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. 

Bob Spurlock

Life is full of adventures, also coming to that proverbial fork in the road moments. Don’t be afraid to take that chance. That happened to me when during working for a fortune 100 company in the corporate world. During that last year, the company decided to go through a corporate restructuring. I was presented with several options. Read More>>

Scott Campbell

I’ve been accused of being an adrenaline junkie. When I was young and more or less indestructible, two of my favorite activities were skiing and mountain climbing. My best days on the slopes were the ones where I felt right on the edge of catastrophe–dropping into something crazy steep or navigating massive mogul fields. Read More>>

Anna & Chris Holmes

One of the biggest risks we took was starting to teach painting classes and investing in our own studio space before we had any guarantee it would work. At the time, that felt huge. We had to spend money on the space, supplies, and advertising while wondering if anyone would actually show up. Read More>>

Dr. Starr Barrett

One meaningful risk I took was expanding GodXess into vegan hair products while also transitioning many of our holistic services into a mobile model to reduce overhead. When I first started GodXess, the focus was primarily on holistic wellness services—things like Reiki, spiritual counseling, and other energy-based healing services. Through working closely with clients, I began noticing a pattern. Read More>>

Ashley Deland

One of the most defining and earliest risks was walking away from a very successful corporate career to become an entrepreneur. At the time, I was working in a high-level marketing role, managing major portfolios and building campaigns and putting on events for million-dollar organizations. From the outside, it looked like the kind of career people spend decades trying to build. Read More>>

Mo Smith

I started my business with a risk. I left my 9-5 job with just enough money to last me 1.5 months. No savings. No concrete business plan. Just the intuitive feeling and KNOWING that it was time to take the leap. Read More>>

Jeffrey Urdang

One of the most defining risks I’ve taken was starting my own art installation and design company, Flagstaff Fine Art Services, while building my career as a painter. At the time, I was exhibiting my work but kept hitting limitations; larger, more immersive ideas required resources and control I didn’t have on my own. Read More>>

Anthony Dyer

I’ve mentioned before a quote I once heard: “Empires are built on taking risks; 9–5s are built on avoiding them.” I’ve always pushed it a step further: “Legacies are built on risk; ordinary is built on avoiding it.” Writing Moon Child forced me to live that out. Because putting your story on paper—your real story—means choosing vulnerability over comfort. Read More>>

Naii Vegas

One of the biggest risks I ever took was deciding to build my design studio in the United States. Creative Buildr Studio was born during the pandemic while I was living in Colombia. At that time, the world felt uncertain, but creatively it was also a moment of reinvention. Read More>>

Sheree Swann

One of the biggest risks I’ve taken recently was deciding to step away from the stability I had built and move to Ghana for a year-long fellowship. On paper, it probably didn’t make the most practical sense. I had a recurring contract that provided steady income, and I also run a business, Wild Seed Butik, that was beginning to find its rhythm. Read More>>

Jessica Wiler

One of the biggest risks I’ve taken was leaving my job as a college lecturer in Singapore after living there for nearly four years. It was, by most standards, a very good situation: stable, fulfilling, and with the added benefit of being able to travel frequently. Read More>>

Jay Grammond

I bought my first 35mm camera back in 1981. By the time I was in college in the late 80s I was doing photography as a side-business. Fast forward to about 2016 when the photography side of things was really getting busy; and my full-time job in Lifelong Learning was very successful. I started really thinking about the idea of going full time with photography. Read More>>

Erica Duran

Risk: Walking away from an online business model that “worked” + disappearing without an explanation to rebuild the ecosystem. I took a risk that looks small from the outside but felt massive in real time: I stopped playing a game I was winning. For years, I had built a highly visible online business. Read More>>

Chris Brock

In 2011 I started my landscape architecture business, but it actually began out of necessity more than a grand plan. At the time the economy was still recovering and jobs in the design and construction industry were scarce. To make things even more challenging, I was living high up in the mountains in Colorado, far from major cities where most landscape architecture work was happening. Read More>>

