You’re working hard, things are going well, piece by piece you’ve built a life you are proud of, you’ve overcome obstacles and challenges, beat the odds and then you find yourself at the center of an unexpected dilemma – do you risk it all to keep growing? What if growing means leaving the job you worked so hard to get or the industry you worked so hard to break into? How we approach risk often has a huge bearing on our journey and so we’ve asked some of the brightest folks we know to share stories of risks they’ve taken.
Molly MacDonald
In general, I am risk averse. I don’t like heights or speed. I am fiscally conservative, but if I believe in something as I did when I thought of the idea to help women with breast cancer, I guess I bet on myself, meaning my abilities. Well, I had the vision and a plan in place. The risk was getting others to believe in me too. At the time we were just getting started, we had rescued our home from foreclosure, as I was unable to work while in treatment and had a hefty COBRA premium. I have learned that I not only have vision, but that I am strategic and tenacious. It helped tremendously that my husband supported my vision, even though he thought I had two heads, but ya know he sleeps with me, so he went along with it. And not only that he is far more detail oriented than I in some respects. He is my true co-founder and does all the sweeping up behind me. . . Read more>>
Kristin Voss
A little more than 7 years ago, I started my own skincare + beauty line: KVossNYC. The products are all certified vegan + organic and curated to bring out and enhance your own natural beauty, not cover you up. The mantra is: Love yourself, Love the world around you, and find beauty in what is natural and real. KVossNYC remains a giant chunk of my heart. I literally started with a mixing bowl, ingredients, and a dream in a very small NYC kitchen. Building that business to what is it today is one of my proudest achievements and it has lead to a lot of positive personal growth. There is nothing cooler than creating something from just an idea in your head. When the pandemic hit, I lost two giant deals I was working on. My sales plummeted. I wasn’t sure if I was going to be able to keep the business going when people stopped buying things that weren’t necessities. But I couldn’t just give up, I had to pivot. Read more>>
Butta B-Rocka
Hi everyone, my name is Butta B-Rocka, I am a highly versatile serial entrepreneur. I am an executive film producer, director, screenwriter, actress and top-charting internationally acclaimed recording artists. I am a recording artist who has released several albums and singles that have been heard around the world. I have collaborated with some of the biggest names in the music industry, including Janet Jackson, Akon, TLC, Kanye West, NAS, Collective Soul, and Zac Brown. Read more>>
Nicolas Sotomayor
My parents made the journey from Chile to the US without knowing the English language and carrying a 2-year-old. That decision must have taken great courage. I couldn’t imagine doing that myself, but I also knew I wanted to leave my comfort zone. The very least I could do is move across the country for love. I met Maki 10 years ago while we were touring Germany. She was a traveling tattoo artist and I was on my way to Oktoberfest. I remained her client throughout the years and we became friends. On my last visit to Los Angeles in 2022, I decided to take her on a proper date. We had amazing conversations about our life goals and ambitions and I knew I had to make a major decision when I returned home to New Jersey. Read more>>
Richard Bakewell
I’ve lived in Los Angeles for 19 years, and I learned that the studios never come knocking at your door to ask you to direct a big budget movie. Last year I decided to take a gamble, and spend a part of my savings on producing and directing my second feature length film called Roswell Delirium. It’s a sci fi 1980s throwback psychological thriller with an all star 80s cast featuring Anthony Michael Hall, Lisa Whelchel, Reggie VelJohnson, Sam Jones, and Dee Wallace. And producing your own film there are no guarantees that anyone will ever want it or even want to watch it for that matter. Read more>>
Anne Watson
Deciding to plant a vineyard is a risk in itself for many reasons. But, planting our vineyard with the aim of creating our own family wine label was a decision that my husband Tim & I made together when we bought our ranch here in Fallbrook, CA almost a decade ago in 2014. And the risks seemed reasonable at the time as he was going to oversee the vineyard as his main occupation, and I would continue my photography business to support us. But, things took an unexpected & devastating turn in 2021 when Tim passed away after an 18-month battle with stomach cancer, and I suddenly found myself at a crossroads with a huge decision to make. Do I fold the business and walk away? Or do I take over where Tim left off, learn-as-I-go about wine growing, and carry on our dream of having a family vineyard on my own? Read more>>
Kathryn Spencer
Moving to San Angelo, TX to open a brand new business. I had never heard of San Angelo until a year prior to moving here, buying a home and opening a business with 2 of my 3 business partners that I was still just getting to know and had only met once. It was a huge leap of faith, a strong belief in what we could do together and a trust fall into what could possibly be one of the best decisions of my life. Moving around and changing homes wasn’t a new concept to me. I grew up in an airline family and then traveled with my husband for 5 years across the country while he took contracts with hospitals as a travel nurse. We had become rather quick on our feet and learned to travel light so we could be flexible and move if and when we wanted or needed. Read more>>
Bobby Corpus
