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.

Marquze Killion

As a child, I suffered from intense night terrors. Art became the only thing that could calm me, and that’s where my love for creating began. What started as survival grew into purpose. After graduating high school at 18, I made the biggest decision of my life leaving Memphis for Los Angeles on my own. I had never left home before. Read more>>

Dr. Annise Mabry

One of the biggest risks I have taken was launching the Restoration Institute at a moment when most people would have chosen safety instead. For nearly a decade, my work lived at the intersection of trauma-informed education, public systems, and nonprofit leadership. Read more>>

DeShaun Davis

Taking a risk for me came later in my career. For most of my time in entertainment, my role was to serve others and support their dreams. I was often the foundation beneath someone else’s “big idea,” helping bring their vision to life while placing my own on the back burner. The greatest risk I had to take was learning to believe in—and bet on—myself. Read more>>

James Michael McLester

The RISK- Answer the question who do you TRUST? I was willing and able to step into uncharted waters- The OCEAN of LIFE and with grace and agility move from tragedy and despair to TRIUMPH and in my Health, Wellness, Music, Relationships, and completion of 2 Exhilarating Curriculums at The Institute for Integrative Nutrition at age 55. Read more>>

Lost in the City Band

A meaningful risk we took was restarting our band, Lost in the City, after it effectively broke up during COVID. Before the pandemic, the band was active and moving forward. When COVID hit, everything stopped at once. Shows disappeared, plans were canceled, and the informal momentum that keeps a band alive just… vanished. Like a lot of people, we shifted into survival mode. Read more>>

Gala Brauer

I moved to the United States all by myself at the age of 18. I did not know the language well, and had no one I knew here. I took an opportunity to come study in the U.S. and settled in little town in the middle of nowhere in Kansas. It was a very challenging period of my life. Read more>>

Steve Castillo

I love to work and hustle, so I couldn’t understand why I went from job to job every two to three years. It wasn’t completely boredom, it was more that I didn’t want to build someone else’s dream on their time while keeping mine on the back burner. Read more>>

Stacia Weddle

One of the biggest risks I’ve taken with my photography wasn’t buying new gear or saying yes to a big shoot, it was uprooting the life and business I had carefully built. I started my photography journey in a community where I poured my heart into building relationships, trust, and a client base from the ground up. Read more>>

Arif Yardimci

Growing up in a small town in Turkey, I never imagined I would one day be helping companies from around the world navigate the U.S. energy market. But dreams have a way of pushing you beyond your comfort zone. Read more>>

Lindsay Ryan

I’ve loved photography since high school. Back then, I was drawn to capturing moments in a way that felt honest and meaningful. Years later, while living in Hawaii, I even had a side gig photographing friends and families. It was never about money… it was about passion. For more than 14 years, I worked in the medical field as a medical assistant in orthopedics. Read more>>

Lori Marini

The Biggest Risk I Ever Took Was Expanding Beyond One System When My Life Depended on It The biggest risk I’ve ever taken didn’t look dramatic. I didn’t quit my career overnight or reject science. The real risk was quieter: expanding beyond the system that trained me when staying inside it was no longer enough to save my life. Read more>>

Sally Mayberry

From Sunsetting a Passion to Launching a Purpose For more than two years, I was the voice behind ‘FriYAY,’ an internal employee podcast I created and launched for the National Park Service during the height of the pandemic. It was more than a project; it was a digital lifeline for employees during a period of global isolation. Read more>>

Helen Blondel

The biggest risk I’ve taken, and I continue to take it every day, is choosing my art and doing music at a professional level. Having went to college and majored in Hospitality Management & going straight into working in the corporate world after graduating, I’m thankful to have that experience. However, I’ve always been called to perform. It’s a very unpredictable industry. Read more>>

Michelle J Margolis

The biggest risk I took was walking away from certainty when it no longer aligned with who I was becoming. I had a stable career, benefits, and a clearly defined trajectory, and I also had a growing awareness that I was playing a role I had outgrown. Read more>>

Jose Torres

One of the biggest risks I’ve ever taken was deciding to fully finance and produce a cinematic audio drama called The Rise of King Asilas. At the time, I had no guarantee it would succeed. In fact, I knew it was a long shot. Read more>>

