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.
Amber Abeid
Going from a commission salon to booth renting was the biggest risk of my career. I was at my old salon for 5 years & had built a steady clientele there but one day I realized I just wasn’t happy, I was just comfortable where I was. I was working more hours than I wanted to, I wasn’t doing the type of hair I was truly passionate about. I felt like I was just an autopilot during my shifts and I was starting to feel burnt out. I decided that once I felt myself losing the passion to do hair, it was time to make a change. So, in 2021, I made the change to go out on my own & booth rent. It’s been a wild ride but if I had the chance to redo it, I wouldn’t change a single thing. I am so much happier doing hair & it shows in my work too & my clients can tell that I love doing what I do. Read more>>
Tara Ghormley
I developed long COVID after my infection in March of 2020. I was able to work full time at a specialty practice for a few years after becoming ill. As time passed, my health worsened due to the workload and long hours. I knew I needed to leave traditional clinical practice and my best friend put forth an idea for a mobile ultrasound and consulting company. I never saw myself as a business owner and in fact had previously decided it was too much hassle to own my own clinic. However, when my friend proposed the idea of a mobile business, I knew it was the perfect opportunity given my personal needs at that time. Read more>>
Marlene Morales
The biggest risk I have taken is leaving my small town. You see, I grew up in a small town called King city in Monterey Bay County. Probably an hour away from Target, an hour away from the mall. Luckily, we had a movie theater and a park to entertain ourselves while growing up. I am really grateful and humble to have grown up away from the city life. I just knew growing up there was way more out there, I was super curious and always loved exploring. Therefore, when I turned 18, I left my small town to attend college and never looked back. Graduated from University and had a job offer back home to become an Environmental Science teacher. Seconds away from signing a contract to be stuck in my hometown and working with high school students. Read more>>
Robin Spielberg
In the late 1980’s, I began playing piano in hotel lobbies and piano bars to support my aspirations to become a successful working actress. I had played piano my entire life, and blessed with a really good memory for a tune, and ability to arrange music quickly, I managed to secure a highly coveted “steady gig” at the Grand Hyatt in New York City, which was situated right above Grand Central Station. Acting jobs came and went, but the piano gig was always there, and it was on this job, that I began trying out incorporating my own original compositions into my sets. Slowly, but surely, and each week, with more confidence. Eventually, I had enough original piano melodies to compromise an entire set (3 hours.) Listeners began complimenting me on the originals and asking if I had a CD for sale. Read more>>
Christopher Lees
A few years ago, we decided to try something different with our business – produce a board game. Horrible Adorables has two main areas of focus – our own artwork that we show around the world and freelance design work for toy companies. A good portion of the art we make falls into the designer toy category (small run art collectibles that reference toy nostalgia and use traditional toy production techniques to create). In 2019 we released a vinyl figure called The Familiar. It was a cute little magical creature with a cape, wizard hat, and satchel with a frog poking out. For the packaging we decided to go with a drawstring pouch to play up the magical theming of the toy. Jordan even joked that we should toss a twenty-sided die in the bag to really push a Dungeons and Dragons reference. Read more>>
Kristin Lindgren
At times one must follow a path no matter the risk. I had to follow my path no matter the risk, I knew it with every fiber of my being. Many have had their calling to follow a path. Have you ever taken a huge risk and it felt like it was something that felt so right that the risk no long mattered? In January 2021 a fire ignited in me with flames I had no control over. We were in the middle of a pandemic and The CDC just announced that it had found at least 22 confirmed cases of the more contagious SARS-CoV-2 variant in Florida. Yet, at the same time, as soon as I heard about an amazing Targeted Cryotherapy device that reduced Fat and Pain, and that no one had it in our area, I instantly knew what I was meant to do. I knew I was meant to open a healing and beauty service with the device. It was not a decision, it was a calling, a divine path. Read more>>
Pier Mason
In life we all have to take risk, but the most satisfying risk are the ones that force the hustle out of you. Hairstyling was a gift that came to me naturally. I styled my sisters, my cousins, all the neighborhood girls, friends, and the list goes on. My entire life I did hair. However, instead of going to school for hair I decided to get my business degree. I working in corporate America for 12 years before I decided I had enough. I put my way through cosmetology school, built clientele, and worked my full time job. Once I felt like I was stable enough, I quit and chose to work in my salon full time. This was the most scariest yet fulfilling risk I had ever taken. Read more>>
