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.

Erin Fangmann

One of the biggest risks we took as founders was turning a simple kitchen-table conversation into a full-blown business and movement. Read More>>

Lee Ann De Reus

At the age of 54, after a 20-year career, I left my job as a tenured university professor to start over. My husband and I took the leap together. Read More>>

Melinda Riego de Dios

From Corporate to Carpentry … In January 2024, I learned I’d be laid off from my corporate role, with my last day landing on June 30th. After 25 years in customer-facing roles, it was the first time I’d faced a layoff—and instead of seeing it as a setback, I embraced it as an opportunity. Read More>>

Eileen Peterson

In 2013 I was offered a job doing what I loved and creating my own original works, but I would need to move the Paju, South Korea to do so. Having lived in the Southern United States my whole life, I couldn’t even fathom what Korea would be like, but I had 48 hours to decide. So, I took the first risk. I said Yes. Read More>>

Ariana Coleman

Growing up I have always been one to take risks. Back then that seemed so small, insignificant and a given. Being an entrepreneur is a risk in itself that I was scared to take. I always had a passion for art and beauty. When I was 17 I decided I would take the risk in doing both as my career. Read More>>

Michelle Gilbert

The biggest risk I’ve taken is leaving corporate America to start Purple Engine Coaching & Consulting. The company I worked for went through a restructuring and my job, among many others, was impacted. My choices were to apply for another job with the company or take a severance and write my own next chapter. Read More>>

George Yuhasz

A few years ago I decided to write a novel, RIGHTEOUS ALLEGIANCE, which would focus on the examination of urgent social issues, the insidious growth of division and extremism, and the consequences of radical ideologies in modern American. My decision to write this story was predicated on the January 6, 2021 attack on the U.S. Read More>>

Shawna Fletcher

The biggest risk I have taken related to my creativity is finally self publishing my first novel. I worked on it for over a decade. At first it was a simple passion project to get the characters out of my head and come to life on paper. Then as I read more and more books, I realized there was a market for my story. Read More>>

Eric Stikna

One meaningful risk I took was transitioning from photography as a side hobby into building it as a legitimate business while continuing my full-time role in education. For years, photography was something I loved — capturing school events, sports games, and community moments. Over time, people began asking if I could photograph their events professionally. Read More>>

Jordan Inthachack

The biggest risk I took was letting go of who I thought I was supposed to be and redefining my dream. Growing up, I was wanted to become a music artist or producer. Music means everything to me. But as I got older, I realized those lanes weren’t for me (and I definitely learned that the hard way, haha). Then I found photography. Read More>>

Briana Deshields

A few years ago I took one of the biggest risks of my life. I walked away from the comfort of working for others and decided to build my own platform, Baeyourself. At the time I was a single mom with no investors, no team, and no safety net. All I had was a vision. Read More>>

Valerie Cortinas

Expanding Before It Felt Comfortable One of the biggest risks I’ve taken didn’t look dramatic from the outside ,but internally, it was significant. I had already built stability through my tax business. I understood the workflow. I had returning clients. I knew how to manage the season and structure my time. It was predictable and as a mother, predictability feels safe. Read More>>

Christina Hamman

I believe we are not meant to move through life alone. Ironically, it took feeling profoundly alone in my own profession to fully understand that. When I became a psychotherapist years ago, I was met with a lack of substantial connection within a group practice, misaligned values, and poor supervision. All of these things contributed significantly to my loneliness and disillusionment. Read More>>

Kerri Naslund-Monday

When They Wouldn’t Listen, I Built It Myself On betting on your own vision — and winning. Let me tell you about the moment I realized that sometimes the biggest risk isn’t the leap you take,it’s staying put on a platform that was never going to grow with you. Read More>>

Khaleel Ray

One Thing I Started doing recently Is showing who I am. To me that’s the most risk ever. In my journey as a artist I was always really scared to really show who I was to the world. Read More>>

Melissa VandenBerg

For 28 years I worked in healthcare as an administrative assistant I loved baking in my down time but often felt like something was missing- like maybe I had missed my calling. About a year ago I was asked to mange and bake for a dessert bar in downtown Grand Rapids full time. Read More>>

PME Ghost

This year I made a promise to myself to be different to branch out. I’ve always made all kinds of different music behind the scenes but I was never comfortable releasing them for different reasons. Some songs were just way too vulnerable, others I just wasn’t confident that they would do well. Read More>>

The Media Prince

They told me independent media was a long shot. They said without a major network backing me, without a big machine pushing my name, I’d never make it in this industry. I heard the whispers. I felt the doubt. There were moments of turmoil where the noise was loud enough to make anyone second-guess their calling. But I didn’t. Read More>>

