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.
Aloha (Haekyung) Lee
When I boarded a one-way flight from Seoul to Los Angeles, I wasn’t just changing my address — I was changing my life. I had already built a career in South Korea, even storyboarding for Netflix’s Squid Game, but I felt an undeniable pull toward animation. It meant leaving behind stability, loved ones, and a clear path for a country where I knew almost no one and an industry famous for its competition. Read more>>
RIA RAJAN
In 2022, after over decade of working as a creative profession as a freelance designer and illustrator, I went back to school to get an MFA in studio art for which I moved across continents from India to the US, to study and make art in NY.
It was a big leap of faith and I landed in NY on the eve of my 37th birthday to get myself a degree and be an artist. Coming back to school, as a mature student, was both challenging and exciting, and wearing multiple hats of being both a student as well as an educator in training put me on both sides of art education, further cementing my love for using art as a tool of critical thinking and meaning making. Read more>>
Olya
The biggest risk I’ve ever taken was moving to New York City on my own and starting my life from scratch at the age of 32. Was it scary and stressful? Absolutely. Was it worth it? Without a doubt.
Before making the leap, I had visited the city a few times and, like so many others, completely fell in love with it. The energy, the people, the possibilities — I began dreaming of one day calling it home. Read more>>
Priscila Alfaro-Barrantes
For 18 years, I worked as a Business college professor before moving into the corporate world. My career had always followed a structured, “safe” path—clear roles, stable income, and predictable expectations. But deep down, I felt called to step into something completely different: starting my own business as an Intuitive Professional. Read more>>
Paul Dufour
Leaving a stable career to build bamboo fly rods full-time felt like jumping into a river without checking the water temp. I’d been making rods in my free time for years—late nights in the shop, weekends at fishing events—but there was always that “safe” backup plan of a steady paycheck.
The turning point came when I realized that every time I sat down to work on a rod, I lost all track of time. I’d go from splitting cane to tying silk wraps in what felt like minutes, only to look up and see it was 2 a.m. That’s when it hit me: this wasn’t just a hobby—it was my calling. Read more>>
Santiago Osorio
Opening a business in a state and city which are both new to me, is very expensive, very competitive, a very complex business landscape, having no family besides my wife in the area for support, knowing very little about the community and not knowing many other professional in the field.
I have made many mistakes and learned from them. But despite of it all, I have been able to move ahead. Read more>>
Dan Rossi
My name is Dan Rossi also known as The New York Hot Dog King. I am an Italian American disabled Marine veteran who currently owns the most famous hot dog cart in front of The Metropolitan Museum of Art on 5th Avenue. My hot dogs are known all over the world for their delicious and authentic New York style. I have been featured on Netflix series;Street Food, Munchies, Snap Judgement as well as my most recent appearance on Watch What Happens Live with Andy Cohen. I recently wrote a memoir, The New York Hot Dog King; From Rags to Riches to less than Rags. Read more>>
Isabella Martino
Having the courage 2 years ago to leave an environment that no longer served me has changed my life’s trajectory in every single way. I gathered my belongings and took an incredible leap of faith to move away from my family home, not confident in the slightest as to what the future would hold. My family was all I had ever known, but when the people closest to you are choosing not to love you in the ways you need — truly feeling seen, heard, understood, or accepted — it weakens your mind, body & spirit. My life didn’t feel like my own and that scared me. Read more>>
Ellis Angel
It started back in 2017 when I was furious about the glaring corruption in Trump’s first term. I had one of those free U.S. Constitution mailers from the ACLU on my desk and started reading. It was immediately clear where the law was being violated, so I began circling the offenses in red Sharpie.
My attention was drawn to the Emoluments Clause—the section that’s supposed to prevent corruption and conflicts of interest. It says that the president cannot accept gifts, payments, or titles from foreign governments, and prohibits additional compensation from the federal government or states. Read more>>
Leah Cordovez
Risks have defined my life.
Two big risks have been inflection points in my life, taking the chance on myself twice has catapulted my life into this wonderful place where my vocation feeds my love for life.