I think one of the biggest challenges of being an author and writer is taking risks. When we write, a part of us is being put into page and paper. You mold together all of your ideas for the world to see, and to share it with just about anyone is always a risk. Ask a writer what they are writing or if you could read an excerpt from their latest novel and they will cringe at the idea sharing it. There’s a risk of people not liking what you wrote or perhaps a lack of understanding too. However, risks can be rewarding when your craft is loved and appreciated. This is exactly how I felt when I began to share my writings with the world and taking that risk. Read more>>
Anna Gieselman
During the COVID-19 pandemic, I made some major changes to the direction of my life and my businesses. From the outside, these changes didn’t appear to be the wisest choices but from the inside of my heart, they felt 100% right. I went from teaching yoga for a busy gym in bustling Austin Texas (where I grew up), to moving to the sleepy town of Santa Fe, NM with no connections or employer to lean on. At the time, I was studying applied neurology which is practice of training the brain in order to heal the nervous system and body. This is a fairly new area of study and for the most part is unheard of in the fitness world. Read more>>
Melissa Roddy
For over twenty years I spent my time living the 9-5 grind growing and nurturing brands and businesses that weren’t my own. I poured myself into companies and teams and was dedicated to the task and people at hand. Often times I’d find myself consumed with a work project, trying to figure out how to take it to the next level. It was fun and exciting, yet it often didn’t align with my passions or interests. Fast forward to a role in corporate banking where I couldn’t connect with the topic and felt a continuous internal tug that my time and energy was not being well spent. I was torn, the 9-5 was secure and steady, and with one of my top 3 needs being security it met what I thought was a critical personal need. Read more>>
Amy Stein
I had a baby at the age of 40 and each day that I walk with my child, I feel the responsibility to be my authentic self. Just before my daughter turned one, we found ourselves on an outing around town and to escape the cold, we walked into a boutique for a cup of tea. The space offered me something that I can only explain as a feeling and three visits later with the owner, I found myself with a treatment room for my Reiki services and the opportunity to grow a business. Unplanned in the moment, I wanted to provide support to individuals in the same way that I myself needed support years ago. Read more>>
Stella Piontek
In 2022, I was feeling the burnout of the seemingly never-ending pandemic, and carrying all of the weight of the past two and a half years on my shoulders. I was feeling empty inside while working in the hospitality field, being a barista and had already poured out all I had to give in the medical field working in a nursing home right when it all broke loose in January of 2020. After these two endeavors I knew that I needed to give myself a change and needed to find out what that change consisted of quickly. I looked around at a few different options and found myself standing in the admissions office of The Academy of Beauty Professionals, a college designated to cosmetology, barbering, esthetics, and nail classes. At the time there was no finite decision on what the game plan was, but I was exploring my options. Read more>>
NATASHA ALLICOCK
Newly married!! I took a risk on love when I met and married the love of my life! My wife inspires me every day to network, grow my business and embrace all the challenges this business comes with. With her support and belief, I moved my Professional/Private Chef business from the DC Metro area where I started, to Fort Lauderdale/Miami/SoFlo area, the melting pot of Caribbean cuisines, and it has been a delicious & exciting journey! I uprooted my life and took a chance on my business and applied the knowledge I acquired over 17+ years and applied it to my new venture in the culinary scene in Miami. Like any risk you take in life and business it comes with obstacles and learning curves. Read more>>
Eva Nicolait
The kind of risk I’m addressing here is the objective in a work. The process of painting is interesting to me because there is risk involved from the first contact to the last. The beginning, for me, is never anywhere near how it ends, and, along the way I encounter cool ideas, the safety of the past, supportable but unexciting solutions, and then, in dismissing all these, the unknown. Having a brush, or whatever, and skills in hand on one’s way to wherever can feel like the edge of a precipice where one can retreat to the safety of past gestures, ideas, or take those things we’ve already done and extend them to somewhere new, or somewhere completely different. The resolution is the point at which intellectual and aesthetic curiosity is satisfied. Read more>>
Sarah Pesso
My life has been full of risks of me believing in myself and taking the plunge. The first big risk I ever took was fully committing and believing in myself and my business. It was taking my first solo trip across the world to Australia. I was a huge move that completely transformed my life as I was forced to grow as a person. I did not come back the same person after that trip. My 3 week trip turned into 4 months and I almost didn’t come home. Another risk I took was investing $12,000 into a business where I connected with multiple 7/8 figure earners and learned so much about the digital world. This was 8 years ago and I am still connected with those people today. Even though the business didn’t really work out, I wouldn’t change a thing because of connections made. Read more>>
Cuzo Key
The biggest risk I took career wise was my last project NIONEK 3. I actually did what it takes to make a complete successful body of music. I didn’t cut corners or go the cheap route like I use to do. I took my time with it. And it was a make or break situation because NIONEK 1 & 2 didn’t hit how I thought it would so NIONE3 was about to be my last time recording music if it didn’t land as well. But it did! Moral of the story is stay true and genuine to your craft and it’ll all work out! Read more>>
