You’re working hard, things are going well, piece by piece you’ve built a life you are proud of, you’ve overcome obstacles and challenges, beat the odds and then you find yourself at the center of an unexpected dilemma – do you risk it all to keep growing? What if growing means leaving the job you worked so hard to get or the industry you worked so hard to break into? How we approach risk often has a huge bearing on our journey and so we’ve asked some of the brightest folks we know to share stories of risks they’ve taken.

Quintin Gerard W.

As a creative, one would imagine that the journey to success would come with challenges you must overcome and decisions you will have to make that may or may not suit your needs at the time. For me, one of the biggest risks in my life I took was dropping out of college, packing up everything I owned and moving to Los Angeles, CA to pursue my dreams of a career in the music business. I had just turned 22 yrs old and thought I was ready for the challenges that I would face attempting to survive in a place new and foreign place where I had very little support. Nonetheless, when you have a calling or let’s say – burning passion that drives you, none of these trivial ideologies affect how you think and perceive your life and ability to achieve your goals. Read more>>

Erinn Weenink

One of the biggest risks I’ve taken in my life was deciding to leave my nursing career behind to pursue photography full-time. It wasn’t a decision I made lightly, and it came after a lot of soul-searching, reflection, and personal challenges. The backstory starts during my time working in the Pediatric ICU. It was a high-stakes, emotionally charged environment, and while I was passionate about helping children and families, the mental and emotional toll of the job began to weigh on me heavily. I was also a mom to young children myself, and the experiences I had at work made me acutely aware of how fleeting and precious life is. On top of that, the pandemic exacerbated the sense of burnout I was already feeling, and I started questioning if this was the path I truly wanted to stay on for the rest of my life. Read more>>

Madison Celt

The idea for my business started with a chance encounter. My fiancé took our dogs to the park and met someone who owned salons. That conversation sparked curiosity, and not long after, he found a listing for a salon for sale—Aviles Hair Studio and Spa. At first, I was against it but the moment I stepped into that salon, I loved it and thought it was so beautiful. Walking through those doors felt like everything was falling into place. Read more>>

Chef D Gooch

Taking the leap to become a chef has been one of the most challenging yet rewarding choices of my life. Embracing my true calling required a strong faith in God as I ventured into unfamiliar territory, competing against talented chefs. Despite feeling called to this purpose, I worried that I was starting too late. Although I had known for years that my passion was cooking, fully committing to it felt daunting. Read more>>

Jordyn Lassaint

One of the biggest risks I’ve ever taken was moving from Houston to Atlanta with only $4,000 in my savings. At the time, I was at a crossroads in my life, feeling that I needed to make a bold move to create the life I envisioned for myself and my children. The decision didn’t come easily—it meant sacrificing time away from my kids, which was the hardest part. However, I knew in my heart that the opportunities I could create for us by stepping outside of my comfort zone were worth the temporary distance. Read more>>

Nicholas Soto

A few years ago, I found myself at a crossroads, juggling two parts of my life that felt incomplete. On one hand, I had a steady job working for an influencer-based automobile marketing company. It was an incredible opportunity, full of perks, connections, and excitement. From the outside, it seemed like a dream job. But deep down, something was missing. My passion—music—was always calling. I thought I might be able to silence it by switching to another promising career, so I left the automobile company for a tech job. Yet again, I found myself unfulfilled. I realized that no matter where I went, my heart wouldn’t let me ignore my dreams: music and flying. Read more>>

Amanda Ramirez

One of the most significant risks I’ve taken was deciding to pursue filmmaking full-time. While I had a stable foundation in television and theater, shifting to independent content creation felt like stepping into the unknown. The decision wasn’t just about changing mediums but about telling stories that mattered deeply to me, even if they didn’t fit conventional molds. Read more>>

Dad Is Fire

The biggest risk I ever took, didn’t feel like a risk. When I was 21 I walked into a real estate agent’s office and said “I am buying a house today, who wants to sell it to me”. I had $800. I had researched and studied real estate for several years. I spent a lot of time at the library (this was the 1990s) learning how I could retire early. None of the agents wanted to talk to me. I was 21, looked 16, and dressed homeless. They had some old man named Elmer assigned to me. A few hours later I made an offer on a house. It was accepted. I then rented the house out until my lease was up. Read more>>