I made a big decision to move from the US back to my home country of Panama not having the security of housing or steady income to attend Medical School. Read more>>
Jenna Johnson
The Biggest risk I’ve ever taken was moving to Houston, TX (never visited prior) to change my career path from working in Corporate America to answering my true calling and betting on myself, to pursue my true calling of being apart of the beauty industry. I became a Licensed Esthetician and this has led me to making big impacts in people’s lives. Read more>>
Rachel Gatschet
At 40, I took the biggest risk of my life — I asked for help.
For 25 years, I was a teacher — not just by profession, but by identity. It was the role I poured myself into with everything I had. Then, almost overnight, I lost it all. I lost a job I had held for eight years. I lost what I believed was my purpose. And in that unraveling, I lost my sense of self. Read more>>
Cierra Sellman
Five years ago, I took a risk that ended up changing my entire life. At the time, it didn’t feel brave, it felt terrifying. My drinking had gotten so bad that I didn’t recognize myself anymore. My daughter had just turned four, and instead of being home to celebrate, I was in an inpatient treatment facility. I remember lying in bed that night wondering if she would ever understand why I wasn’t there, or if she’d ever forgive me. Read more>>
Lisa Keslar
Life is full of risk, but for me, it’s often shown up in the career choices I’ve made. Early on, I chose to work in entrepreneurial organizations and smaller family businesses instead of the “safer” route of established corporations. That path was a risk in itself—smaller firms are less stable, roles are less defined, and you have to wear many hats. But I took those chances because I believed in the people I was working with, the products or services we were building, and I knew I had the tools in my toolbox to make an impact. Read more>>
Jennifer Horstman
Life is always about taking risks. I have taken a few major ones in my adulthood. In my mid-20’s, I was working for a large insurance company – Making good money for my age, had great benefits, allowed me to own my own home and…. I was miserable. I cried at my desk almost every day. So I quit and went back to school full-time while working 3 part-time jobs to pay the bills. After 2 years, I graduated with my second Bachelor’s Degree, this time in Interior Design. It set me on a course with my current career and I have never looked back – Best decision ever! Read more>>
Patricia Maltz
My life has been a series of taking risks, although I’m not sure it was a conscious decision at the time of the incident, it was just what I was supposed to do. Here’s the backstory – grew up on a farm in southern Minnesota milking cows and breaking horses. Attended a one room country schoolhouse and at 7th grade went to town school. I had a brief stint in nurse’s training but that wasn’t my destiny. Read more>>
Matthieu Meynier
If you work in a creative field, risk is part of the terrain. Sometimes it’s obvious — moving to a new country, launching a business, reinventing yourself. Other times it’s quiet — saying yes to a project you’ve never done before, turning down work that doesn’t align with your values, or starting over in a place where no one knows your name. Read more>>
Sebastian Roundtree
When I was in my mid-twenties, I did something reckless: I quit my job so I could perform and write more. I didn’t have any real plan, nor any real savings–just a fiery rainbow of passion deep in my bones. I bounced between friends’ couches and my dad’s spare room, living off scraps, favors, and whatever I could charm out of the day. Read more>>
Sophie Werner
Music has been a part of my life for as long as I can remember. From singing in the shower and writing songs in my bedroom to performing on a few beautiful stages in LA, I feel blessed. I always found comfort, identity, and a way to express myself in music. It’s been in my soul from the very beginning, even when no one else really understood. Read more>>
Maxwell Bruner
Risk. It’s something anyone in a creative profession, especially acting, has to get comfortable with. One of the biggest risks I’ve ever taken was deciding to move to Los Angeles and leave everything I’d ever known behind. It wasn’t easy and it certainly wasn’t always fun, but in my experience, the biggest risks often lead to the biggest rewards. Read more>>
Megan Dunbar
I’ve always been a strategic risk-taker throughout my adult life. Some of those risks didn’t pan out, but the ones that did have shaped who I am and unlocked my true potential. The biggest example of this was my decision to move to Charlotte, North Carolina, to pursue a career in motorsports. Read more>>
Lauren Loretnz De Haas
The first risk was just starting. It the summer of 1995 and for 15 years I had taught ballet at a local studio when the thought first occurred to me. Why not provide the dancers with another performance opportunity in addition to the end of year recital? What if I formed a company to just do the Nutcracker? It was summer and December just a few months away. So all the first decisions happened in a whirlwind. Application for Nonprofit status, getting a theatre, figuring out costumes and sets, holding auditions, casting the show, figuring out how to sell tickets. But the biggest risk, would people come? With starting capitol of a $3000 limit on a new credit card the Triangle Youth Ballet Nutcracker was born and continued to grow. Read more>>
