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.
Jackie Bachmeier
I’ve probably taken many risks over my lifetime thus far. Adventure risks like zip-lining in the Costa Rica Rain Forest, snow skiing, snowmobiling, riding dirt bikes, and waterskiing could all be forms of risk taking. But, by far the biggest risk I’ve taken to date was starting my personal training business with very little experience or knowledge of the industry. Read more>>
Jennifer Machado- Newman
I took a risk by turning my hobby into a full-time career. I had grown up farming alongside my dad. I loved learning from the farm experiences as a child. Growing flowers was always a passion of mine. I kept gardening as a hobby in my adult life but worked in the medical field. Read More>>
Moses Hall
In 2019, I made the boldest move of my career: I stepped away from the safety of working under another brokerage and launched MoHall Commercial & Urban Development. It wasn’t just about building a business—it was about building something that reflected my vision, my values, and my community. Read more>>
Lindsay Renee Chapman
One of the biggest risks I’ve taken was leaving a secure, salaried position in New Orleans to pursue freelance event production and consulting full time—without a clear roadmap or safety net. At the time, I was working as an Executive Assistant and Hospitality Coordinator for a well-established restaurant group. The job was steady, and I had built strong relationships there, but over time, I began to feel boxed in. I had always thrived in fast-paced, creative environments, and I missed the spark that came with producing large-scale events and working in diverse spaces with a range of clients. Read more>>
Mystix Mercury
In my eyes being a musician is a risk. You risk your time, energy, creativity and soul to share your music to an audience you aren’t sure will accept or listen to your sound.
When I was 15 I dreamed about singing in front of large audiences and performing my own music but I never stepped out of my comfort zone to try at the time. I filmed covers I sang to my digital camera and uploaded on youtube. This was me getting the confidence to do more.. I made mini vlogs about my day. Read more>>
Philip Schrei
Back in 2018 I was living every bladesmith’s day‑dream: sparks flying, shop stereo cranked, orders stacked higher than my anvil. I’d just auditioned for Forged in Fire, the hit reality tv show on the History Channel—and a few months later I was on set, sweating under studio lights instead of Texas sun. Session 6 Episode 17 ” The Partisan” aired June 2019, I walked away champion, and business boomed…for about five minutes. Read more>>
Coriander Focus
In march of 2020 I lost my job, lost my relationship of nine years, and lost my housing. I realized that I had a choice to either continue to live in an apartment I couldn’t afford being sad in the middle of a pandemic or I could choose the plot twist. Read more>>
Yohanna Baez
One of the biggest risks I ever took was deciding to build an entire multi-platform universe from scratch, without institutional backing, without a safety net, and without waiting for permission. After years of working across media, producing films, collaborating on campaigns, and ghostwriting narratives for other people’s visions, I reached a breaking point. I was sitting on an idea that kept haunting me: a sci-fi story grounded in the streets of New York, shaped by Caribbean diaspora, nightlife, designer drug culture, and radical tenderness. Instead of endlessly pitching it to gatekeepers or trying to squeeze it into a single format, I decided to bet on myself and expand it across multiple platforms: podcast, manga, video game, and animation. All with an amazing soundtrack! I call it All Night Deli, but you can call it weird! Read more>>
Kamala Brown
“Had I known the full journey, I wouldn’t have taken the first step. But not knowing was the gift.”
The risk that changed everything was stepping away from a life that made perfect sense on paper—and no sense in my soul.
