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.

Derek Jolley | Creator, Organizer, & Humanist

My Dad taught me that risk is the price you pay for opportunity. The only appropriate risks, he said, are the ones which opportunity outweighs. I’ve been playing in bands with my best friends since I was 11 years old, and have tried hard to only take appropriate risks for the sake of golden opportunities, but as fate would have it, that doesn’t always work out. As an openly queer individual, I have faced a great deal of adversity and harm while working to bolster creative communities. Read more>>

Tanya Thamkruphat | Poet and author

Risk-taking, I think, is a positive thing. Without taking risks in life, we might be missing out on wonderful opportunities and connections. My parents took a risk by leaving their family, friends, and home behind when they moved to America in the late 1970s in hopes of a better future for themselves. So, risk-taking has been in my blood. Read more>>

Jebbs Rodrigues | Jewelry Designer & Store Franchise Owner

As an entrepreneur, taking risks is an inherent part of the journey. While there’s no guaranteed formula for success, taking calculated risks can help you seize opportunities and propel your business forward. Remember, successful risk-taking involves finding the right balance between caution and boldness. By adopting a strategic and calculated approach, you can navigate the entrepreneurial landscape more effectively and increase your chances of success. Read more>>

Rob Wiltsey | Founder & CEO of VideoFresh

Taking risks is a pre-requisite for success. Not all risks are worth taking, but growing a business is impossible without risk taking. Read more>>

Quentin Hill | CEO of iliac Golf, Owner of 72 and Sunny Real Estate, Co-founder of HG Authentics and Jesus In A Bottle Non Profit

Taking risks has played a large role in my professional life to this point. From the age of 15 to 20, I worked on various projects and businesses while saving every penny I could living at home. Simultaneously, I was given the opportunity to model for my favorite golf apparel company, iliac Golf. In 2020, the owner of iliac Golf shared his desire to sell his company. Read more>>

 

ibti | Photographer & Creative Director

I think taking risks is the key to success. I’d rather take a risk and see where it leads me, even if it doesn’t work out, but at least i will live my life without any regrets. Read more>>

Alex Michael Torres | Actor/Model

One of my favorite quotes I say all the time is “No Risk, No Story.” When I decided to pursue this career path, people in my life would say it was too risky or unrealistic to pursue and it would be better to pick something safe. The problem is if you never take a risk and go after what you want, you will never get it. Read more>>

Trey Everett | Playwright, Author, Musician

I think risk has such a negative connotation in the zeitgeist. Especially when it comes to pursuing a life as an artist. When I think about risk, I try to broaden the definition by simply thinking about following the impulse. As an artist, I think inspiration hits suddenly, and intensely. Whether it be a new book idea, a new play idea, a new song idea, whatever the inspiration brings, it comes unexpectedly. Choosing to listen to that impulse, and really lean in, to me, is choosing risk. Read more>>

Diego Ramirez | Filmmaker

Risk is almost everything in filmmaking really. Not only can it be an expensive occupation (if you allow it to be), but it can also be a gambling one at that…and I’m a horrible gambler believe it or not. Read more>>

Babiibleu Jess | Cosplayer & Content Creator

I believe without risk there is no reward. However, it’s essential always to have a backup plan. After being laid off from my flight attendant career of more than 5 years during the pandemic. I had to sit with myself and ask what my next step was going to lead me. I considered going back to school or taking up a trade. In the end, I took a leap of faith and decided to pursue content creation and live streaming on Twitch. Read more>>

David Heckenberg | Singer/Songwriter

We live in a money driven society where it feels like money equals freedom, but that couldn’t be further from the truth. Freedom of the human spirit is alive and well and unconditional. On the surface there are two categories for me, 1) people places and things that lift me up, and 2) people places and things that attempt to suck the life out of me. I’m not really at the mercy of either, only temporarily seemingly so. Read more>>

Denise Williams-Jones | RDA, Dental Speaker and Consultant

It is necessary to take risks in life. I have talked about this with many people and asked them if they could change one thing in their life, what would it be? Most said they wish they would have done more, taken more chances, and not been afraid. They wished they would have taken a risk on things. Read more>>

Yijuan Reggie” Zhao | Film Editor”

Broadly speaking, taking any project itself is risk-taking for an editor. People say there are three rewrites in filmmaking. First, the writer writes the script. Second, the script gets rewritten when they shoot the film. Finally, the third rewrite happens when the editing process begins. An editor can read the script before they accept the job; Read more>>

Sean Grand | Producer/Artist Manager & A&R

Risk is about thinking about exposure to danger. It’s situational. Danger can be big or small. Risk can be low on something very dangerous. It can be high on something very safe. Read more>>

Yuqin Hong | Filmmaker/Producer

Risk is indeed an intriguing and complex concept. Throughout our lives, countless choices accompany us, and each choice represents a risk in itself. Many people emphasize the need for caution and rationality when facing risks. However, I wish to advocate for the voice of sensibility. Read more>>

Freangel The Artist | Artist

I think no one as ever achieved greatness by playing safe. Taking risks has been far more enjoyable, fulfilling and much more of a learning experience than not. Personally, taking risks means two things: believing in my ability to overcome obstacles and also believing in the invisible connection to a greater/unperceivable energy that is aware of my genuine desires and that no matter how hard it gets, in the end, things will always workout. Read more>>

Kenya Rothstein | Attorney and Podcaster

I think there’s something to be said about taking risks. Risks involve doing something where you don’t know what the end result is going to be. It’s intimidating and fearsome to walk a path you’re creating as you go. But taking risks is also really rewarding—even if things don’t work out the way you thought they would. Read more>>

Avery Watts | Founder & Director of South LA Soul & P.E. Teacher/ Athletic Director

This idea came to me in college while in my dorm room. I played rugby at Cal State Fullerton, and while it was a great time, absolutely an experience I would do the exact same way 100 times over, there was a disparity in where the players who had prior rugby experience were coming from. Read more>>

Ezekiel Bridges | Actor Writer & Producer

Taking risks is one of the great ways to grow in life! Every time you take a risk and put yourself out there, the universe will respond. Sometimes, that response will surprise and enlighten you on new possibilities! Read more>>