Monica Gross

The biggest risk I’ve taken is trying stand-up comedy. I had no idea where to start – I just googled ‘open mics near me’ and started going by myself and performing.This entire journey has been a risk because stand-up comedy is something I feel so passionately about but it is also so uncertain and ambiguous. There’s no set career path, you can never know if your performance is going to go well, you never know what gigs are going to come your way. Going from something as stable and safe as accounting to stand-up comedy is a risk but I know I’m on the right path, because when I found stand-up comedy, it felt as though a part of me that was always missing was finally found. Read more>>

Allison Ernst

For myself, entrepreneurship wasn’t a sudden leap – it was a carefully charted journey. The dream of owning my own business first took hold in 2006, but rather than rushing in unprepared, I chose to build a solid foundation as I didn’t yet have the means or assets to climb that mountain. Over two decades in retail, including groundbreaking roles like becoming The Journeys Group’s first female loss prevention manager, each position added crucial experience. It wasn’t until after a hard look at my life and career that the timing finally felt right. With support from friends and fellow small business owners, I took the risk to launch Prevail Boutique in 2021, which evolved into today’s Stacked by Prevail – proving that sometimes the longest roads lead to the best destinations. Read more>>

Julia D’amelio

It was 2023. I was half way through my Doctorate in Clinical Nutrition program when I found myself unfulfilled, stuck, and stagnant. I was a full time student balancing night classes with clinical hours, while also working for my family business nearly full time in an office job. At this point I had been in college for nine and a half years, growing tired of the student role, and feeling sorry for myself that I worked behind the desk of a funeral home, and not in an well renowned nutrition clinic. I thought to myself, “How many days am I going to let pass before finding the courage to change my life?” Read more>>

Kate Ray

Reflecting on my journey, I realized that pursuing my dreams was a significant risk, but one I was willing to take. From a young age, I felt a deep calling to help animals, regardless of their species, and I’ve always sought opportunities to do so—whether in a zoo, veterinary practice, or emergency medicine. While I found fulfillment in my job, I felt a lingering emptiness; I ached to make a greater impact on the community around me. My lifelong dream of establishing an animal rescue often felt out of reach, complicated by uncertainty about where to begin. Read more>>

Macy Lane

For years, I have dreamed of being a writer. First, I envisioned myself working for a fashion magazine in New York City. I started college as a journalism major, but I never felt confident or supported, so I switched my field of study to education. I spent 20 plus years in the classroom, with a big gap in the middle while I stayed home raising my three boys, and all the while, I dreamed of writing. Read more>>

Marie P. Anderson

When I called my father, a retired rocket scientist, to share my plan to write a book on how to become a model, he scoffed, “Who’s going to read what you have to say?” From his perspective, I was still the kid who struggled in school, rarely got A’s, acted out in class, and couldn’t sit still. (Only later did I learn I had dyslexia, ADHD, PTSD, and anxiety from early childhood trauma.) Read more>>

Glensky Inagas

At 20, I made a decision that changed everything. I had a business that was pulling in solid cash flow—six figures annually—working with something as simple as dog walking. Life was comfortable, predictable, and profitable. But I knew that comfort wasn’t where I wanted to stay. I didn’t want to be the guy who built a business, cashed in, and stayed in one lane for life. I wanted more. Read more>>

Charlie Walkrich

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>>

Alena Butkevica

As I mentioned earlier, I am a well-established oromaxillofacial surgeon with numerous awards and have performed over 15,000 surgeries. I have been an international lecturer and run a private practice with a waiting list of six to eight months for the past 30 years. Life was excellent. However, I faced a challenge: I was aging, and nothing seemed to work for me. The only way I could maintain a youthful appearance—something that patients appreciate and trust in a doctor in my field—was through surgery. I have always been reluctant to resort to injections or surgery for cosmetic reasons because I am fully aware of their short- and long-term side effects, which the world is beginning to acknowledge. On social media platforms like Instagram, many renowned plastic surgeons my age showcase impressive immediate results on women, yet you will hardly see any surgeons who have undergone surgery themselves; most prefer to age naturally. Read more>>

