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.
Moriah Mylod
My story as an artist is taking one risk after the other, but there is one particular story in mind that spun my life in a whole new trajectory. While living in Phoenix, AZ at the age of 19, I was in a near-fatal car accident that turned my life upside down. Read More>>
Lauren Denison
The Backstory: In early 2025, I was at a breaking point. I was navigating a separation from an emotionally abusive marriage, raising two young boys (ages 3 and under 1) largely on my own, and managing multiple chronic illnesses including fibromyalgia, arthritis, and PTSD. Read More>>
Chief Griffey
When I first decided to make music, I remember being at work and had a thought that I’m working here and I have a million dollar talent. Read More>>
Jesse Forte
I’ve taken risks that most people call wild. As an artist I’ve dropped tracks when rent was due and performed like it was the Grammys even when the crowd was three people and a bartender. As a pilot I’ve flown through turbulence with my heart in my throat and my wallet screaming every time the engine started. Read More>>
Dr. Cortesha Cowan
The Risk That Built a Movement: How One Step of Faith Became Mothers Helping Mothers Twenty years ago this month, I made a decision that changed my life and the lives of so many others. I started Mothers Helping Mothers with no money, no formal education in nonprofit work, and absolutely no idea what I was doing. Read More>>
Sara Ann Todd
After 15 years in government service, I made the difficult decision to step away from a stable, well-established career and launch my own business. For much of my career, I believed deeply in the mission of public service and the ability of government to make a positive difference. Read More>>
Hannah Whitney
When Cherry Street Brewing began planning our Halcyon location, Alisa Tanner-Wall sat me down and asked whether I wanted to move into management or take a leap into building an events and catering program from the ground up. At that time, there wasn’t a program—just an Excel sheet and a private room at our Vickery location. Read More>>
Tremaine Hemans, Esq.
The biggest risk I have ever taken was betting on myself in starting my business. I was working a job where I loved the actual work, but I was uncomfortable in the environment I was in. I would get serious ‘Sunday scaries’ and my 2 hours commute each way to work only to be greeted with unnecessary reprimands and micromanagement began to weigh on me. Read More>>
Ashley Melton
When I first decided to start Parenting Pathways, I was fresh out of college with no big savings account, no network, just a heart full of passion and a dream I couldn’t shake. I was still trying to figure out my own life, but something about this vision kept tugging at me. I couldn’t ignore it. Read More>>
Anthony Trujillo
My biggest risk is putting myself out there, even when everybody has doubted me. It would be my friends family and opponents. A lot lot of times there were some doubts, but I just keep pushing forward. Keep writing keep learning keep speaking the truth. Keeping faith in god, Jesus, and ,myself. Mentored by my cousin ARMENiO. Read More>>
Diana Moll
The biggest risk I’ve ever taken was starting my business — ‘literally’ from scratch. After years in the corporate world as a Vice President/ Fiduciary Trust Officer, I never imagined becoming an entrepreneur. The idea actually came from my daughters, who saw how much I enjoyed helping friends and family organize their homes. Read More>>
Heriberto Gomez
Almost 30 years ago, I was managing a small restaurant in Palatine, IL, when the owner offered me the opportunity to buy the business from him. I was scared since I had never owned a business before, but I decided to take the chance. Read More>>
Leah Forney
The biggest risk I’ve taken recently was creating and leading my very first event, the Courage Couture Gala. The inspiration actually came from watching a reality show about fundraising events in fashion, and God dropped it in my spirit that I could do something similar for my business and the work I do supporting survivors of color who have experienced sexual violence. Read More>>
Mel Bowers
When I launched Relax and Release, people thought I was out of my mind. I was creating something Huntsville had never seen before a wellness space that offered Japanese head spa treatments, sleep tests, allergy testing, and quiet rooms for mental reset all under one roof. It wasn’t just a spa; it was a sanctuary for the tired, the stressed, and the overlooked. Read More>>
vince young
I am taking a risk every day actually, but the biggest I took was stepping back from the 9 to 5 scene and trying to invest in myself. I lost a lot of friends. A lot of close relationships, time and money. I’ve seen small results, but I gotta go bigger. Almost every risk, is not without cost. Read More>>
