Tony Robbins says the #1 human need is certainty, but do you know what the second need is? It’s uncertainty. This tug of war between the competing needs of safety and risk are at the heart of so many dilemmas we face in life and for most folks the goal isn’t to eliminate risk – rather it’s to understand this core human need. In our view, the best way to understand or learn is through stories and so we’ve asked some very talented entrepreneurs and creatives to tell us the stories behind some of the risks they’ve taken.

Debra Hopkins

Sharing our most vulnerable thoughts and feelings can be a powerful act of courage, even when it feels risky. Though the emotional toll of revealing long-held secrets and feelings of shame can be difficult, it can also lead to deeper connections and understanding. Speaking out can inspire healing despite the doubts that may keep us isolated. Read more>>

Jroach

The biggest risk I’ve ever taken started with a decision that most people around me thought was crazy. I was on track to become a computer engineer, studying something practical, something stable. I had a full-time job offer waiting for me after graduation, a path that was laid out with security and predictability. But deep down, I knew it wasn’t for me. I couldn’t see myself spending my life behind a desk, coding away while my real passions—modeling, acting, and music—remained just dreams. Read more>>

Kellema “kelley” Evans

The biggest risk I ever took was to become an actress. I tried it as a hobby when I relocated to Atlanta just to see if I could do it! My first stage play was titled “ REAL” I played the typical baby momma with the drama. I nailed it! Now I have done a lot more of it! Plays, Short Films and a few projects including background, that have landed on Tubi and YouTube. Now, I was never the popular kid growing up, so I kinda fought a lot! I had to because I would get picked on. I was the girl known in the neighborhood for always fighting. But around my family. I was up and rising star!! lol . I would impersonate family members and was really good at it. My uncle use to say you need to be on someone television! He named me Miss Hollywood!! Read more>>

Jane Goto

My definition of a risk is something that has no guaranteed outcome. That’s really scary and you never know how it’s actually going to go, that’s what makes it a risk. It’s always a risk to follow your dreams, especially enormous ones when it comes to entertainment or entrepreneurship. It was a risk for me to pack up my whole life and move across the country to LA in order to pursue my dreams of modeling and content creation. It’s always a risk to audition and submit myself to a project where I may or may not book the role. It’s a risk posting content on social media not knowing if the content will get the right engagement. Starting my own business, amongst all my others dreams was risky too (that’s a lot to handle at once). Read more>>

Pam Ewell

Anytime I do an art piece, I feel I am taking a risk. It’s putting yourself out there for criticism and judgement. I’m a sensitive soul so that is usually frightening. I am usually rewarded for stepping up by sweet comments or helpful narratives that even help me see my own work from a different perspective. Read more>>

Sonia Daptardar

Risk was never my comfort zone. Even as a child, I thrived on structure and predictability. My world was meticulously organized with color-coded folders, daily calendar updates, and an unwavering commitment to knowing what came next. For me, risk was the opposite of security—a leap into the unknown I wasn’t eager to take. Read more>>

Rae Karim

One of the most rewarding risks I took was deciding to pitch my organization Good Grief Now!™. I was a student in an entrepreneurial cohort and the last part of the class involved a pitch competition. I had attended all the classes, did the work, developed my pitch from 30 words to 100 words to 300 words. I received amazing coaching tips on what to add to the pitch and I received incredible feedback from a trial run BUT I was standing firm on the fact that I wasn’t going to pitch. I felt like because I didn’t have a product, and only had a service that it wouldn’t be enough. Read more>>

Mashallo Samilo

Taking creative path in our country is a risk for there is no structure of creative industry. We don’t have lucrative music labels hence poor artist management. So most of the times, artists work and save a little to pay for studio fees inclusive of musical players. Good artistic works require financial support for example there was this time that i needed money to travel to Mangochi to fine tune my manuscript of Wokoma Nyasa. I had to save and get a loan to execute my project. And marketing of artistic works is also another challenge as it isn’t easy like sellling food stuff. Read more>>