Jesse Petersen
When I was a teenager, I told people I wanted to be an artist. That felt risky in itself, because I didn’t know any successful artists, only my recreation center teacher and a group of retired women in my weekly watercolor class. They encouraged me, but when it came time for college I chose the safer route of graphic design. Read more>>
Maren Curtis
I was raped two months into my freshman year at CU Boulder. How it happened, where it happened, and with who made it clear to me that coming forward wouldn’t be safe, so like many victims I repressed. Though we can try, there is no way to eliminate the memory of sexual violence from our bodies, even if we push it out of our minds. I lacked a support system and was surrounded by a rape culture that thrived off fear and secret keeping. Much later I’d discover most of the women I’d known had been raped or assaulted at one point or another, often at a party just as I had been. I don’t know anyone who went to the police, we all knew the depth of their ineffectiveness and their connections to rape myths and the Greek system that dominated the school’s social rules. Read more>>
Jess Marie
A big risk I took was deciding to start my podcast. It all started with a social media post that was extremely vulnerable. I put a lot of personal information out there for everyone to see. The response from that social media post transformed into me starting my podcast and sharing vulnerable information about myself but also giving others the space to share their stories. Read more>>
Dido Balla
When I was about 20 years old, I was a University student in Benin, West Africa, studying law in French, my native language. About a semester in, I had the realization that studying law from Benin was not conducive to the future that I wanted for myself. In this future, I saw myself speaking English and living in the US, so I decided to stop university and try to learn English. This decision led me to Ghana, a neighboring country where English was the first language. I spent a year in Ghana trying to learn English but I was not very successful because my friends and I spent most of our time speaking French. Read more>>
Paul Witmer
Life for me blew up at the tender age of 52..lol resulting in my packing up a used Prius (I purchased 2 days before quitting my job in IL.) with my 2 cars, clothes, and 2K all the money I had in this world! I moved into my parents Mobile home and began anew….
No career path, no friends, only my parents and my brother here in Colorado. As I made friends by going to Meet Ups in Denver I eventually befriended a guy who needed a townhome updated and offered to let me live there—Operation: GET OUT OF MY 77 year old parents home began! Read more>>
Kaylie Pacini
I have always had a love of acting, and since I was little I knew it was my calling. I am originally from a small town in Utah, I love home however it’s not necessarily the place to start up an acting career. So after I graduated High school I applied for college in LA. My mom and family have always been very supportive of me and my passions so when I told her about my audition she was thrilled. When I told everyone else it was a mix of reactions, there were the people who I looked up to told me I was throwing my life away, not being realistic, and started up saying I couldn’t do it. Read more>>
Jordyn Brummett
I fell in love with art when my high school art teacher took me under her wing. She encouraged me, pushed me, and helped me see myself as an artist. I wanted to pursue art school, but my parents were hesitant, so I chose what we all thought was the “practical” path — graphic design. Read more>>
Kyla Kay
A few years ago, I was working in a stable corporate job – the kind with predictable hours, a steady pay check, and a clear career path. On paper, it was everything you’d want for security and stability. But inside, I knew something was missing. I had always loved the world of performing arts, and musical theatre had been a lifelong passion. I found myself daydreaming about creating something of my own, something that would allow kids to experience the same magic and confidence that performing had given me. Read more>>
Shianna Blei
I was working as the manager of a cafe at the time. This quaint cafe serves more than just coffee and pastries; it also supports the arts and music in the community, hosting art shows, music events, and writing clubs, among several other programs. To put it another way, I was unexpectedly placed in an environment that fueled my creative path and encouraged me to pursue my art. I have always been a creative in some form and have experimented with different mediums, but I keep coming back to painting. Shy at first to share my work with those around me, I eventually worked up the courage, with the help of my husband, to show my boss my paintings. Read more>>
Angelica Blyden
