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.

Karen DeBonis

“How will readers judge me if I share my truth?” It’s a question all memoirists have to consider. Telling our stories is a risk we take. When I began writing my memoir Growth: A Mother, her Son, and the Brain Tumor They Survived, my heart pounded at the thought of exposing my lifelong Achilles heel: people-pleasing. Read more>>

J Terrell Jeter

I believe in taking risks now. Before the pandemic, I was playing it safe. I was in Louisiana to stay close to family. They were my “safety” blanket. The job I had at that time was mediocre, but I knew my full potential wasn’t being tapped. So I interviewed for a job on December 18th in Dallas. I received news on December 19th that I was being hired and on December 20th, I packed up one suitcase and instantly moved. I didn’t second guess or listen to all the “what-ifs” in my head. I just jumped and it was one of the best decisions that I have made. Read more>>

Elizabeth Gottshall

Having a 9-5 office job was never in the cards for me. No matter how hard I tried to make myself choose the more “stable” career option, I was always brought back to art in its various forms from creative writing to studio art to photography. My path through the different art forms led me to film, which combined my favorite mediums, writing and photography. Being a visual storyteller has been tough, especially since we are inundated with so many stories through social media and streaming. But, if anything, it’s shown me that there is always a place for my story to be told and there will always be someone out there who will watch and listen. Read more>>

Sylvia Valde

If you don’t take a risk you won’t find out ! Life is a gafe full of risk you just have to take them Read more>>

Brianna Benitez

This was in the beginning of my photography business. During the spring, I took many photos and uploaded them on my Instagram and Facebook pages. One day I received an email from a local newspaper in California. The email stated that they wanted to interview me for their newspaper. At first, my reaction was crazy. I didn’t know then if it was a scam or real. It was a risky moment for me due to receiving scam emails. I had received emails from other small companies that wanted to work with me but, ended up not working out. When I did my research and looked at their website, I was impressed with the email I received. Read more>>

Danielle Towle

When I started my photography business I was really just doing it as a hobby. I wanted to take better pictures of my kids and I began by taking photos of family and friends for free or next to nothing. I quickly realized that I love it and it could turn this into extra income for my family. Read more>>

Ariel Kochbarski

I’ve taken many risks over my 20 years of fashion apparel experience. I started my own consulting company in 2016. I restarted it post pandemic in June 2020 but pivoted to styling full time. I’m currently taking another risk by starting my own brand, ARIKO. ARIKO is a clothing line inspired by my life in both fashion and surfing. I want to fill a void for items that I want to wear that I do not see other brands making in this space. I have been in this field of deciding what people wear for a long time. I have the connections to make a real impact and I have such a fun time creating my brand that it doesn’t feel like work. I was disappointed by the current surf brands assortment and wanted to make things I wanted to wear. Read more>>

Brenda Sanders

After almost a decade of toiling in the corporate world, I found myself standing at the crossroads of life, an early retirement and a gnawing sense of emptiness in my heart. The once-promising career had lost its luster, and I longed for something more meaningful. One morning, I sat in my office with nothing to do sipping coffee and staring out of the window where the sun filtered through the blinds creating a tranquil ambiance. As I gazed out into the world around me, I began to cry and pray to the God, asking for guidance on what I need to do next. I needed to discover my true purpose in life, something that would fill the void in my soul. Read more>>

Israel Miller

Taking risks is how we grow as artists. Whether we realize it or not risks always push us to be greater and put us in higher positions to succeed. My biggest risk that I have taken was picking up a camera and curating art in the first place. When I picked up the camera for the first time, it gave me a sense of freedom but what I was not aware of is how many risks I would have to take throughout this profession. Telling my parents that this is what I want to do not only now but for the remainder of my life, prioritizing shoots and personal projects over my schoolwork, and just choosing everyday to keep on creating even though I have no idea if my passion can reach the prosperity I believe it can. My life’s work can be seen as a risk. Read more>>

Traci Wright Martin

It’s important as a creative to put your work out there. For awhile, I kept working hard on the artwork and not trying for exhibitions that I wanted to participate in, because I thought the work wasn’t ready. One day I decided to not overthink it and just entered a show I had my eye on. I got in, and it was my first time to show in a gallery in New York City. Not only did I get in to the juried show, I also had the privilege of earning a third place award. I’m proud of my desire to work hard on my art, but I realized that I can also overthink and hinder my opportunities in that state and it can keep me from moving forward. Taking risks and putting ourselves out there can be really rewarding. Read more>>

Tia Metaxas

The biggest risk I have taken is trying to relocate from Australia to New York. I have always loved New York and wanted to spend more time here and collaborate with more brands and people however for years it felt out of reach. It was actually during covid that I had more space and time and I decided to finally follow my dreams to try and live in my favourite city. I even quit my job to try and come here and travel in 2022. It’s not the easiest thing, but I must say that it has been an exciting rollercoaster ride. I have loved New York since my first visit ten years ago & I said to myself if I could live and work anywhere it would be New York. I took the risk because I thought if not now- then when? There is nowhere else as exciting, creative and that feels like home. Read more>>

Priscilla Emprechtinger

Life is all about taking big risks. Read more>>

Katie Lewis

To the average person, the largest risk that you can take is taking your entire income and relying on a business that you own and operate. To me, the biggest risk that I could take as a professional, even from the age of 13, was relying on someone else to provide me with the income that I want, paired with the schedule that I want to have. I’d rather be hopelessly broke than to have my own tail on the hook with some corporation with their own ideas of what my work/life balance should look like. When I was 9 years old I was given a riding lesson for my birthday. By that age I was already hopelessly in love with all things equine and I came from a stable family, but not one that had excess funds to throw around. Read more>>

Meredith Shafer

With my career, I have taken some risks that have probably looked crazy from the outside. For fifteen years I was the Executive Director of a large multi-million dollar foundation—I loved my job! I really thought I’d do that job until I died. It was fun, I got to meet tons of wonderful people, and my favorite part of the job was giving away the grants that our organization chose for other nonprofits in the area. Read more>>

Tresta Ward

Stepping into the unknown to be financially stable. Read more>>