Clare Guintu

The first small risk I took was creating an Instagram account (@clareguintu) to share my poetry and artwork in 2019. All I wanted to do was share my work with others and meet fellow writers in the community. Months later, I met so many talented, supportive, and kind creators who inspired me to express myself in various ways. Read more>>

Brenda Hudson

In September 2024, I lost my job, and I chose to view it as a sign from God to pursue my passion for content creation. While it was undoubtedly challenging, especially with the uncertainties of income and the fear of how I would make ends meet, I found comfort in the scripture Matthew 6:34. That reminder gave me the strength to trust that everything would work out. Though I’m still growing in this journey and haven’t reached major milestones yet, I’m truly enjoying the work I’m doing. It’s been a risk worth taking! Read more>>

Lucas Stolze

I believe one of the biggest risks I took in life was to migrate to another country without having anyone to rely on. I moved from Brazil to the U.S. to pursue a bachelor’s degree in mechanical engineering at Purdue University. After a study abroad program in the U.S. where I spent one year here, I was so fascinated with the country that I decided to move to the U.S. for good and finish my studies. It was a really risky move because I sold everything that I had back home in order to pay for my expenses here until I could land a job and survive on my own means. Read more>>

Jimisha Patel

From the moment I first donned a white coat, medicine was never just a career for me, it was a calling. I spent eight grueling years immersed in training, navigating the labyrinth of medical school, residency, and the relentless pursuit of knowledge, all with one unwavering purpose: to help families and heal children. And for a decade after, I did just that, practicing pediatrics in a traditional setting, following the well-paved path of modern medicine. Read more>>

Jackie A.

On January 6, 2025, I decided to resign from my corporate job, where I had been leading a team of 34 healthcare IT professionals and earning $180,000 a year. Fueled by my experiences with racial discrimination, this choice marked my bold leap away from corporate America, which had been my life for 17 years.

Embracing the unknown, I became an independent travel representative and launched my own travel business; despite having no prior experience in network marketing or the travel industry, I had a mission: build a workplace where my community would not endure racism and help them travel safely and affordably while empowering others to establish their successful travel businesses and build generational wealth. Read more>>

Josette Diaz

Thomas Jefferson is credited with saying “With great risk comes great reward.”

We can apply this to so many situations in life. Risk says one thing to your mind and another to your body. To your mind, it says, be fearless, be brave, you never know unless you try, and so on. To your body, it can instill fear, doubt, and feelings of not good enough. Read more>>

Signul Ez

Risk and chaos have often walked hand in hand with the paths I’ve had no choice but to tread. My first big life risk I’d taken happened when I was twenty. Coming from a family with no connections and limited resources I had no idea what to do after high school. I spent a few of those early years living in nyc trying to find a niche. Everything from door to door salesman to cafe barista. It was horrible, I wasn’t able to hold down any of the jobs I’d applied for. I found some solace once I had come up with the idea to start my own art company called “Faces for Sale”. I’d made a thin 3 door foldable kiosk out of ply wood and once unfolded acted as a mini art display for my works. I had to carry the huge installation everytime I went out to vend, it was exhausting but I still persisted and set up my works illegally in the subways of Nyc on a regular basis. Constantly arguing back and forth with subway law enforcement. Read more>>

Tiffany Lewis

Taking risks has truly shaped my journey. One of the biggest risks I took was resigning from my teaching career in 2020 to go full-time into business. At that point, I had already been running my first business since 2018, but leaving behind a career that I’d spent years building, especially in a field I was passionate about, was a major leap of faith. I knew it would mean letting go of financial security, the comfort of a predictable routine, and the support system I had as an educator. Read more>>

