Risk-taking is at the heart of making a difference, but often we’ve been conditioned to avoid risk as much as possible. So, we asked some successful risk-takers to talk to us about how they developed their comfort with taking risk.

Emily Gray

Taking risks had been something I never really did earlier in life. It took a lot of self reflection, therapy and life experiences to develop the confidence to bet on myself and my happiness. I think I had to burn out completely to be able to light a small flame of change! That’s where the magic of just starting, just trying and doing it scared came from. Read More>>

Marissa Bond

How will you know if you never try?

I don’t take risks blindly. I think about my actions and the logistics before starting, but starting can often be the scariest and riskiest part of achieving your goals. Nothing in life is going to be perfectly easy, and I have learned (and still am learning) to trust myself and my abilities to take on challenges and risks. Read More>>

Tamaya Livingston

My capacity for taking risks has been cultivated through a blend of early experiential learning and a deepening of my faith. I vividly recall learning a fundamental lesson early in life: direct experience often serves as the most profound teacher. This realization, coupled with the unwavering encouragement of my mother to explore diverse activities – from Girl Scouts to various sports and clubs – instilled in me not only a willingness to try new things but also the crucial ability to bounce back from setbacks, though bouncing back is a little bit harder as an adult, I still find the journey rewarding and hopeful. Read More>>

Alycia Rogus

Honestly my whole life I have always played it safe and was fearful of trying new things and failing. It wasn’t until last year when I had a strong calling to photography that my husband encouraged me to leave teaching and pour my heart into this passion. Ever since then I have challenged myself to say yes to any opportunity that comes my way even if it scares me. It has been the most rewarding year because so many amazing blessings have come from me putting myself out there and saying yes. Read More>>

Lauren Rogers

My introduction to risk taking came early, and intentionally. When I was a kid, my dad would take me to playgrounds and have me climb to the top of the play structure. Then, he’d tell me to jump. I’d always jump, and he’d always catch me. I was lucky to come from a family that encouraged risk taking, and offered the emotional safety I needed to feel comfortable going out on a limb. Read More>>

Lana Phan

It definitely wasn’t easy for me, and it’s still something I struggle with. I am someone who has been very risk averse all my life and I think that’s pretty typical for first generation Asian Americans, it’s part of our culture to play it safe and be conservative especially when your parents built their lives from a place of significant economic disadvantage. Read More>>

Desmond Denton

Crossing Continents: How Desmond Denton Rebuilt His Life and Voice in America

When South African filmmaker Desmond Denton and his wife packed up their lives and boarded a flight to the United States with their young children, Katelyn and Logan, they weren’t just chasing new opportunities—they were stepping into the unknown. It was a leap of faith that meant starting from scratch in a new country, far from familiar faces, rhythms, and creative ecosystems. It was also the beginning of a powerful chapter in Desmond’s story—one rooted in courage, reinvention, and purpose. Read More>>

Ruby

Risk is when you’re not in control of all the factors that are crucial for your success, but you can reduce the risk by doing your best and giving your maximum effort in the areas that depend on you. You have to be prepared for it to be tough, for you to want to give up, and for your personal life to suffer. You will need help along the way, but you have to endure the effort, do the hard work, and most importantly, keep your vision alive and believe in it. Read More>>

Tapio

As a filmmaker, I had to take various risks, such as using different technologies and new skillsets, spending more time and money than what was initially expected, challenging audiences through narratives, and introducing a personal story that makes myself extremely vulnerable. Although I was not quite comfortable with taking risks when I was small due to the academically high-profile schools I attended and the Japanese social expectation of keeping good grades as well as conforming to other people, it was this encouragement from my parents that kept giving me a great reminder to take risks in creative fields and my daily lives: “do something different from what others do, and do something people don’t expect you to do.” Read More>>

Platinum Pianist

I first learned to take risks after reading The Alchemist, a book my mom gave me when I was young. While I didn’t grasp everything then, its core message stuck with me: the journey matters more than the destination. It taught me that setbacks shape who we become and that taking risks in pursuit of our dreams is not just necessary—it’s what gives life meaning. Read More>>