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.

Suzan Fete

I’ve been Artistic Director and Co-founder of Renaissance Theaterworks (RTW) since our inception in 1993. RTW is a professional theater company in Milwaukee with a focus on gender equity.

Theater is hard. It is a constant struggle of too much work and never enough money. Even the best people fail way more often than they succeed. Sometimes It can feel hopeless. And, theater is the most thrilling, craziest adventure you get to share with other people. There is nothing else like it. Read more>>

Marina Cruz

Marina Cruz Lopez, born on December of 1980, from Mexican parents. Born in Nezahualcóyotl, Mexico. Studied in Nezahualcóyotl’s public schools, also at a all women’s school in Mexico. In 1998 immigrated to the USA, at the age of 17. She graduated from Berkeley High School in 2001, works as a server, is an activist; and is one of the parent leaders of Latinos Unidos de Berkeley. She has also obtained her California Association for Bilingual Education (CABE) License. She is also a poetry lover, it is her hobby; and her biggest inspiration are the kids from all over the world. One of her favorite mottos is “practice the art of the non violence”. Her poems are inspired by the places shes been and the people shes met along the path of her life. She continues to learn and educate herself by taking courses, and she will continue until she reaches her goals. Read more>>

Laura Belmonte

Things felt stagnant here, in the Swamp. Jake and I decided to seize an opportunity to write songs and music in a fresh new location. It was a risk we were willing to take for Lost In Clovers. I call it the ‘pilgrimage to the Blue Ridge Mountains’ ; we lived and breathed the ‘Appalachian emo’ air in Roanoke, VA. We packed up everything, left everyone we knew and the Music scene we were apart of. Drove 7ish hours west with the hope of finding something new in ourselves. For the time spent in a new place I filled up a whole journal with my experiences. Jake and I created Venus of the Swamp E.P , Tales of a Chesapeake Lighthouse E.P, Truth about Sasquatch and Ego Death. We are really proud of the depths we went to in these sounds. We have since moved back to the Swamp, things cannot stay stagnant forever.. Read more>>

Tracy Mangum

I spent most of my life being incredible introverted, shy, and unsure of myself. My first weeks of working as a high school video store clerk forced me to interact with people and began a process of forcing me to be more social and open up about my love of film. Customers would ask me to recommend films to them and at first I would panic. This person was looking for a film to enjoy on a Friday night and I risked ruining their entire weekend if I suggested a movie they didn’t like. I didn’t want that pressure, but instead of running and hiding in the children’s section I began asking a series of questions to get a better understanding of what kind of movie they wanted. Was it a thriller? Read more>>

Violeta Sandoval

Growing up undocumented, I avoided risk at all costs. I did not want to do anything that could put myself and my family at risk. Every decision I made was carefully considered. I spent my earlier years planning out my life, study hard, get a degree and steady career, get married and live happily ever after. Of course, that did not happen. However, at the age of 22, I found myself at rock bottom, after a failed marriage and running out of money for college. I felt trapped and my future was unclear. Read more>>

Tina Kiniry

At 21 years old, I took a risk that would shape the rest of my life—I bought my first modeling agency. From a young age, I had always been passionate about the modeling and acting industry, captivated by the artistry, ambition, and creativity that shaped it. But I never imagined that one day, I’d be in the position to take the reins of my own company. Read more>>

Jocelyn CALAC

I’ll talk here about a small risk I took by going to see a well-known photographer in my city who had a job opening.
I requested a meeting, and on the day of the meeting, I immediately explained to him that I didn’t want the job but that I was taking advantage of this opportunity to meet with him, apologizing for taking up his time. He could have taken it badly and fired me right away. Read more>>

Carolyn He

Zoom audio-feedback is ghastly. This I discovered during a weekly WiSTEM Leadership meeting, wincing as a distorted version of my proposal echoed awkwardly.

