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.
Estefania Peynetti
Moving to Miami, to new country. Starting my business all over from scratch is a very crazy risk I took. For somebody who doesn’t like change, lived in the same city, have the best friends since I was a kid. I still can’t believe I did this. About a year ago I moved from Mexico City to Miami, and my business moved with me. I started let them have cake from scratch from my parents kitchen in 2014. I grew my business slowly for9 years in Mexico but the pandemic and the countrys situation hit hard. I didn’t see my business going where I wanted to go. I took a huge risk and invested in renting space here and began the remodeling process which took two years, a year ago I moved here to work on getting ready and now 3months ago I Finally opened let them have cake miami. Ithaca been tough learning many things in a new country and trying to start over and get new customers from scratch but everyday we see progress! Read more>>
Miranda Loftis
When I graduated high school in 2017, I was told that I now need to go to college and know what I wanted to do for the rest of my life. It seemed like the only thing to do because of a false belief that was programmed into my mind from a young age. Back then I was an athlete, I had endured a lot of injuries and worked with physical therapists. They had a great impact on me, so it seemed only right to pursue that as a career to help others. The only thing I had right in what I wanted was to help others. I then proceeded to go to college for three years. By the end of my first year I started to realize that physical therapy wasn’t for me. At that time, I was, for the first time, getting really into going to electronic shows and festivals like Electric Forest. There I tried psychedelic medicines for the first time that year, which led me to really digging deep within my unconscious and unlocking parts of myself that were hidden. I also starting seeing all the worlds problems in HD and wanting to find the roots to these problems. Read more>>
Nicole Scimone
This year I made one of the scariest decisions of my life, to leave my corporate job, while not really knowing what was on the other side, or having a concrete plan. I have a loving husband and two young children, a mortgage to pay, and a million reasons I should have stayed put. Despite how scary it was, it was a choice I HAD to make, it was the right choice. Read more>>
Kandyce Jackson
Retiring from my career of 17 years earlier this year has been my biggest risk thus far. As scary as it was, I took the leap and have no regrets. I am still getting acclimated to full time entrepreneurship, from creating and sticking to a schedule to balancing finances. Having patience and grace with myself has been key. Read more>>
Gabriel Hihira
I came from a small village in rural NZ. Was always active and loved sports. My family and extended family were all actively in sports so I was drawn to the competition aspect of it but more so the acceptance and camaraderie of my team-mates. This lead to some very sporty teenage years, and a few opportunities at high levels. I had always dreamed of playing basketball at a professional level but that was not on the cards outside of representing my city/region. But volleyball was a different story, I enjoyed it but had picked it up quite late so lagged in the detailed skillset my team-mates all had, but the athleticism from my sporting years shined through. A few opportunities came from that inside NZ but the biggest one was to move overseas (Australia) and have the chance to train full-time with some of the best volleyball players in the world at the time. The kicker was I had a team-mate already set up and willing to help me out with accommodation and a part-time job to allow my dream to come to reality. Read more>>
Polly Acioli
One of the biggest decisions and risks I’ve ever taken was moving from Brazil to Houston, leaving behind a well-established photography studio and a loyal client base. In Brazil, I had a thriving business, a full schedule, and a reputation I had carefully built over the years. It was secure, comfortable, and provided stability. But at the same time, I felt a pull—a desire for growth and new challenges that I knew I could only find outside my comfort zone. Read more>>
Xintian Tina Wang
One of the biggest risks I’ve taken was moving to the U.S. from Hangzhou, China, at 18 to pursue a career in storytelling. Growing up, I was taught to keep my head down, listen more than I spoke, and avoid standing out—a common mindset in my cultural upbringing. But I had an undeniable urge to challenge these norms. I wanted to tell stories, especially those of marginalized voices, and to create space for new perspectives. Read more>>
Zahra Premji
