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.

Bree Angela

My story on how I got to where I am and where I hope to go creatively has always been fueled by risk taking. While growing up, my grandfather made sure to show us photo slides and albums of relatives from his side as well as my grandmother’s after Sunday dinner. This always fascinated me! There were so many stories passed down about the entrepreneurial spirit of those who had arrived in America before us. I thought they were so brave and took such a risk to come to this country and to work in NYC. Read more>>

Jay Zeager

They say that fate will guide you in certain directions that will have an imprint on your life. In February 2016, I ran into an acquaintance who was a well known auctioneer in South Florida and someone I had worked with on a previous charity event. (He as the Auctioneer and me as the Emcee) At the time, I had only done a couple of benefit auctions and he suggested that if I was serious about pursuing it further, I needed to get licensed. He also invited me to be a spotter for him at one of the largest events in South Florida. Read more>>

Lisa Peranzo

I always gave my workouts priority. After getting hurt in an Army ROTC training exercise, I knew that my physical capabilities directly translated into my overall health. But being a fitness instructor was not something I directly dove into upon recovering from my injury. I felt like I needed to follow the traditional trajectory of going into corporate America, and fitness could be a side hustle. For a long time, that setup was beneficial but I never felt fulfilled. Read more>>

Neelou Malekpour

Finding my path to my current career was not rational or linear, at all. I received my undergrad degree in English lit with an emphasis in creative writing because I LOVED to read and write. Then for some reason, I went to law school – I hated every minute of it and wanted to quit at the end of each semester but I graduated three years later. Soon after, I started a career in peacekeeping, working at the United Nations, which I was very passionate about. I’ve always wanted to help people, in a real tangible way but at the time (I hear it’s different now) the advancement opportunities for women were extremely competitive, somewhat shady, and I was uninterested in the politics there so after a few years I left. Read more>>

Karen Lustgarten

I am a risk taker in business. It seems to be in my nature. When I see a need that’s not being filled in my area of expertise (media), I like to create a pathway–a business–to fill it. I have created a few pathways to meeting business needs over the years. In San Francisco, it was starting classes in dance and exercise with a new twist that hadn’t been done before. That led to writing books on the subject (one on the NY Times Best Seller list), to a TV show (Emmy nomination), to a syndicated newspaper column and more. Read more>>

Marjorie Waldo

The biggest risk I’ve ever taken – in my career at least – is changing careers in my fifties! I was an educator, teacher and principal, for 28 years. I never imagined that I would leave that passion – particularly focused on high risk students, specifically drop-out recovery. When I made a decision to do so, I was afraid. Excited, but afraid. I am not a mainstreamer. I have BIG passions and BIG dreams and made a decision decades ago to let those lead me in my career. I graduated with a degree in Drama from the University of Virginia, and I consider myself a poet, and I have always believed the Arts are meaningful and important for all of us, but to work in the field? Read more>>

Cheryl Carpinello

Writers take many risks from the beginning of an idea through the writing, editing, publishing, and marketing of that ida. And being a writer, I’m right there every time I start a new project. My newest project is my 5-book series, Feathers of the Phoenix. Two teens summoned by another time face death and danger in their search for the Five Feathers of the Phoenix required to raise the lost island of Atlantis. Several factors make this series the biggest risk I’ve ever taken with my writing. Read more>>

Adam Stroder

Entrepreneurship does not come easy. Oftentimes it is born from necessity. I went through many career-focused educational changes over the years, and when the time came that I found a major I really enjoyed, I was no longer able to get school funding to complete my degree. Being a new homeowner and new father all within a year of this, I decided I had to make a move. I had built a wood deck, fence, and dog bed for my family using basic second hand tools, Read more>>

Kiley Burke

I would 1000% have to say the biggest risk I’ve taken was leaving my job to start full time as an artist. I had been working as a restaurant manager and, while my schedule was flexible, often times requested days off would suddenly become days where I was required to be at work and taking more than 2 days off in a row was pretty impossible. I had the dream of traveling for art shows, and realistically I knew that I wouldn’t be able to do it as long as I was working for the company I was with. Read more>>

Christina Humphries

After taking a spontaneous road trip to Breckenridge, Colorado in October of 2018 from where we were living near Cincinnati, we decided to make Colorado our home. I’m not sure why, but we never thoroughly questioned our decision, even though we had every reason to be terrified and unsure. At the time, we had two toddlers in tow and had just reached a great place with our photography business in the midwest. Read more>>

Dr. Tongie

As I sit here overlooking the Caribbean and Atlantic Oceans…with Gladys Knight exclaiming how she “heard what she heard through the grapevine, (e.g., no doubt someone meddling in her business causing her distress…hahahahah) and how she’s indeed questing her disposition…my Son “Chris”…that same Son that questioned how I could ever have the audacity to NEVER TAKE RISKS…I can’t help but reflect on how my taking RISKS…OVER AND OVER AND OVER have manifested some of the most magnificent and disheartening experiences I’ve ever known. See, it’s in the RISKS that you live. Read more>>