My dilemma began with Zoom audio-feedback, but quickly evolved into a matter of Women in STEM’s organizational stability. My proposal to temporarily halt Ambassador Onboarding—the foundation of WiSTEM’s network of thousands—seemed entirely counter-intuitive to our growth. Was it too much work? Too much change? Risk? Back in September, I never would’ve considered freezing Onboarding, except now I suspected we needed to slow down for sustainable growth. Read more>>

Quynh Vu

The Biggest Risk of My Life: Leaving Pharmacy for Real Estate

I walked away from a six-figure pharmacy career to become a full-time land investor. Sounds crazy, right? But here’s why it was the best decision I ever made.

For years, I followed the traditional path—advanced degrees, a secure job, and a steady paycheck. But despite the financial stability, I felt trapped. Long hours, constant stress, and no control over my time made me realize: this isn’t the freedom I worked so hard for. Read more>>

Alexandra Powell

The biggest risk I ever took was moving to Hong Kong at the age of 23. My grandfather and father encouraged me to go work in Asia for a tenure of 6 months to in order to learn product development for a family run Asia Import business. The goal was for me to learn our product development at factory level in order to understand our family business, Heritage Mint Limited, which distributed non food products to 30,000 grocery retail chains across North America. Six months turned into twelve of the best years of my life where I was immersed in the Asian culture and met incredible, intelligent, driven like minded people from around the world. Read more>>

Idan Shoham

In early 2020, I arrived in Australia with my saxophone, a loop station, and a dream of traveling and making music. Then, COVID-19 hit. Borders closed, and I found myself stranded in Fremantle with no gigs, no income, and no clear plan. I was faced with two choices: stay with no resources and wait for the world to open up, or fly back to Israel. Read more>>

Landrie Miller

I had just gotten married and found out I was expecting a child. My husband and I needed to ensure our success as new parents, and decided to open our own business. We had a few ideas, but most of them seemed out of reach. We shared a love for Halloween and wanted to pursue a business related to the holiday. So we could not only love what we do, but also bring a uniqueness to the city. So many other things had been done before, and we needed to stand out amongst other businesses. After much deliberation and planning, we opened Spoox Bootique. Neither of us had ever owned our own business and it was a bit intimidating and downright scary. But with lots of support from our friends, family and the community, we’ve been open for 13 years! It has been an amazing adventure and I am so grateful we took the risk! I couldn’t imagine doing anything else! Read more>>

Andrea Vowels

A risk I have taken is committing to staying home as a full time mom and content creator after having both our boys! I was a kindergarten teacher for 7 years and also had my home account as a way to share all my love for interior design. In the past 3 years we have had our two boys and we took a risk for me to stay home, not knowing if we could manage that (money wise) and it has been the best thing we ever did. I love being able to focus on my page and sharing all our favorite finds we use daily with our family! Read more>>

Jadyn Shea

One of the biggest risks I took in my photography business was when I invested in my first high-end camera and lens setup. At the time, I was still building my brand, and every dollar I made went right back into my business. I had been working with an entry-level camera for a while, and while it got the job done, I knew I was reaching a plateau. I needed better equipment to boost my work and attract the clientele I always dreamed of working with. Read more>>

Kyle Gilmore

The biggest professional risk I’ve taken was transitioning from my landscaping career to becoming a full-time realtor. Coming from a blue-collar background, the idea of leaving a guaranteed paycheck was scary. But I found that taking this step towards my purpose was the best decision I ever made. I’ve been raised to believe that if you don’t show up and clock in to your job you’re not getting paid. Taking a job where I’m putting all my bets on myself is a big risk, especially entering a world I knew so little about. I’ve felt comfortable in this decision because of 3 major things. 1 I was burnt out of my labor-intensive job landscaping. I loved the work, but ultimately, I was always more interested in finance, global economics, and politics. Any time I wasn’t speaking to a coworker, I was listening to a podcast about current events or business development. I wasn’t being pushed mentally. Read more>>

