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.
Anthony Dimaria

I grew up in a strict and conservative household. It was a risk-averse atmosphere centered on rules – and a lot of them. Ever since I can remember, I would test the limits of those rules. I wanted to know why they existed. What was the philosophy and methodology they originated from? How much would they actually be enforced? Although my parents were not big on explanations, they were big on enforcement. Despite this, I kept testing the limits within our household. However, in public, I was terrified of doing something ‘risky’. Actually, I was terrified of doing anything at all, really. I’ve had anxiety from a young age – anything regarding public speaking, having attention on me in public, or having to perform publicly put my mind, body, and spirit in a state of stress. Read more>>
Pejman Zare

I decided early on that I wanted to live with minimal regrets. I told myself that when I’m 80, I don’t want to look back and wonder, what if I had taken those chances? The quote “Doubt kills more dreams than failure ever will” resonates deeply with me—if I let doubt stop me, I’ll never know how far I could’ve gone.
To develop my ability to take risks, I start by weighing potential outcomes. I ask myself: What are the chances of success, and what’s truly at stake? Some risks are straightforward—like the chance of surviving a jump from a building without a parachute—while others, such as launching a new product or business, are more complex and require deeper research and market insight. Read more>>
Alejandro Ansoleaga

I feel like risk is relative. What one person might find to be incredibly bold might just come naturally or at least more naturally to someone else. I dropped what was shaping out to be a good career to move to Los Angeles in pursuit of a life in show business where the prospects are of course incredibly low. I’m also not fazed by public speaking and have jumped out of a perfectly good airplane over one hundred and eighty times. On the surface a person might go as far as thinking that I could be fearless but those things just happen to be right up my alley. On the other hand, until recently the idea of sharing my work was absolutely paralyzing. That and commitment but you’ll have to talk to my exes about that. Read more>>
The Soda Shop Movement Company

We both feel that if there’s something you want in the world that doesn’t exist, it’s up to you to bring it into existence. As much as we love the ballet classics, both of us feel that the art of moving has a place in the 21st century, and we wish to amplify the kinds of stories that are more representative of the world we live in today.
As scary (and risky) as it is to start a professional dance company from scratch, dancers are quite used to navigating these kinds of challenges. The business of being a professional dancer is nothing but risk. We risk our bodies every time we step into the studio or on the stage, not to mention that our careers (regardless of how “successful” they are) are finite. Because we love the art form, we dance because we have to, not because we want to, which also makes us vulnerable to those looking to exploit our passion. We find fulfillment not in our paycheck but in the art we create, which is always a risk, sometimes terrifying, and more times than not…completely worth it. Read more>>
Evan Bellingar

There was no official recession declared in 2023 or 2024, but for me and my business: we were in a terrible spot. In late 2024 I had been retired for almost a year having left a stable, good paying job after years and years of nothing but economic success. The graph of my net worth that I WAY too obsessively updated just went up month after month and year after year until I retired, and now it felt like it was in freefall. I retired from my dayjob because my wine brand needed attention, my long term rentals were doing great, and we now had 4 short term rentals. Then the hits started coming: huge repair bills, higher interest rates meant that we couldn’t get cash out at refinances anymore, short term rental rates went down and vacancies went up. Selling grapes into the worst market in 20 years didn’t happen, and wine tasting tourism was down 30 percent. The tailwinds that had propelled my success turned to headwinds, all at once, and didn’t care that I considered myself “a good businessman” or “I’m good with money”. Read more>>
Simon Gissler

Well, like any skill it gets easier with practice. I definitely haven’t always been as bold as I’d like, and it’s something that some days I’m still working on. I look back on parts of my life so far and have moments where I think “Oh, I wish I’d stepped out of my shell and shared my truer self with the people around me” or “I wish I’d just jumped right in and started making more art earlier.” I think having periods where I realize I’m not living as fully or honestly as I artistically could be make me hungry enough to make more drastic moves. Read more>>
Kirsten Womack

I developed the ability to take risks by hanging out with, watching and learning from my father. He was an incredible example of courage and perseverance. As a Black man in spaces where he was often the only one, he boldly pursued his passions and defied societal norms. He was an organic farmer in the 1970s—long before it was a trend—working tirelessly to grow and nurture vegetables in a way that honored the earth. Beyond that, he was a barber, a hunter, a fisherman, and raised horses. My father’s willingness to embrace challenges, carve his own path, and stay true to his values taught me that taking risks isn’t about fearlessness—it’s about moving forward despite the fear. His example continues to inspire me to take bold chances in my own life. Read more>>
Pearl P

I developed my ability to take risks from my parents. My mother immigrated from Grenada to the US in her 30s by herself. Despite having a lack of resources, my mom made the best of what she had in hopes that it would pay off and provide a better life for herself and hopefully her future family.
My father is a military veteran who went through many obstacles and hurdles while in the military. He now continues to advocate for veterans and also serves the community as a counselor. Both my parents had very humble beginnings, but the trajectory of their lives changed the moment they decided to take a risk and sacrifice in order to get to where they wanted to be in life. Read more>>
Bethany Diaz

Taking risks wasn’t always natural for me. For years, I put my passion for art on the back burner in exchange for stable, predictable income. But when I lost my 9 to 5 last year, I realized that life had handed me a unique opportunity to start fresh. I could either let fear hold me back, or I could embrace this moment to take a chance on myself.
The biggest shift in my mindset came from recognizing that the worst-case scenario of taking a risk wasn’t as frightening as I had once thought. I had already experienced a major setback—being let go—so in many ways, the only way to go was up. I started seeing risks as opportunities to grow, learn, and really pursue something that had always been a part of me but was buried under the weight of routine. Read more>>
Ottavia Giola