OTR Nick

Growing up with sickle cell I always believed life itself was a risk, from doctors telling me I wouldn’t live past a certain age to multiple surgeries, I never wanted to live mediocre. Read More>>

AriLyn McKelvey

Leaving my old life behind. Read More>>

Michelle Nirumandrad

The first time I jumped out of a plane, it was supposed to be a one-time thing. I was overweight, unsure of myself, and definitely not someone people would describe as a thrill-seeker. But I said yes anyway. When the door opened, I was terrified — and completely alive. That jump didn’t just change my hobbies; it changed how I see myself. Read More>>

JW Wright

The idea of going from the construction management industry to opening a Martial arts school was a scary one! I never thought I wanted my hobbie to turn into a job. But what I soon realized was that when you follow your passion it’s easy for people to see and want to support. Read More>>

Jeramy Purley

Throughout my life, I have consistently taken calculated risks. I rely on my own judgment, as when proposing positive initiatives, the initial response from others is often negative. Once someone responds negatively to me or my ideas, I refrain from further discussion and avoid sharing my plans with that individual in the future. Read More>>

Inessa Createssa

The fundamental risk of my life started when I was 12 years old. Choosing a creative path at that age means stepping into a world that does not come with an instruction manual. While my classmates were focused on a traditional school life with parties and dates, I launched my first YouTube channel. Read More>>

maiana Rose

Taking a risk is not a story… from my perspective, risk is a lifestyle, and I am living it. Becoming an author felt accidental, but it wasn’t. Committing to a year-long book tour for my second book, Oh, The Dudes That You’ll Date!, and integrating it with my personal life and brand was a risk. Read More>>

Catherine Lang-Cline

I always wince a little when people say that business owners or leaders are risk takers. The people I have seen as the most successful, myself included, are better described as curious. From the outside, it may seem like I was taking a risk when I decided to start a business and knew very little about doing it. Read More>>

Stephanie Gilewicz

We have taken so many risks in the life of our business it has become a large part of our MO. Read More>>

Just Zero

I’ve always believed it’s riskier not to move. Staying in the “what if,” circling half-formed ideas, waiting for certainty — that’s the real gamble. I’ve never been reckless, but I’ve consistently chosen the path where growth was unavoidable. I tend to bet on outcomes where I win either way. If something succeeds, that’s great. If it fails, I leave with skill, experience, and clarity. Read More>>

Savanna Reliford

I have always been a risk taker long before I even knew what risk meant. One of my favorite stories about myself isn’t something I remember clearly, but something my late Granny Barbara didn’t let me forget. She kept a drawing I made when I was four or five years old. Read More>>

Penny Mendez

La vida, a veces, parece detenerse antes de haber comenzado realmente. A los 16 años, mientras el mundo se abría para otros con promesas de futuro, el mío se transformó en una responsabilidad gigante: me convertí en madre. En ese instante, guardé mis sueños de niña en un cajón con llave y aprendí que sobrevivir era la única prioridad. Read More>>

Deepspawn_Logic

The biggest risk I’m taking right now is becoming comfortable with my voice and putting my words to my music for everyone to hear. It makes me feel vulnerable and powerful at the same time, like I’m standing on the edge of something and I don’t know if I’ll fly or fall. Read More>>

Rahmar Duffy

To fully paint the picture, we have to go back in time. When I first began my journey as a DJ back in 2016, I was a month away from my 24th birthday.  Skipping ahead—in a few months I’ll be 34. Needless to say, a lot has happened within those 10 years. Some truly amazing things, others not so much. Read More>>

Machaela Wooden

I have taken on a lot of big risks in my life such as moving away hours from my family starting a whole new life reestablishing myself. Through the transition and the new journey I have been on, life of course has had its ups & downs, but through the grace of God & the love & support I have obtained from my family & close friends, I have overcame everything and been great along the way. Read More>>

Mykerah Mackey-Robinson

One of the most significant risks I have taken was choosing to build my leadership consulting work in alignment with my calling rather than my comfort. Read More>>

 Jada Mullins

We all know taking risks can be scary. Right ? It’s very uncertain of what may happen next and honestly as a business owner the risk taking never stops. You literally bet on yourself every important move you take but this is where faith comes in. I took the biggest risk in quitting my 9-5 to flourish in my business. Read More>>

Donald L Dowridge Jr.

The biggest risk taken was on November 22nd, 1996! As the first Black Male Manager of the OCR/BCS Department at the U. S. Post Office Main in Tampa, Florida, I was invited by my son to speak in his 5th grade class, my intentions first of all was to be present as a great dad would. Read More>>