Terra Weiss
Hoping to become a best-selling author is undoubtedly, as a pie in the sky venture—only to be topped by dreaming to make it big in show business. It’s a risky proposition. For me, there was added risk because I was a thirty-eight year old mother of a year and a half old: not exactly the ideal time to be reinventing myself after climbing the corporate ladder doing marketing copywriting for tech companies. But the heart wants what the heart wants—and I was driven to tell my story So, day by day, I’d sit at my laptop and type away during my daughter’s naps and her time with Nana. Fast-forward six months, and I had my first draft of my first novel. Hooray! I signed up for a conference to pitch my story to agents and editors. To my shock, it went well! I got requests, which gave me the encouragement to keep going. Read more>>
Krista Parks
Being an entrepreneur is a risk in and of itself… if you know you know. But after starting my wellness facility from the ground up and running it for 8 years, I decided to change paths. I still love health and wellness and its a big part of what I’m still doing, although in a different way now, and thankfully the employee who bought it is doing amazing things there still! But I had to make the decision to take a risk on myself. Working for yourself is hard. You have to develop such a strong sense of trust in yourself and your team and deciding to change directions was scary. People thought I was crazy, not to mention having this realization in the middle of the 2020 Pandemic… Read more>>
Jasmine Blackbear
I would definitely say I was the black sheep of the family growing up. I grew up being into alternative fashion and music which my family didn’t necessarily get. I also had the idea of not attending college once I graduated high school, my parents were super against it. They would tell me things like “that’s not a real job”,” you’ll struggle with that career”, etc. I however believe in having faith in yourself, I think you can be successful in any career path you decide on as long you believe that. Read more>>
Derrick Henderson
Taking risks in life is a necessity, but the biggest risk I believe we can ever take as a person is learning who you really are inside. No fluff, no lies, just deep self reflection and knowledge of oneself, Really looking within ourselves and really being honest about the mistakes we make, the choices we decided to make that affect others around us, what we really and truly like, love, feel, desire or what solely fulfills us without relying on any another person to do it for us. Taking this risk gives clarity of the mind and soul, this eventually led me back to what I truly loved doing after a decorated medical and military career, which is creating art. Read more>>
Tracy Graham
A couple of years ago I felt the Lord calling me to make a change in my vocation. I had been a teacher and coach for 20 years at that point and changing careers felt like a crazy idea. I wanted to be faithful so I took the leap. A friend of mine, JP Findley, had asked me if I would be interested in joining his real estate group at Rogers Healy and Associates. After much prayer and talking with my husband, I felt like this was where the Lord was leading. Now, two years into my real estate career, I can say it was the best decision I have ever made! I absolutely love being able to help everyone from first-time home buyers to investors looking for new ventures. This career is so much fun and I love meeting new people from all walks of life. I am so blessed I get to do this every single day! Read more>>
Briana Butler
The biggest risk I have taken lately has been to go forward with a complete rebrand of my business after only re-launching the current version 5 years ago. After the pandemic I learned so much about my abilities as a business owner, and I learned how to push through slow times. Now rebranding is a big risk because since 2021 I have made a name for my business/brand and people were just started to know me, my business name, and my business values however I had to take a big risk of rebranding to ensure my business & brand matched each other and that my advertising would truly capture my target market. It took about 4 months of working with a design team, and another 4 months of figuring out all the background details for this new brand to come to fruition and I could not be happier with my choice to rebrand! Read more>>
Jefferson Mathis
Just the thought of forgoing your typical 9-5 job to pursue one’s dreams is already risky. To actually turn those thoughts into reality is 100x more risky in my opinion. Where do you start? Are you actually ready for something like this? Why leave something secure for something that you could easily fail doing? These were all in my head as I decided to move to a new state to chase my dream. Let me back up. I started with photography when I was about 16 years old. Back then, it was just my friends and I skateboarding and wakeboarding all the time and I used photography as a way to document our riding and progression. Read more>>
Jessica Cornel
Starting my social media agency was a risk that didn’t make sense on paper. I had just received my Master’s degree in Public Relations, finished 2 years at a public relations agency, and had a few freelance clients I loved to work with after my 9 to 5. I was financially comfortable and ready to settle down a traditional life with my small family. But for 8 months, I had been repressing this feeling of being out of place where I was in life – like what I was doing, what I was meant to do, and like I was meant for something more. Deep down, I felt like I was missing out on life just by working 9 to 5, having to ask for PTO, and feeling like I was married to work without a choice. I wanted to go to work because I felt passionate about what I did and because I loved every single piece of what I did! Read more>>
Sage Bower