The biggest risk I’ve taken was leaving my 20-year career as an occupational therapist, including 16 years in my previous job, to become a Life Coach. I had a stable income, health benefits, summers off, and a pension waiting for me. I worked close to home and had strong relationships with many colleagues. But I was increasingly frustrated, undervalued, and overworked. The lack of purpose and alignment in my job was draining my health, well-being, and relationships. I was constantly stressed, irritable, and exhausted, struggling to keep up with everything. Read more>>
Taylor Cicali
Gaming has always been my passion, and I even dabbled in streaming for fun. But when I met my now-husband, Anthony ‘Hoagie’ Cicali, he showed me that streaming could be more than a hobby—it could become a semi professional career. With his support, I joined a stream and started with a team called Nerdthusiast, engaging with audiences, and learning the ropes. At first were tough, but over time, my community has been growing and I have enjoyed the process so far. Read more>>
Robbie C. Ward
The biggest risk I’ve ever taken is one that I am still right in the middle of. I’m currently finishing my debut short film, which I began back in 2017, and I never imagined it would take so much time and energy. When I began, I had just parted ways with DEDSA, my former band. I initially began animating because I wanted to create memorable videos to further my music career. However, as my Crohn’s Disease became more and more debilitating, performing and touring became far less possible, and I found myself falling more deeply in love with film until I came to the clear decision that I needed to find a new path forward. Read more>>
Lizeth Felix
A few years ago, I was living what most people would call a “safe” life. I had steady, reliable jobs—ones that, honestly, looked pretty impressive on paper. I worked as a counselor for a company, then as a therapist for a government program, and even as a PERT clinician for the police department. It was the kind of work where you didn’t have to worry about where your next paycheck was coming from. My path felt secure, predictable—even enviable to some. Read more>>
Alex Julie
In 2021, I attended a two-week Ecodharma training at the Rocky Mountain Ecodharma Retreat Center. During the retreat, we were invited to spend two days alone in the mountains with minimal distractions—staying within a 20-foot radius, fasting, and relinquishing timepieces if we chose. This solitude came after days of meditation, embodiment practices, rituals, and Dharma talks about humanity’s relationship with the Earth, leaving me deeply attuned to the environment and my inner world. Read more>>
Garrett Alexander Watson
Taking a risk Id like to call this passage: ‘ As an Actor: Beyond the Glory and All The Fame. ‘ I think many of us today see our favorite actors on tv and film and commercials and get really excited. Because it’s SO entertaining. But what did it take for that person to get there? How did they make the journey? Well, everyone’s journey is completely different, and I will say, they all required major risk. So, let’s talk about risk. I began in the commercial market a few years back. I believe it’s been 7. And that trek really was interesting because I learned fast to bring headshots and show up 10-15 minutes early in person for my auditions. Obviously that changed during covid, but I will say that every actor should be focused on making sure their self tape set ups are done well and they’re bringing their all because zoom has brought a lot more competition! And you will be doing tons of auditions throughout the year, so make sure you learn to throttle yourself so you don’t burnout. Audition burnout is real. Please take care of yourselves. Read more>>
Cesar Santana
Being an entrepreneur is a risk because it requires stepping into the unknown. You invest time, money, and energy with no guaranteed success, face uncertainty, and navigate challenges like competition and market demand. But with risk comes the potential for big rewards! So, stepping into this fashion world has been a whole roller coaster ride, but I would not change it for nothing, Read more>>
Maria Antonia Vallejo
In 2023, I left a stable job to pursue my passion for fashion journalism and storytelling. I launched The Latin Issue, a digital magazine dedicated to showcasing Latin American talent and sustainable practices. It was a bold step with no guarantees of success, but I knew I’d regret not trying. Starting from scratch was challenging, but the platform gained traction, becoming a space for emerging designers and conscious fashion enthusiasts. This risk taught me that following your passion, even when uncertain, can lead to the most fulfilling rewards. Read more>>
Blvxxkk
At the end of 2023, I stood at a moment of profound clarity. For a long time, I had poured my heart into being an empath coach. It was work that felt aligned at the time—helping others navigate their sensitivities and emotions—but deep inside, I felt an unease I couldn’t ignore. Something was shifting, and I knew I could no longer stay where I was. Read more>>