Jerry McGlade

The biggest risk I have taken was making a career change that prioritized long-term potential over immediate stability. Early on, I was in a role that was technically solid and relatively secure. The safe play would have been to stay specialized and keep things predictable. Read more>>

Luc Jorgart

One of the biggest risks I took was when I moved to Japan to continue my legal studies, knowing there were no guarantees waiting on the other side. At the time, I had already completed my undergraduate law degree in the UK. Read more>>

Nate Paxton

The greatest risk I’ve ever taken is becoming a preferred walk on at Georgia State University, while my family was battling homelessness and poverty. This was a huge wrist because we were struggling financially not knowing where we were going to stay the next night, but also I was on straight student loans so I was putting myself in debt chasing a dream. Read more>>

Alexandra Kerlin

One of the biggest risks I ever took was investing $30,000 into a coaching program from someone I had just met online. I worked really hard to put myself through and complete my Master of Arts in Holistic Health Studies. I was working full-time in wellness at a local food co-op after graduation at the time, still paying off massive debt. Read more>>

Jervon Galloway

Taking a risk? Betting on yourself? Have you ever done so with so much faith take you don’t see anything besides your future & end goal? I did so last year May 2025 at the age of 28 years old. That risk was moving across the country to a major city that I knew no one at all neither did I have a plan. Read more>>

Miriam Boucher

When I was 21 years old and graduating from my undergrad, I started looking for places as far from my norm as possible. I wanted to challenge myself and put my passion for wildlife conservation and research to the test. My thought was to look for opportunities to live and work abroad because I love to travel. Read more>>

Shaquil Reeves

The biggest risk I’ve taken was leaving my hometown—Kansas City, Missouri—to pursue acting. I grew up in the inner city, and where I’m from, a lot of people don’t branch out. You take the safe route because it’s familiar. I’ve been out here for ten years now, and while it’s definitely the harder path, it’s been worth it. Read more>>

Edgar Sermeno

You take risks everyday that you wake up and do something we call life. There are good one and bad ones. But we will only know the outcome after we do that. In business it’s a high risk in the reason for is because the come up is a journey of it’s own. Read more>>

Amanda Banzali

When I had the opportunity to start my waxing studio, it all happened by chance! At the time, I was a stay at home mom and had purchased a “Black Friday Package” from a local service provider to treat myself. I showed up to her location which was situated in a salon suite. Read more>>

Isaiah Thomas

It’s a risk to put yourself out there and write books, write an article, start a business, get married, start a clothing brand, or start a podcast. Taking a risk requires most often, to just jump out in the unknown and make mistakes until you learn how to navigate it. Read more>>

Jori Bowman

I want to encourage you to step into what calls you. I made a choice to dive into a career that was looked down on by the average person. I decided to trust in ideas for my spiritual business. I want to help folks get a clear conscious on the doubtful thoughts, emotions and ideas that are flowing in their mind. Read more>>

Laura Messick

Quitting my full time career as a successful hairstylist without truly having much to fall back on is the biggest risk I think I’ve taken to date! I had been in the beauty industry for over a decade, had an amazing clientele, was booked out for at least 8 weeks a lot of the time, and. . . I was no longer happy. Read more>>

Colden Blades

Everything in this life is a risk. At least that’s the way I’ve always viewed it. Whether you’re getting in your car and risking an accident or asking a girl out and risking rejection, the list of daily gambles goes on. Hell if you try avoiding risk altogether the only thing you’re going to find yourself truly avoiding is a life worth living. Read more>>

Kristina Libby

I’ve been a business owner for a while, on and off. I always seem to be starting up something. But my biggest risk was actually stepping outside my business to embrace my more creative self. I began to take seriously my painting, then my writing and most recently my storytelling. Read more>>

Luiza Gottschalk

After 20 years of solid work in Brazil, arriving in NYC for a debut exhibition in Chelsea is undoubtedly a risk (at least that’s what I’ve heard from the experts and advisors in the art world). It feels like starting from scratch all over again. NYC is a major international art world itself—“What if your work isn’t accepted in the market? What will you do?” This kind of question reached me. I think about it this way: if I were an engineer constructing a bridge, it would be quite irresponsible not to have everything meticulously planed. But I am an artist—I wish to carve my own paths; I have no interest in walking well-trodden roads. Read more>>