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.

Katiebeth Brandt

The air crackled with a mix of excitement and terror. August 1st, 2024, a date that would forever alter the course of our lives. It began with a phone call, an unexpected opportunity to purchase a 40-kennel facility, complete with a grooming salon and a sprawling half-acre training field on the other side of town.

For years, our dog training business had been a labor of love, conducted from our home and within the familiar confines of our community. It was a comfortable existence, a steady stream of furry clients and the satisfaction of witnessing dogs flourish. Yet, a nagging desire for something more, something grander, had always lurked beneath the surface. This unexpected offer felt like fate knocking, a chance to transform our passion into a tangible, thriving entity. Read more>>

Traci Keen

One of the biggest risks I’ve taken was stepping into the CEO role of a struggling startup in 2022, just months after joining the company. The organization faced daunting challenges—operational inefficiencies, legal hurdles, and leadership gaps. The situation was uncertain, and conventional wisdom might have said to walk away, being a CEO is both personally and professionally filled with risk. But I saw an opportunity to solve significant problems using my unique toolbox: a diverse blend of financial acumen, design thinking, and the resilience I’ve built over years of navigating complex situations. Read more>>

Varuni Palacios

All my life I’ve taken risks. I’m not someone who can sit for long on an idea. I have one rule, sleep on it. And then, if it sticks with me, I pursuit it, or it eats me alive. Some of my favorite personal risks include pivoting into entrepreneurship after spending 15 years in corporate America; moving across the country from NYC to LA to build a family; and being open and vulnerable with my emotions since I was a child. My mother always called me rebel. To everyone else, it looked like I was always taking risks, but to me, I was really just following my own gut instincts. Read more>>

Charity Harris

Starting my company was one of the biggest risks I’ve ever taken. As a disabled woman who had never been able to find a “regular” job due to disability bias, the idea of launching a business was both exhilarating and terrifying. I had no financial safety net, no investors, and no guarantees of success. Yet, I felt a deep conviction that I was meant to do this—not just for myself, but for others like me and the children I hoped to inspire through my stories. Read more>>

Emily Walsh

I had the opportunity to study at the Yale School of Music on a full scholarship when I was only 16 years old. I came to the US alone as we didn’t have the means for my mother to join, and I didn’t see my family for two years. In retrospect, the culture shock and being alone in a foreign country at such a young age was a big risk, but it led me to build my career and life here – including meeting my wonderful husband. Read more>>

Kweem

One of the most defining risks I took was in deciding to step away from my comfort zone and start my own business. For years, I worked in environments where I was often the only Black person in the room, navigating systemic barriers to my success. I had big dreams and ideas, but I kept telling myself I should follow a more traditional route—something “safe” and “easy.” I even tried to fit into existing structures, working for others, in hopes of finding stability. But deep down, I knew that wasn’t where I was supposed to be. Read more>>

Jessica Siegfried

In 2017, I took a leap of faith and started Thrive Creative Design. For over 17 years, I honed my skills in the advertising industry, taking on diverse roles across various agencies and steadily climbing the ranks. My journey began in print, working for a monthly lifestyle magazine while still in college. From there, I transitioned to a traditional agency and eventually expanded my expertise at a digital agency. Read more>>

Milkin’ It

Our podcast is not big nor do we make money from it but one risk we take is making investments into the podcast where we won’t see a return anytime soon. We are believing that someday it will happen but its a risk we are willing to take. We started with the equipment that Arturo has from his video production company Apollo Studios. From there we slowly started adding equipment and extra items as we saw needed. From using a 360 camera and 4 microphones to have lighting, a camera and an audio board. We are having fun with this endeavor and honestly that is all that matters. Read more>>

Petra Schott

The entire painting process for me is an act of continuous risk-taking, an exploration that demands both courage and vulnerability. From the moment I begin a painting, I enter into a dialogue with the canvas, where unexpected moments of beauty often emerge. These fragments—whether a stroke, a texture, or a delicate interplay of color—can feel like treasures, holding the promise of something complete. Yet, paradoxically, these are often the very elements I must sacrifice to move forward. Overpainting these beloved parts is not an easy decision; it feels like an act of destruction, but it is necessary to open the next door. Read more>>

