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.

Cindy Mejia

The biggest risk I’ve taken has been betting on myself and following my heart. I’ve always been the type of person who likes to analyze every move. I need to know the outcome, the numbers, and whether something will be a guaranteed win before I take action. Read More>>

Arron Gray Lee

In August 2024, God called me to leave my job. At first, I wondered if I was absolutely crazy. But after prayer, fasting, and truly seeking His voice, He confirmed it: this was the risk He was asking me to take. A holy risk. A faith-filled risk. A risk that made no sense on paper but made perfect sense in my spirit. Read More>>

Deby Dearman

I am a singer who lost my voice — and for a time, lost my way. My hubby and I are partners in life, love, and mission. For years, singing together had been our way of expressing who we were with the world. Our songs traveled the globe and were sung in churches worldwide. When singing was taken from me, I was beyond devastated. Read More>>

Meranda Crosby

I’d say my entire business was founded on a risk. Fresh into my twenties, I was living in California with a great job at a highly respected company. I had health benefits, a consistent income, opportunities for career advancement, and an amazing group of friends. Despite all this stability, a part of me felt deeply unsettled. Read More>>

Rebekah Moore Murphy

The biggest risk I’ve ever taken was stepping away from a successful, established design firm to start something entirely my own, during a season of professional transition, motherhood, and uncertainty. Read More>>

CINTIMA

Starting CINTIMA was, at its core, an act of risk. We chose to professionalize intimacy in the film and television industry at a time when the industry was still uncertain about what that even meant. There were no established paths, no precedents to follow, and no assurance that studios or unions would embrace this work. Read More>>

Molly Bolte

Risks are just that, risky. Putting myself out there to develop the little notes on my phone into children’s books was like stepping into the unknown. Would people read it? Would anyone like it? Was I qualified to do this? And HOW do I even do this? Read More>>

Robert Zeler

 

I’d say the biggest risk I’ve taken came right after my 2023 accident. I was stuck in a 9-5 that didn’t fit, hunting for something more meaningful. From late 2023 through 2024, I dove deep into AI—focusing on how it actually works in practice, not just the tech specs. That set the stage for May 2025. Read More>>

Ebony Jeanette

Risk-taking is an art. It’s a sweaty, often teary-eyed and sometimes even blood-soaked driving force behind every creative conquest worth jumping at. One of the most defining risks I ever took was right after college. I packed up my entire life in Columbus, Ohio and moved across the country to Los Angeles, CA for an unpaid internship at Century Media Records and no backup plan. Read More>>

Ebonnie Modisett

The biggest risk I ever took was choosing to bet on myself, especially during one of the hardest times of my life. I’ve always loved beauty and doing makeup, but after losing my mom and brother during COVID, everything changed for me. I realized how short life is and how important it is to do something that truly matters. That’s when I found esthetician school.  Read More>> 

Amani Williams

Deciding to move out on my own was one of the biggest risks I’ve ever taken. I’ve lived with my family for years, surrounded by comfort and familiarity, but I began to feel the need for independence and space to grow. The thought of managing rent, bills, and being completely on my own was intimidating, but I knew staying would hold me back. Read More>>

Megan Van Sipe

The whole decision to chase after a big audacious goal is a risk. The idea felt impossible, with little resources and no insider knowledge, I had to just take one baby step forward at a time. For four years I was comfortable with the passive way I was running my business, designing notebooks and planners to be printed on demand and shipped by Amazon. Read More>>

Matt Malyon

Taking risks has been central to my life’s journey—the invitations to risk that I declined, and those I accepted. There is a way to look at a life and see how both decisions have shaped one journey. Read More>> 

Ashley Chouinard

When my husband Bill and I took over Wild Blue Adventure Co. we were brand new to the business world. Bill is a flight nurse and I am a teacher so we thought we would run Wild Blue in our spare time and it would be a fun passion project Read More>>

Liane Vaz

The year is 2025. The economy is not having a fun time. Small businesses are suffering. The political sphere has much to be desired. I decide to open up my own private brick and mortar goldsmithing studio and shop – despite all signs pointing me to play it safe. Read More>>

Gerald Hearns

Taking a Risk — The Birth of Too Cool Alkaline Water

“Taking a risk isn’t just about doing something uncertain. Sometimes, it’s about following a calling that others can’t yet see while moving on faith and confidence.” Read More>>

Ana Bueno

Before I ever became a chef, I was an entrepreneur in a completely different field — a demanding, high-pressure, male-dominated environment where results mattered more than wellbeing. I learned discipline, resilience, and strategy, but I also learned how easily we can lose connection with ourselves when we operate only from our minds and never from our bodies. Read More>>

Sandra Rios

A Calculated Risk Brings a New Sunrise for Hart to Home Texas

A bold move by Sandra Rios and her business partner David Rios has transformed their partnership into a thriving, life-changing venture. What began as a professional collaboration to improve housing placements for veterans, seniors, people with mental illness, and individuals with disabilities has evolved into a powerful personal and professional union. Read More>>