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.

Tiffany Anich Mansito

Risk-taking was woven into my story from the very beginning. My parents were young entrepreneurs who started their first industrial supply business with just $500 borrowed from each of their grandparents. I watched them build that company from the ground up, eventually selling it just two years later for a meaningful profit. They went on to start a second, larger business that they owned for over three decades. Read More>>

Aleisha Cappellano

15 years ago, within a 6 month month period, I lost a close friend and a boyfriend to suicide and then 6 months later lost my father to a sudden heart attack. All three losses hit me really hard and I became severely depressed and felt very lost. I spent a good amount of time soul searching and trying to figure out who I was and what I wanted my life to look like and I came to the realization that life is extremely short and can be taken away in an instant. Read More>>

Mary Grodman

I developed my ability to take risks gradually, through a combination of experiences, education, and reflection. It started when I was young and spent summers working at camps. I found that every new responsibility—whether leading a group, handling an unexpected challenge, or speaking up in a difficult moment—pushed me to step outside my comfort zone. Over time, I became more confident in my ability to make decisions and adapt, even when the outcome wasn’t guaranteed. Read More>>

MagicalLeeMe

I originally grew up in the Boston, Massachusetts area and I spent my whole life there. I had hit a point where I had been feeling stuck for a few years and then the pandemic hit. At first it felt like things were falling apart because my job had laid off a bunch of employees including myself. It was then that I took some time to really start thinking about what I actually wanted in life. My partner and I had been talking for years about how we wanted to move to Florida to get our social media to take off and try to work on becoming full time content creators. Read More>>

Brian Mulvey

I developed my ability to take risks through a mix of early life experiences and decisions I’ve had to make as an adult. Growing up, I played a lot of poker—not just for fun, but seriously enough that I came to appreciate the psychology of risk. Poker taught me how to make decisions under pressure, weigh probabilities, trust my instincts, and stay focused when you have a lot on the line. That mindset stuck with me. Read More>>

Jen Paul

I’ve always enjoyed a good adventure and at the age of 6 I remember hunting for golf balls near the golf course and selling them at a stand. Throughout high school and college I enjoyed taking part in groups that challenged me to grow. In college I followed in my Dad’s footsteps and graduated with a Bachelor’s in Business. However, I had always felt called to be an educator. Years later, after taking a hard look at myself and working to overcome personal trauma, I returned to school to do just that. Read More>>

Ruhana Nova Ra

Risk has become a special language of faith, intuition, trust, and inner security. I didn’t just learn to take risks. I lived them, again and again, until they became part of my rhythm.

I grew up in an environment shaped by constant movement. We were always changing homes, schools, and communities, and while it was disorienting at times, it taught me how to adapt with dynamism. I learned to make the unfamiliar feel like home, and that built the muscle to try new things, leap into the unknown with curiosity and instinct, rather than fear. Read More>>