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.

Jamil Gordon

In Birmingham, there was a driven and enterprising high school student, name jay, who had a vision. He was passionate about organizing events and had a knack for bringing people together. Tyler decided to create a promotional group aimed at organizing exciting parties and events for his peers. He poured his heart and soul into this venture, tirelessly networking, planning, and promoting. Initially, things were promising. His events gained popularity, and Jay’s promotional group started to make a name for itself. However, success often comes with challenges, and Tyler faced his fair share. Some of his closest friends and collaborators, envious of his success, turned their backs on him. They undermined his efforts. Read more>>

LaRae Day

“The year 1519, Hernán Cortés arrived in the ‘New World’ with 600 men, and upon arrival, made history by ‘burning his ships.’ This sent a clear message to his men. There is no turning back! Two years later, he succeeded in his complete conquest of the Aztec empire.” – As a working runway model, I’ve learned that, at times, in order to achieve success in this life we must “burn the boats”so to speak. Read more>>

Mya Fillingham

I was passionate in health and wellness and was dedicated to my yoga practice. I had dreamt of sharing my love for yoga and wellness with others. I have an autoimnune disease of type 1 diabetes, where my pancreas no longer produces insulin and dependent of insulin for the rest of my life. This disease is not cureable and is out of my control. I have learned to cope with it it by embracing that this is part of my new life style and this is when I started to practice yoga. Yoga has changed my life positvily not just physically, but mentally and emotionally. Read more>>

Ben Smith

The biggest risk that I ever took was betting on myself, by trusting God and setting out to work for myself. I get these little (read: BIG) ideas that I call downloads. When I listen to these downloads and put in the work, historically, they have always worked out. However, sometimes they take a bit longer to come to pass. Specifically, quitting a nice paying job, that brought me daily frustration that was equal to or greater than that same frustration of “gigging”, but with no creative outlet, to doing the Splice Cream Truck full-time, which of course has its own unique set of challenges, including but not limited to not getting paid on time, (if at all), breakdowns, last minute cancellations, and exhaustion. With that being said, I am so glad to have taken the risk because I am happier knowing that I am existing within my purpose while making other folks happy! Read more>>

Mabel Cezar

I am a Brazilian actress, dubbing actress and voice director with almost 30 years of experience in localization in Brazil. I am from Brazil and I moved to Los Angeles 2 years ago. I am the only female voice on Brazil’s largest TV broadcast, Rede Globo. Until I joined, 10 years ago, there was no female announcer on Brazilian TV. It was a milestone in the history of Brazilian television. Read more>>

Kat Stauffer

I blame the Aries in me. I suppose most risks feel similar. A pull towards action without explicit confirmation there will be support. “Take a step and the ground will appear,” they say. But when steps of risk affect those around you, especially as a solo parent, there are so many more cautions that come up. Read more>>

Travis Mickel

I grew up in a quaint New Jersey town, feeling out of place from a young age. Convinced that I was destined for greater things, I took the leap after college and landed in the hustle and bustle of New York City, joining the ranks of a prestigious luxury fashion brand, Prada. For 8 years, my identity revolved around my role there, immersed in the high-paced world of fashion and achieving notable success. Starting in sales, I progressed to coordinating events for top clients, working closely with celebrities and their teams, and living a jet-setting lifestyle that seemed like a dream to many. Read more>>

Rosie Gellman

In my journey to my current practice, I have taken multiple risks, and set up myself and my family for some large ventures. I was born and raised in Texas, left for college, but returned for medical school and my initial training. I started my training in a 3-year program in Pediatrics in Texas. While about halfway through, I was grappling with the challenge of the system requiring a Pediatrician to see 30-40 patients a day and only able to spend 5-10 minutes with each encounter. Beyond this, many patients I was seeing were presenting for mental health concerns, and I had neither the time nor the knowledge to help address these problems. Read more>>