Alexis Stapleton
So I think the biggest risk I have ever taken, was definitely going to New York City to chase my dreams in modeling. The modeling work in New York is so cut throat and competitive. You have to really keep your head up, and remember what the end goal is for yourself. It definitely was not an easy rush for me to take. I got signed with an agency up there, and it was definitely something I worked very hard for. But like I said New York is very intimidating and cut throat. I spent a month there, doing so many photo shoots, and going to castings through my new agency I got signed too. All in all I think it shaped into a stronger model and woman. Read more>>
Alissa Wyle
One of the biggest risks I’ve taken was dropping out of University. As many do. I went right from high school to college, majoring in contemporary dance. At the time the only photography I was doing was for my own sentimentality. I had not yet tried portraiture, what later would spearhead my career. I decided to leave school despite the dream I was holding on to at the time of being a professional contemporary dancer, because the everyday life of training for that dream was withering my self confidence and leaving me feeling deeply unmotivated. I had always been a driven person, able to work hard toward my goals, but as I got deeper into this dance program, the more I watched myself drag my feet. Read more>>
Ozgur Yesilbas
Being defined and defining myself as a shy and reserved person, even writing about myself I would classify as taking a risk withouth assessing how big or how small it is. The biggest one that I would say is when I decided use the opportunity provided by my brother to become a tattoo artist. Just like my older brother, I too graduated from one of the top high schools in my country and immediately enrolled in university. Read more>>
Kate & DJ Hoessle
Rain splattered across the windowpanes, boxes strewn about our empty house, that was our home; was because now it would be someone else’s, both our hearts felt as gray as the weather outside. How did we get here? What were we doing? We were on the precipice of everything we ever wanted and now that our dream was turning to reality, it felt more like a nightmare. We were risking it all. Casting aside the, “American Dream” we had worked so hard to build to chase a life of adventure in far off lands, but in those final moments before the jump, fear raged in our veins. It was now or never; so we jumped. Read more>>
Ashley Shihab
The biggest risk I have ever taken was following the little voice that kept whispering to me “there has got to be more to life than this.” That quiet voice knew that if I didn’t uncover my passion and purpose and if I spent my whole life in Corporate America where I didn’t belong, my authentic self would wither away and I would never feel truly fulfilled and at peace. It would have been easier to stay in my comfort zone that at the time consisted of working at a soul sucking job, going to the gym, watching TV, rinse and repeat. But if I had done that I would have always felt stuck and my life would have been so blah! Read more>>
Sommer Leigh Plotnick
I took a risk and walked away from high paying job to follow my passions, as a holistic facilitator and educator. In 2015 I relocated back to Las Vegas after divorce. I was a single mother to a 16-year-old daughter who was accustomed to a solid middle-class lifestyle. It was important to me that I showed her that women can be resilient, diversified be financially successful. I took a job as a mortgage banker, specializing in refinance loans. It was a great paying job in a toxic masculine environment. I found myself feeling overwhelmed and out of touch with my purpose. I needed to readjust…To be brave and take a risk. Read more>>
Shannon Brydges
Opening MALOFTA VINTAGE in a physical space was a big risk for me. I did not think I was ready and I have always been oh so very risk averse. Certainty, guaranteed income, safety – I love those things. I was currently working a full time job at a place I had spent 14 years and my vintage business was primarily through Etsy – just a side hustle. Still, it was growing and so I was curious: how much would it cost to open a space? It was my dream. I just wanted information. Read more>>
Tenisha Hicks
The most comfortable place in the world is staying in your comfort zone, right? Well, I guess I like being a masochist because starting a business in a place that you’re just not the “type of person” to run such a business is extremely uncomfortable. Opening and operating Isha Esthetics and Wellness is a labor of love. It’s my way of providing a safe space for Black women and a very marginalized community in Utah looking for a place to heal, grow, and glow their fullest. Being in business for 6 years, it shows me just how valuable a routine that is around self-care and the horrible misconceptions that there is if you take the time to do so. Especially as a Black woman. Read more>>
Catherine Simon