Nino Daniel

This is definitely a question that is going to be applied towards TWO risks I’ve taken. The first risk comes in the form of starting my own dance class. Let me take you back to November 2015. I had been applying to graduate and doctoral programs in an effort to become a psychologist. I did all of the applications, the interviews and NOTHING. Not one admission to the 8+ schools I had applied to. The final “No” was given to me in January of 2016. At this point, I felt hopeless and very lost with what to do with my life. Read more>>

Stephanie Hanrahan

The personal and professional freedom I have now is directly related to a risk I took while sitting at my kitchen table one balmy evening in September. For almost three decades, I had been living a duplicitous life: posting my prettiest moments and concealing my cracks. I was certain that if the world, or simply the people in my inner circle, knew my truth I would be pitied and penalized. I kept my truest self hidden and only allowed her to be seen in the short captions of a private Instagram account; Read more>>

Matthew Broyles

Back in 2007, it felt as if I had maybe taken too many risks. Having returned from a four-year sojourn in New York City without much to show for it, a pile of debt from making my first album, and a toddler in the house, the time seemed ripe to try and find some stability. I took a job at a bank in Dallas, working for general counsel, making binders for the board and generally being safe. The following September, the biggest financial crisis since 1929 broke the floor under my boring bank job, and it became clear to me that nothing is truly safe. Read more>>

Scott Uhl

Spiral Cell is a pretty different music project, and it’s always been hard to find who the core audience is for the project. With previous bands that I was a part of, it was a lot easier to know that the fans of rock would generally be a fan of the band. “If you like Linkin’ Park, you’ll like this band…. if you like Halestorm, you’ll like this band…” etc. Read more>>

Stefan Dr Harzen

I grew up in Germany, and when I was in high school, I contemplated three career paths: brain surgeon, commercial pilot, and marine mammal scientist studying wild dolphins. While all three were fascinating and promising, it was the adventures Jacque Cousteau and Hans Hass portrayed in their films about the underwater world that made me decide to pursue a life of studying dolphins. Read more>>

JoAnna Pendergrass, DVM

One of the biggest risks that I’ve taken in my life was starting my freelance medical writing business. As I was nearing graduation from veterinary school, I knew that private veterinary practice was not for me. I struggled with deciding what my next step would be after graduation. I decided on research. However, just a few months into my 2-year research fellowship after veterinary school, I realized that the research world wasn’t for me, either. Read more>>

April Taylor

I’ve taken many risks over the years, but one risk in particular was moving from my hometown in California and moving all the way to Georgia. It was a huge risk because I had built a reputation and a great clientele in Sacramento,Ca and I was walking out on faith to where absolutely no one knew me or what I had done in my photography career. It was terribly hard, I actually took 1 whole year off from my business to make sure my family settled in with this big move . Read more>>

Thomas Matthews

As a settled and safe creative director for a calm and predictable firm, I became disillusioned with the day to day drudgery of the ordinary. Ads the son of an American Literature professor, I had always been a voracious reader and imagine myself a potential writer. Call it a mid-life crisis, but I resigned from my job, put myself in front of my Mac and began writing a novel. It came easy and I was hooked. Read more>>

Gregg Pearlman

my future. Once I turned 22 – I felt the best investment I could make would be in myself. So – my stock money was used towards my education to be a Record Producer. I enrolled into a Recording Engineer school in Los Angeles and moved to the world’s entertainment capitol. The school also taught Live Sound Reinforcement. Read more>>

Astoria Stubbs

Life is definitely all about taking risk. Most recently with covid-19 I really had to sit back and reevaluate things that were important to me. one thing being my authentic self in and outside of my brand. It’s a distinct difference in the brand or persona you put out and who you as the business owner and business are. As a hairstylist im like a therapist helping clients while im doing their desired service. As I have been on my own journey of spirituality i found reiki resonated with me. I began to see how it could help me in the work i already do with my customers when it comes to healing. Reiki is like healing hands its the use of energy and chakras to removal unwanted energies and disease. Read more>>

Rebecca Baum

As an artist, I never thought I would own a business. I didn’t enjoy thinking about money, and didn’t really understand what a business was. That all changed when I stumbled upon a little art school for sale in Old Colorado City – With no formal business education, background, or general understanding of what I was in for, I took a risk and dove in. Here’s my story. My husband and I moved from Pennsylvania to Colorado in 2018. We chose Colorado Springs for the beauty, nature, and the size of the city. Read more>>

Kris Wrede

In 1993 I was going to take a job at Aveda in Chicago, one of the first free standing stores in the U.S. I had been studying aromatherapy for 3 years, and I told a friend about the job. She said why would you do that? Your products are so good you should just start your own business. So, I did! I travelled around Chicago with my backpack on my bike, on the bus and on the ‘L’, going from door to door in shops I wanted to have my products in. It was a HUGE risk and every day in business is a risk. I always say you have to reinvent yourself every day. I worked at a pizza place as a waitress at lunch, and I worked the night shift at a group home for developmentally challenged adults. Read more>>