Tricia Dycka
At the end of 2023, I stood at a moment of profound clarity. For a long time, I had poured my heart into being an empath coach. It was work that felt aligned at the time—helping others navigate their sensitivities and emotions—but deep inside, I felt an unease I couldn’t ignore. Something was shifting, and I knew I could no longer stay where I was. Read more>>
Wiseonearjay
The Risk That Redefined Me: WiseOneArjay’s Journey to Independence For WiseOneArjay, the risk that reshaped his life and career wasn’t just about music—it was about betting on himself when the odds felt stacked against him. “I’ll never forget the day I decided to walk away from my 9-to-5 to pursue music full-time,” Arjay begins. “I was working a steady job, doing what everyone said I should be doing—paying bills, providing for my family—but I wasn’t happy. I had all this creative energy bottled up, and I knew music was my purpose. I just couldn’t ignore it anymore.” Read more>>
Tamera Jones
From the moment I entered this world, I’ve been breaking barriers. Born premature at just 2 pounds, 4 ounces, and without medical complications, I am a living testament to resilience and overcoming odds. That resilience has defined my journey and shaped my identity as someone unafraid to take risks. Growing up primarily in a single-parent household, I had a front-row seat to courage and determination. My mother, raising two children while working multiple jobs, shattered stereotypes by earning her accounting degree in less than four years—a remarkable feat in a male-dominated field. She didn’t just survive; she aimed to thrive and was a trailblazer, instilling in me the mindset that excuses were never an option, and challenges were simply opportunities in disguise. Read more>>
Anna Lundmark
I worked at a marketing agency before starting my own business and I always wanted to venture out on my own. I did some consulting work but I never found my path. That was until I realized that my Autistic sister in law needed a path too, and she needed someone to help create it for her. I suggested that we build a business together, using her interest for beauty and my passion for marketing. Every part of me wanted to play it safe and save up to buy product before we launched. However, I knew this wouldn’t happen immediately, and it wasn’t certain it would work. So my fiancé suggested that I do pre-sales. The idea of selling something I didn’t have yet terrified me. There were so many what if’s that came to mind. What if the products don’t come, what if something’s wrong, what if people get angry waiting, etc. But I decided to launch pre-sales, posted on social media, and within two weeks we had made enough to place our first order of product. Two months later, we were able to ship it out, and the business has financed itself ever since. Read more>>
Melanie Haselmayr
In the early days of CURATED., we operated as a staging and furniture rental company, addressing a clear and steady market need. However, as we worked within the industry, we recognized a significant gap in the luxury interior design market. Clients were seeking a design firm that could not only craft bespoke, high-end interiors – but also execute those visions with exceptional precision and efficiency. This realization led to a pivotal decision to transform CURATED. into a full-service luxury interior design firm. The shift required us to completely redefine our business model, including restructuring our services and expanding our team to meet the elevated demands of this niche market. So that’s what we did. Read more>>
Zoe Stallings
One of the most significant risks I’ve taken in my life was choosing to pursue a career in counseling, specifically sex therapy. From a young age, I knew I wanted to help people by becoming a counselor. It wasn’t long before I discovered my passion for sex therapy, a field that deeply resonated with me and where I felt I could make a real difference. However, this decision was met with resistance and skepticism from many people close to me. I was told repeatedly that sex therapy wasn’t a “real job” or that it was too provocative, and I was warned that I would never be able to make enough money to support myself in such a niche career. I remember having to send my aunt quarterly research articles on the impact of mental health after she would send me computer science education/job opportunities(her career path). Read more>>
Vanessa Richaud