My professional life has been a bit of a windy road to say the least. I graduated from UNC-CH with a degree in Recreation Administration and Leisure Studies with the intent to run a summer camp, preferably for children with disabilities. My first job after college was in a Recreation Center and while I enjoyed it, I was craving more intellectual stimulation. I perused the community college course list hoping for a class on reupholstering or refinishing furniture, but the only one available was Emergency Medical Technician. As a life-long learner, I decided it couldn’t hurt to have some medical skills. That decision changed my life. Read more>>
Virginia Wall Gruenert
I wrote my first play in 2007 about four women and the effect alcoholism (theirs or a loved one’s) has on their lives. I was inspired by my husband, who at the time was four years sober. He was so impressed by the play that he hunted down an empty building to rent in Washington, PA, and we built a theater from the ground up. We were still relatively new to the Pittsburgh area and didn’t know many local theater artists yet, so I played all four parts. The play, “Shaken & Stirred,” ended up being named “Best Play of 2007” by the local paper. Thus off the WALL Productions was born, and my husband is now twenty years sober. Read more>>
Sarah Zimmer
Starting my own physical therapy practice in Boulder, Colorado felt like the biggest risk I’d ever taken in my adult life. At that point in my career, I had been out of school for just 1 year and feeling completely lost. I wasn’t loving the insurance-driving clinical environment, and I really felt like I wasn’t being the best practitioner I knew I could be. The first job I interviewed for was for an independent contractor position with a chiropractor. I had no idea what being an independent contractor meant, but I learned very quickly that I needed to be my own business, market myself, and obtain my own patient load without help. I had zero background in business, but I knew I’d be able to learn along the way. Read more>>
Joel Livingston
I am a basketball coach for a local high school in the North Texas area. I will begin my twenty-third year teaching and twenty-second year coaching basketball. In my career, I have coached both boys and girls basketball with both having challenges as well as positivity. I have coached a number of sports; basketball, volleyball, track and football. I have worked at college camps such as Baylor University, Texas, and Texas Christian University teaching the game of basketball. I have made it a point to further my education for the game of basketball to learn as much as I can to give the players whom I coach a great experience. Read more>>
Kristen Fedeli
I would say the biggest risk that I’ve taken in my life is quitting my teaching/counseling career of 12 years to pursue business ownership and working outside of the educational system. Ever since I was a little girl, I had always wanted to be a teacher because my role model and best friend, my Grandma Janet, was a teacher and reading supervisor. She would bring me her old grade books, lesson plan books, text books, pens — all the things to make a girl’s dream of “playing school” a reality. I was hooked. I went to Penn State to get my teaching certificate and I taught 5th grade for 7 years. Read more>>
Sylvia Kelsey
My entire adult life has been a series of thoughts turned in to reality. I never really pondered the idea of fear or even for once backed down from something I wanted to do. When I was faced with challenges in my marriage and I had to make a decision to stay or leave, I choose to leave because I knew there was better awaiting me if I dared to risk starting over new. The journey after marriage was long, but with each step forward life got easier, and things felt better. Doors began to open to new adventures and those doors led me to finding the person I am today. The journey through feeling rejected and being in emotional pain, has helped me to become a bigger risk taker which led me to write my new book, Ask Abundantly – Daily tips to help you live the life you desire. Read more>>
Matt Poon
One of the biggest risks I’ve taken was opening my own private practice in the middle of 2020. Throughout my graduate training I had always aspired to work in university counseling and work my way toward being a training director or outreach coordinator. I found tremendous meaning in prevention work and being able to make mental health services more accessible to communities who ordinarily wouldn’t seek out treatment due to stigma, financial barriers, or negative previous experiences. As I worked longer and longer in university counseling, I witnessed how mental health services were shifting away from a community or prevention model and toward a more short term and crisis management approach. It was throughout 2019 that I noticed how dissatisfied, unfulfilled, and overwhelmed I was despite being on a wonderful team. It was at the end of that year that I decided that I wanted a different relationship with my work that involved more balance, flexibility and creativity. Read more>>
Three Ladies in Wilmington 3LW
