You’re working hard, things are going well, piece by piece you’ve built a life you are proud of, you’ve overcome obstacles and challenges, beat the odds and then you find yourself at the center of an unexpected dilemma – do you risk it all to keep growing? What if growing means leaving the job you worked so hard to get or the industry you worked so hard to break into? How we approach risk often has a huge bearing on our journey and so we’ve asked some of the brightest folks we know to share stories of risks they’ve taken.

Dillan Lowrie

One of the biggest risks I’ve taken was taking a year off from school to fully focus on my photography business. A year ago, I was juggling classes while building my photography business on the side, and it reached a point where I realized I couldn’t keep doing both well. Read More>>

Don Che

The risk level increases daily given the situations I’m faced with! Rather my music career, or coming up with new designs that will attract fans, and shoppers alike. Music changes every second of every day, and the demand to deliver for me at least is to remain one step ahead of the normal pack! Read More>>

Megan Pennington

 

One day in 2018, I decided to pack up my car and travel from Pittsburgh to Chicago to pursue my music career. Long nights on the road landed me quite a few gigs, and opened doors for me that were previously unimaginable. Since taking that risk, I have found the confidence and ability to travel the country as a performer. Read More>>

Ashton Reynolds

The biggest risk that I took was deciding to truly give my life to Christ. This was a decision that was made as I was going through the toughest time of my life: 2015. That was the year my mother passed away. Read More>>

Yvonna Russell

When I decided to share my creative writing, I had to choose between traditional publishing and self-publishing. This is my second career, so I have some experience with agents, auditioning, and rejection. Being an actor was entrepreneurial, so I knew I could navigate the world of creative writing with the same discipline. The big difference is my satisfaction with direct-to-consumer e-commerce. Read More>>

Megan Butts

With big dreams, I rented a cozy 500 sq. ft. space, just enough room for 10 kids at a time. I hosted small classes and special Parents’ Night Out events… and something magical happened. Families kept coming back. Creativity filled the room. Soon, birthday parties were added, laughter got louder, and Craft Lab quickly outgrew its first home. Read More>>

Dani Guevarez

The risk I took was giving Jesus my career. I took that risk fully in July 2025. I was acting in commercials, stage plays, and film. For years, He had been getting my attention, calling me to step away, but I wasn’t ready to let go. Read More>>

Terraca Bobo-Wright

As a single mom who had just had my son, I hated my body. I also hated the gym lol so I took a risk and started my own dance fitness brand because I’ve loved dance since I was a child. I learned that dance was a great way to get in shape so I went for it. Read More>>

Samantha Mahon

One of the biggest risks I’ve taken in my life hasn’t been just one moment—it’s been a series of intentional and risky leaps ‘of faith’ where I felt called to ‘build the plane while flying’ and chose alignment over comfort, and integrity over fear. Read More>>

Aiden Branss

It was August 28th, 2020. I specifically remember the date because it was the day after actor Chadwick Boseman passed away. I was 16 years old, and during this time of my life, I was really struggling with anxiety and insomnia. Being trapped inside my family’s small two-bedroom apartment for months was eating me alive. The COVID-19 pandemic showed no signs of slowing down. Read More>>

Ora Lockett

In the early stages of my work, I focused primarily on selling products. Over time, I realized that the greater impact came not from the products themselves, but from creating content that challenges people to think differently—especially about natural alternatives to conventional health approaches. Read More>>

Meredith ‘Phee’ Avery

The biggest risk I ever took was deciding to stop treating my creativity like a luxury. For years, I split myself in two. One version of me did what was necessary to survive. The other wrote, made music, and waited for permission that never came. Creativity was something I squeezed in after responsibility, not something I was allowed to build a life around. Read More>>

Julia Deckman

At the beginning of 2020, I was working part-time at a local art supply shop and painting out of a small studio at Redux Contemporary Art Center. When COVID hit, I was terrified—not just about the world, but about my future as an artist. Would art still matter when everything felt so uncertain? Quarantine unexpectedly brought clarity. Read More>>

Erin McGuire-Henson

I think the biggest risk I have taken recently is writing and publishing my book, The Art of Unraveling. It is risky, because it is such a personal story with very raw stories from my life, some of which people who know me well don’t even know. Read More>>

Christy Knutson

Founding Near has been the biggest risk of my professional life, but not in the way that is often talked about. It’s not one big leap but rather the slow, steady toll of showing up every day for something that may never work. I underestimated the cost of building in a space this personal. My partner and I have bootstrapped everything. Read More>>