In 2010, I left my successful career as a chartered town planner. I had a first-class degree, awards, and a stable, respected role. It was a massive professional risk. Read more>>
Dr. Shumonte Cooper
In late 2018, I stood at a crossroads—a place many dreamers find themselves. I had a vision that burned deep within me: to launch a nonprofit that would radically change the way communities—especially underserved and often forgotten ones—received support in the wake of disasters. I envisioned rapid response, emotional and spiritual care, and real relief delivered not just with hands, but with heart. But visions don’t pay bills, and dreams don’t fill trucks with supplies. Read more>>
Adrian Miramontes
Taking risks has been at the core of my journey as an artist. In fact, choosing to pursue my artistic passion over a more conventional path was one of the first major risks I ever took. I was in college studying graphic design, but over time, I found myself burning out and losing my connection to the work. At the same time, my passion for dance was steadily growing. Being raised in Los Angeles, I was surrounded by some of the best dancers in the world, and that environment lit a fire in me. I took it as a sign — a calling — to follow that path more seriously. Read more>>
Suzanne Groves
After graduating in 1987 from The University of Texas at Austin with a bachelor’s degree in English, I thought I would be able to find gainful employment as a writer. Unfortunately, newspapers and magazines were struggling given the recession, so the only job I could find was as an assistant manager for a clothing store. The pay was enough for me to cover my bills, but I was miserable…I didn’t enjoy the work and I worried I would never be able to find the path to do what I loved: writing. After working at the store for six months, I had had enough so without another job in sight, I up and quit, even as I had no savings and my parents had already made it clear I was off their “payroll”. Read more>>
Silke Van Loenen
Approximately 20 years ago, I went through a rough patch. I was combining a full-time job and studying for a bachelor’s degree. I held a job I was good at, and at the same time that job wasn´t good for me. There was mortgage stress because I needed that job to afford the monthly payments. Next to that my relationship wasn’t bringing the happiness I was looking for. So, too many things going on, too much stress and stressors and one day I just couldn’t function how I should have. There I was, mid 30s: burnt out, sick leave, single. 20 years later I still don´t know which straw broke the camel´s back, the only thing I knew was that I had to change something. But what? Something deep down in me told me that I needed a 180-degree turn. Read more>>
Monique Edwards
I took a significant risk by leaving behind a stable and promising career as a realtor in Toronto, as well as stepping away from studying for the MCAT and applying to medical school. These are paths that would have likely guaranteed financial security and a clear professional future. Instead, I made the bold decision to move to New York and pursue a Master of Fine Arts, a path that comes with high financial costs and no guaranteed income. Despite the uncertainty, I chose to follow my passion for art, storytelling, and representation, believing that the pursuit of purpose and creative fulfillment was worth more than the safety of a conventional career. Read more>>
Michelle
The biggest risk I ever took was walking away from a business I built from the ground up—a business that was successful on paper, generated a multi six-figure income, and that our family relied on. I had poured years of time, energy, and identity into it. But the truth was, it was draining me. I was having anxiety attacks daily, and the emotional cost was bleeding into my marriage, my health, my ability to be a present and happy mother. Read more>>
Janette Wong
People often say that the biggest risk for business owners or entrepreneurs is to leave a corporate job and start their business. But having gone through that journey, I found that relatively easy. Instead, the biggest risk I’ve ever taken was choosing to do things MY way. To go against everything I’d learned. To strip away all the parts of myself I’d picked up to survive — and actually figure out who I was underneath it all, and to do things in MY time, on MY schedule, and creating my personal brand around the true, authentic me. Read more>>
Mike Shishkin
I used to run a successful agency in Russia. We worked with top brands, grew 40% year over year — everything was going well. But I wanted something else — to be relevant globally.
In 2020, I moved to Barcelona. It felt like the right place: international, creative, close to the UK, the U.S. and the rest of Europe. I saw it as a future HQ for building a global business.
Then the war started. Russia invaded Ukraine. Sanctions hit. Companies began leaving the market. Read more>>
Maureen Kerr
Sometimes what initially seems like a setback turns out to be a stroke of luck. In December of 2019, I left a job and career that I had spent over 30 years learning, cultivating and practicing. My departure was unplanned, but I decided to enjoy the holidays, spent several weeks traveling overseas, and then came back to…yes…the COVID pandemic. The unexpected quiet time, away from my usual hectic day-to-day schedule gave me the opportunity to reassess my goals and recalibrate my thinking. I decided not to return to what had been, up until then, my steady and stable career. Read more>>
Luisana Mendez
One of the biggest risks I’ve taken in my life was leaving my home country, Venezuela, in 2018.