Amber Walker

When I began my aerial yoga journey. I started doing yoga when I got medically retired from the Navy. I was diagnosed with lupus and a rare neuromuscular disease called myasthenia gravis, I had lost 70% of my mobility and suffered great nervous system and muscular issues because of the illness. Becoming a yogi while embracing ancient healing techniques which included meditating and sound healing sessions from 4-5 hours day sometimes guided me into the path way of yoga and aerial yoga. After doing regular yoga and pilates for a year, I was able to have the endurance and strength to begin Lyra, aerial hammock, and aerial silk. I am now in remission and am practicing as a professional! Read more>>

Autumn Adeyan

Understanding that you must always choose between change to pursue a different outcome and repeating tired cycles, is a lesson that must be understood more than once in this lifetime.

I chose to start my podcast after realizing I wanted to do something different, while not quite knowing what the end result might be. Would it become an organization, remain a passion project that I nurture on the side, or transform into something else entirely? I was (and still am) unsure, but despite not having certainty, I knew I wanted to create, for the purpose of celebrating the truth that brings together the communities that influence me. Read more>>

Erica Branz

I took a leap of faith by transitioning to full-time at Branz Nutrition Counseling after leaving my role as a dietitian at a local eating disorder treatment center—despite having only one patient on my caseload. A full-time caseload is typically 27 patients, though I wasn’t aware of that at the time. This expectation has since shaped our standards for dietitians at Branz. Read more>>

Zachariah Crooks

At the time, I was working as a team lead and therapist at a community mental health agency. I was in my fourth year in this position, and my career path was growing. Yet, I really wasn’t happy with providing counseling to the clientele we were serving. One day, a series of events unfolded at work, and I decided it was time to make a change. What I ended up doing was demoting myself and taking a new position at a different location within the company. I spent four months in a position that was exciting at first, but the excitement wore off quickly. I pondered for a short period about what I wanted to do with my career path. Read more>>

Cynthia Tom

I’ve developed an art based healing program A PLACE OF HER OWN(founded 15 years ago) and intuitively blending my visual art business (40+ years) into the body and intention of this program.

I focus on healing,spirituality and social justice/feminism. Read more>>

Stacey Levine

I took a risk in trying to write books via pushing language, writing against conventional realism, and creating fictional worlds based on not on sensible, coherent plot, but absurdism (to some degree). I don’t have one single theme or identity to establish in my writing, no case to plead, but my novels & stories are actually political, very much tuned into the ways humans hog power in situations or relationships, and how other people fully & willingly hand over their power. It seems inexplicable sometimes, but there are reasons in each case why a person does either of those things. These are the conditions inside the folds of daily life that demand to be examined. Read more>>

Steve Wilson

The biggest risk I ever took was jumping head first into the music business full time. I gave up any stability I had known, work life, financial, etc and just literally took the leap of faith. It was a decision made together with my wife, who is also in the business, and we just decided that we only get one trip around the sun, why should we spend it “working for the man” when we should be doing what we love and following our dreams. We really had to decide what was important and what we were okay with giving up. Read more>>

Toni Dunbar

When my son was seven years old now 26 I decided to move to Washington DC for a job. I was a single mom with a little boy going into middle school. We were unaware of our surroundings and did not have family or friends in the area. I decided to make the move for a better life for us.. Leaving my first purchased home and Family was a huge and difficult decision, but I knew that I had to do something for me and my son to help expand our Experiences and outlook. Read more>>

Quiana A. Jackson

The biggest risk I ever took was when God told me to quit my job and step into full-time podcasting. At the time, I had worked in the medical field for 14 years. It was a steady job, provided security for my family, and made sense to everyone around me. But deep in my spirit, I knew God was calling me to something greater. Read more>>