I was 10 years old when my dad started having me work in his business. My dad and Uncle taught me everything from bookkeeping to sales, I was blessed enough to have a head start in what owning a business was really like. I quickly learned what it was like to be an entrepreneur when I took a big risk at 21 years old to start my own business. I franchised Chill N Nitrogen Ice Cream at 20 years old and was talking to the corporate team before that at 19 years old. At first it was absolutely scary to think what did I just get myself into and now I have successfully had my business open for almost 3 years this 2025. Read more>>
Chris Smith
One of the biggest risks I’ve taken was turning my passion for fishing into a full-fledged business, AdVenture Bro. It started as a hobby where I shared fishing content online. At the time, I was working a stable job, and taking a leap into social media marketing and content creation full-time was a daunting prospect. But I believed in the potential of my idea to connect with a community and create value. Read more>>
Taquala Woods
In 2021, during the height of the COVID-19 pandemic, I created a business focused on a planning and registration course to help clients establish their own small businesses. At the time, I was incarcerated and noticed the lack of programs offering education on business planning and entrepreneurship. In September 2021, upon my release, I carried this idea and business venture forward with determination. Despite not knowing much about my competition or how other entrepreneurs were scaling their businesses, I took a leap of faith. I began attending seminars and learning various trades to expand my knowledge and refine my skills. Read more>>
Joely Hackmann
It all started in my small town of Basehor, Kansas. Ever since my freshman year of High School I have had a go getter attitude. I was always looking for something more to do that could challenge me, excite me, and give me a little extra cash to spend. Most of my friends where focused on grades, sports, or just hanging out. My freshman year of High School I asked my family to buy me a camera to started this adventure. While still being in high school I didn’t know how to manage finances, book clients or market myself. Without the help of my school Innovation academy program I couldn’t have learned all of this. Read more>>
Fynn Jane Coleman
Taking risks often feels like stepping into the unknown, and it’s especially daunting when it involves your hard-earned money. For me, the decision to invest in a hotel renovation at the start of this year was one of the most daring moments of my life. While I’ve always been an analytical thinker—one who tends to overanalyze things to the point of resurrection—this opportunity required a leap of faith in an industry that was entirely unfamiliar to me. Read more>>
Jordan Johnson
Opening my healing arts business was one of the biggest risks I’ve ever taken. To step into an unfamiliar world and to tap into my authentic expression publicly, made me aware of how being yourself in today’s world really opens the door to risk-taking. In a world that constantly tells us to conform, embracing your most authentic self is a revolutionary act. I felt an angelic call to step into the intuitive arts, which required courage and a deep trust in the guidance of the unseen. These paths, often misunderstood or seen as fringe, offer some of the most profound ways to connect with the truth of who we are—and help others do the same. Read more>>
Amy Atchley
In May 2020, My husband, Brian and I sat on the couch. Our kids (3rd and 5th grades) were home, distance learning. I was a high school Special Education Teacher, frustrated by the low pay and high stress of teaching. My students, increasingly anxious about the state of the world, felt that those in power weren’t acting quickly enough to address climate change. They felt we were leaving them with a global disaster to clean up. I always felt like teaching was the best way for me to spend my time to leave the world better than I found it. But I was realizing that I could not wait for my students to grow up and be the solution. I needed to do what I could to move the needle, now, and any amount. Read more>>
Dominique Paredes
Breaking the Silence For as long as I could remember, social situations felt like climbing a steep mountain with no end in sight. Even the thought of speaking up in a room full of people made my chest tighten and my heart race. Social anxiety wasn’t just a part of my life—it felt like a barrier that defined it. So, when the idea of starting on social media first crossed my mind, it seemed like an impossible dream. How could someone who could barely talk to strangers in person put themselves out there for the world to see? Read more>>
Brady Allio
