The chapters in our stories are often marked by wins and losses. Getting a new job, getting fired. Getting a life-threatening medical diagnosis, beating it and getting a clean bill of health. Too often, due to a societal expectation of modesty and humility we are discouraged from talking about the risks we’ve taken that led to those ups and downs – because often those risks draw attention to how we are responsible for the outcomes – positive or negative. But those risks matter. Those stories matter. We asked some brilliant entrepreneurs, artists, creatives, and leaders to tell us those stories – the stories of the risks they’ve taken, and we’ve shared them with you below.

Edwin Portillo

Taking a risk is pretty much the story of my life. I was born in America, moved back to El Salvador at age 5, and then had a huge decision to make at 18… do I stay in a country that I know the language, the culture, that I am familiar with? Or do I take a risk and leave it all behind to pursue a completely different life? Read more>>

Kiara Davis

One of the greatest steps of faith I’ve ever taken is the one I’m currently walking in. I’m choosing to fully trust God (Jesus) with every gift He’s placed within me as I return to the modeling industry after taking a step back to reflect, grow, and realign. During this time, I realized that I had been holding myself back—doubting the very dreams and ideas that God had placed on my heart. Read more>>

Patrice McBeath

Stepping out and starting my private practice was a huge risk for me. I was raised to believe that success had a blueprint: go to school, get a good job with benefits, stay loyal, and retire with a pension. That was the model. Stability was the goal. Safety was success. Entrepreneurship? That wasn’t something we were taught—it was something other people did. Not us. Not me. Read more>>

Tiia Potry

One of the biggest risk I’ve taken was leaving behind a stable career in the marketing industry to follow my soul calling and create Inner Wild, a wellness brand offering retreats and holistic wellness. Read more>>

Sue Krizman

Risk taking is in my DNA. I have always been described as a disrupter: “Quietly disrupting the status quo as I go.” And, yes, sometimes I’m quietly the silent instigator. Well, to be honest, sometimes I’m bold and loud. I have also been described as seeing things others cannot see. (That qualifies as a superpower, I’m certain.) Read more>>

Khara Hindi

In 2020, when the pandemic hit and the world started shutting down, my business as a natural products broker took a hit like so many others. Stores were limiting reps, demos were canceled, and for the first time in a long while, things felt uncertain. Read more>>

Mariana Morais

At just 15 years old, while most of my friends were figuring out high school, I took a leap and chose something completely different—I decided to become a professional makeup artist. It felt risky for so many reasons. I was young, inexperienced, and stepping into an industry full of seasoned professionals. But I had a deep love for makeup. Read more>>

Amy Joob

In the summer of 2023, we made a move across the country from Chicago, Illinois to Naples, Florida. We sold and donated 2/3 of our belongings, our guinea pigs, and our home and re-located on the Florida Gulf Coast. We took the risk of a lifetime as both me and my husband are entrepreneurs and own our own businesses. We took the plunge with our high school son and dog and sent our daughter off to college in Colorado. Initially, it was a challenging adjustment but we are thankful to all be in states and places with beautiful views and surroundings and a fresh start after the pandemic, covid, lockdowns, and limited opportunities. Read more>>

Cody Brooks

One of the biggest risks I’ve taken was betting on myself—turning a tough setback into the start of something entirely new.

I started martial arts as a kid, and it quickly became more than just a hobby—it was a way of life. As I grew older, I dove deep into multiple styles, eventually becoming an instructor. Alongside that, I worked in the medical field, where I gained a strong foundation in health, wellness, and how the body works. Those two worlds—martial arts and healthcare—shaped how I saw strength, discipline, and helping others. Read more>>

Jeffrie Favianny

The biggest risk I’ve taken was leaving the corporate world to pursue life as a full-time creative.
As the eldest of four and an immigrant, I carried a heavy, self-imposed pressure to “make it” in the most traditional sense—by going to a top university and landing a prestigious job. And I did. I went to the #1 public university in the country, UC Berkeley, and then joined what was, at the time, the #1 tech company in the world: Google.  Read more>>

Thea Bedell

Taking a leap into the unknown by opening my own therapeutic mental health clinic has been both exhilarating and daunting. It required me to confront my fears, challenge the status quo, and embrace the uncertainties that come with starting something new. But ultimately, the desire to cultivate a sanctuary where everyone feels safe and comfortable has been my guiding light throughout this journey. Read more>>