Ruth-Ann Thorn

In the world of entrepreneurship, the path is rarely straightforward. For me, it started in 1988, at a time when my circumstances felt far from ideal. With only a ninth-grade education under my belt, I took my first step into the art business, not knowing that this would be the foundation for an exhilarating journey filled with challenges and triumphs. Read More>>

Ian Harvey

One of the biggest risks we ever took was deciding to build Smokers Abbey Austin around connection instead of convenience. When we first opened, the “safe” play would’ve been obvious: carry the big-name brands, push volume, move people through quickly, and lean hard into retail. That model works—especially in a city like Austin. But it didn’t feel right to us. Read More>>

Laura Mendiola

The biggest risk I’ve ever taken wasn’t jumping into something new — it was walking away from a version of myself I’d spent over a decade building. I worked in the beauty industry for over fifteen years. Hair, makeup, weddings, full clientele, full reputation — I built that career from scratch. It taught me everything: timing, people-reading, intuition, pacing, energy, self-reliance. It was my world. Read More>>

Christine Kotlarski

Opening my own practice was a leap of faith. Leaving a full time job with benefits to become a self-employed therapist was a huge risk. It was all on me as a single person, a one woman show. I didn’t have a partner’s income or benefits as a safety net. Will I earn enough to pay my bills? what about healthcare? Will clients find me? Read More>>

Steve Twinley

In mid-2023, something had to change. I was Managing Director of a life science recruitment company, with 17 years’ experience, and I was getting burned out. My home life was amazing. Happily married, with two children aged 13 and 11. Read More>>

Monica Lofstrom

For a long time, my work revolved around telling other people’s stories. I built and led a global luxury magazine, interviewed artists, designers, entrepreneurs, and thought leaders, and helped shape narratives that gave voice to others’ creativity and vision. From the outside, it looked like a dream career — and in many ways, it was. Read More>>

Erika E. Wade

Pursuing a career in the arts, especially in today’s world, is a risk in so many ways. Every day, I wake up and ground myself in gratitude for some of those risks paying off. I choose to tell stories that are sometimes hard to hear. Read More>>

Melissa McGowan

A big risk I took recently was saying yes to my first destination wedding in Mexico. While I had photographed weddings before, taking my work out of the country felt intimidating. There were so many unknowns, and fear almost convinced me to say no. What pushed me forward was my clients’ trust in me. Read More>>

Emily Bettdur

The absolute biggest risk I’ve taken in my life is ending my marriage to a man and coming out as a lesbian. This was also the scariest thing I’ve ever done, but it completely changed the trajectory of my life for the better. Read More>>

Stephen Ryan

Starting Fetch The Sun was a real leap of faith. We weren’t just launching another pet brand—we were intentionally creating a new sub-industry and positioning ourselves as one of the first true lifestyle brands for dog owners who love the outdoors. That meant taking on significant financial risk upfront: trademarks, original designs, initial inventory, professional photoshoots, advertising, PR—the list adds up fast. Read More>>

Laura Levine-Pinedo

I was raised off of West 238th Street and Broadway, and growing up in that neighborhood, you develop a specific kind of DNA; you learn early on that there is no one who understands the word resilience more than a true Bronxite. For years, I have been deeply rooted in the restaurant and hospitality industry, navigating its high-pressure environment and fast-paced demands. Read More>>

Josh Stein

In 2015, after fifteen years in the wine business, I closed the winery no one would ever have expected me to open in the first place. Read More>>

Madeline Bastida

Taking a risk, for me, meant choosing to step into the unknown for someone I love. A few years ago, I made the decision to bring my dad from Puerto Rico to Washington after noticing changes in his memory that I couldn’t ignore. It wasn’t a clear or easy decision. Read More>>

Jame Geathers

The biggest risk that I have taken was stepping onto the TEDx stage in 2018. I had (and still have) a paralyzing fear of public speaking. Furthermore, the topic and the contents of my talk were not for the faint of heart. I exposed a very private part of my life, one that many of my clients and friends had no idea about. Read More>>

Fernanda Niemeier

Taking a Risk My name is Fernanda Niemeier. I am 30 years of age, a proud mom to four wonderful children, and currently expecting my fifth. I studied International Business with a minor in Finance and graduated from The University of Texas at Dallas in 2017. Read More>>

Priscilla Caballero

Risk for me is a choice I make every day. I chose a path of service that requires walking directly into uncertainty alongside others. As a housing specialist, domestic abuse advocate, and financial educator, I work with survivors of violence, families facing eviction, and individuals navigating homelessness. Read More>>