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.
Tarina Khatun
That’s where the word bold truly comes into play. If you are bold, I believe taking risks is the first step to proving it to yourself and the world.
In 2009, an event occurred that shaped my life. I was forced into a child marriage, and what followed was non-consensual sex—which is rape—something my soul could never accept. I gathered the courage to approach my mother, asking her to file for a divorce. However, she dismissed my plea, insisting that it was tradition and something I had to endure. Read more>>
Angelique Shah
I grew up the only, and oldest daughter in a family of 7 brothers. I was always the one fighting to protect my younger bothers from bullies. My mom would worry for me as I held onto the city buses in the Bronx, riding my roller skates.
I was the big sister that did jumps off of ramps with my bicycle. I was the first person to leave home for the military, and travel all over the world. I wanted to show my brothers no fear, that they could do anything they wanted if they tried and didn’t let fear hold them back. Read more>>
Ashen Music
I’ve been fearless ever since the beginning. That doesn’t mean that I don’t experience fear though. I learn how to manipulate my fear the way it would manipulate me. Instead of playing “safe” I play big. The bigger you dream, the more you can lose. But how do you turn those losses into stepping stones? You stop feeling like you’ve lost. You stop telling yourself that. And you man up and keep going. That promise you made to yourself cannot be broken under ANY circumstance. YOU are the key. Self- belief is mightier than risk. Risk is a possibility. Self-belief is a knowing. Read more>>
Vi Vo
Hi, first of all, Happy New Year and thanks so much for having me, Bold Journey team!
My ability to take risk has always been inspired by my Dad. He is a true leader, bold entrepreneur and genuine teacher of my life. I witnessed the perseverance, bold risk taking and integrity of him through both challenges and victories. Maybe the word “risk taker” has run in my blood! (laughing). My family told me I have a stubborn heart and it’s true! My life has been full of unlimited possibilities and I firmly believe the Universe favors the bold. And sometimes, it will test you to see if you really want what you want. Read more>>
Camila Hargett
My ability to take risks developed through a combination of life experiences, resilience, and a commitment to growth. Growing up in Chile, I learned the importance of resourcefulness and adaptability—values that have been foundational in my personal and professional life.
When I launched Sezhel Consulting a year ago, it was a major leap of faith. Starting a business is never without its challenges, and taking that step required me to embrace uncertainty while staying focused on the impact I wanted to create. The decision to build a consulting firm that helps businesses grow wasn’t just about risk-taking; it was about believing in my ability to turn my vision into reality. Read more>>
Transit Nomad
Don’t be afraid to take risks when it’s necessary. The biggest risk I’ve taken was moving my businesses from Ukraine to the United States. I had no idea if it was going to work as I would have to start my marketing from scratch. Even though I had the experience and I knew what to do, it took me several months to start getting clients. In the meantime, I had to work other jobs to support myself. Once my marketing efforts started to pay off, my income went up substantially and I used that profit to start new businesses. At this time I own and operate 13 small businesses that focus on event services and I’m very happy I made the move. We have a saying in Ukraine: “Those who don’t take the risk don’t get to drink champagne. Read more>>
Penny D.
For most of my life I didn’t have a reason or a purpose. From a young age my life was full of drugs, risky behaviors and a general lack of desire to live. After some severe suicide attempts I can to realize that my life would end if I continued on the same path. I then decided to sober up. It took years of failures and dozens of destroyed relationships before I actually made it any length of time without any substances.
Getting sober was the hardest thing I’ve ever done. Quitting drugs was a determination to live. It was an admittance that I had some purpose even if that purpose hasn’t been decided yet. From that experience I learned that nothing I do is too important or too horrific. I can do anything I want. It makes taking risks easier. Nothing I do will ever be as difficult as getting sober so there’s no point in not doing the things. Read more>>
Emily Freymann
One key step to motivating yourself and others to take risks and overcome fears is identifying the benefits of doing so. What positive outcomes can you achieve? How will it help you grow or improve? Focusing on these benefits creates a compelling vision that encourages action.
Support your employees by showing them that you have their back when risks don’t go as planned. This reassurance empowers them to step out of their comfort zones.
If you struggle with voicing your opinion online due to fear of criticism, adopt a service mindset: “I’m here to help.” This approach can lead to constructive feedback, turning criticism into an unexpected benefit. Read more>>
Quanella Jordan
It’s a combination of life experience, my role as a mother and wife, and the demands of running a doula business. At 44, I’ve learned that risks are often disguised as opportunities waiting to be embraced. As a Black woman, I’ve faced unique challenges that required me to trust my instincts and make bold decisions, whether it was advocating for a mother during labor or deciding to build my own business from the ground up. Being a wife and mother has also taught me resilience and adaptability, which naturally translated into my professional life. Every risk I’ve taken has been a lesson in courage and faith, and those lessons fuel my commitment to supporting families in some of the most vulnerable yet rewarding moments of their lives. Read more>>
Chiara And Sasha Bertoletti And Gatti
I think I took that from my mother.
She was known in my family for having a crazy streak that would emerge every so often, usually in the form of a big dream—sometimes bigger than she could handle. For instance, she once opened an arcade bar in the early 90s in our small village in Italy.
We almost lost our house when the whole thing sank, and she had to work tirelessly to recover while also juggling life as a mother of three. (That’s probably where I got my inclination for hospitality and my hard-working mindset.) On the other hand, she had a remarkable gift for inspiring others to climb aboard her latest dream ship. Read more>>
Kaptured X Kyle
For much of my life, I associated the term “risk” with a negative connotation, viewing it as a dichotomy between a good choice and a poorer one. As both a child and a young adult, I would not have described myself as a risk-taker; in fact, I shied away from risks, primarily due to my concern for my reputation.
However, my best friend, Caleb, has profoundly inspired me to embrace risk-taking. His fearless nature is one of the qualities I admire most about him. Caleb possessed an ability to navigate unpredictable situations without a set plan, adapting effortlessly to any environment or social setting. Caleb’s adaptability became the model for my own approach to taking risks.
I have come to understand that while taking risks can indeed be daunting, it can also be rewarding. For me, the concept of risk has transformed from a “tug-of-war” between good and bad into an action that challenges my comfort zone. An example of this newfound perspective was when I photographed a New York Fashion Week show for Sherri Hill at 6 PM, despite having a return flight home at 8 PM. Read more>>
Monaye Marcia
I developed my ability to take risks by embracing discomfort as a sign of growth. Life’s challenges taught me that the most significant breakthroughs happen when uneasiness is present and you ‘allow’ it versus shoving it away to return to comfort.
I also rediscovered that situations that happen in life are neutral and your thoughts are the game-changer. I reframed risks as opportunities—less about what could go wrong and more about what I could learn, achieve, or inspire in others.
I’m not saying I jump without looking. I assess the potential outcomes, weigh the pros and cons, and then make bold moves. It’s like playing chess—each risk is a strategic step toward success. Read more>>