Tasleem Lee

On March 29, 2025 I took a risk and decided that I was going to host a fashion and art show. I collaborated with an Artist named Carlos Marquez and we held our first showcase together at his art studio where he does his work. I was pressed for time but I was able to create five looks for the show. This was a big risk for me but I realize that without a risk there is no reward. Read more>>

Jose [Tony] Haber

One risk I’ve taken that’s had a significant impact on my life is launching my business, which specializes in reviving classic Cuban brands and creating high-quality beverages. Growing up Cuban-American, I was deeply influenced by my family’s heritage and the rich culture of Cuba. I saw an opportunity to share this culture with the world, but it required taking a leap of faith and investing time, effort, and resources into building a business from the ground up. Read more>>

Alyson Phillips

“Do something that scares you every day.” – Eleanor Roosevelt. Enough discomfort can cause us to take a “big” risk. Through risk taking, I didn’t find comfort, but I did find challenges that I’m suited to face. My 25 year corporate journey began as a female engineer and wove through many aspects of product commercialization and global business leadership. The consistent thread was my drive to implement change for the better. As uncertainty increased, many people grasped for more control. The unfortunate effect was reduced creativity. That situation was diminishing the value of my unique skill set. It felt like walls were closing in on me, limiting my contributions, my freedom and ultimately my happiness.  Read more>>

Jordan Rae Herron

Taking a risk in the “holy wood” machine whose gears are greased by silicon, plastic, and the oil of sweaty men carrying lots of skeletons is knowing who you are as a craftsman, as an artist, as a leader; sticking to your morals. Knowing when to speak up, knowing when to walk away, staying true to cinema is taking a risk these days. Read more>>

Ben Pilon

If we first zoom out, starting Minimal Market as an idea was a risk (as most businesses are). Our particular business model is placing a big bet that people are ready to significantly shift how they shop and live toward a more sustainable and healthy focus. There seems to be growing awareness to the fact that not every food, household, and personal/health care product is created equal. In fact, many would argue that perhaps these products are more problematic than their marketing would suggest. However, there are significant hurdles to changing the status quo. Read more>>

Nancy Baron

Sharing new work with the public always feels like a risk—though never quite as intense as it did when I first started showing. Artists are often their own toughest critics, so gathering the courage to present work to curators, editors, publishers, or collectors can be intimidating. Read more>>

Michael O’Brien

For as long as I can remember, I’ve carried this dream in my heart—to become a model. Not just for the glamour, but for the feeling of being seen, accepted, celebrated for who I am. As a kid, I’d retreat into my bedroom, close the door, and get lost in America’s Next Top Model. It wasn’t just a show to me—it was a fantasy, a window into a world I longed to be part of. I’d watch those photo shoots and runway challenges and quietly hope that one day, it could be me up there. But when I looked in the mirror, I didn’t see anyone who fit that mold. Read more>>

Vin

Saying yes to the endeavor of audiobook narration and voiceover was like frosting on the cake of becoming Vin.
But before even that first bite, came a lot of struggles, shedding of old skin, and fear

In the summer of 2023, I quit my job/career (of 15 years) to pursue something new. I wasn’t being challenged where I was and there was certainly no room for creativity or growth, Plus I was extremely burned out. For anyone that values financial stability, they would’ve looked at my bank account, looked at my letter of resignation… and imploded. But I knew I was worth more and I knew I deserved to give myself a shot. Read more>>

Anisa Turner

In the music industry we take risk everyday. As an artist manager the risk I take are a little different. I’ve once risked it all to make sure we did everything that needed to be done so that we could meet a deadline. Risking it all in this game could be missing meals, missing fun, missing family, and sometimes missing opportunities and money. But in the end it’s all worth it. It’s all part of the game. Read more>>

Chrissy

A defining moment of risk-taking that paid off came in 2018, when we began working with Dakota County Juvenile Services, supporting youth experiencing complex trauma rooted in systemic racism, poverty, and a lack of access to mental health care. While we had years of experience using mind-body practices to support people in crisis—both children and adults—we weren’t sure how these tools would translate within a juvenile corrections setting. Read more>>

Miki Wright

It may sound crazy, but I took my Cosmetology Licensing Exam in Texas on Tuesday, then packed up my car on Wednesday to drive half way across the country to start my career as a Hairstylist in Washington, DC. Of course, I didn’t have any family or friends to start build a clientele, so I worked temporary Admin jobs while I took my time to find just the right place to start my career. Read more>>