Jasmine Garner

Entrepreneurs tend to be natural risk-takers, and I’ve never been afraid to take a risk when I believe I can achieve something. Those who play it safe don’t believe miracles or impossible situations can happen to them. I recall the time I took a risk to jump out into the modeling and acting world. Previously I had given up on the dream because I thought I couldn’t be in this industry as a Christian. Believe it or not, God proved me wrong about that. Read more>>

Anthony Zuber

So far in my life, I have taken many risks. Some have paid off, while others have taught me invaluable lessons. One of the more recent risks I took was creating Point Electric LLC. Before this, I ran a subcontracting business for three years. That was my first business, but ultimately, it didn’t work out, leaving me with $100,000 in business debt. I returned to work as a W-2 employee in a management position to pay off the debt, which took me one and a half years. That period was incredibly stressful. Read more>>

Julian Garcia

One of the biggest risks I’ve ever taken in my life was quitting a job because I had to chase my dreams. At the time, I had no money, I was heavily in debt, and I was entering an incredibly competitive field where no one knew me, and I didn’t have much of a portfolio to prove my abilities. It was a reckless decision, but I had reached a breaking point—I was tired of not doing what I truly wanted. Read more>>

Matteo Mosterts

People often talk about risk like it’s this big, dramatic thing, but for me, most of the so-called “risks” I’ve taken—moving to a new continent, investing in myself, or diving headfirst into overly ambitious projects—never really felt like risks. They just felt like the next steps on the path I was already on.

The hardest part of being an artist isn’t the leap itself; it’s putting your faith in something as abstract as your own talent. There’s no manual or test to tell you, “Yep, you’ve got what it takes.” You just have to trust in the work you’re doing and take that leap, knowing full well that a lot of people who try don’t get there. Read more>>

Lesley S. King

For nearly twenty-five years I made a living as a travel writer. I loved the job. It took me to a cooking school in Provence, France and to an ecolodge in Costa Rica, among many other posh and beautiful places. However, my body grew tired from all the travel and I had a deep desire to write about the inner world rather than outer places. Meanwhile, the whole travel-writing world was shifting. Because of the internet, magazines and guidebooks, from which I made my living, were closing down. I knew I had to pivot. Read more>>

Yelena Reese

I believe one of the biggest risks we take is choosing to pave our own path, especially when it “doesn’t make sense” in the context of what you’ve always known, what you found safety in, and most importantly – what brought you validation and success. This is my story – walking away from an established freelancing career that already gave me reasonable freedom, good money, comfort, ease and validation. On the outside it seemed like I found the path that offered me everything I had asked for. And it did. Because up to that point what I was asking for was safety, certainty, stability. Which all serve a beautiful purpose. But as we grow and evolve, our asks become something bigger. Read more>>

Dr. Cameka Smith

As an entrepreneur, you are always taking a risk. For myself, when I
launched The BOSS Network fifteen years ago, I had a vision to support women
of color along their entrepreneurial journey. At the time, I was beginning my initial
foray into entrepreneurship after it became evident that my own career in
education was coming to a close. While that experience was challenging, I
learned to use it as leverage for what was next for me. I became passionate
about supporting other Black women who needed the education, information and
resources to navigate and lead their businesses. Read more>>

Ashton Bingham

One of the biggest risks we’ve ever taken was traveling to India to film The Robocall, a documentary series that exposed the inner workings of international scam call centers. It was a risk that came with significant safety concerns, but one that we knew could make a real difference in the fight against global fraud. Read more>>

Yiwen Qian

“What’s wrong with your back?” These words, spoken by my mother, came after a normal dance practice. I had just showered and was drying my hair when my mother, who was standing behind me, saw something unusual. She swept away my hair to examine my back, which looked unbalanced. I had experienced pain while dancing before, but I thought it was just regular wear and tear from such an arduous activity. However, after a visit to the hospital, I was diagnosed with scoliosis and was recommended for immediate surgery. The thought of lying on an operating table while surgeons inserted steel rods into my spine terrified me, as it would likely mean the end of my dance career. Read more>>