At that time, I was an established professional— a civil engineer with a master’s degree in urban planning and over 14 years of experience in both the public and private sectors. I had my own business, ongoing projects, financial stability, and a strong support network of family and friends. But the deepening political, economic, and social crisis in Venezuela forced me to make a painful and life-changing decision: to emigrate. Read more>>
Isabel March
I started my photography business 17 years ago. I am the mother of 4 amazing kiddos…all who were still little (ranging from ages 13-5) when I quit my extremely well paying corporate job (I was an attorney) that had amazing benefits to follow my gut, take a giant risk and leap of faith to start this “wing and a prayer” business (as my sister put it). Read more>>
Mikki Sodergren
My risk-taking journey has been almost my entire adult life, which has led to a unique full-circle moment that I never expected. When I was a teenager, I fell in love with opera. I dreamed of one day singing on the stage of the Metropolitan Opera in New York, and having an illustrious solo operatic career as a mezzo-soprano, following in the footsteps of some of my favorite artists, such as Frederica von Stade and Elina Garanca. I dedicated my life to this pursuit at a young age, leaving my high school and hometown at the age of 16 to attend a prestigious arts boarding high school called Interlochen Arts Academy, in northern Michigan. I missed prom and other formative high school moments with my group of friends, all in the name of dutifully studying classical music at the highest level. I spent summers in college studying at vocal intensives to further hone my craft, make connections, and serve the art. Read more>>
Alicia Tardugno
One of the biggest risks I ever took was walking away from the safety net of a steady paycheck to bet on myself and launch my creative business, Wicked Focused Creative Media. I had a successful career, a comfortable routine, and every reason to stay on the traditional path—but I also had a gut feeling that I was built for something more aligned with my passions, my energy, and my purpose. Read more>>
Matt Liang
As a freelance cinematographer, I have come to realize that my entire career is built on taking risks. I grew up in Hong Kong, where my perspective on life and work was shaped by a different set of expectations. Moving to Canada as a young adult was my first big leap into the unknown, and it was not long before I took another bold step. I moved to New York City to pursue my passion for film and I had never even visited the city prior to that. I felt that it was where I needed to be and that decision was its own kind of risk. I dove into a new culture, and stepped into a field that although I loved, I knew so little about. But it was a risk worth taking. Read more>>
Nancy Stohlman
I believe the work of all art IS to risk. It’s a huge risk, for example, to set out on the journey of writing a book—not knowing if it will be any good, or whether you will even finish. And then there is the risk of having to put yourself out there in all the many ways—it’s just a mathematical reality that noncreative don’t get nearly as many rejections in life as creatives do. But that’s part of the gig, it lets you know you are in the arena, lets you know you are alive and working. And then, of course, there’s all the risk involved in the content of the art—the purpose, the emotional thrust behind it. Will people like it? Will they like me? To put yourself out there anyway, staying clear to the vision of your art, midwifing it into existence even when some people won’t like that—all of that takes enormous courage. Read more>>
Dee Manuel Cloud
That’s the question I asked ChatGPT. And she (yes, my ChatGPT is a “she” because who else always has the answers?) responded:
“To take a risk means to step into the unknown or do something despite the possibility of failure, loss, or discomfort. It often involves making a decision or taking an action without knowing for sure what the outcome will be—but doing it anyway because the potential reward, growth, or impact is worth it.”
Basically, it’s doing the damn thing even though your inner voice is screaming, “Uhh, are we sure about this?!” Read more>>
Jill Sohayda
Life is full of options to take a risk. Knowing which path can be difficult but if you never try, you will never know.
My first big risk was going to medical school. Initially, I had planned to go to graduate school to do research in biochemistry but after spending some time in a lab, I realized that being isolated in a room doing repetitive tests, and minimal interaction with other people, I needed to do something different. I started working at a hospital during undergrad and loved it. I decided to apply to medical school. Financially that was. a big gamble for me, but it worked out! Read more>>
Lauren Markham
My life, (maybe everyone’s) is the accumulation of perpetual risk. They might be subtle everyday decisions, but even with those—aren’t we all weighing the risk-reward ratio? Like which road will get me to my destination fastest or what kind of meal will make me feel best and hit the spot? Then, there are the objectively riskier decisions that impact every aspect of our lives and even change our trajectory. Read more>>
Katera
I grew up just outside of Columbia, SC and always thought I’d move to Atlanta after high school. But I ended up going to college at the University of South Carolina, got a full-time job, and never made the move… until now. May will make one year since I finally took the leap and moved to Atlanta. In my head, it still sounds a little wild—moving here in my mid/late 30s—but I knew I couldn’t live with myself if I didn’t at least try. It’s been a pretty interesting year. The transition had its bumps, but honestly… I’m really glad I did it. Read more>>
RAPHAELLA DAWSON
Starting my jewelry business was a big risk, but it was one I felt deeply passionate about. As a 33-year-old mother of two, I knew I would be juggling a lot—family responsibilities, financial considerations, and the uncertainty of entrepreneurship. But I also saw an opportunity to create something meaningful, not just for myself but for my children—to show them that dreams are worth chasing. Read more>>
Elle Ibarra
When I was in middle school, I watched 13 going on 30 for the first time and I remember instantly falling in love with Jenna Rink’s job as an Editor for Poise. From that moment on, I became obsessed with the idea of working for a fashion magazine and moving to New York one day. Years later, I ended up applying to universities to study computer science or nursing because art just didn’t feel like a reasonable route. But by the time I was a senior at UC Davis, I was reminded of my passion for art and realized that I needed to pursue it. I ended up applying to hundreds of magazine internships in New York. Read more>>
Fischer Wallace
My life/business has only been about risks and following my gut. Always believing that money was a renewable resource.
