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.

Pamela Ellis

Life changed for me 9 years ago after I gotten divorced after 27 years. I closed my clothing boutique in Terre Haute, IN after my divorce and moved to Fort Lauderdale, FL. I began working for a boutique on the beach and then started working in the couture department at Nordstrom in Aventura. After 2 years of being in Fort Lauderdale, I decided why not become a flight attendant. I left Fort Lauderdale and was based out of Louisville, Ky. I flew for Mesa Airlines on American Eagle. I did this for a year and a half. I knew my heart was in fashion so I resigned from flying and went working for my girlfriend, Juetta West at her boutique in Daytona, FL as her store manager. Read more>>

Sharmaine Longsworth

Not too long ago, my life was all about comfort and stability. I was happily working as a physical therapist in Illinois, with a cozy home and a routine that felt just right. But deep down, I felt this nagging urge for something more—something that would stretch my limits and challenge me in ways I hadn’t experienced before. So, after countless discussions with my family, we made a bold decision: we packed up our lives and moved to Texas to open my own physical therapy practice, Physiophyx. The thought of leaving everything behind—our friends, our neighborhood, and my secure job—was terrifying. But I knew I had to follow this dream. Read more>>

Lisa Lovelace

synonymous with in-person sessions, sitting across from clients in a quiet room. I had been working as a therapist for several years, and while I loved the work, I started noticing a growing gap in access to care. Clients would cancel due to travel issues, bad weather, or work commitments. Some, especially those in rural areas or with disabilities, found it challenging to access therapy altogether. I began to wonder if there was a more flexible way to offer these vital services. Read more>>

Avery Kwong

I haven’t always had an occupation in the arts. In college, I studied to become a structural engineer, however, soon realized that it wasn’t for me. So I went into construction management, destined for higher pay and less desk time. Even that wasn’t satisfactory. Even with stable income and job security, I felt more out of place than ever before. I wanted something more fulfilling. Music has always been a big part of my life, and being able to introduce my passions to others is an incredible feeling, so teaching was almost a no-brainer. Photography, on the other hand, was more unexpected. I’ve never been a stranger to taking photographs, but I never imagined myself getting paid to do it. To move from my hometown down to San Diego to pursue teaching AND photography was the biggest risk I’ve ever taken and one of the best decisions of my life – both personally and professionally. Read more>>

Felissia Mae

Taking a risk can be big or small. In the last few months I decided to take a risk. It was a risk I didn’t necessarily see as a risk at the time yet now looking back it definitely was one. About a year ago I had found two different colleges I wanted to attend, they both were colleges that seemed great for me yet they had two different career paths. One was in holistic health and one was in my creative endeavors as an artist. I didn’t know too much about either yet I did know they both were calling my name. I struggled listening to my intuition at the time and was going through various different challenges as well. It was an overwhelming time for me yet it was a very new chapter in my life, I just knew I wanted to continue to work on myself and look into a new direction that could aid in my journey so far. Read more>>

Karizma Chestnut

The biggest risk I’ve ever taken was starting my photography business at 18 as a Black female entrepreneur. Rather than following the typical path of attending college, I chose to pursue my passion directly, believing it would enable me to pursue my career aspirations more swiftly.. Taking that leap has been incredibly rewarding, and I’ve been fortunate to experience success in my business for the past five years. Read more>>

Lamisha Jones

The journey to becoming a business owner is fraught with challenges. It demands significant sacrifices, evokes deep emotions, and often leaves one feeling trapped. Although the path may be lengthy, the rewards are ultimately worthwhile. Throughout this journey, I experienced feelings of delay and denial, yet in the end, divine intervention prevailed. There were numerous instances when life seemed incomprehensible, and I contemplated giving up, wishing to reclaim my investments. The struggles were real, and the calculations did not add up. Everything felt precarious, and the fear of losing it all was daunting. Rejections were part of the experience, as three individuals expressed their disapproval. Read more>>

Nickolas Alu

Risk is a fundamental part of success in entertainment or otherwise, it always will come down to the moments you chose to bet on yourself. I have a lot of stories of times I took a risk and it hurt me and I had to learn a great lesson because of it. On the flip side, I only have a few stories where I took a risk and never looked back. Here’s one of the more notable risks in my life which lead me into the journey I’m living today. I went to vocational school for audio engineering and from there I mainly recorded and worked with solo acts like myself. One day a friend of my roommate comes over and him and I get along pretty well off rip. Music wasn’t brought up at all for months, we would actually speak on old video games and make jokes for the few minutes we ran into each other. About 6 months or so later, he mentioned being in a metal band, showed me a record and I remember I had asked him to hear more. Read more>>

