is. ” What is the most important thing to you in life? What would make you truly happy? Is it having a lot of money, security, a family , making the world better? No answer is wrong, it’s figuring out what is truly important to you. For me it was career. We spend most of our life working so I wanted to do something I Love. The other factors was location! I love nature so have to be by the mountains or beach. I hate the cold so I wanted somewhere warm. My final factor was what am I passionate about? Helping People and cannabis! Read more>>

Allie Mosier | Evolutionary Astrologer & Reiki Practitioner

Taking risks is a natural part of life, and something that most of us do at different points in our life. I believe it’s what leads to growth and change, and can orient us on our desired path. With that said, it’s important to take risks when it feels right intuitively or internally. Taking a risk can feel like a natural progression of your life, and that’s how it unfolded for me. I took a risk by leaving my stable corporate job near the end of 2020. Some people may have considered this risky, Read more>>

Yvonne Parma | CEO | Creative Marketing Director

The biggest risk I had to take was giving up my 9 to 5 job, I had a steady pay check, having that secure income each month, stability and reliability, but I felt limited with my capability and creativity in my job even though I loved it. My boyfriend at the time, would constantly say to me “imagine ALL this effort and commitment you invest to grow others people businesses was in YOUR OWN business!” That Always made me think. Read more>>