NaTori Aliyah

Late 2022, I decided to work a regular 9-5 job in retail. I had no experience but i was in a creative funk & needed a steady source of income until could figure out if being a performer & creative was what I really wanted to do. I was hired on the spot & promoted to a manager position two weeks later. It was a job that paid my bills but I wasn’t satisfied. I was 5 months in and I felt like although the job pays me, I’m letting myself down. This wasn’t the dream. Instead of just quitting, I trusted God & worked another 5 months. I learned so much within those 5 months about patience, and discipline, and just to have faith. Read more>>

Shayne Cerebe

Reflecting on my journey, the pivotal risk I took was signing up for my 200-hour yoga teacher training, an endeavor that served as a catalyst for profound personal and professional growth. Two years into college, I found myself at a physical, mental, and emotional low. As a former competitive swimmer, the transition to college life had taken a toll on my health, leading to weight gain and various physical issues. Recognizing the need for a gentler form of exercise, I stumbled upon an Instagram account featuring yoga inversions, sparking my curiosity. Read more>>

Orma Smith

I went to school to become a corporate lawyer. My undergraduate degree is in Economics and Business Administration. My sophomore year in college I did an internship at a law firm and discovered that I did not want to be a lawyer. The following year, while studying abroad in West Africa, I did some soul searching. I made the decision to finish the degree, but I took a different path. My first “real” job out of college was as an English teacher at my alma mater. That started my 20-year career in education. During that time, I acquired a Master’s degree in Counseling and two counseling licenses-school and mental health. Read more>>

Stacey Millett

I feel confident in saying that being a small business owner comes with great risk and even greater rewards. I became a small business owner while still in college, I am now in my early forties and realize that my evaluation of venturing out on my own came with a lot less stress and twenty-year-old carefree confidence. Now, later in life, my persistence, passion, and hard work have pushed me through any rough patches over the twenty years. Read more>>

Katie Tucker

I took a risk and left my career as a Research Psychologist as a civilian for the US Navy when my oldest son was 5 months old without a detailed plan of what was next. I have always been self driven but the unknown was scary and maybe a little exciting. Who knew I would find a passion in fitness and helping other likeminded women. I have kept my personal training certification not only through the pandemic by teaching classes over zoom and but also while having three other babies. Read more>>

Jasmine Sykes

The biggest risk I had to take in life other than natural childbirth, is moving to a new city to follow my dreams. Stepping into the unknown, not knowing if this dream of mine would prosper, I moved from my hometown Milwaukee, WI to Atlanta, GA in March of 2017, then to Los Angeles California in 2022. Growing up in Milwaukee, WI where the largest incarcerated zip code is 53206, entrepreneurship was not visibly promising. With very limited resources, support and space to grow, my thought process was “I had to make it out of my city, not just for myself, but for every young woman who person who come from where I am from with a vision.” Read more>>

Sevyn Bevoy

You are your biggest critic and the only person that can stop you. How do you know what you can do if you don’t take a risk? You take a risk everyday just stepping outside the door and you don’t stop yourself from doing that. So whatever it is, at least try it once. I took a risk to by putting myself out there to attempt modeling in another country and if I didn’t, I wouldn’t be where I am now. Read more>>

Gabriel Acosta

Taking photos and carrying your camera with you motivates you to look for unusual things, but going to unexpected places often involves taking a risk of not knowing where you are going and what you are going to find. As part of my photography journeys I decided that it would be good to explore the Baja California desert but this time my approach was going to be different, I would decide to travel to Mexico and explore many parts of the Baja California desert by foot (my favorite way to photograph a place). Read more>>

Esther G

Starting FireBar Labs was one of the most significant risks I’ve ever taken. In life, as in business, there are no guarantees. With the economy constantly shifting and seeing how things like the housing market and inflation were moving, I knew I had to make an intelligent choice with the savings I’d accumulated. Letting it sit in a bank account wasn’t going to cut it; I wanted to invest in something meaningful. Read more>>

Flaviya Kaklyugina

We always have to take a risk if we want to grow. I have taken many risks in my life, sometimes I did not have much choice though, other times I was following my heart. The first risk I took when I left my parents’ home with only $126 in my pocket. I moved to a different country with those money and luckily I found a job within the first 3 weeks. Some mornings I would wake up crying, but I always knew that those challenges were temporary and that my life would be different in 5 years from there. Read more>>

