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.

Renée Gotcher

The biggest risk I’ve taken as an entrepreneur is owning a private integrated arts and academics program for local homeschooling families. When my family joined this unique community in 2015, it was the perfect fit for my artsy girls but a completely new endeavor for me. I began teaching history, literature, and worldview in the classroom for the first time. Read more>>

Jami Buckner

In 2019, I held the position of counter manager for Lancôme, but unfortunately, I found myself unfulfilled in the role. As a makeup artist on the side, my passion for the craft continued to grow, yet I felt hindered by the demands of my primary job. The company’s emphasis on sales numbers overshadowed the artistic aspects of cosmetics sales, which was particularly disappointing given Lancôme’s stature in the industry. The focus on upselling and adding extras created a sense of dread for me, making it challenging to come to work. After several years with the brand, I made the decision to devote myself fully to being a professional makeup artist. I submitted my resignation and have not looked back since. It was the most prudent decision I have ever made, and I am proud to have taken a risk on myself. Read more>>

Minh-thu Lam

At my last career, I had almost a fairy tale story in an industry that is pretty cut throat and grimy. I spent 9 years in the auto industry and started and finished my career at the same place. I was working for the #1 luxury auto dealer in the world and working in 1 place over the course of my career, especially as a female was extremely rare. Read more>>

Jeidi Carrion-fajardo

A huge part of my identity and who I am as a person is my sexual orientation as a Lesbian. I haven’t always gotten the privilege to say this as confidently and loudly as I do today. Growing up in a latino household, where the only reality I knew was a hetronormative one, in which I would eventually end up marrying a man and having a family like every Latina is expected to do. It was an extremeley upsetting light of the end of tunnel. Not only was this stripping me of my professional aspirations and dreams but also one where I got to be true to who I was and who I loved. As I grew up with this standard being drilled into me, I eventually conformed and attempted to engage in hetrosexual relationships that always felt very unfilling and empty. Read more>>

Suzanne Boothby

Creative careers are full of risks, and I think so many early choices in my life helped create a foundation where I became more comfortable with uncertainty and betting on my ability to take a risk and have it pay off.

One of my earliest risks was traveling to New Zealand for a year in my early 20s. I had been working for a magazine in Chicago, and it was a great, steady job. But I had wanderlust and really wanted to see the world before I became too settled into a routine. I became interested in New Zealand, as it was a place known for gorgeous landscapes, organic agriculture, and a rich indigenous culture. I also had a kiwi editor when I worked at Mother Jones magazine, who was always telling me stories about NZ. Read more>>

Reid Harris

The original plan was to just stay for 3 months in 2021, but after falling in love with the city and its vibrant music scene, I decided to give New York a real shot. The energy here, combined with the opportunities to grow both personally and professionally, made it clear that staying longer was the right choice. It’s been an amazing journey so far, and I’ve really embraced the challenges and rewards that come with being in such a wild city. Read more>>

Chase Lin

During my first year at California Lutheran University, I made one of the biggest decisions of my life—I chose to drop out and pursue my business idea full-time. It wasn’t an easy decision, especially after having spent years preparing for college while attending La Cañada High School. Like many others, I was on the traditional path of education, but deep down, I felt a strong pull toward entrepreneurship. Read more>>

Priscilla Garcia

The biggest risk I’ve taken was switching careers and finding what I wanted to do in life. Prior to the pandemic, I worked for a well-known musical instrument company as an HR representative, went to school for business management and got certified with employment law. I thought I wanted to do this for the rest of my life. However, I found myself feeling burnt out, and coming home frustrated (working 12 hour days, and being on-call) from my job. On the weekends, I would go visit my mom and she started doing house pet grooming. She would ask me if I wanted to help her and, naturally, said yes. Read more>>

Jessica Oduro

In September of 2023, I was sitting on my living room couch having a mental breakdown. I was a year and a half into my corporate consulting job when I decided I needed to quit. I always knew I wouldn’t be in the corporate space forever, as I was doing social media part time and that was my passion. Read more>>

Dominic Moore-dunson

Starting The Remember Balloons was one of the most profound and challenging decisions I’ve ever made, both as an artist and as a provider for my family. The idea for the project emerged from a deeply personal place, and though it was rooted in love and a desire to spark meaningful conversations, I knew pursuing it would come with significant risks—financially, emotionally, and artistically. Read more>>