Creating “Three Ladies in Wilmington” was a risk due to the innovative approach it took in providing casual but meaningful opportunities for Black professionals to meet and connect socially and intentionally. By focusing on fostering a sense of community and facilitating networking, the event aimed to address the lack of inclusive spaces for Black professionals in Wilmington. The risk stemmed from the challenges associated with introducing a new concept and breaking away from traditional networking norms. The success of “Three Ladies in Wilmington” relied heavily on overcoming societal barriers and ingrained expectations regarding professional interactions. Read more>>
Robb Ortel
I remember a few years after my kids were born while I was working a 9-5 job managing a group home for developmentally challenged adults, that I made the risky decision to quit my job and commit, full time, to following my dream of being an airbrush artist. My kids were only 2 and 5 years old. My wife, at the time, was only working part time. It was a scary scenario to risk the job security I had to follow a dream. But had I not taken that risk I would not be where I am today. I have a successful career custom painting motorcycles and guitars, I was the in-house airbrush artist for Orange County Choppers and on the reality show American Chopper, I created a successful clothing line, and I have a really cool television show on Amazon Prime that I created called Robb Ortel’s Art Attack. Read more>>
Tracy Livecchi
Almost everything I have done in my life has come with risks. From moving across the country and away from my family home to exercsing on a regular basis. That is because I was born with a very complex congenital heart defect. Throughout my life, I have had more cardiac surgeries and procedures than I can count. I’ve had a pacemaker since I was 12 years old, and am now completely dependent on it for every one of my heart beats. My doctors didn’t ever expect me to live as long as I have, and I was warned along the way about the many risks connected to things most people take for granted. Read more>>
Meryska Taylor
Once upon a time, in the midst of a global pandemic, a brave and determined woman named Meryska found herself at a crossroads in life. For six long years, she had dedicated her time and energy to a major health insurance company, only to be unexpectedly let go. As a newly single mother of two, she faced the daunting challenge of providing for her family with no financial support other than her own and occasional help from her loved ones. But Meryska was not one to be easily defeated. She had always possessed a talent for styling hair and maintaining locs, which had been her cherished side hobby for family and friends. With no other immediate options in sight, she decided to take a leap of faith and turn her passion into a business. Read more>>
Joshua Levinson
I recently retired from a 24 year career as a music teacher in the New York City Department of Education school system. The decision to teach was mostly based on the desire to live a more stable life replete with a steady income and of course the promise of.life-long healthcare and a decent pension, Yes, it was a decision based on pragmatism, but it followed many years of an unsuccessful struggle to make money as a musician in New York. Retirement coincided with covid. I started and completed my fifth CD in February/March of 2020 only to have all music making stop the second week of March. Read more>>
Amelia Romano
I have chosen to pursue the performance of classical music (mostly chromatic, involving movement between half and whole steps; equivalent to black keys in piano) using a mostly set key, white key instrument). This requires me to adapt works written for piano and pedal harp and flip levers throughout the performance of a work, but rewards me with a wide-ranging rich repertoire featuring works from Chopin and Debussy to Glass and Bruebeck. Read more>>
Whitney Blake Myrick
I feel like any creative takes risks in some way any time they put their work out there. It is so fulfilling but sometimes terrifying. I still struggle to overcome the fear at times…but I’m proud of how far I have come when I look back to where I started. The first time I performed in public was one of those terrifying instances. Other than my ten-year obsession with karaoke, I had only played guitar and sung for friends. I think I had posted one video on Facebook at that point. Read more>>
Shariee Jones
I believe that taking a risk on starting any business is necessary if you believe in yourself. I went to college to study Consumer Education in Fashion Merchandising, Business Administration in Technology, and Counseling. However, I learned a lot about business from trial and error. I sacrificed time and money like any real business owner in order to develop and grow my business. I legally started my company Divine Army in 2018 but had been using the name far longer. This was my third time starting a business and since I included God in this last venture, I believed that Divine Army would become something that could create generational wealth. Read more>>
Gwendolyn Rehm