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Philly, mid-2000s. MySpace is poppin’, I’m creating lipstick shades to match my outfits, and rocking my pink Doc Martens at the Art Institute. My bag is full of fabric swatches, patterns and charcoal drawings… until Muzic Class pops up on my page. A local band of artistic genre-bending geniuses mixing, hip-hop, pop, and rock. Ahead of their time. Untouchable. Read more>>
Kristina Van Orden
I have been blessed to have so many experiences in my life that encouraged me to pivot, embrace change, and remain open to opportunity. In 2016 I was traveling through Mexico with my son and fell in love with an area of Nayarit. The next year I purchased a small piece of land with the intention of retiring there. My dream of retirement became something else. Over the next few years I changed the course of my career – I was an accomplished executive at a Fortune 500 company. But I felt I wasn’t living my dharma. Corporate restructuring created a window in 2021, and I decided to start all over again as a yoga and fitness professional. My passion for wellness and guiding others through physical, mental and spiritual practice propelled me to fast track my formal education, study and certify so I may fulfill my inner calling of encouraging health and peace. Read more>>
Kelsey Askew
Leaving my corporate job at Nike to pursue freelance work was the biggest and most soul-led risk I have ever taken. I had worked hard to land a creative position at a globally recognized brand, and from the outside, it looked like I had made it. But inside, I felt a creative restlessness that I could not ignore. I have always made art from the heart, from painting dog portraits as a teen to building a design career through grit, curiosity, and deep care for the people I work with. Sitting in a corporate office, I began to realize I was craving more than creative freedom. I wanted a deeper connection to my work and how it impacted the world. Read more>>
Kathleen Caprario-Ulrich
I love words and have been an avid reader my entire life. Whether taking the form of an artist statement, social media posts, or a grant or residency application…words are an important part of my visual art practice. However, as much as I appreciate words and use them to support my artwork, I never considered myself a writer. I was a visual artist. I couldn’t be both…or could I? Read more>>
Katia Conte
Shortly after my oldest daughter passed away in 2020, I took the biggest risk of my life: I started a pediatric cancer non-profit to support families affected by pediatric cancer. At the time, I had no roadmap, no major funders lined up, and no guarantee it would work. All I had was a deep sense that it needed to exist—and the fear that maybe I was wrong. Read more>>
Tyrone Player II
One of the biggest risks I’ve ever taken was leaving the job I held for 21 years to pursue a career in real estate. It was my first real adult job. I was able to grow within the company, and I genuinely appreciated the relationships I built and the mission we stood for. I learned early on how important it is to value both your internal and external customers. I loved the impact I was able to make on people’s lives, both personally and professionally. Read more>>
Alyssa Black
The biggest risk I ever took was the bravest gift I gave myself—I took a risk on me. For so long, I was living in the shadow of who I truly am, caught in the busy, the noise, the “shoulds,” never fully stepping into my own light.
But one day, I decided to be like a seed—buried, unsure, but ready to break through the soil. I chose to nurture myself with healing, kindness, and fierce love—mind, body, and soul—knowing that growth often feels uncomfortable before it blooms. Read more>>
Nicole Clark
For five years, Hue Loco—my hand-dyed yarn business—operated out of a rental space that we eventually outgrew. When the building was sold and the new landlords turned out to be a nightmare, I knew this would be the catalyst for change—and that we needed more. I nearly signed a lease on a larger space, but the rent was essentially the cost of a mortgage. I just couldn’t do it. That’s when I made a huge decision: to buy a building for Hue Loco. It was the scariest professional leap I’ve ever taken. It took almost a year to find the right place—it was painful. A couple of deals fell through, and what I ended up with was a 7,400-square-foot former automotive shop. It was actually the best-case scenario for the type of space I needed, but it was a total dump and required a lot of updating. Read more>>
Elizabeth Fletcher
Several years before I became a yoga teacher and then a yoga therapist, I was working as a freelance business writer. Between gigs, I was traveling to Guatemala, a country to which I felt a deep, if inexplicable, connection. During one trip, an expat friend told me about local daykeepers who offered Maya horoscope readings. During my reading, one of the daykeepers said I was meant to follow a spiritual path. Whether I went to an ashram in India or returned to Guatemala, she said I needed to be trained in “magic female energy.” I had no reference for what this meant, but I felt an embodied “yes” in my gut, along with a draw back to Guatemala. Read more>>