When I’m afraid of taking a risk usually I tend to overthink it at first, but then I push myself to act. It’s still something I am working on. The moment I start thinking too much, I know I need to stop and just take the leap. For example, when I was working as an art director I was uncertain about leaving everything I knew to pursue something entirely different as photography. Leaving my city, my family, my friends to move to the opposite part of the world by myself. Everyone around me had different opinions, and I was torn, but in the end I just did it. I didn’t even realize I was moving to another country until I was already on the plane and by then it was too late to turn back. A year later, it hit me how significant that step had been, and I felt an immense sense of pride and realization in having made that choice. Read more>>
Dinu Antonescu

When I was three years old, my father brought me skiing for the first time. What began as a father son hobby, ended up shaping me into the person I am today. What was a way to stay active in the winter, turned into a teacher. As I grew older, my passion for skiing turned into one for competitive ski racing, a world based on learning how to take risks through focused practice. When I first began skiing, I faced disappointment after disappointment, persevering through a lack of results, despite my consistent training. As time went on, I dedicated myself to practicing more and more: four times a week, waking up at 5:00am on the weekends, and training twice on weekdays. Read more>>
Rachel Hazzard

I developed my ability to take risks by learning to trust myself and my vision. In the beginning, it wasn’t easy—I faced doubt, fear, and uncertainty like anyone else. But I realized that growth and success rarely happen within a comfort zone. I started small, taking calculated risks and learning from both my wins and setbacks.
A key turning point was understanding that every failure is a lesson. I stopped seeing risks as potential losses and started viewing them as investments in my future. Surrounding myself with mentors and a supportive network also gave me the confidence to take bigger leaps. They helped me see that the scariest decisions often lead to the most rewarding outcomes. Read more>>
Margaret (mo) Smith

I was sitting in this meeting and began to feel my anger grow about the lack of progress and how it was affecting me. I felt this anger rolling around in my stomach, chest and throat- and I didn’t know how to express it. As I felt this feeling bubble up- all of a sudden my hearing started to fade and my vision began to go black. I didn’t realize it at the time- but I think I was starting to experience my first panic attack.
I have been the tall, quiet, shy and observant girl for most of my life- up until my early 30’s. As the first born child of four kids- I was responsible, compassionate and I wanted everyone around me to be happy. I took very few risks and did whatever I could to play it safe and stay under the radar. I didn’t want to be the focus of anyone’s attention- I was afraid of being bullied, made fun of and ostracized any further than I felt I was. Read more>>
Alxne

At a very young age, me and my mother got evicted from our house. I had to stop going to high school dropout freshman year and get a full-time job and I wasn’t even a legal adult yet. After a few weeks of sleepless nights in my mom’s car, no shower little to eat, I made a conscious decision to move to Florida, where I embrace the EDM music industry, and met a lot of rave producers. Taking big leaps of faith was kind of my signature move. I wouldn’t be who I am today if I wasn’t a high risk high reward type of personality. Read more>>
David Quinones

I’ve always tried to live by the motto: *“Take risks and be daring!”* Looking back, it’s clear that this mindset has shaped who I am today. Life has thrown its fair share of challenges my way, but without taking risks, I wouldn’t have grown or discovered my true potential.
Growing up, I struggled with the fear of standing out. Like many kids, I just wanted to fit in and avoid embarrassing myself. I grew up in the heart of the ghetto, and while it came with its challenges, it was home. I had friends who often went to great lengths to be accepted by others, but I didn’t want to follow that path. Instead, I sought authenticity—though, at the time, I wasn’t sure how to achieve it. Read more>>
Alexander Coleman

It all started with a deep desire for something better—something more than what was being offered to me. I come from a community where stepping outside the box of what’s considered a “normal” way of life isn’t common. If I had stayed in that mindset, I wouldn’t have made it as far as I have today.
I took a chance on myself by starting my own podcast, joining a reality show, and stepping into a producer role. I chose to believe in the gifts God blessed me with and to step out on faith. That leap of faith has made all the difference, and I’m so grateful for the journey. Read more>>
Murray Sawchuck

If you want to be successful you have to take RISKS. If you don’t you will not push the boundaries of things you don’t even know you’re capable of. Risks put you outside of your boundaries and make you strive for something better. It’s easy to get a 9 to 5 job, stay in your lane and live a simple life and that works for many, but if you are an entrepreneur you are looking for that golden egg or the pot of gold at the end of the rainbow. I worked for over 18 different companies from the age of 11 – 19 back in Vancouver, Canada but every time I was working whether if be cooking fish and chips, delivering news paper, being a lifeguard or fixing bikes, I always thought, I COULD OWN THIS STORE and do better, make more and have more control over my life and finances, that’s how I developed my ability for risks… I wanted a better life for me! Read more>>
Meg Malone

I was not an inherent risk-taker. As a kid, I was cautious and internal. I became aware very early on that I was different from the other kids I had access to. My head was full of stories and art. I wanted to create and live this big, bold life, but I had no idea where or how to start. Because I felt like an odd-ball, I gravitated towards more comfortable situations where I could vanish. I wove this world in the walls where I could slip away, go unnoticed, and be in-between the realities that made very little sense to me. Read more>>