Risk is the most common topic that comes up in our conversations with entrepreneurs and so each week we ask entrepreneurs to talk to us on the record about how they think about risk.

Andrew Holmes | Antiques Dealer

The antiques trade is built on risk, its the ultimate risky business, experience undoubtedly mitigates risk to a certain extent but bravery is essential. strangely I have found that the more money I make the more risk averse I have become. It’s a trade where you never stop learning and even the oldest veterans confess to making mistakes still, there’s a lot of split second decisions that have to be made and sometimes there is collateral damage. I try and buy with gut feeling which is entirely unscientific but ultimately its an unscientific business. Read more>>

Gagan Singh | Music Composer, Producer & Creative Executive

I have always believed in taking calculated risks. From the moment I was young, I knew I had a gift in creating musi. Taking risks is an every day part of the game in the music business. As a composer and a record producer, I bet on my creative skills and talents to propel whatever project I’m working on, helping me move forward. No risk, no reward. You can’t play small and expect big results. Taking risks at the right time is crucial. Read more>>

Bridget / Liza Connelly / Mcgowan | Co-Owners of After Hours Vintage

Bridget – I’m a risk taker. The way I see it is it is not taking the risk and staying complacent is riskier than taking a chance. If the risky decision turns out to be a nightmare you gain a hilarious story to tell at dinner parties. I have a lot of hilarious stories. Quitting my near decade long job at Delta Airlines LAX was probably the biggest “career” risk of my life. I had to give up first class flights to France. When you fly (standby), you’d risk getting stuck. The risk of potentially not getting a seat on the plane was what made it fun. Read more>>

Tatiana Khoury | Graphic Designer

Viewing something as a risk is a psychological choice. My perspective on risk is that it’s a challenge that you were meant to endure for one reason or another. In my mind, I subconsciously replace the word “risk” with “challenge.” I view it as an unsolved problem, a challenge calling my name to be resolved. The beauty of being in a predicament and having my back against the wall is that I’m forced to solve a problem. This fuels me because I find myself to be most creative when I am faced with a problem to solve. Read more>>

Tuo Jiang | Producer/Lighting Designer/LiveSound Engineer

Whenever I think about a risk, it is about the way you manage it. In my own opinion, a risk is something that a person perceives it with fear of failure. The longer you hold on to the fear, the risk is likely to keep building up. So you either analyze the risk and come up with solutions to face the risk or you just walk away from the risk completely. For example, I was doing lighting for some big shows in my work place. Read more>>

Seohyun Jeong | Designer & Illustrator

As a designer, I believe that taking risks has been a big part of my journey. Whenever I tried something new—whether it was making a style guide, building a brand, or designing food packaging—I faced challenges that were outside my usual work. But each project helped me grow. Read more>>

Mriana | Actor and Model

Risks are an important part of the film industry. like Abel Morales said “when it feels scary to jump, that is exactly when you jump.” I moved to Los Angeles 3 weeks after my 19th birthday. I didn’t know anyone in California but like all opportunities, I trusted my instincts. I felt a rush of fear and excitement, which was the perfect cocktail for my career. As an actor, to stand out you constantly take risks regardless of the norm. Each step will take me to the right path, you don’t know what lies ahead of you until you discover it. Read more>>

Wendy Nolasco | Makeup Artist

Risk can be intimidating, but it’s essential for success in any area of our lives. Embracing growth requires an open mind and a willingness to welcome new opportunities and blessings. For instance, if Oprah Winfrey hadn’t taken the risk to leave her job and start her show, she might still be in a role that others deemed best for her, rather than achieving her current success. Ultimately, only you can truly understand and pursue what’s best for you. We must learn to become okay with others not seeing our vision, later they will understand. I have experienced this first hand. Read more>>

Hanan Margoles | Photographer and Graphic Designer

Personally, I believe that as an artist, embracing risk is essential—not just in the work you create, but in the journey you take to reach your goals. Art itself thrives on pushing boundaries, and if you’re not willing to explore the unknown, you’re likely limiting your potential for growth and discovery. In my career, taking risks has manifested in many ways, whether it’s experimenting with new styles, mediums, or approaches that don’t necessarily guarantee immediate success but offer the potential for something greater. Read more>>

Jillian Valentin | A multi-hyphenate creative- VoiceActor/Singer, Artist, Author/illustrator, & Creative Marketing Director in web

Since I was a little girl I never followed the norm. I went against everything I was told I should follow when it came to a career. If I wasn’t happy somewhere, I left. I never wanted to just do the “9 to 5” & follow the same “normal path”. At that time it was risky chasing dreams with no real fallback, but even in the non plan I knew what I was doing. If you don’t take risks you end up with regrets & that scared me more than having a real 5 or 10 year plan. Read more>>

Kane Navasard | Artist

No risk, no reward. It’s as simple as that. You can’t be afraid to fail. There are plenty of lessons to be learned when you make mistakes along the journey. Some time ago, I took a leap of faith and opened a private tattoo studio in Los Angeles after working at a shop in Orange County. I had poured all of my savings into opening the studio, unaware if it was going to work out. I was engulfed in anxiety as I wondered if my clients would follow, if I’d be able to stay on top of my bills, and whether I could sustain this long-term. Read more>>

Wesley Guimarães | Actor & Creative Director

I think risk-taking is the fuel behind any serious creative pursuit. When I look at the state of the world right now, I am even more certain that being an artist in times like these is intrinsically a monumental risk. During the age of mass production and consumption, existing as artists and artisans is, to me, an extraordinary leap of faith. Read more>>

Rohan Das | Film Director & Producer

Taking risks is essential, especially when you have nothing to lose. In such moments, the fear of failure diminishes, replaced by the freedom to pursue bold ambitions. When you’re at rock bottom, the only direction left is upward. The very act of taking a risk propels you closer to your goal, even if you don’t achieve it immediately. Each step forward, no matter how uncertain, builds momentum. It’s this momentum that sustains the dream, fueling the fire to keep pushing onward, refining your vision, and making the objective more tangible with every move.  Read more>>

Claire Yee | Creative Director, Artist, Illustrator, Concept Artist

In my sophomore year of high school, when I was deciding to pursue art as a career, I was grappling with the question of whether it was the right path for me. At the same time, I was at the peak of my Taekwondo journey—placing at Nationals and training with world-class coaches. It was an incredibly difficult decision to make such a complete shift, essentially sacrificing my athletic career for art. I had to take a step back and reflect on what I truly wanted. Read more>>

JuliaDawn

Personally, I believe taking risks is absolutely necessary to achieve any kind of growth or expansion in life. Whether it’s personal development or career-driven growth, if you’re afraid to take that leap into the unknown, how could you ever discover what you’re truly capable of achieving? I think the word ‘risk’ itself is often intertwined with fear, but I hope more people begin to see fear as a guiding factor. For me, fear can act like a road map. Whatever seems scary in your mind but doesn’t unsettle your gut, that’s the path you should follow. No matter what doubts your mind brings up, trust your instincts. Keep moving forward—and when you come across an unfamiliar yet intriguing opportunity, take it. You can always find your way back if needed. Read more>>