Tina Barnes
I would say that the biggest risk I have ever taken was moving to Canada with no job, family back in Michigan, and ready to continue my business, PrettyOnMe Beauty, in a brand new country. PrettyOnMe Beauty was first established as PrettyOnMe LLC in Detroit, MI in 2014, but at the time, I found that Detroit wasn’t as fashion-forward as I wanted it to be. Read More>>
Amanda Frock
Taking a risk, that is truthfully what got me here. A big, life changing, no one truly believing in you but yourself (and maybe one or two others once they see your kinda crazy), multiples trying to convince you not to, kind of risk. It’s how I am here. Read More>>
Sunny Ray Hipple
The biggest risk I’ve ever taken was betting on myself and my creative gifts. I chose to step away from the predictable path to build a life and business rooted in creativity and intuition. For years, I worked in environments that valued deadlines over creativity and flow—places where I felt disconnected from my own artistic voice. Read More>>
Charles Traylor
Taking risks is part of my daily life. I am 83 years old so I have been at it for a long time. I am an architect, and taking risks quickly became for me the measures of last resort. My wife, Corinne, and I eloped, because we could not afford a wedding. We were both unemployed. We just jumped in. Read More>>
Anders Lindwall
For a lot of us, we have dreams or fantasies of doing or achieving something radical or unconventional, but feel just out of reach, or impossible for a variety of reasons and responsibilities. For me, it was to make a movie – a movie of moral and social significance, and release it theatrically nationwide. Read More>>
Teodora Todorova
One of the biggest risks I’ve ever taken was opening my own hair salon, Moonflower Hair Studio. I had always dreamed of creating a space that felt more like a home than a business — a place where people could relax, feel seen, and leave not just looking good, but feeling restored. Read More>>
Claire Deegan
One of the biggest risks I’ve taken in my career was deciding to launch Ella Rose Aesthetics as a solopreneur in Omaha, Nebraska. To give you the full picture, let’s rewind a bit to the backstory. For years, I worked as a Nurse Practitioner in a high-stress hospital environment. Read More>>
Tasha Gorel
Floating in the middle of an aquamarine lake, surrounded by Mother Earth’s jagged masterpieces, I read John Muir’s meditations to my sister riding alongside me in our inflatable kayak. Somehow, we were the only humans boating Tenaya Lake on that iconic September morning. I let my foot droop over the side of the plastic platoon, my body instantly relaxing from the freezing dip. Read More>>
Susan Weiss
For the majority of my photography projects i begin with no definite concept in mind. I just begin photographing. Sometimes it can take months until falling into place. Examples with this questionnaire are all of projects that began in this manner.. Read More>>
Desiree Young
I’ve been writing all my life. It’s always been how I expressed myself and processed my internal world. In 2017 as I was driving home for work, I asked God what my marketable skill was; what was the thing that He created me for. He said writing and gave me the idea for my first novel. Read More>>
Lauren Pan
I’ve always been someone who believes in leaning into discomfort, and that’s a philosophy that has guided my entire career. I always knew I wanted to have my own business, especially one that could make a difference in the housing industry. Read More>>
Kelley Cervenka Coker
A big risk I took was quitting my full-time job to pursue content creation without a plan, just the feeling of being called to follow my dreams. To understand why I would take such a risk, with a very nano following and no clients lined up, we have to rewind to one year prior to my departure from my job, 2023. Read More>>
Marcia Guthrie and Sophia Castillo N/A
I’ve worked in real estate for most of my adult life and have taken a great deal of risks over the years, but the biggest ventures I’ve ever undertaken in this industry have always been alongside my husband or daughter—my greatest partners in both business and in life. Read More>>
Gabriel Grant
Shareholder Democracy is transforming corporate governance by empowering civil society organizations to represent owners of publicly traded companies, giving voice to owners’ values. https://www.shareholderdemocracy.org/ Read More>>
Marie Dunn
In 2018, after completing my first book of erotic poetry under my pseudo name -Toya J, I was met with the harsh reality of the publishing world for first-time authors. Despite my excitement and creative fire, I quickly realized how difficult it was to break through without connections, resources, or industry knowledge. Read More>>
Ashley Clark