Mansi Mehra

For 16 years, Los Angeles had been my home. I built my life there—a thriving community, a reliable routine, and a comfort zone that felt like an impenetrable bubble. Yet, as much as I loved the City of Angels, I found myself yearning for something new, something challenging. The thought of uprooting everything and driving cross-country to New York—with just my dog as my travel companion—felt like a leap into the unknown. But sometimes, taking a risk is exactly what you need to rediscover yourself. Read more>>

Ashleigh Netter

One of the biggest leaps I took was choosing to bet on myself during one of the stormiest times in my life. Everything seemed stable—my career, my personal life, my dreams for the future—until it all came crashing down in just a few hours. I felt heartbroken, lost, and unsure of my next steps. But in that challenging moment, I made a decision that would transform my life: I chose to believe in myself and take charge of my future. Read more>>

Echo Zhan

In June of this year, I made the decision to quit my design job at a tech company to pursue building my lighting brand, KĀDNS, full-time. It was my first job after graduation, offering me the chance to experience design roles within a large corporation while providing the financial stability to support product development for my lighting designs on the side. Read more>>

Stephanie Grosvenor

I feel like my whole adult life from the age on 25 onwards has revolved around taking risks in pursuit of the life I wanted to create. In 2014, I quit my job in steel construction, bought a plane ticket, packed anything I needed into a carry on bag and flew across the world to the US. I had never been to the US, nor did I know anyone here, but I was determined to create a something magical. What was intended to be 2 years of working abroad turned into a life altering adventure. I worked, I travelled to places I only ever dreamed about, I made friends who became family and found my passion & purpose in this life. In 2018 I went back to school part time to study nutrition & functional medicine. Read more>>

Carrie Ann McCormick

I am currently living my biggest risk! I left my career in public education a little earlier than anticipated, in April of this year. So, just less than 6 months ago I took a major leap into my business of yoga, writing, and embodiment practices. I am exploring the part of me that loves to perform, teach, learn, and grow, just in completely new capacities. I had been saying that I felt that I was spent after my days in the classroom for a number of years. I felt a sense that I had an opportunity to really make a go of it and that is what I’ve done – at age 50! Read more>>

Ron Kao

Growing up in New York, I always had the violin in my life. I was classically trained and fortunate enough to perform at Carnegie Hall on multiple occasions, a dream for any young musician. I even played for special high school moments like prom proposals and Valentine’s Day carnations, though I never imagined it would lead to anything beyond these casual performances. At that time, I was on a different path altogether—I entered college as a Premed Neuroscience student, aiming for a career in medicine, a path I thought would make my family proud. Deep down, though, I knew it wasn’t what I wanted, but admitting that—especially to my parents—seemed impossible. Read more>>

Najah Berry

Taking the bold step to rebrand Girl code cosmetics into Pretty Skin By Girl Code , was a significant risk, but one driven by a vision to elevate the brand to new heights. Embracing this change meant venturing into uncharted territory, with the potential to redefine our identity and resonate more deeply with our audience. This decision was not made lightly; it involved meticulous planning and a deep understanding of our customers’ evolving needs. By rebranding, we aimed to enhance our commitment to inclusivity and luxury, ensuring that every product not only meets but exceeds expectations. This journey, while fraught with challenges, ultimately reflects our dedication to growth and innovation, positioning PrettySkin by Girl Code as a leader in the luxury body care market. Read more>>

Mandy Kron

I graduated in 2008 with dual Bachelor’s degrees in Art and Music Performance. I was thrilled to secure a full-time, art-related job that I started immediately after graduation. I was a retail display artist and I worked for a company that did multiple “floor set” changes throughout the year, requiring an in-house artist. I built furniture and temporary walls, and created window displays and other decorative elements. It was based on the company’s direction for a certain “look” each season, but I had the freedom to adapt the concepts to fit our location. Though this sounds like a dream, it was unfortunately a very unpleasant place to work. Everyone was overworked, under paid and never received recognition for their efforts; a terrible combination that creates a toxic work environment. Read more>>