Sarah Scott

In both business and athletics, I have always viewed risk more as an opportunity for success than a possibility of failure, for risk is the first step toward reward! For me, risk represents an opportunity for success. The Chinese symbol for risk consists of two interrelated symbols representing both “opportunity” and “danger”! Read more>>

Jake Tripp

One of the biggest risks I’ve taken was a caving expedition where I spent the night underground in one of Utah’s deepest caves. We were about 10 hours deep into the cave in damp alpine conditions. We were tasked with opening up new passage in the cave that had previously been underwater. The water had receded this year, allowing us to put on dry suits and duck under. While we didn’t make it through our destination, we were able to open up new passage that had previously been undiscovered. There are many inherent risks to caving, but hypothermia is the primary concern for alpine caving. This is just one of my many outdoor (or underground hobbies) like canyoneering, rock climbing, and mountaineering. Read more>>

MJ Caballero

Great rewards come with great risks. I have always thought that I have nothing to lose. For example, when you apply for a job, if you end up not getting it, you are not really losing anything because you didn’t have the job in the first place. Having that mindset of taking risks with nothing to lose it’s one of the reasons that has brought me to where I am here today. Read more>>

Ferrell Marshall

During the turmoil of the Great Recession of 2008-2009, I chose to leave my safe, predictable, and lucrative 20+ year career at PricewaterhouseCoopers to pursue my creative endeavors. Granted, timing could have been better but the truth was that I had been promoted into a role that was not a good fit. I was working stressful 70+ hour weeks and no matter how hard I worked, I felt like a failure and ended most days in tears. This went on for three years when finally, after much soul searching and profound conversations with my now late husband, George, who was my biggest fan, I made the decision to LEAP! It was surreal and scary. Who would I be if I did not have a title, salary and a 401K?! Read more>>

Bryan Toton

The most pivotal moment of my life was when I first fully submitted my life to Jesus and understood my life’s purpose. I grew up believing I was a Christian, but consistently valued habitual sin over my relationship with Jesus. I was absent from church for 14 years, but thankfully, God called me to renew my faith in Him prior to beginning my master’s in engineering. I had just read through the book “The Deflame Diet” and ended up launching a website, “Eat for Prosperity,” to teach others how to prevent and reverse chronic illnesses. Read more>>

Janice Jo Lee

As an independent musician and spoken word poet, I am a one person record company. If I want to tour and reach new audiences, that is a project I take on from scratch. It is a huge financial and artistic risk to enter new markets. The main thing I do is perform live for audiences. I am driven to do it because I know that my concert is valuable. I know that I create music medicine, that performing for people is a nourishing experience for all of us. Read more>>

Stephen Correa

In the year 2021, I found myself at a crossroads. I was working a regular 9-to-5 job, but my heart was always in the rhythm and beats of music. I was a part-time DJ, spinning tracks at private events and weddings for a company called RJM Entertainment. I loved the thrill of controlling the mood of a room, the power of music coursing through my veins. But it was just a side gig, something I did for fun, not something I could make a living out of. Or so I thought. Read more>>

Chris Dunlap

Early in my career I was working in higher education, as a rising star, young Director but I always had this itch to try something completely different. I was always super curious about the tech world and sales. I had a brother in cyber security and a best friend in Tech and their day to day sounded exciting. So, one year, I just went for it. I took a huge leap and joined this small tech startup. Man, it was exciting at first—like jumping into the deep end without knowing how to swim. But, as luck would have it, things didn’t go as planned, and shortly after joining, there I was, jobless for the first time ever. It was kind of a shock, you know, but I told myself that this would be the greatest year of my life. Read more>>

Lyna Knight

I learned early on that making your path in this life, career, and happiness, comes with risks. I moved to Tampa Bay from a small rural town many years ago, taking a clerical position with a company I knew very little about. I learned the business and opened a title insurance company several years later. After many years, I sold the business and took the biggest risk of all and began farming blueberries. Read more>>

