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.

Ariel Levin

The biggest risk I have taken in recent years would be making the decision to drop out of college to pursue an entrepreneurial career. It was January 2018, and I had just made an incredibly spontaneous decision to move to Miami for college to get a degree in Nutrition & Dietetics. When I graduated high school, I took a gap year because I was lost with no direction or or any idea on what I wanted to do with my life. Read more>>

Alejandro González Charles

Last year, my colleagues and business partners AD Dolphin, Joshua Engle, and I embarked on an exciting venture: the creation of the That’s F***ed Up Podcast. Originally, my role was intended to be that of a behind-the-scenes producer and show runner. However, after persuasive discussions with my co-host AD Dolphin, I decided to also participate as an on-camera talent. Considering the controversial nature of our discussions and the current climate in the United States, I must admit I had concerns about the potential consequences for my future. Read more>>

Corey Lynch

I am still very new to being a business owner and it didn’t come about with a huge leap of faith like I expected it. I left my job back in April, thinking I would only be taking a few months to work on, what at the time, was a side hustle. I was interviewing for jobs throughout, but nothing seemed to be sticking. I had some great interview processes where I got all the way to the final stages and thoughts I would be getting an offer. After months of frustration, I decided it was a sign for me to get serious and try to give my all to my business. On top of the frustration, I was also beginning to realize how much I didn’t want to go back to that life. Read more>>

Archana Liggins

I have a servant’s heart and as an upcoming leader in the community, I wanted to work to build the community and support families in need. I was scared but determined to alleviate the burden of accessing personal care items in underserved communities. My new motto from that time on – DO IT SCARED! I founded BAG Lady Outreach non-profit (501c3) organization in January 2019 based on my belief that every underserved person deserves to have dignity through access to hygiene products. Read more>>

Julia Henning

My life has been a series of risks. I wouldn’t have discovered the person I am today and the person I am returning to if it hadn’t been for my risk-taking lifestyle. Taking a risk requires a profound faith in the unknown. We don’t yet know ourselves prior to the risk we embark on, but we trust that the risk grants opportunity. I might admit that my earliest risk occurred in childhood when I asked myself, “Who is Julia?” in the mirror one day. The decision to self-actualize early in life was most likely my greatest risk. But that’s not a very entertaining story, is it? The risk that may have brought me to this precise moment dates back to 2018. Read more>>

Tiffany Heard

Risk: Hosting day group trips to Rosarito Mexico. Tijuana is approximately 45 min away from Rosarito, Mx and is often known to be very dangerous. Yet after spending a weekend in a beautiful Airbnb near the coast, eating tacos and seafood and going ATV riding. I knew that I couldn’t pass up the opportunity to bring other women to this country. Since 2022, we have taken over 5o women across the border to have lobster lunch, horseback riding and bonding with other people they may not know. Read more>>

Nicole Oliverio

I still remember being a young girl, no older than 5, sitting in my grandmother’s living by her bay window. She would be sitting on the hassock listening to me tell a story and writing it out for me. For as long as I can remember, I wanted to be a writer, author, storyteller. As I entered my high school and college years, I still loved writing but my focus turned to journalism. I interned at two television stations in Boston, where I grew up, and spent four years working at the Boston Herald. My major never changed, it was always communications and I always wanted to be a reporter – and I was. Read more>>

Tara Polley

Being a Realtor encompasses more than mere house sales; it involves fostering connections, having a profound understanding of the local community, grasping the regional lifestyle, and assisting individuals in achieving their dream of owning a piece of California. When the producers of American Dream Tv approached me to represent our community and spotlight the wine country region, I found the proposition both intriguing and nerve-wracking. On a personal level, I’m not at ease in front of the camera, tend to be introverted, and prefer to avoid excessive attention. However, at my core, I firmly believe that growth happens outside your comfort zone. So, I took a leap of faith and accepted the role despite my initial apprehensions. Read more>>

Maggie Piazza Carroll

Accepted a full-time job in a country I had never been to before. Granted, it was Greece so I figured it would interesting, beautiful, historic, delicious (lemon potatoes)… and surprise, it was all of those things and more! At the time I was experiencing some personal difficulties, so when I saw a posting for this storytelling role at the International Rescue Committee I thought “why not at least try”? I ended up being offered and accepting the role… getting to live in not only Greece for a while, but also Italy which is where I’m from. Read more>>

Nuria Richards

Many people close to me know that I identify with the concept of “opportunity cost,” the value of the next-best alternative when a decision is made; it’s what is given up. It’s a brain twister but relates to something that we have all done at some point in our lives: thinking what would have happened if we had chosen the other option… the other career, the other partner, the other city, the lives we live in parallel worlds. Read more>>