For years, life was defined by the loop of necessity. I chased rent through claims departments, retail counters, and medical offices, always pushing toward the promise of a career and stability, only to end up burned out or sick. Every lost position proving again that I was not built for the system I tried so hard to fit into. Read More>>
Blair Harper
It was after I returned to a retail job I thought I’d never go back to. I laid on the floor, self pity, failed dreams, lack of direction or respect…and I thought ‘I have a truck, people need stuff moved, what’s the worst that can happen if I put a $5 ad on Craigslist? It worked. I got maybe 3 jobs a week for $50. Read More>>
Julio Lugo
I’ve taken many risks in my life, but as a majority of small business owners would probably say, not necessarily big or small but the most profound risk I’ve taken is making the leap from working for someone else to working for myself. There is always that voice of doubt, is this going to work? What happens if it doesn’t? What if I’m wrong? Read More>>
Anne Ferguson
I’ve taken many risks in my life, each one becoming a stepping stone toward the woman I am today. The first big leap came in my late 20’s when I packed up my car, my cat, and a few belongings, and left Tennessee for the wide unknown world heading to Washington State. Read More>>
Nicholas Truscelli
Every aspect of my life whether it be my music, skateboarding, or trying to become a pararescueman/operator revolves around taking risks, and learning from failure. At first it may sound a bit pessimistic considering you would expect ‘success’ to follow up eventually after the ‘failure’ portion of what I just mentioned. However, that sums up my whole athlete/creative/wanna be operator journey so far. Read More>>
Petey Mac
In 2024, I felt a strong pull to go fully independent with my business rather than continue contracting for larger PR firms. At the time, I didn’t have enough clients to cover more than a month of living expenses, but deep down, I knew it was the next step I needed to take—and I had a peace about it. Read More>>
WeiJen Liao
One of the most significant risks I took was over a decade ago when I left my hometown in Asia to study abroad in the U.S. without fluency in English and without a clear career path. That leap of faith has been transformative, leading me to growth as an actor and as a person. Read More>>
Mar Di Meglio
Everything in life carries a risk. From the moment we begin making choices, we start gambling, sometimes with opportunities, sometimes with comfort, and sometimes with who we are. My first risks were not about danger or adrenaline; they were about identity. As a kid, I did not choose soccer, tennis, or field hockey like everyone else. I chose singing. Read More>>
Nancy Woodworth-Hill
Sometimes we need to be invited to step up to a task. Sometimes, it’s a bit closer to being volun-told. It began with Barbara’s invitation to coffee, a story, and the news that her regular local newspaper column to appear in two days’ time had already announced the open community meeting she wanted me to lead. To say this was unexpected is an understatement. Read More>>
Jackie Edwards
From a young age, I was taught that the ultimate dream was a college degree and a stable 9-to-5 in corporate America. But deep down, I always felt like the black sheep, always craving something different, something more. After graduating from the University of Florida with a degree in Telecommunications, I planned to pursue broadcast journalism. Read More>>
Keisha McMillen
In 2020, I was hired as the operations manager for my city’s local arts council, which I considered a dream job. A few years earlier, I had worked for them as an intern and camp coordinator for a program called “Arts in the Park,” where neighborhood kids could experience visual and performing arts led by teaching artists. Read More>>
Daniela de la Piedra
One of the biggest risks I’ve taken was leaving my 13 year legal career to start something brand new all on my own. The pandemic was the turning point for me and it was the pause I didn’t know I so desperately needed. My life was going so fast that I hadn’t realized how burned out, bored, and misaligned I had become in my career. Read More>>
Kaitlyn Bathel
I decided to go into the field of education for a few reasons: being passionate about supporting future generations, working in a setting to advocate for change, and having the same holidays off as my children. Read More>>
Alan Catz
Leaving my home country, Argentina, to study at Berklee College of Music in Boston was the biggest risk I’ve taken. I left my friends, family, and cultural traditions for a place where everything worked differently. I arrived alone, had to navigate life in my second language, and quickly learn new systems: visa rules, banking and credit, healthcare, leases, taxes, public transit, and a completely different academic and studio workflow. Read More>>