As I have grown up, health and wellness and the diversity of what that means for all of us has become incredibly important to me. In a world that is focused on the grind and making the most money at any cost, I have chosen a path where the goal is to slow down my own life and to inspire others to slow down and to prioritize their own wellbeing. As part of a society that moves so quickly, this is a risky decision. Building a business structured around wellness and mindfulness means that I, myself have had to put instant gratification and financial success on the back burner and rely on my support network while I build a life which represents the change in the world I wish to see. I am very grateful for the support I have received along the way and I am looking forward to what the future holds while remaining grounded in the beauty and chaos of the present. Read more>>
Marlo Miller
We are all scared of taking risks especially life changing ones. The biggest fear is not making it in business or any area of our lives but as my mom always said, what’s the worst that can happen, you will be in the same position you are now if you do fail. She was right. Owning a business is not for the faint of heart, lots of struggle, time and effort. Building relationships is key In any business. Read more>>
Choyce Schwartz
Sometimes in life you have to be willing to take risks. That includes sacrifices. When I was in college working multiple jobs I had to risk not making enough money to invest more time into my craft, spending more hours in the studio, and interning without pay in order to learn from the best in my field. Overtime I grew into my craft gaining experience and honing my skills. When I focused on the commitment to my work that’s when the money came and it eventually became my full-time career. Taking risks in music has helped me make it into not only a career but a life I can enjoy while not feeling like work. Read more>>
Rashad Jiles
Rashad Eats The World was born from my travels as a flight attendant. During the pandemic I wasn’t able to visit some of my favorite places and eat some of my favorite foods like Aguachiles in Mexico, which feels like my back yard since I live in Texas, and other things like the bold spices of the Caribbean and unique foods of Europe. So I decided to get in the kitchen and make it myself! I noticed sharing my knowledge and experience with an audience on social media was really taking off. It felt like my followers were living through me! I love that feeling. Exposing them to new things or even providing more insight on things they were curious about. Read more>>
Heather Ann Hughes
In the intriguing chapters of my life that unfolded from the questions posed, I stumbled upon a truth that transcended fears and embraced the essence of authenticity. I am who I am and the risks I’ve taken were not mere leaps of faith but daring strides toward wholeness and purpose. From my years immersed in corporate America, where I poured my heart and soul into the world of Interior Design, to my passion for animals and their profound healing power, every step of my journey has shaped me into the person I am today. As the pages turned, the universe gently nudged me toward my true calling—a calling that grew stronger with each passing day. While I thrived as a designer and found joy in serving clients, there was an unmistakable yearning deep within me—a magnetic pull towards animals and a desire to explore their language and healing energies. Read more>>
Nikendra Green
I had been working for FedEx for about two and a half years and I would always tell myself this is going to be my last job, I knew I wanted to work for myself and take my DJ career to another level. I didn’t know exactly how it would turn out not having a job because I had been working since high school. I knew if I never took the risk of leaving FedEx I would never know what opportunities I could receive being an entrepreneur. June 2021 I resigned from FedEx and put my faith in God and I believed that I would not fail!!! I prospered and received an financial overflow once leaving Fedex and I knew I had made the right decision for my career and it was one of the best decisions I had ever made. Read more>>
Angel Sostre
One of the biggest risk that I have ever taken (and choose to take daily) is to truly accept who I am. As a female in transition, becoming my true self is a day to day activity. From attires to allowing my mind to wonder, delegate and an enjoy its power as a female. This has been the most mesmerizing decision I’ve made thus far. Allowing myself to fully transform into my true self has been impactful not only in my life but also the life of those around me. Its a beautiful day in the neighborhood, let’s go for more. Shall we? Read more>>
Jaclyn Wagner
The risk I took was changing my entire career and going into cosmetic tattooing. I was a pastry chef before working in this industry and I had been doing my thing for quite some time. When my little sister came home with her eyebrows microbladed; I just thought it was so cool. I felt like working in kitchens wasn’t my true calling and I felt really stuck where I was. Working in the cosmetic tattoo industry offered me a space to be creative and help others feel like their best selves. The work I’m doing now makes me feel so fulfilled and excited to come into work. Read more>>
QP. WorldWide
It was a hot Atlanta summer night. Down to my last 700 hundred dollars and every other streams I had was none existent. It looked like I was having more month than money. An like diamonds dug out a mind (S/O Killer Mike) a jewel hit me. WORLDWIDE MONOPOLY. The entire creation of my business was a risk. Short on money but loaded with ideas. I finally put real action behind one. I always wanted to have my own business but the way I pictured it formulating is nothing close to how it happened. I was a novice with ambition of being a boss. An the pressures of life birthed a new conglomerate. Risk breeds rewards and The timid never touch the trophy. Read more>>