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.

Brianna Dutcher | Wedding & Lifestyle Photographer

Ever since I was young, my mom always called me the daredevil child. I have always been the one to take risks and try something new, even if it was absolutely nuts. I knew that starting my own business as a wedding photographer in a highly saturated market could absolutely be a nightmare, but I also knew my passion for making art and capturing couples was stronger than that fear. There are so many highs and lows opening any kind of business, but luckily the work is so rewarding, and the people I get to meet along the way, have made every single risk worth it. Read more>>

LIL MILE | International artist/singer

I always like to say that if you want it, go for it. Take a risk! Don’t always play it safe because you will die wondering. We have only one life and you have to go out of your routine to get what you want, or you will loose the chance. Taking risks played an important role in my life, in fact one of my biggest risk that I take is when I was 19 years old, I left my daily routine in Italy and I decided to move to the United States to play college basketball and do music, even if I didn’t know English or had so much money. I built the person that I am now, and I’m still learning. Read more>>

Carliss Bussey Jr | Entrepreneur

The way I approach taking a risk is before going into a particular risk is that it’s 50/50. I tend to think of every possible outcome before I proceed to take the risk. I have never had success just going raw & unplanned, for me when I’m organized with solutions planned out. Success tends to follow. Taking risks have played the biggest factor in my life starting after my senior year of high school. Risk from mentality, sports, school , business , lifestyle , living and more have had there pros and cons that I had to learn from. Read more>>

Asher Phoenix | Photographer, Storyteller, Mental Health Advocate

Risk-taking is the foundation of the authentically creative and successful life that I have today. A week after turning 20, I moved from the middle-of-nowhere Kansas to Los Angeles for a real chance at a creative life. I hopped on a plane with 3 grand in my pocket, manifesting that the universe would have back back when I needed it. And that, it has. Because of that risk, I’ve had the opportunity to become a live music photographer and seasoned storyteller. Even riskier than a cross country move, however, has been coming out and living authentically as a transgender person. In revealing my identity, I understood the risk of losing connection with my family. Read more>>

Shuoran Zhou | Metalsmith, jewelry artist

One’s willingness and courage to take risks are always admirable, in my opinion. I applaud to those who take risks in their life and career, and so is how I navigate my own. I like accepting challenge, which also is my coping mechanism when facing uncertainty and unexpected changes in life. I do think by taking risks, whether succeeding or failing at the end, it is a painstaking but rewarding way of learning, growing, and breaking through one’s limits and comfort zone. I have been taking risks in every step of my life so far. Read more>>

Bet Miller | Barre Instructor & Studio Owner

My whole life I have played it safe, most likely from a fear of failure. If you keep risk low then your chances of being disappointed are greatly decreased. But as I age and grow I understand how debilitating fear can be to accomplishing something you truly love. I could see what I wanted and could envision myself there but kept making excuses to not taking any risk. Until one day it all just clicked. Someone casually said the clique term “life is too short” and I suddenly realized that it’s true! I no longer wanted to live in the shadow of regret and fear. And ever since that day, the risk of starting a business has been immensely rewarding. Read more>>

Skylar Economy | Film Director & Producer

When I first embarked on this whirlwind journey as a filmmaker, it was tough. After college, I moved to LA to break into the film industry – starting out as a Production Assistant. During this time, I was simultaneously filming my first film in the Bay Area – which I had gotten funding for through grants and Indiegogo. This meant long, 5-to-6-hour drives every weekend from LA to the Bay Area, and back to LA to make it to work on Monday morning. It was exhausting. Not only was I working every day in LA on the weekdays, but I was also working every weekend – I forgot what it was like to have a day off. Read more>>

Essie Faye Taylor | Servant Leader, Teacher, Author, Podcaster, Improviser

Risk-taking is a natural part of life. Risk confronts us so very often–it’s present at every fork in the road. Every decision that we make has risks involved. I am a risk-taker. I am a person that takes a chance, in the face of fear. I love to try new things, different experiences, and challenging tasks. Risk-taking has been essential to my career path and creative growth. Read more>>

Jon Cheung | Small Business Owner

My understand of risk has grown and deepened since becoming a business owner/entrepreneur. I first understood it as an abstract concept based on the dictionary, basically that there’s a chance something could go wrong. Then as I became more familiar and experienced different aspects of risk, it began to take shape and I was able to see how it impacted my life. I observed that because we are not perfect and cannot predict or guarantee anything with absolute certainty, risk will always be a part of life. Read more>>

Richard Williams | Composer

Choosing to pursue music as a career was a complete risk in the first place. I could have had a secure job but I chose to take the risk to learn how to compose. I was trying to challenge myself and pursue something that I thought is innately valuable – beautiful music. Throughout my career I have taken a number of risks. I spend the time and money to pursue many opportunities, and many of them don’t pan out, but a good number of them have panned out. Read more>>

Gentry Hale | Freelance Environmental Journalist

Life is made up of a series of risks and rewards. At a young age, I realized that taking risks and facing discomfort is when you grow and develop. I decided to base my entire career around risk. As a freelance journalist working for yourself, you have no consistent income, no reliable paychecks and no guaranteed work; it is a huge risk. In return, however, you can live the most exciting life you could dream of. You can write stories on whatever interests you, you can travel to places you’ve always wanted to go, you can take deep dives into the topics that excite you and you have an excuse never to stop learning and growing as an individual and as a business. Read more>>

meryem slimani | photographer & art director

I am as they say a high functioning anxious person that is also dealing with depression and ptsd so I see risks and dangers everywhere which might keep you in a constant state of terror and always opting out of anything out of your comfort zone. But contrary to that I somehow always jumped into things even though they scared the living hell out of me. I remember throwing up before every ballet and violin recital when I was a kid but also hyperventilating in rollercoasters or ziplines. Being scared never seemed to be something that held me back but it has always cost me a whole lot of energy and effort to still do whatever it was that freaked me out even until this day. Read more>>