John ‘Lex’ Robinson

For me, risk isn’t about recklessness — it’s about alignment. The most pivotal risks I’ve taken were about standing in truth, even when it meant standing alone. There are two moments in my journey where that became crystal clear. Read more>>

Tracee Barlow

When I launched my hat line, “In His Image,” it was more than just starting a brand—it was stepping into a prophetic vision without a clear map. It was a huge risk for me, not because I didn’t believe in the message, but because I didn’t know who else would. I questioned whether people would see the heart behind it, hear the message through it, or even feel called to wear something so bold, so rooted in faith, and so personal. Read more>>

Deshanay Brinkley

One of the biggest risks I’ve ever taken was leaving the security of my 9-to-5 job to fully commit to building my own business.
I had been working as a teacher—a role I didn’t take lightly, especially because I have a heart for children and believe in the power of guidance and impact. But over time, I found myself emotionally and spiritually drained. On paper, everything seemed fine: a steady paycheck, a respectable role, and a clear daily routine. But internally, there was a war in my heart. I felt unfulfilled and disconnected from the purpose I knew God had placed in me. Read more>>

Vaishali Joshi

Header: At 22, five years into living in Canada, I was ill-equipped to take this risk. But it paid forward in droves! At just 17 years old, I boarded a plane alone from Kenya to Canada. My parents took a huge risk by sending me half-way around the world for a clearly defined – “better future”. All their hard work into my development as a student, dancer and daughter now rested on my somewhat little shoulders to carry forward and make good of. I was to become a doctor.  Read more>>

Sydney Rumsey

In 2023, already halfway through my junior year of college, I changed my major from film production to fashion-business management, which has been the most life-changing decision I’ve ever made. But attending school for more than 4 years was not an option for me. So I was tasked with the challenge of catching up on 70 credits to complete my new degree, with only 3 semesters left, potentially risking not receiving my degree at all. While I admired the art of filmmaking, and still do, I knew I wanted to start a business as a fashion stylist. I constantly found myself sitting in film classes imagining a different future for myself, so I decided it was now or never. Read more>>

Matt Razook

Starting my hair color brand was, without question, the biggest risk I’ve ever taken. I had no investors, no financial cushion – honestly, not even a savings account. Just a vision, a gut feeling, and a pretty loud refusal to keep waiting for ‘the right time.’ I was already a working hairstylist with years in the industry, and I kept seeing the same gaps: lack of transparency, inconsistent product quality, and a general disregard for the artist’s experience. So I decided to stop waiting for someone else to fix it and build what I wanted to see. I mixed my first batches at home, filled every pouch by hand, and launched with zero marketing budget – just word of mouth, social media, and sheer stubborn belief. Read more>>

Adam Martin

Being a music producer and artist there are many risks with creating and collaborating with other creatives. You run the risk of someone stealing your intellectual property, not getting paid, personal drama, the list goes on. One risk I wanted to share was the decision to start sharing music with the world at the age of 12. Not just on a local small town scale but the WORLD. I remember getting a few listens in the beginning, and then my sophomore year of high school, I sold my first beat. I was lit at the thought of it but also a humbling moment. I thought wow, if I sold one, whats stopping me from selling another. 100k streams later, I became my own artist and added my nephew as an executive producer to Streetz Productions. Read more>>

Brianna Lyons-Willis

In 2023, I took one of the biggest risks of my life—I founded The Niche Mentorship Program and its sister initiative, The Niche Social Club. It wasn’t just about launching an organization—it was about filling a void I had personally experienced growing up without a dedicated mentor, and building the kind of support system I wished I’d had. Read more>>

Richard Trebus

I started my career working for a non-profit organization whose mission is to support persons with intellectual and developmental disabilities (IDD) through community homes, work enrichment, and social connections. I loved the people and the work environment! It was challenging, but deeply transformative as well. Working for a non-profit is hard work. You tend to wear many hats and get stretched physically and emotionally. But it is also a rich personal and professional skill building setting. Read more>>

Stuart Anthony

You’re right—it is a leap. But Lakeside Valley Vineyards was never just about launching a business. It was about following a vision that felt rooted in the land itself. We stood on that hillside, looking out over the lake and the mountains beyond, and knew this was a place meant to be shared. A place that could offer something lasting. Read more>>