JAMES

In college I studied finance and data analytics. I worked in data analytics during school and quickly found out I didn’t enjoy it. Shortly after graduating I started work as a financial adviser. I quickly found out I didn’t enjoy that either. Music, though, had always been a passion of mine. Feeling a bit lost with my career choice, I decided to finally pick up music production on the side, after work. I quickly found out I enjoyed the hell out of it – more than any work I had ever done. At the start I was by no means good, but I sure enjoyed doing it. Read more>>

Jordan Gilbert

I owned and operated successful, nightclubs and bars and was making a huge name for myself in the industry. I was traveling the world at a super young age doing what I loved! My business partner and I founded and launched a liquor company and I was being called for training and speaking engagements. The best part was that I was really good at it. After a speaking at the Night Club & Bar show in Las Vegas I was hired to do consulting in Mongolia. Read more>>

 Jade Hustler

One of the key traits of a creative is risk taking.. I personally, am not afraid to put something new out into the world that might be laughed at. The moment you don’t mind being dismissed as crazy or unusual you often generate the most innovative ideas.I’m not a fan of being stagnant or wasting my fears on should’ve could’ve would’ve! I am the walking proof of failing & trying again, but I’m also the walking proof & well respected for coming out on top when I’ve failed. Read more>>

Lex Kilgour

I have taken my fair share of risks when it comes to career choices and my current one, to most, will sound like no exception. But each risk has taught me resilience, and I think for those of us in creative industries we understand how each challenge has strengthened our ability to step forward with greater confidence. For many, taking that first leap happens when we go to University. I remember hearing a statistic when I was graduating high school: that my generation was most likely to have 5 careers over the course of our lifetime. Well I’m somewhere on my 3rd or 4th at this point so… let’s see how I got here. Read more>>

Vickey Finkley-Brown

One of the biggest risks I’ve taken was not renewing my teaching license. I retired disabled in June of 2014 because of complications with lupus. I intended to keep my license active, just in case. Once my health was somewhat stable and I could begin to think about my next steps, I could no longer see a classroom in my future. My license was set to renew in 2015. All I needed to do was take a class with the SC Department of Education and complete the paperwork. The closer the date came, the lighter my shoulders felt. When the date passed, I took my first real breath of freedom. I wasn’t sure what I would do but I knew it had not to do with teaching high school students. Read more>>

Emily Kane Miller

As someone who would never have described themselves as an entrepreneur, the decision to step away from a stable job to found my own company was scary. From the moment I graduated law school, I worked in government or for a large corporation. For the better part of a decade, I built a social impact career in-house, and loved being part of a bigger team. Read more>>

Huntley Castner

Many times I have had people ask me why I have chosen my life as a restaurant industry executive and painter. They often suggest my life would have been far easier if I had chosen less risky professions and hobbies. They might be right; the restaurant industry has a high rate of failure and low margins. I am fortunate enough to have attended Stanford University as an undergrad and UCLA’s MBA program, then started my career in investment banking and management consulting. They say, “If you’d stayed on that track, you’d likely have made millions and be retired by now”. But, that was not my path. Read more>>

Kelly Shannon

On the final day of the year in 2016, I sent my letter of resignation to my boss at my old job. I’d worked in the Marketing department for a luxury automotive brand for several years. My physical and mental health was deteriorating, and I realized I was the only person who could help myself get out of a toxic situation and turn things around. I had no job I was leaving for, so I ended up staying for the majority of that year doing my normal day-to-day job, finishing up projects, hiring and training my replacement, all the while frantically anxious on what to do with my life. I grew up with an Interior Designer mother, and my friends had told me repeatedly over the years that I should be doing design. So finally, I listened. Read more>>

Shenna Whitley

To advance in life, in general, risks have to be taken. For many of us, we are programed to take emotionally government risks. You know the, just go for it – “what you do you have to lose” risk. Overtime, we will start to develop the educated/calculated risks. These comes from the wisdom bestowed upon us from the emotional risks that either worked out in our favor or became a hard but well-learned lesson. Read more>>