Gwendoline Van Doosselaere

The founding and launching of Artemis Divorce Coaching and The Divorce School for Women was — and continues to be — a risk. Stepping into entrepreneurship is not foreign to me. Knowing what it takes to run a small business is not unknown. Turning the lens on myself, however — flattening the gap between the product and myself and my work — is entirely new. Read More>>

Donellia L

I’ve always been someone who takes risks, but the one that changed me the most was walking away from something that looked secure and choosing to rebuild my life on my own terms. In 2024, I was working as a Branding Director at a real estate company in Chicago. Read More>>

Apollonia Crush

One of the biggest risks I took was stepping fully into my creative path and building my brand, Crushin Visuals, instead of staying comfortable in a stable routine. I had security, but I felt stuck. I knew I had a bigger vision in videography and storytelling, so I chose to bet on myself, even without guaranteed income or opportunities. Read More>>

Kailey Hall

A defining risk I took was starting PHEEL. At the time, I was a Marketing Director in what many would consider a “dream role.” On paper, it didn’t make sense to leave, I had stability, success, and everything I thought I was supposed to want. But deep down, I knew it wasn’t where I was meant to stay. Read More>>

Bob Stahl

Taking the Risk of Being Seen: How I Went from Hiding My Gift to Building a Business Around It There is a moment most psychics don’t talk about. The one before the business cards, before the website, before the first client sits across from you. The moment you decide whether to keep this thing quiet or tell people. That was the real risk for me. Read More>>

Jasmine Seewald Godeaux

The first step to being an artist is taking a risk. I started drawing digitally when I was 11 years old, but for years I never showed anyone my work. I was afraid of exposing what I thought was “bad” about my art, so I kept everything hidden—every drawing, whether I thought it was good or not. Read More>>

Debby Flowers

It’s really hard to contemplate giving up a well paying job with good benefits for the questionable income and no (traditional) benefits. To trade that employment for the opportunity to pursue a full-time farm life was a big scary risk. In 2022 after working for our county social services department for 14 years, I took that risk. Read More>>

Mikhail Marcus

One of the biggest risks I have taken was opening my own gym, Webhead Fitness WERQhouse. I did not step into it with a big savings account, investors, or a real safety net. I had very little liquid cash to get things going. What I had was vision, hunger, faith, and the belief that I was supposed to build something that could truly change lives. Read More>>

Anna Fox

I left Europe for the Florida sun, the stunning white-sand beaches, and a lifestyle I had always dreamed of. It was everything I imagined — until the very sun that drew me here brought an unexpected challenge: a diagnosis of skin cancer. Determined to understand my own skin, I enrolled in aesthetics school — and almost immediately found myself fielding questions from people around me. Read More>>

Cassie Link

There are two risks that I have taken recently that have brought me to where I am today. I finished with my Master of Occupational Therapy (MOT) in Fall 2021 and have been working as an Occupational Therapist (OTR/L) since 2022. Read More>>

Ray Sheehan

As a performer, every live show you play contains risk. Some have more than others, though that is where it all happens… in the risk. You are risking showing your truest form to the world and to the room itself. It is not always glamorous; there is a reason people hide things within themselves. Read More>>

sara palma

One of the biggest risks I’ve ever taken was moving to the United States on my own at 24. At the time, I was navigating personal loss and a deep sense that my life needed to change. I didn’t have a clear plan—I just knew I couldn’t stay where I was. Read More>>

Allyson Tomchin, LCSW

I could talk about taking a risk when I got divorced and was left to raise my daughter alone or I can tell you about taking a risk and starting a psychotherapy private practice which is 23 years old now but I think I would rather share my first experience that I can remember in taking a risk. I was 8 years old. Read More>>

Steven Rodriguez

Just being a Street Photographer period and putting my work out in the world. Naturally introverted as a person and facing the public with only my camera goes against my better judgement. My photography is, to me, a personal journal and how my eye sees the world. I’m out there taking pictures of myself through others. Read More>>