With every move I have had to supplement my freelance income with a steady job. In most every town I chose something in the non profit world that involved helping the community. In Seattle I worked as admin for “Soulumination” which is a group of photographers providing family portraits to children suffering life threatening diseases and to parents who have a terminal illness. Soulumination.org Read more>>
Anna Przy
I lived my entire life with the assumption that there was a “right” way to move through my lifetime. I had to get the degree, and the job, and then work my way up the ladder – the American Dream was drilled into me. I did everything the way I thought I should, I got the degree and I got the job, and I worked my way to the top! I was an event planner for 13 years, I had purchased a portion of the company and was a sitting board member. I thought this was going to be what the rest of my life looked like. When the pandemic derailed everything for me as an event planner in 2020 I was given time, time to be alone with myself, time to reflect on my life and it was as if somebody finally shook me and said “is this even what you want?!” Read more>>
Gala Magriñá
In 2018, while I was running M Crown Productions, my design and production agency, I realized that the commercial and residential interior design work we began to do was more fulfilling (and less stressful) than producing live events and exhibitions. I was pouring all my energy into something that people would get to experience for only a day or two, versus working deeply with people or brands to create a space that they would use every day. I found more meaning in that kind of lasting impact. Read more>>
Naim Dewod
As I sit here contemplating risk, I’ve realized that every choice we make involves stepping into the unknown. We accept small risks daily—driving to work, taking our kids to school, even opening up in relationships. These risks fuel personal growth, spark soul-searching, and reveal what we’re truly capable of. Read more>>
Mariko Rollins
A lot of people preach to follow your intuition, but it can be difficult to know the exact moment that it matters most. I had a pivotal moment with my intuition last summer when I knew I had to make a drastic change in my professional life or my physical and spirit bodies simply would not make it. I was overburdened with stress by toxic bosses and I could probably tell stories of 100 or more experiences I had, almost daily, leading up to truly listening to what my intuition was telling me, resulting in a huge life change. As a very experienced Mystic and Healer operating in business I have learned to follow my intuition first, then qualify my decisions based on data, but sometimes it takes months for the data to present itself, which can be frustrating. Read more>>
Stephanie Pham
Growing up as an Asian American, there were strong cultural expectations around stability, academic success, and choosing practical career paths. These expectations were rooted in the sacrifices my family made to create a better future for me. Read more>>
Elizabeth Wyant
One of the biggest risks I ever took was leaving behind a stable career in education to open a nail salon with my brother—even though neither of us had any experience running a business. I had my cosmetology license since 2014, but I had chosen a different path and worked as an elementary school teacher. Teaching gave me a steady paycheck, benefits, and security—but I felt unfulfilled. I always kept my love for nails alive on the side, and after living in South Korea for three years, I became deeply inspired by their artistry and approach to nail care. I dreamed of creating something like that here, but it felt too big, too risky. Read more>>
Debbie Lee De Jesus
Music has always been a part of my life and the key to who I am as a person; however, I was always intimidated of writing my own music for fear of what public opinion would be. One night I decided that I was going to give it a shot, and I wrote and recorded a song about what I was going through. My first performance of it was a complete disaster but I performed it a few times more and it was life changing. From that moment on I wrote other songs that resonated with listeners, and it has been wonderful. It’s about being able to convey a message through my music and knowing that I gave the ability for someone relate to it, letting them know that someone has been in their shoes and knows what they are feeling. This has been the biggest risk, being able to be vulnerable with the public with my music. Read more>>
Haven English