Paige Carter

My first major risk was transitioning from a 9-5 job to becoming a freelance makeup artist. At the time, I had finally landed my dream job at MAC Cosmetics, a brand I had admired for years. MAC was the top name in the makeup industry, and being a MAC artist was a badge of honor. I had been trying to get in since 2012, and after multiple attempts, I was hired in 2015. Initially brought on as a freelancer, I was offered a permanent position within a week. Read more>>

Sydney Wang

When I first arrived at UCLA in September 2021 to begin my undergraduate studies in music composition, never in my wildest dreams did I imagine that just over three years later, I would be preparing to travel to Wichita as répétiteur in a production of Don Giovanni.

In retrospect, many stars in my life had been gradually aligning over the years for this moment to happen. I’d studied piano since I was four, and had played in chamber groups for over a decade. At UCLA, I quickly discovered an interest in new and contemporary music, and became a frequent performer of new works by UCLA composers. Simultaneously, I’d found great enjoyment in accompanying my performance major friends, and began doing it whenever I had the chance. I found particular joy in accompanying singers. Read more>>

Kristen Deandrade

One of the biggest risks I’ve taken was creating the Little Legs Big Heart Foundation. Growing up, I wasn’t part of the Little People of America (LPA) or any community centered around skeletal dysplasia. The reason was painfully clear: LPA frowned upon limb lengthening, an option my parents made available to me when I was young. When I ultimately chose to undergo the procedures, I faced chastisement from adult members of the dwarfism community, who told me, “Shame on you for trying to undo diversity.”Read more>>

Carla Paola Gonzalez Lillo

Have you ever experienced that moment in your life when you felt you had reached the pinnacle of your career, achieved steady progress, and found yourself in a financially stable and organized place? Everything seemed to be on track, right?

Now, imagine giving all of that up—right at that very moment—in pursuit of a dream you believe to be greater, yet with no guarantees, no certainties, just a leap of faith. It’s like diving into a pool without knowing if there’s any water. Read more>>

Ares Kennedy Alternative R&b Singer-songwriter

The biggest risk I’ve ever taken was choosing music over the “safe” path I was already on—a career in political communications. For someone like me—a Black, queer man from a tough background—that decision wasn’t just about changing jobs. It was about taking control of my life, healing from my past, and betting on myself in a world that often tells people like me to stay in their place. I grew up in chaos. My parents were in the picture up until I was 13—one was locked up in federal prison, and the other just gave up on being a parent. That left me and my 14 siblings to fend for ourselves. By the time I was 15, my siblings were all in foster care, aside from the ones who were grown. Luckily, my aunt took me and my sister in. Read more>>

Mina

Last year i was invited to be apart of our city’s “Winedown Wednesday”, an event held the third Wednesday of every month. This event showcases some of the amazing talent in our city, and gives them the space and opportunity to shine bright. Prior to this event, i have never been apart of any arts event in town. Nervous was an understatement, and i found myself going back and forth on whether i was actually going to join. I was comfortable with what i was doing at the times, mostly commissions and original pieces when i had the time, but I wanted to grow more as an artist. I do have a full-time job which unfortunately, takes up a lot of my time and energy. But my dream is to be a full time Artist and i knew i would have to push myself past what i know. Read more>>

Jamelle Sanders

Honestly, the biggest risk I ever decided to take was leaping into the world of entrepreneurship. Some people were really excited for me and wished me the best. However, I quickly learned that I had many critics and skeptics who did not believe in me or my vision for my business. In fact, I will never forget when I started to share the news about the start of the business and the launch fo the website many years ago. While some people were really excited and immediately rushed to buy my services, others immediately started to share with me all the reasons why my business would not work. I was called too ambitious, a dreamer and some made it clear that they did not believe that I would succeed. In those early days, I will never forget hearing from someone that I needed to stop trying to be big. Read more>>