Melissa Rathbun

The risk I took in creating NewWard Development, LLC wasn’t just in the strategies I adopted or the pivots I made—it was in the decision to start the company in the first place. At that time, I was a single mother raising two young daughters, trying to provide for them and balance the demands of parenting. I had spent years in corporate America, and returning to that world seemed like the safest option. Corporate jobs offer a steady paycheck, benefits, and the kind of stability that any parent would naturally prioritize, especially when their children are depending on them. Read more>>

Ta’quana Whaley-vedrine

Taking risks can be very scary, especially if you’re an over thinker. I definitely over think every thing/situation but I like trying new things, I love challenges! Throughout high school I was so conflicted on which career path to take. I was gearing more so to enlisting into the Navy but I knew my parents didn’t want that for me and I wasn’t sure I wanted that for me. Then I wanted to become a dentist but once I started college I grew to love biology so much that I’ve changed my major a few times from Psychology to biology to Public health. Let’s just say I was all over the place back then. Read more>>

Maxwell Kade

I would say one of the bigger types of risks I’ve taken is emailing colleges around me to see if I could come shoot football and basketball games. The biggest cause of nerves for me was that I was just a high school kid (and I’m still young and newer to the profession) who had just started photography, with no real portfolio photos, no real experience. I would just Email CMU or Northwoods and say basically “Hello, I’m a senior at Freeland high school looking to build my portfolio. I was just wondering if I could possibly get a pass to shoot (insert sport) game?” It definitely took a few tries and figuring out who to email, but I eventually started being able to get into games and really started falling in love with photography. Read more>>

Renee Nicholson

When I was offered the position of Humanities Center Director at West Virginia University, I believed it would be the job I retired from. What I would find out is that the job wasn’t even the one I’d interviewed for. I was offered the directorship in the late spring of 2020, and officially started in July 2020. Immediately, the pandemic would challenge what the Center was, or could be. I also naively accepted two directorships at the same time, which I thought I could manage–an academic program and the Center. The academic work always took more time away from the Center, which had to be re-imagined for a remote role. To compensate, I worked more and more hours. Read more>>

Alyssa Womble Mays

Launching Makeup by Alyssa was a huge risk for me. I had just gotten out of grad school and was teaching full time. I have always loved beauty and being creative and the thought of launching my own business was scary. I had no clue what I was doing, other than the makeup, and had a vision of where I wanted to go but wasn’t quite sure how I’d get there. To know me is to know I’m a professional overthinker. I think about everything and if everything wasn’t enough I analyze the details of everything and what it could be leaving no what if unexplored. I was afraid. Would anyone take me seriously? Would anyone want to be my client? Would people really be willing to pay to get their makeup done? Am I comfortable building a brand and communicating with people I don’t know? There were so many unknowns. Read more>>

Kim Brooks

I’ve taken many risks (or leaps of faith) in my life! I’d say the risks I’ve taken were all at times when my decisions didn’t seem to make much logical sense. They were at times when I felt completely led and determined to go all in on an unforeseeable path. I just knew in my bones it was something I was meant to do or try. The first “risk” or leap of faith was leaving my 12 year teaching job in Maryland and moving to Morocco to teach at an American school. I was only in my 2nd year of being a reading specialist, which was a job I worked so hard to get. Although, I had no idea what to expect and was overwhelmed by the decision, I just focused on one step at a time. I told myself that it was only for 2 years and that I could go back to my job in MD anytime I wanted. It ended up being one of the best decisions I’ve ever made in my life and led to me teach internationally for 5 years (in Morocco and Taiwan).  Read more>>

Deandra Brown

eighth time in just three years. Each layoff had been a blow, not just financially but emotionally. I was navigating a world that felt increasingly uncertain, with bills piling up and a family to support. I had always been driven, resourceful, and passionate about helping others find fulfilling careers, but after eight setbacks, I began questioning if I was on the right path. Yet, it was during this lowest point that I took the biggest risk of my life: I decided to stop relying on others to define my career and build something of my own. Read more>>

Mengeh Windlander

​I think taking risks is the backbone of this career. You are constantly putting yourself out there to be seen and judged, hoping to connect and make an impact. It can be terrifying at times-being so vulnerable and open to the public eye, not always knowing how it will be received or perceived, but to constantly take risks and at the same time, being so passionate about something that you love is what truly makes it so beautiful and worth it in the end. Moving to America leaving everything I knew behind to pursue a career here, not knowing whether I would be successful or not has been a huge risk, but an extremely rewarding one filled with life lessons, character development and beautiful connections. Read more>>