I started my photography business soon after having my first child. My husband and I had only been married less than a year when she was born. We were living pay check to pay check trying to survive. Getting food from food banks, friends, or church’s. I realized that being a stay at home mom and soley surviving off my husbands income wasn’t going to work. I also had worked as a cna before having my first child and I did not want to work those crazy hours and miss out on my child growing up. Those first few years are the best so I asked myself “what could I do that I would make a decent living doing but also enjoy doing?”. Read more>>
Kim Rogers “Worm Queen “
I took a big risk in July of 2021 and went on Tik Tok with a 60 second video and talked about a parasite cleanse I had tried that started my healing journey. Having no idea that sharing my story would go viral and start me down this path of helping others heal too and lead me to start the RogersHood empire I’ve created. Read more>>
Cindi Yaklich
Last year was an emotional one for me. By the end, I realized I needed to step back from the constant pressure to sell and give myself space to explore the creative ideas circling in my mind. While I loved my studio, I knew I had to cut costs if I was going to pause art shows and festivals and focus inward. Fortunately, I found an amazing new space for half the price—it truly felt like kismet. Read more>>
Benjamin Lerman
My life has been a series of risky decisions. I decided early on (right out of high school) to forgo the traditional path of college and instead study Kung Fu in a monastery in China. It was short-lived, but an interesting detour all the same. Upon my return to the States, I once again attempted a more traditional route, only to find myself pulled toward a new dream: to pursue a career as a performer and acrobat in Las Vegas. Read more>>
Tiffany Berger
Leaving the classroom to launch Breathworx614 was one of the biggest leaps of faith I’ve ever taken. At the time, I was the primary provider of health insurance in my marriage, had three dependents—as well as a baby on the way—and was walking away from a secure job in education. But I also felt a deeper calling pulling me in a new direction. As a teacher, I often found myself dysregulated while trying to help students and their families regulate themselves. The toll it took on my nervous system signaled that something needed to shift. Read more>>
Kristian McKay
I met my executive producer while living in South America. I was making a handful of small films that screened in local cinemas—quiet, personal stories made on a shoestring. One day, I got an email from him. He was passing through and asked if I’d meet him for breakfast. I wasn’t sure what it was about, but I said yes. Over coffee, he flipped through a stack of pitches right there at the table. He told me he liked my work, asked what I was thinking about next. I hadn’t really planned that far ahead. I mentioned a few ideas, and he pointed to one and said, “I want to make this with you.” Read more>>
Nick Kohlmeier
I’ve been tattooing for going on 13 years. It all started by taking a huge risk. I was 32 and not feeling fulfilled in what I was doing in life. Almost feeling like I had hit rock bottom in life. I had love tattoos ever since I was a teenager. The whole lifestyle. Punk rock, skateboarding and seeing all those guys with tattoos really spoke to me. I started getting tattooed as soon as I turned 18. I had a background in art and drew ever since I was a kid. I had stop drawing for a while, but decided to pick up the pencil again in my late 20s. As soon as I thought I was good enough again, I started to seek out an apprenticeship. I could never find one in my hometown of St. Louis, but one day a friend in Michigan who was a piercer told me one of their artists was looking for an apprentice. Read more>>
Charlyn Quirino
A risk I’ve taken was opening up the tattoo shop and starting a business in 2020 which was during the height of Covid-19. I knew this was a huge risk but my passion outgrew the fear i had in this business in becoming a flop. This was also (at the time) going to be the first All-femme tattoo and piercing shop in the San Fernando valley with a Filipina that’s a woman, who tattoos that is owning this business. There’s not a lot of that in the 818 Valley. I was not sure if the male dominated tattoo industry would be shook about the changes. I was not sure how they would react, because in all honesty having an all femme tattoo shop that is very queer friendly- is such a better space for all femme and queer people, all people actually who are intimidated and or have had a negative experience with a regular tattoo shop. There is a huge amount and unspoken number of shops who are currently running that have sexually assaulted and or are predatory against clients, apprentices and or their workers. Read more>>