Yvonne Tijerina

My biggest risk so far happened in two parts. When I was faced with the choice to be a rid or die for my own toxicity or my own freedom. When I was a young adult, I married at twenty-one. Marring young wasn’t wrong what was wrong was the way it matured. For years I suffered “in moderate silence, I fought with and against my former spouse. Why? Because I was too stubborn and scared to walk away from what had become toxic to me. I felt that enduring the relationship was what was right and expected of me. I was consumed with the opinions of others about my life. Even with them being unaware of all the venomous parts of my marriage with my ex-husband”. Read more>>

Bryan Norcross

In 1978, I was managing the news department at the ABC affiliate in Louisville, KY. It was a tumultuous time in the city. Teachers and firefighters went on strike, and Mother Nature was out of control. Relentless cold arrived in mid-January with most days only reaching the teens or 20s. Snow from a brutal late-January blizzard didn’t melt until mid-March. Read more>>

Peter G. Kalivas

WHAT is risk? It’s about being different and owning it, in support of your mission, purpose and vision. My 20 year San Diego based company, The PGK DANCE Project’s mission, purpose, vision is: • To be a platform that works to produce and present diverse professional dance that is representative of the world around us in ways that enhance our quality of life. Read more>>

Grizelda Garza

Nobody can really be sure if risks will pay off, no matter how calculated they may be. But this should not stop you from taking risks which has always been my mindset. I’d rather try and fail at something than to say “What If” Growing up in Texas. I’ve been told numerous times that Fashion will not be successful in Texas., that my dreams & goals would be more realistic if I moved to New York or California. I just never really settled for the advice given to me and have always done things my own way even if I would be wrong. Read more>>

Tylisha McKinney

Being an entrepreneur can be not only scary but it’s challenging as well. There’s so many how to’s, why’s, and where do I start, and where do I go next Who do I need to speak to, funding, resource, resource, and more resources. Well, for me being an entrepreneur was always in the plan for me ever since I was a little girl. I would help my grandmother from time to time at a snack bar that she owned at the North Dade Neighborhood Center in Opa-locka. My grandmother is my greatest inspiration when it comes to entrepreneurship. She always instilled in us to always have something for yourself and to never be comfortable working for somebody else. Read more>>

Autumn Taylor

Whether Risky or Risqué, I have always been one to take them. It is extremely difficult to be a business owner and get your business off the ground. It take patience but most importantly risk that make you take that leap of faith. I wanted to launch a brand that allowed me to empower women the way I empower myself which is through lingerie. It couldn’t just be any lingerie brand, it needed to have passion and purpose, I took many risks during the time of House of BEREs creation. Read more>>

Kate Johnston

I started my career as a hairstylist when I was 18 and had just graduated from high school. I knew early on that I wanted to be the best hairstylist I could be, but was never sure if I’d ever want to open my own salon. After working in salons for 10 years at the time, I was very hesitant to open my own salon because I saw how hard my bosses worked and how stressful owning a salon could be. Read more>>

Melissa Drumm

As an Artist it is a daily practice to take a risk! While studying painting and printmaking in Undergraduate school a friends parent asked me “How do you plan on making a living?”. The thought had never occurred to me. Becoming an Artist was naturally innate. I did entertain teaching during graduate school but did not find it to be a calling at the time. In terms of a career choice the Arts is a big gamble. It is however never a risk in terms of joy, excitement, endless opportunity and a life of pushing your imagination. Also, the practice of risk taking in trying new materials, combinations and techniques is my greatest fascination. Read more>>

Jenn Cook

In 2013 I left what I believed to be the safety of corporate America, putting my trust, integrity, and illusion of stability in someone else’s hands, to start teaching yoga, doing Thai bodywork, and making jewelry full time. It was my second time being laid off in 5 years, and I was no stranger to working multiple jobs in order to make ends meet. I figured if I was going to work hard and struggle financially, I might as well do what I loved in environments where I felt supported and inspired. Read more>>

Somy Ali

I grew up in a home of domestic violence and I was sexually abused by the house help when I was five years old. Then at 14, I was raped in a park by a 17-year-old man. From the age of 16-24 when I was an actress in Bollywood, I was in a relationship with a top actor who was extremely verbally, physically and sexually abusive. I took all the bad that happened to me and gave birth to my organization, No More Tears. Read more>>

Moh Yakubi

If you speak to many successful people then most will tell you about the hardship they had to go through to make it where they are at right now. To me one of the biggest risks was restarting my career in a different field than I though I would be in. My family and I fled Baghdad, Iraq, the country I was born an raised in for 18 years, and went to Jordan after the USA/Iraq war in 2003. I have studied computer engineering for 4 years in Amman, Jordan while applying for refuge. Read more>>