This year I took the risk to rent a location instead of running my music studio out of the church I was working for. It was really nice to have the free space where I could also teach students from the community, but I was limited to a very small window of time. A friend helped me launch an idea for a week long morning only summer camp, but the church location couldn’t support. This prompted me to search for a space to call my own. Finding a location within my price range was a challenge, but I was able to find. a fantastic space. When I moved to the new studio, I had 15 weekly students. 3 months later, not including camps, I am up to 35 weekly students, while working the limited hours I had planned all along. Read more>>
Derek Bauder
Leaving the Military to pursue a career as a Filmmaker was the most considerable risk I’ve ever taken. In 2014, I enlisted in the U.S. Coast Guard right out of High School to earn free college in hopes of attending film school. I chose the Coast Guard as my Branch of Service because my Father was a Coastie, and the idea of saving lives as a profession sounded noble. I went to Boot Camp in Cape May, New Jersey, and was stationed in Port Angeles, Washington, on Coast Guard Cutter Active. I was a deckhand performing typical ship work and participating in Counter Narcotics operations. Read more>>
Jonathan Cruz
We take risks every day. We are all familiar taking calculated risks pushing us towards a desired outcome, but a lot of the time doing nothing is a risk. Ive always felt that the risk of trying is better than the risk of sitting on the sidelines. Things always work out if you give it your all don’t play the victim and go get it! In 2016 Katie Cruz and I decided to take a risk and open a boutique fitness studio in a rural community. Based off the current census we would need every single resident to become a member in order to thrive. Through good intentions, excellent programing, passion for the product, strong branding and a community that had a thirst to be healthy our business HIIT Logic thrived. We then went on to open an additional 4 studios including multiple during COVID. The perceived risk of opening where, how and when we did was more of an opportunity. In fact Id prefer “seizing the opportunity” as opposed to taking a risk. We currently are growing stronger than ever both as a business and as a community. Read more>>
Beth Morrison
My decision to start my own company in New York City is by far the biggest risk I’ve ever taken in my life/ career. I didn’t know anyone in NYC and I didn’t have any money, so I was really starting at ground zero with an idea, a dream, and some chutzpah. There have been many hard moments along the journey but the good far outweighs the bad. Read more>>
Brittany Byrd
Life is truly about taking risks. You never know what opportunities arise when you are willing to put aside your fears, worries, and SOAR: soar into your future filled with an abundance of success and happiness. We get so focused on “what if we FAIL”, but the thing is, how would you ever know if you never try for yourself? Are you willing to live your life on a “should of, could of, would of”, or are you ready to actually do what it takes to succeed? Once I realized all of that, on top of understanding that ultimately, we as individuals choose our own future with the decisions we make (not including things that are out of our control in life), it was like instant tunnel vision to succeeding in life. Trial and errors will come. Read more>>
Dan Misdea
The biggest risk I’ve taken in my life was quitting my job to focus on cartooning and illustration. After graduating with an Economics degree, I spent several years working in accounting in finance. I was making comics in my spare time while trying to advance my career, but it started to feel like I was burning the candle at both ends. It got to the point where I had to either sink my teeth into my career or explore a passion that needed my full attention. Read more>>
TJ Thorne
From the time I was a kid, I was always taking risks. Growing up in a rural area meant that my childhood was filled with climbing trees, riding dirt bikes, jumping off of roofs, and as I grew older, skateboarding, snowboarding, and playing ice hockey. After I graduated high school I left my hometown just outside of Pittsburgh, PA to move to Portland, OR. I loaded up my Honda Civic and pulled a U-haul 2,500 miles to a place that I had never been and knew no one. I didn’t even secure a place to live until halfway into my journey. Read more>>
Dr. Andrew Rimby
In March 2020, right at the start of the pandemic, Stony Brook University, where I was teaching during my PhD program, had informed all of us that we had to switch from in-person teaching to virtual teaching. I had a nuanced conversation with my students about best teaching practices when we switched to online learning, but we thought there was a possibility that we would see each other in-person in about a month. However, we all know how that turned out. The first week of working from home, I was also hard at work on my dissertation, was going as smoothly as possible since I had an exercise routine (intense walking outside), and then I learned that my Nana had passed away at her assisted living facility. Since I knew of the risk of traveling because of the coronavirus, I packed a suitcase that would last me for about two weeks so I could be with my parents for an extended period. Read more>>