Tyshone Peterson

Growing up in a small country town, I always had big dreams of sharing my art with people. My environment was pretty dysfunctional, and creativity, art and music became my outlet, my first love, and my therapy. It was the one thing that made sense to me and eventually turned into my profession. Despite my passion, I always lived in fear and preferred to play things safe. Read more>>

Bogdan & Nicole Ionescu

Starting a business is a huge risk in and of itself, regardless of the circumstances. So, me deciding to retire from the Army and Nicole choosing not to go back to work as a scientist were even bigger risks. We were both doing very well in our respective careers, but our priorities changed after having kids. Now, we’re unemployed, raising six and four-year-old sons, while trying to grow a business. It sounds scary when I say it that way, but that’s the reality. Had we both continued climbing the ladder in our careers, we would have only become busier and busier. Just grinding, you know? For me, that would have meant significantly more time spent away from my family. Read more>>

Robyn Savage

I was so ready to go all in. There I was, finally out on my own, building my dream. I had a thriving wedding planning business that was fully booked and in high demand. The clients were there, the success was flowing, and everything was growing—but something was still off. Two years in, I sold it all and started again.

This time, I launched a coaching business to help new entrepreneurs turn their big ideas into sustainable, profitable realities. I teamed up with my best friend, who also happened to be my business partner, and together we went full throttle. We built a vibrant community, launched a podcast, ran global retreats, and worked with hundreds of clients worldwide. Read more>>

Ryan Saroli

The biggest risk I took was launching Flygreen in 2023, entering a competitive private aviation market with a new, tech-driven model. We faced established competitors and an uncertain post-pandemic environment. Our idea was to offer flexibility with short-notice flights and no upfront fees, challenging the traditional private jet model. We built a tech platform that streamlined aircraft sourcing, allowing clients to book flights in just a few hours. Despite the uncertainty, we took the plunge, focusing on innovation and customer experience. Read more>>

Sheri Rathburn

Nineteen years ago I took a huge risk and it began with a dream.

In 2006 I was in the midst of a personal storm where every level of my very existence was being challenged, shifted and shaken all at once. My marriage of 20 years was ending, I was running my thriving interior design business and raising my two very young sons all while in deep self healing and self discovery on every level. Read more>>

Mark Pryor

The biggest risk I’ve ever taken was giving God a chance. I know probably not the answer you were expecting. I’m sure you were thinking the times I dipped into cryptos, NFTS, GameStop/amc (shoutout to those who remember that) or even sports betting. However truly my biggest risk was taken a chance on God. Why? Well let me explain a bit about myself. Prepare yourself this is about to get deep. I grew up in a non religious household, but my parents wanting a better education for me sent me to a private catholic school. The way they pushed religion onto us just didn’t sit well with me. I was so rebellious that I would’ve believed that pigs could fly before I believed God existed.  Read more>>

Ayeesha Barnes

The biggest risk one can ever take is betting on themselves when everyone around them may have doubts. Others may not understand your vision at the moment but it is not for them to see always believe in yourself and your vision and just go for it ! I can tend to be a chronic overthinker and I’ve learned along the years that does nothing but hold me back from what I will inevitably do anyways! Go for it the worst that may happen is you don’t succeed but all that means is you know what not to do the next time because giving up is never an option. Read more>>

Taking a risk means having Faith in an outcome that is not immediately visible. As an entrepreneur, I believe taking risk is essential; if you don’t push yourself to take risk, you will never discover the extent of your potential. Limiting beliefs serve as the root to all problems. When I embarked on my entrepreneurial journey at the age of 13, it was inherently a risk. Although I did not fully understand what I was getting myself into, I recognized that it brought me joy. All I needed was to have Faith as small as a mustard seed to initiate that first step, which ultimately contributes to my success today. Read more>>

Lexie Glisson

Risk is a word that can evoke fear or excitement, sometimes both. For me, taking a risk meant stepping away from a life I had spent years building and dreaming about, all to follow a calling I never expected. It was a leap into the unknown—one fueled by injuries, self-discovery, and a deep desire to help others connect with themselves and the natural world. Read more>>