Ari Hawthorne

Opening my own business has undoubtedly been the biggest risk I’ve ever taken, and it’s definitely been life-changing. For years I’ve worked as a trainer and therapist, building a solid and loyal client base, but I always felt like something was missing, I was limited in how much I could truly help people without a dedicated space-without a “hub” that I could design to provide the full support I knew people needed. Read more>>

Jennifer Silva Redmond

My whole adult life is sort of a story of taking risks, large and small. I dropped out of college at 18 and ran off to Los Angeles and then New York to be an actress. Then, in 1989, just when I was getting a toehold in the business, I took a risk going sailing for a year in Mexico with my new husband. After a decade of sailing, writing, and editing, I took a job with Sunbelt Publications, a small indie publisher in San Diego in 2000. Then in 2011, I went freelance. The first year I had to practically give away my services, and I attended a lot of conferences and writers groups before finding enough authors who needed my services. My work clearly impressed people; I have been an independent book editor ever since. Read more>>

Liberty Bernal

In my early 20s, I took a risk that completely transformed my life, although it didn’t start out as some grand vision. At the time, I was a franchisee of two fitness studios. I loved the experience, but I also felt this pull to create something uniquely my own—a space where I could bring my vision for fitness and empowerment to life. Read more>>

Rose Wheel

One of the biggest risks I’ve taken recently was to leave my stable corporate job to start my own wellness business. It was a decision that weighed heavily on me because I had spent over 15 years in the same industry. I loved my role, the deep connections I formed, and the stability it provided. However, over time, I began to feel a growing desire to make a larger impact, particularly in helping other business professionals manage stress, burnout, and find a better balance in their lives. Read more>>

Maria Juarez

In just one week, I made the decision to move from Mexico to California—a leap of faith and probably one of the biggest risks I’ve ever taken. It made me wonder: what would have happened if I’d stayed? What if I had never tried?

I’ve always been an ambitious person, constantly seeking growth and challenges. At 20, I was working on incredible projects, dedicating my time into sharing all the knowledge I’d gained with others through dance. Being a dance teacher is the most fulfilling job; I get to meet so many people, connect with them on such a deep level and empower them to chase their dreams. My goal has always been to be the mentor I needed when I was younger. Read more>>

Sandie Eggers

The story I’m about to tell you is still unfolding. But I’m convinced that this risk is well-worth it, helping me to better align with my values and to better fulfill my purpose.

That risk? To live less by my understanding and more by faith. You may ask “What do you mean, specifically?” Well, that means to let go of a “sure thing” like seeking contract work and to embrace the greater uncertainty of freelance work in the faith-based market .Read more>>

Elizabeth (beth) Bilharz Of River Valley Canines

As a breeder, our main focus has always been on improving the health, and temperament of the breed and types we work with. We have spent years carefully selecting breeding pairs based on their genetic health, structure for proper function, and overall temperament to produce puppies that are not only beautiful but also physically and mentally sound. Read more>>

The most significant risk I ever took was breaking up with Alcohol, aka getting good and sober one day at a time, by entering rehab on July 23, 2019.

I had no idea if this would “work,” fix me, help me, or save me from the hell I was in, but honestly, I had run out of options, and my people were getting sick and tired of my drinking as well. Something had to change, and thank God, it led me to such utter despair that rehab felt like a good idea. Read more>>

Sameena Mughal

In 2015, I was stuck. Like head caught in a turtleneck stuck. I had been teaching high school for a long time and wasn’t feeling challenged. As a solution-based person, I tried to think of what I could do to get my head out of the turtleneck. I decided to look. Read more>>

Kyle Brown

One of the most pivotal risks I ever took came in 2001, just a year after graduating college. At the time, I was navigating the corporate world, following a stable and predictable path doing technology sales. I found myself sitting in the 10th interview of the day at one of the most prestigious investment banks on the planet. My brother worked there, and with his mentorship and my proven sales record, I felt confident. This was my chance to secure a high-paying, secure position in the world of finance—a dream for many. Read more>>

Kalie Fish

The most profound risk I’ve ever taken is the risk of giving up consistency and security in order to have freedom. One day, I finally made the decision to leave behind the stability of a steady paycheck, health insurance, and other benefits. With this decision, I chose to take full responsibility for my income; relying on my work ethic, perseverance, and drive to meet my professional, financial, personal and family goals. I am a Type-A kind of person; I love a plan and I love consistency. So the logistics of moving from a salaried employee position to being a self-employed, 1099 contractor and business owner was incredibly scary for these reasons. And although the reasons for my fear are valid, if I could, I would go back in time and tell myself to take the leap sooner! Read more>>