Several times, I worked on a couple of films on the same day, back-to-back, from beginning to wrap. I would spread myself out too thin and would have to find a last-minute assistant to cover for me, for several hours on one film project, while I worked on another film. I discussed with both directors for both film projects and figured out my strategies and plans. Then I would speak with my assistant. I would inform them what to do, along with giving them makeup continuity pictures that I had done for the past days on the set, from the beginning of the project along with notes in the folder as well. I knew it was a huge risk, and could possibly impact my career, but I managed to prove to myself and others that I could do a couple of projects back to back. I would sometimes work 20-26 hours when I do a couple of projects at the same time, I would always schedule a little downtime here and there to eat and rest for a few minutes on set, or drive from one set to another set. Read more>>
Annamaria Tushaj
Leaving my secure corporate job in HR Management when my son was born! When my son was born, and there was a complication with childcare, so I had to make a very tough decision to leave my career or stay home with my son. I chose to take a leap of faith and stay home with my son, knowing that I would lose my full-time income and there would be a break in my career when or if I decided to go back. It was a huge risk for our family. Read more>>
Brittany Buchanan
Starting Black Muva Convos was a risk I never thought I’d have the courage to take. At first, it wasn’t even an idea for a business or a movement. It was a personal challenge. My marriage had ended, my sense of self had unraveled, and motherhood, had completely consumed me. I couldn’t recognize the woman staring back at me in the mirror. That’s when I decided to do something just for me. Read more>>
Zarina Williams
Nine years ago, I took a life-changing risk by moving from Kazakhstan to the USA to pursue my dream of working in the fashion industry. It was a leap into the unknown—I had no clear plan, limited resources, and a culture completely foreign to me. I shared a tiny space with multiple roommates, often skipped meals to save money, and faced scams that tested my resilience. But every challenge shaped me, teaching me the value of perseverance and adaptability. Read more>>
Megan Harris M.
A few years after becoming a single mother, I found employment at MedStar Georgetown University Hospital. Because I was raising my oldest by myself, my coworkers advised me to become a nurse. I loved what I did for my patients, so I started school so I could take my nursing prerequisites to get into the nursing program. I had always been a creator, though. Writing, drawing, and designing were my whole life– I had goals of pursuing art after graduating high school. But I had suddenly given up on my art, figuring it wasn’t the most practical thing to do as a single mom. I continued taking my nursing prereqs, but I also began studying several English courses beyond the basic coursework for the general education requirement. While trying to convince myself nursing was what I needed to do, I was having a hard time letting go of who I once was before I began working at the hospital, feeling extreme regret at having let go of my visual art. Read more>>
Erica Wiley
Putting in my notice with my former employer, without any clear idea of what the future might hold, was one of the most pivotal – and terrifying – days of my life. All I had was a vision of what I wanted my business to be, an LLC name, and one of my last paychecks to get started. That’s it. Looking back, it was easily the biggest risk I’ve ever taken. Read more>>
Kee West
I was faced with a moment of going for what I desired, knowing that another desired the same as me. There was complete honesty and transparency of what we both wanted. In which, they wanted exactly what I wanted. I hoped in every part of me, that it was for me. So, I stayed diligent, pure of heart, love, and soul, with every good intention, trying and trusting in the Divine focused on my mission, knowing that both a yes and a no were alignment with what they had for me. This risk was scary for me because once you make the move you cannot come back from it. The thoughts of society’s opinion crossed my mind. Once you make that choice the only way is through and everything else that comes with it. However, I chose to not let that stop me. Fear cannot come with me where I am headed. The Divine has always shown me that they won’t leave me hanging. I chose to go for it. It was the best decision I made. Read more>>
Nico “nnil” Pires
It might sound silly, but the biggest risk I’ve taken and been rewarded for was making a TikTok video. I’ll explain: I had operated on Instagram for years as a multi-disciplinary artist. I’ve taught danced, performed and street busked, I’ve produced and distributed music, I’ve modeled and done photography, among other things…but I couldn’t wrap my head around doing them as a business. I had been doing Tarot a couple of years for fun, and a friend of mine told me I should do it on TikTok, (which I devalued and despised at the time). Read more>>
Clara Stevens