 Jenny McGrath

Blending movement, embodiment, and somatic awareness into a mental health practice felt like taking a big risk. Unfortunately, the psychology world has often imagined as though we exist as floating heads. Talk therapy has been the primary way folks have dealt with mental health issues since Freud. While it felt risky to me in the “Europatriarchal” (Minna Salami) way that healing is done- I’ve found along the way that engaging the body and movement for healing are nothing new for indigenous practices and ways of being. Read more>>

Amanda Rose

I went to college for Acting for Film and Television, and graduated into the 2008 recession. I was in Toronto, Ontario, Canada, where the film industry is entirely reliant on US film companies coming up north for their projects. During the recession, for the first time in decades, the Canadian Dollar was stronger than the US dollar, so no one was coming to film up here. In one fell swoop it felt as if my dreams had been smashed to bits. I got an agent, and still auditioned for the few roles that were around, but ultimately I didn’t work for a year. Read more>>

Brandi Calhoun

Life is full of risks. When you decide to get married or have kids, or take a job or make a move, those are all life-changing risks. But the biggest one we’ve taken by far is starting our business. We’ve been working for so many years to get to a place where we can finally open and right before COVID happened, we were looking for a spot and we were ready to start moving forward. When everything shut down, we were stuck. Going through COVID and the uncertainty of life at that time really pushed us to be brave enough to just dive in once things opened back up.  Read more>>

Ingrid Edshteyn

One of a series of risks I took over the last few years was deciding to move to a state that I have dreamed of living in since I was a kid, and then going against the grain on professional career advice by starting out my own medical practice, alongside a fitness training business. We had been living in NYC for several years, had been working in a good job in preventive medicine for several months, and then we plunged into a big move to the west coast, not having any local family, friends, or secured job lined up. It’s definitely been a challenge, but we listened to what was calling us – the joy of being outdoors: going on regular hikes, swimming in the ocean, exploring the varieties of people and places in the LA area, and developing new friendships with wonderful people. Read more>>

Lynda Goldman

My Illegal Art Story (an act of risk and rebellion) “You need to be a lawyer to make a good living,” was whispered in my ear almost from the day I was born. My father was a lawyer, and both my brothers ended up following his calling. Read more>>

Zylia Knowlin

In 2019, I published my first book, The Memoirs of an Empress. I was underemployed and raising my four children alone. It was a financial risk as I self-published my book. That meant having to finance my book 100% on my own. It is a risk I don’t regret. My book has opened doors for me. It has renewed me and helped me to see my greatest potential. It has strengthened me. Read more>>

Linda Khoshaba

I worked for an established clinic for almost a decade and I was about to get the biggest raise of my career. I was only a few days away from signing my new contract and then COVID hit the world. Instead of getting my well-deserved raise, I found out that the entire company was going to give pay cuts to all employees as a way to save money during the pandemic. Not only did I miss out on the income, I then learned I was going to work exclusively from home while watching my 2 young children who were under 2 and 5 years old. In addition to that, I had learned that my father became ill and was admitted to the hospital and never left, ultimately passed away after being there for 8 weeks. Read more>>

Stephanie Carpenter

I’ve always been a big risk taker. I’ve never stayed just in the safe comfortable area in business for much time. I always am thinking what’s next. From the beginning of my career as a cosmetologist I’d get everything that I felt I could learn from and use it towards my experience. The first job I had in a salon I watched and learned how to run a salon. I was a receptionist / makeup artist during the work hours and went to school at night for my trade. I always continued to look forward and see where I could go next to evolve. Read more>>

Evelyn Sun

Every time I work on rigging characters and see how they act lively in the game; I always feel great happiness and I really appreciate that I took the risk to change my career. In my undergrad school, I studied electrical engineering as my major, which my parents recommended would provide me with a secure job and income. However, in my heart, I always have a strong fascination with art and games. I always enjoyed painting and sketching for the whole day, observing light and shade on the object. When I applied for grad school, I decided to pivot my major into entertainment technology to pursue my passion for art. Read more>>

Chenelle Bragg

I think the biggest risk I’ve taken is opening up a business during the Covid pandemic, while businesses were closing, I’m over here with the bright idea to open a business, a food industry business at that, we all know food industry businesses usually fail within the first year, I was fortunate enough to be able to make it longer than that and I was also able to transition from a restaurant to a food truck. Read more>>

Ionia Wilson

One risk that I believe has made a large impact on my life and career is moving across the country from Florida to Arizona. To a lot of people. a move may not seem like much but to someone who has never left their hometown of Tampa FL. It was life changing. At the time of the decision, my husband and I were looking to change jobs and he mentioned wanting to look at other states (he has lived in quite a few dfferent states before). I told him I would be completely on board as simple as going to the store. I felt nothing tying me to my city and needed a change. Although this was a risk, it was still a calculated one. Read more>>