Katherine Yannucci

In 2004, I took a leap of faith that forever changed the course of my personal and career life. Up until then, I had poured myself into the fashion industry, earning my Bachelor of Science in Fashion Design from Syracuse University and working as a Fashion Designer in New York and Miami for nearly a decade. I genuinely believed I would spend the rest of my life in that fast-paced, creative world. But life had other plans. Everything shifted when I was diagnosed with Graves’ disease, a condition that causes hyperthyroidism. Suddenly, my body and mind was not the same and I couldn’t ignore it. Battling symptoms of this illness forced me to pause and reassess what truly mattered. Friends and practitioners recommended yoga as a way to ease symptoms, and it was through this practice that I found not only relief but a new calling. Read more>>

Bridggett Bess

The greatest risk I have ever taken was my attempt to move to London England after I obtained my BFA (Bachelor of Fine Arts) from North Carolina A&T State University. Coming off of a big win, receiving the Irene Ryan award for Best Actress in the Southeast region. The Irene Ryan Acting Scholarships provide recognition, honor, and financial assistance to outstanding student performers wishing to pursue further education. The Irene Ryan Foundation awards sixteen regional and two national scholarships annually. I also performed as the Lead Actress at the Kennedy Center in the winning production David Richmond. Our play was number one in the country. My performance garnered the attention of the Dean at Savannah College of Art and Design. I was offered a full ride to grad school! Read more>>

Machiel Bornman

Not that long ago I lived and worked in South Africa not knowing anyone in the USA when I saw an opportunity to do a mediumship workshop in California. The odds were against me, but my intuition kept pushing to do it. My mind kept reminding me of the logistical challenges – how much it would cost, having to apply for a visa to the US, navigating my way through a new country seemed very frightening. I took the leap of faith – I booked the tickets and made my way to San Diego not knowing what to expect at the very least. It took months of planning and preparation, but when the plane landed in California I instantly felt at home. One step lead to the next, I made a friend here and I made a friend there. And I met an amazing community through the mediumship workshop. Through them I managed to find a job as a nanny for a new born and lived with an incredible family for some time. I still see the kid often and will attend his 7th birthday soon! I recently obtained my citizenship to the USA and work as a psychic medium in California. Read more>>

Oretayo Fatokun

One of the biggest risks I took was pursuing music while still holding down a full-time job. It wasn’t just a financial risk—it consumed every part of my life. I threw all my income into my music, despite having people around me constantly draining my resources. I handed over money to advertisers and music marketers, and while some of those ventures ended up being financial losses, they taught me invaluable lessons about the industry. It felt like a gamble every time I invested, but I believed in the long-term vision. Read more>>

Alexys Williams

Business will always have risks—it’s just part of the journey! One of my most significant risks was deciding to go full-time with my photography business. It was scary not knowing if it would sustain itself over the next year or if people would even want to work with me. As someone in a creative field, those doubts can sometimes feel overwhelming. But taking that leap, pushing myself to take the risk, and fully committing to this passion has been incredibly rewarding. Looking back, I’m so thankful I trusted myself and made that decision—I couldn’t be happier with how it’s turned out. Now, these “risks” have become part of my daily interactions, and they’re what make my job so much more fulfilling. Read more>>

Damarrus Grant

I took a risk when I decided to make a feature film without having the money or necessary resources readily available. Even more intimidating, I had no blueprint for completing a full-length film, as my experience up to that point had only been in short films. But the idea—creating a horror story about a property manager who terrorizes her tenants—felt timely and relatable, especially living in Los Angeles, where many people I knew shared amusing but frustrating stories about their own experiences. Read more>>

Anna Simpson

At 54, after spending 20 years as a massage therapist, I took what felt like the biggest risk of my career: starting a new business from scratch in a field no one in my area had heard of—sound baths. Typically, at that stage in life, you think about winding down your work, not launching something brand new. But I felt called to this work so strongly. I loved attending sound baths myself, and I knew deep down that I had to bring this experience to others. Read more>>

Ashtyn Smith

Taking a risk of starting a private label clothing company. It was a pretty hefty investment and I’m not someone that shops a lot or spends a lot of money. So taking the risk and going for it was such a hard thing for me to do as I was starting from scratch with the company. The whole idea of the company was such a God thing I couldn’t ignore it anymore. He put it really heavy on my heart and really lined everything up. I did a lot of praying about it and he continued to open doors and put me in positions in life where I could finally say yes and go for it. Read more>>

Tina Kiaosouvath

When I moved out to Arizona 5 years ago, I didn’t have a plan other than moving to be closer to my family. I was a stay at home mom with a 1 year old son and a newborn daughter. A few months later Covid surprised the world. This was during the time when a lot of businesses shut down, but I was fortunate to be hired at a pharmaceutical manufacturing company. 6 months passed and I’ve always been a person to have the urge to learn and grow. Many have told me I would be absolutely crazy to leave a stable job for an offer I had at a start up company with possible endless knowledge I could gain. Even due to the circumstances of the world being in a crisis, I still decided to leave. Read more>>