Before August 2024, I dedicated hundreds of hours to Junior State America (JSA), a 90-year old organization dedicated to youth participation in debate and mock-congress conventions, with 6,000+ members and 8 regions nationally. I first served as Chapter President at my own school, where I hosted meetings and tripled my club’s membership. Then, throughout my three years in JSA, I increased my leadership responsibilities on the student-run Cabinet, and I was ultimately elected as Ohio River Valley Governor in April 2024. My role was to lead the 30+ schools in my region and direct the Expansion Department nationally. Over the summer, I fully committed myself to developing ideas to better the future of JSA. Instead of an internship, I spent 15+ hours a week on planning summer programs and organizing leadership conventions. And then, in August 2024 during the first month of my senior year of high school, JSA abruptly shut down. Read more>>
Simon Martin
Becoming an actor was within itself a risk. A risk I wasn’t ready to take until I was 25. But let’s start from the beginning. From a young age I always wanted to be an actor, a clown, an artist, a creative or an entertainer. I loved evoking emotions out of an audience, and ever since I was little, I dreamed of being an actor. But, unfortunately, following my dreams and pursuing this art wasn’t in the cards at the time; my head was lost in the clouds of addiction and would continue to be until I was 25. February 5th, 2017, I took the biggest risk of my life; I decided to get sober, straighten my life out and chase my dreams. For years, I told myself that chasing this pipe dream of acting was way too risky and that becoming an actor was near impossible, but I thought getting sober was impossible, and I conquered it. Why couldn’t I conquer this? I took the leap of faith and started acting in 2017, I haven’t looked back since. Read more>>
Brooklyn Moran
The biggest risk I’ve ever taken was investing in myself and beginning my salon suite business. I have been behind the chair since 2014 and I had always worked under another stylist. This is fairly typical in the industry and at that time, stylists, were at the mercy of their salon owners. What schedule you worked, how much you made, the types of appointments you preformed, how long it took you to perform the, the clients you serviced, ect. was all pre determined. I’m not saying that is bad in any way for someone who needs leadership and growth, but I was at a point where my life had different needs. I’m the breadwinner of my family, I was a new mom, and I had just gone over my monthly finances and came to the realization that I was going to be significantly short on my rent and there seemed to be nothing I could do about it. That was the moment I knew I had to take control. I only had about 30 days to prepare mentally and financially to open a successful business, leave the salon I was currently working at, and continue to provide for my family. Read more>>
Emily Burnham
After starting a YouTube channel about one of my favorite passions in life, the Gospel of Jesus Christ, I knew I wanted to create a therapy YouTube channel after obtaining my Master’s Degree in Marriage and Family Therapy that integrated therapeutic teachings with gospel principles. However, during my graduate program, I received judgmental comments from professors when I brought up my religious values that led me to feel like I had to separate my spiritual self from my therapist self within my own conceptualization of who I was as a person. Their messaging made me feel like I wouldn’t be seen as “unbiased” or “professional” if I viewed case conceptualizations through a religious framework or brought up religious values with my colleagues. I was never in jeopardy of violating ethical principles in therapy sessions by preaching religion, but I did worry about clients coming across videos of me sharing religious views and then feeling judged or unsafe. Read more>>
Eboni Garvin
A risk that I’ve taken is deciding to become an Herbalife Health Coach. I’m a full time math educator and most people know that we as educators don’t get paid our worth. I knew that I needed additional income, especially after the effects of covid. I tried to make extra income in a few other areas: Amway and Primerica. Coming to an opportunity meeting, trying to see what’s possible for me. And even though what they had to offer works and was good, and beneficial, it wasn’t consistent. So I wasn’t exactly sold on giving Herbalife a try. Read more>>
Paige Barbee
In 2018, I took the most significant risk of my professional life by opening my retail store in Nashville. My husband and I had recently moved to the city for his new job, and I had quit mine. We settled into an apartment that was cozy but certainly not ideal for my jewelry making, which, as you can imagine, isn’t the quietest of crafts. I had dreams of finally running my jewelry business full-time, so I embarked on a search for the perfect studio. Read more>>