Mic Most

In life, some moments demand audacity—the kind that forces you to confront fear and uncertainty, knowing that the stakes couldn’t be higher. That moment came when I chose to represent myself in two family civil suits: a contentious child custody battle and a divorce proceeding. Standing on the precipice of these challenges, I understood that my decision to go pro se—without formal legal representation—was both a monumental risk and a leap of faith. Read more>>

Kelly Cazarez

My Beauty Career Journey: Embracing Risks and Passion My journey in the beauty industry began immediately after I graduated high school in 2002. I enrolled at Paul Mitchell Cosmetology School, setting off on an incredible path into the world of beauty. Soon after, I found myself in Los Angeles, California, where I had the privilege of assisting some of the top hairstylists. It was during this exhilarating time that I discovered my true passion for skin and makeup. Read more>>

Jenyse Mcginnis

In 2024, I took a leap of faith that catapulted my career and redefined my future. As I entered my final semester at Michigan State University, my primary goal was securing a stable, well-paying job after graduation. I was studying Creative Advertising with a focus on Art Direction and dreamed of landing a role in graphic design or social media—something that would let me be creative and work on exciting projects. By February, I thought I had achieved that goal. I accepted a position with a company in Traverse City. The people seemed great, the benefits were solid, and the job aligned with my interests. But there was a catch—it was six hours away from everything and everyone I knew. Read more>>

Mariel Bayona

I think deciding to be an artist, is a risk in itself. To choose to go on a creative path, is almost like signing a contract to go against all odds in every direction in today’s society and culture. The life of an artist is difficult and harsh in our world that we live in today… however, worth it! Every day I have a thought: when I wake up every morning, I ask myself if I want to continue to be an artist today and keep creating. I ask myself if this a risk worth taking, or should I change paths and choose a more “conventional” profession?… My answer is always YES to the risk. Why? Because being an artist and/or creative is not just a “job” or a “profession”; it is my identity. It is everything from the start of a thought to the trace of a line on paper or skin. I’m in love with what I do.  Read more>>

Laura Williams

Years ago, I co-owned a fine art publishing print studio in Atlanta, GA. It wasn’t just a business; it was a living, breathing space where creativity thrived. We were three years in, and things were good. The kind of good that lulls you into thinking you’ve found your forever groove. The business was prospering, and I adored collaborating with other artists, leading our team of printmakers, and working as a master printer. It was hands-on, heart-in, all-encompassing work. Read more>>

Ken Cunningham

A risk I took was moving to the United States at age 23. I was born and raised in Japan to an American father and a Japanese mother, so moving to the U.S. was both exciting and anxiety-provoking. At the time, I didn’t really think of it as a big risk, but looking back, it was. I had completed my undergraduate law degree in Japan and landed a job at a major Japanese airline company. I quit shortly after, which probably seemed foolish to some. But the truth is I was never passionate about that job and was always interested in learning more about the field of psychology and counseling. Read more>>

Eleana Pena

Many of us have dreams and goals. Some dreams are big and some are small. As soon as I graduated college, I felt deep down inside me I had to take a life changing risk. That risk was to relocate to a major big city so I can explore both my creative and career opportunities. Taking a life changing risk can be overwhelming and scary, but I knew I had to leave my comfort zone and what I knew in order to grow and develop my career. Growth never happens when you stay in your comfort zone. You never will know what you’re made of until you step out the box. After graduating college and completing film school, I felt a nudge that it was time to take a risk. Read more>>

Payton King

One of the biggest risks I’ve taken – and one that is still unfolding – involves a bold decision we’ve made at our floral business. As you know, the wedding and event industry is fast-paced, with many seasonal pressures. While summer can be a slower period for us, June, in particular, is often our “quiet” month, at least here in Texas, because it’s too hot. So, it feels like the right time for a leap! My team and I have decided to take almost an entire month off this June to travel to Italy and Switzerland for both a floral design class and an experience of a lifetime. The goal was not just to travel but to immerse ourselves in new experiences, gain inspiration, and, most importantly, take a floral design class in Italy. We will learn from some of the best in the world, and my entire team is coming along for the journey. Read more>>