Carissa Tompkins

The biggest risk I have taken is starting my personal training business. I started in July of 2024 but didn’t go full time until November 28th of 2024. I was training at a corporate gym. I was let go due to the new owners terminating training at that location. That pushed me into going all in with my business. If I had never started the process in July, I would have been panicked when they let me go. Instead it was risk worth taking as in the long run I set myself up for a smooth transition. My biggest piece of advice for new business owners is go for that opportunity. As long as it aligns with what your goals are with your business, don’t be afraid to take the step. Read more>>

Ishakeyva Arnaud

One of the biggest risks I’ve ever taken was stepping away from a traditional career path to fully commit to my passion for empowering others through speaking and writing. It was a decision that carried both excitement and uncertainty. I had a steady income and a clear path in front of me, but something in my heart told me there was more something bigger waiting for me to create. The moment I decided to take the leap, I felt a mixture of fear and exhilaration. I didn’t have all the answers or guarantees, but I knew that staying in my comfort zone meant silencing the calling that burned inside me. I began building IB Natasha LLC with nothing more than a vision, my voice, and the determination to make a difference in people’s lives. Read more>>

Neal Wright

Since starting Wave Collector back in 2015 or so, I’ve always thought of myself as an artist, but never a businessperson or marketer. For years I talked about how bad I was at self-promotion, marketing, and business. Finally, at the end of 2023, I decided that I was tired of putting out music in the same old way without getting much traction.

I decided at that point that I could be as good or as bad as I wanted at promotion, marketing, and business. I committed to learning about music marketing and started experimenting with different marketing techniques. It took a little while, but I began to get the hang of it and started getting a lot more listeners. Read more>>

Sandra Coates

The risk was taking a chance to believe that the mindset I had been given to empower women and girls of all sizes, backgrounds and cultures was going to really do something significant. In my background, I struggled so much and for so long with body image, self esteem and confidence in who I was. Being 5’11” mean’t I always stood out and was looked at. battled with food addiction and bouts of disordered eating. (I was a very successful athlete in high school and into the beginning of college. ) Read more>>

Victoria Yampolsky

As an entrepreneur, I take risks all the time, whether it’s launching new programs or products, or changing my company’s direction during COVID.

The first big risk I took was starting my first company in media and entertainment and leaving my lucrative job on Wall Street. I didn’t know much about film or entrepreneurship, but my passion for storytelling and the desire to try outweighed the fear of failing. In the end, I didn’t succeed, but I learned a lot along the way. This experience led me to start the company I have today, The Startup Station. Read more>>

Brooke Aymes

Risk taking is a theme that has occurred throughout my life. When I was younger, I would get into trouble because I was always taking risks. Throughout my adolescent years, I experimented with substance use and that risk raking behavior brought me to my knees in my early adulthood when I was suffering from a heroin addiction. At age 23, I took a risk on myself for a change and entered into recovery from substance use. That was terrifying to let go of substances and to change my entire lifestyle. Read more>>

Michelle Franklin

Starting LRX Lux Rejuvenate was one of the biggest risks I’ve ever taken. I walked away from a six-figure job, dipped into my savings and retirement, and launched my own company—while pregnant with my third child.
At the time, I was working for one of the largest healthcare organizations in the world, managing a large project and collaborating with both divisional and corporate teams. I was working around the clock and thriving in my role, until the moment I told my leadership I was four months pregnant. That’s when everything changed overnight. I found myself cornered by my superiors, with pressure to sign a document that would have been detrimental to both my health and the health of my unborn child. It was a turning point—I made the decision to leave. Read more>>

Vanessa Sanchez

At the end of 2019 I decided to take the leap and jump full time into self employment. This was very scary to do as a single mom with no support or parents to help guide me. However, I did see a lot of opportunity around me for accounting work and tea selling. Having my son pushed me to create the life I want now vs later or never. Little did I know a worldwide pandemic would hit in 2020! Somehow I got busier than ever while also able to slow down and be a present mother. There’s many times I look back and think “how did I get anything done?”. I’ve learned that although I am hard on myself and push myself to the limits and sometimes feel like I’m not doing enough (when I’m quite literally doing the most), it’s that part of me that continues to propel me to grow to new heights. Read more>>