Rakeeda Austin

Becoming a full time business owner with no money and not a lot of inventory. Had just bought my house not that long ago and had just gotten a brand new car. I had to take a big risk on making that decision especially since I had a previously been on a leave of absence from working in corporate America and was robbed at gunpoint while at work and was terminated while on the leave of absence. I didn’t have anything but my faith and God allowed blessings to come into my life and I was about to navigate through being a full time business owner for almost 4 years strong now. Read more>>

Trevor Darden

Well my story begins as a child learning the inside and outs as a musician early childhood. With a piano sitting in my grandparents living room. Or as they called it a ( Den ) Set aside from being partly raised from my grandparents I had been playing and learning melodies as a infant. Deciding how and when my life could turn out this way was not up to me or through my actual birth parents. My older cousin also taught nourished me as a musician he had been playing the trumpet. A marvelous instrument. He would sit down with me and go over certain scales that he was taught. My older cousin ( Antwon Boone ) was in a band. Not just a regular band or performing band but school band.  Read more>>

Mona Caruso

Ten years ago I decided to leave my very successful 25 year corporate career to be at home more for my three boys. I always held two jobs while I became a mother. My Corporate job was my bread and butter and teaching Pilates was my passion. When I left corporate I decided to build a home studio unattached to my home so I could pursue Pilates full time knowing I could create a schedule that would not interfere with my priorities at home. It was the best decision I ever made. I started teach privates and duets and I have been blessed with good fortune. I have expanded twice and now teach 4 person classes and privates and am completely booked again! I will not expand again because keeping my classes intimate provides me the opportunity to create semi-private experiences for all my clients. I absolutely love what I do and am so grateful that I can be home for my family and pursue my passion. Read more>>

Lauren Elizabeth

Anyone who owns a business understands the amount of risk and hard work that goes into being your own boss, late last year I decided to open my books as a makeup artist full-time and although it looks easy as I portray across my platforms I also share how it was super time-consuming and one of my biggest projects ever. Being both a creator and makeup artist has its struggles from being held to higher standards, and often can be a struggle building my clientele. I find that taking this risk was the best yet, the amount of opportunities that have been sent my way is unbelievable. One thing about risks, like mine, is that at first, it may seem like the worst risk ever, but I’ve learned along the way that some risks are a process of time and patience. Read more>>

Jah Garcia

All risks create impact. A Ripple. For me everything came to be, what seems to be within a short period of time. An act of fast decisions tapping into intuition. I had went to visit my mom and brothers down in texas, coming from Wisconsin back in 2014 I needed family. I needed to hear their voices and be in their presence. I spent alot of my life back and forth states. Life was full of stressors for me. Fast forward a few months. I was on my way back to Wisconsin to grab my belongings finding myself and new dwellings, in a motel room. Strange circumstances but that was always life for me. Always something. The first 3 days I spent in deep thought. Alone. In a place that felt dirty, dark and heavy. Although I never was one to pray I did for those 3 days wondering how did life bring me here. In a place where I felt as if all my life I tried and tried for others but never for myself. Read more>>

JP Garcia Jr.

Back in November 2023, I lost my job as a Lead Designer for a home decor company in Littleton, CO. It wasn’t a total surprise, given the economic impact COVID had on the home improvement industry. Sadly, the company didn’t survive much longer after that. Without a job and needing to cover my home, food, and pets, I had a decision to make: should I keep searching for an office position as a designer, or take the leap into self-employment? As many people know, job hunting these days often leads to dead ends, with most applications going through recruiters just collecting information. Read more>>

Jules Marsh

Kelpful has had quite the journey since the starry eyed dreams of having a seaweed farm back in 2017. We learned very quickly that it wasn’t possible to have a seaweed farm in the open ocean in California, yet. This led us down two paths: networking and supporting the industry and agencies in making that possible & wild harvesting seaweed so that if/when we had our own farm, we would know how to process it and also build the market and consumer awareness. From 2020 to 2023 we developed phenomenal food and self-care products, built a well-known brand, and were in stores like Whole Foods. We went this direction because at the time, and it’s still true today, it’s what the seaweed industry in the US really needed. Read more>>

Jennifer Campos

I had constructed my life and identity around being a “working woman,” juggling multiple careers that I embraced wholeheartedly. My sense of self was rooted in my talents and commitment. While working at an ad agency where I learned and flourished in various departments, I was also dancing professionally and styling projects for different artists. I was a fusion of all arts. I’ve always been the kind of person who stays active. A typical day involved going to my 9-5 office job, rushing home to shower, preparing a quick salad, and heading off to either a gig, class or rehearsal, which sometimes stretched into the early hours. I was always on the go Read more>>