Taylor Hammer & Taylor Ehle

Starting Thistle House was, without a doubt, a leap of faith. At the time, we were still considered young designers—full of ambition but admittedly not experts in the industry or in running a business. What we did have, however, was a clear vision, a deep love for modern floral design, and the willingness to take risks in order to build something truly special. Read more>>

Taciana Mcdaniel

My entire culinary journey has been about taking risk and a leap of faith in the unknown. After high school in Chicago and even during my senior year, I began to get a pull to go into a creative career. I had an interest in fashion and at my high school, food science was my elective. One day, a celebrity private chef came in to talk about culinary arts. I come from a line of great home cooks and food has always brought our family and friends together. Although I wasn’t in the kitchen helping, I know it had an influence upon my interest. When the time for a decision for college came, I expressed my interest in both fashion and culinary, and due to the no traditional view, my parents urged me to go to traditional university. Read more>>

Audie Wood

I taught Sociology at Western Kentucky University for four years as an adjunct professor. Although I was severely underpaid and faced financial struggles, I managed to be comfortable in my situation. I received support from my department head, taught a subject I loved, and had amazing students. However, I realized that love and passion alone do not pay the bills. I kept thinking, “I need to find a way out. I need to find a way to do what I love, support myself, and enjoy life. ” Read more>>

Kaptured By Kyle

Choosing to pursue a career as a photographer represents the most significant risk I take each day. Owning a business entails numerous sacrifices, the most notable being the missed opportunities to attend events and gatherings hosted by family and friends. It is indeed ironic that my profession revolves around preserving memories, yet I often miss the chance to create my own. However, I recognize that this career has afforded me the opportunity to travel the world and provide for my family. Ultimately, I believe the risks I undertake are worthwhile. Read more>>

Beau & Brandy Burridge

We had been living in New York, watching countless YouTube channels about living and traveling on a sailboat fulltime, wondering what it would be like to have that kind of freedom. One night, we found a listing for a 35-foot sailboat online. It was cheap—almost too cheap—but it felt like an opportunity we couldn’t pass up. The catch? We knew nothing about sailing or sailboats. Read more>>

Melanie Luke

Opening a brick & mortar shop was the biggest risk I’ve ever taken. Financing it using retirement funds via a C-Corp was the second biggest risk. I was 43 years old and was presented with the opportunity to buy a building and open a small business. There are a lot of ways to finance things and borrowing a large sum of money with an interest rate on top of that was the least appealing way to me at that time. I put in the research, wrote the business plan, received a neighborhood grant for facade improvement, and opened The Flying Squirrel in 2014. We filled a void in the community by providing a space and service for children, families, and fans of old-timey ice cream and toy shoppes. Read more>>

Christy Howard

I never imagined leaving the security of a high-paying corporate career to embark on an uncertain journey, guided only by faith and a calling I couldn’t ignore. For decades, I navigated the structured corporate world in different cities and industries, excelling in operations, strategy, and business development. But something was missing; I felt a persistent nudge—one that grew louder with time. It was a whisper from God, urging me to use my experiences, lessons, and skills in a different way—to help others who were struggling to see themselves as valuable solutions in the job market. Read more>>

Kaylee Meyer

Some people ease into adulthood—I did what every parent dreads. I dropped out of art school, not to “find myself,” but because I couldn’t shake the feeling that life was happening beyond the classroom. What a waste, I thought, to be so alive, so acutely aware of the world, only to sit in a windowless room, learning about the environment without ever seeing it. Surprisingly, my grand act of rebellion didn’t involve moving to a cabin in the woods (though I did consider it). Instead, I set out to build something of my own—something real, messy, and entirely mine. Read more>>