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.
Lucy Beato
One of the most life-changing risks I’ve taken was moving from New York to Florida to start a new life. I left behind my family, my career, and my friends, all in pursuit of something bigger—becoming an entrepreneur. At the time, it felt like a huge leap of faith. I was leaving behind the comfort of everything I knew for the unknown. The decision wasn’t easy. I had a lot of fears: I didn’t know anyone in Florida, I didn’t have any formal experience in entrepreneurship or leadership, and I was stepping into an industry I had no prior exposure to. Starting from scratch in a completely new place, where everything was unfamiliar, was both thrilling and terrifying at the same time. Read more>>
Sandy Weberman
In 2023, I faced a crossroads. My design business wasn’t bringing in enough clients, and with three kids in private school, the financial pressure was intense. I had a safe option – a position as a teacher’s assistant at my kids’ school that would help cover tuition. The responsible choice seemed clear. But something didn’t feel right. When I asked my husband for advice, he didn’t give me a yes or no. Instead, he said he believed in my abilities and would support whatever I decided. We made a deal – I’d give my business one more year. If I couldn’t match what I’d earn as a teacher’s assistant, I’d switch careers. Read more>>
Paloma Schell
Moving to a new country was undoubtedly one of the biggest risks I have ever taken. Deciding to leave Brazil, where I had an established career as a newborn and children’s photographer, to start over from scratch in the United States was both challenging and transformative. This decision stemmed from my desire to provide better opportunities for my children and to explore new horizons in photography. However, the journey was far from easy. I had to adapt to a new culture, face the challenge of learning a language I was not fluent in, and help my children integrate into a completely different environment—all while trying to rebuild my career and earn the trust of new clients. Read more>>
Alexandrea G.
For me the biggest risk I ever took was leaving my full time job to start my art business. At the time I was working in a therapy office as the marketing manager and intake coordinator. It was fulfilling work but it was heavy work. I found myself not being able to create art. The thing that was the most important to me wasn’t happening! I decided to get a part time retail position until I was ready to make the big jump to full time! That day came November 27th 2019. I did it, I took the jump! I was finally going to bet on myself! I was going to make this work! Read more>>
James Wallace
The biggest risk I took was taking a chance on myself & betting it all that I would blow I believed in my craft that much too the point where I was losing more than I was gaining but I laid them bricks till it became a wall & now it’s s a compound, but if I never took that risk I would never be here in this position today, so I say just keep at it until you see those risks turn to pure gold. Read more>>
Anu Kumar
One of the biggest risks I’ve taken in my life was stepping away from a well-established career in business strategy to pursue a year dedicated to exploring my art. I have an MBA and spent 15 years developing a career that provided financial stability. Though I thrived in the corporate world, I never felt fully aligned with my purpose. It wasn’t until a moment of burnout that I decided to take a leap of faith: I left my corporate role to rediscover my creative side. Read more>>
Cheryl Wilson
When I first started in my painting journey ten (10) years ago, I did as most artists do, I explored painting styles of many types. I was sorta all over the place, but knew this was all a part of the journey to find my true style, the style that defined me in my personal art journey. To get to where I am today, I had to take these steps to know what I loved. During this time of exploration, I remember someone giving me the advice… “paint what others want, that way you will sell!!” That lasted for a short time as not only were my paintings nothing like what I loved, but I knew others did not see my heart in my work. There was no passion and I knew this. Every stroke felt hollow, like I was slowly losing the essence of who I was as an artist and my work looked uninspiring. Read more>>
James Fung
The biggest professional risk I took was when my business partner Whitney Maehara and I decided to make the creative, financial, and professional investment and take over as Principals and owners of our residential interior design studio NB Design Group (NBDG). NBDG, based in Seattle, Washington was founded in 1988. I started as a designer with the firm in 2013 and after working closely with the founding principal had the opportunity to purchase the company as co-principal in 2017 when the founder decided that she wanted to retire. While this was obviously an exciting opportunity it was also a huge risk that came with a lot of hefty decisions that had to be made. Read more>>
Kimberly Jimenez
Life is about taking risk. The risk I took was starting my modeling career with no experience at all, while also having no self esteem. I had always had a passion for modeling but never thought it would be something I would actually be capable of doing. My first fashion show was modeling quinceañera dresses, which is when I realized that is what I wanted to do in the future. Time passed by and Ana Castro from Path Academy reached out to me. She opened up my path in modeling. I have gained so much experience in runways, photo shoots, and many more areas. I have grown to be confident with myself and my work. I would say taking that risk is something I will never regret taking. Living life with no limits is what I live by. Read more>>
Guy Balbaert
I was working for Bose globally when a US colleague came up with a product idea that would allow bands to rehearse silently using headphones with full control of all sources. It was a game changer idea that needed to be built from the ground up. We (Steve Skillings and I) then both left our well payed jobs and launched JamHub about a year later after having sourced investments from multiple partners. It was a massive undertaking for a very small team, but we had a working product and through our joint networks, drive and market knowledge we had a full global distribution network up and running only one year later. The challenge from then became constant growth, new product creation and keeping investment money (read cashflow) in check. It was a hell of a rollercoaster ride to run this company to the level we envisioned, until we found an investor in Singapore that bought the company and the additional software platform ‘Bandlab’ – online collaboration tool for musicians – that we had conceived and is now a creative tool for millions of musicians globally. Read more>>
Duachaka Her
As creatives and artists, life is about taking risks, whether we want to or not. In my experience, it has been the only way to move forward and get yourself out there. I feel like my art career has not been linear in any sense. I went from graduating college back in 2015, to a working a full-time day job, to leaving my day job in 2017 to be a stay-at-home mom and trying to start my art business, to going back to work a part-time day job a year later. Although working a day job met my financial needs, there was always a part of me that wanted more personal fulfillment. I knew that if I wanted to grow my art business, I had to be spending more time building it. Read more>>
Erin Brooks
My biggest risk I’ve taken is deciding to take the step in becoming a streamer and playing my games online for the world to see. I got my start in July of 2023, after much convincing from someone who had been trying to get me to do so since January of that year because they saw how much I loved to game. At my last job being a healthcare professional, any chance I had on my breaks or lunch, I’d be on my phone gaming to the point where I even had my coworkers and manager gathered around invested in my gameplays. Looking back at it, that served as a prerequisite to my streaming/ content creator career today. Honestly, if you told me at that time I’d be playing games and making money from my passion of gaming, I would’ve just laughed it off but it’s turned into a beautiful career and I’ve met so many wonderful, genuine individuals. Read more>>
Mick Silvers
The risk I took was leaving my steady job in non-profit work on Skid Row to step into the uncertainty of private practice. For seven years, I worked alongside a community that taught me more than any lecture or textbook ever could. Skid Row shaped me as a therapist in ways no textbook or training ever could. It taught me the power of presence, the raw strength of human resilience, authentic courage, and the innate need for connection that lives in us all. Working there demanded that I shed pretense, embrace discomfort, and meet people exactly where they were. In August, I made the leap. It was a decision fraught with risks. Leaving a secure paycheck behind, I had no financial safety net if I failed. There was no guarantee clients would come, no promise that my efforts would succeed. On top of that, I battled the ever-present voice of impostor syndrome, a belief rooted in my own upbringing. Growing up, I didn’t think I’d amount to much because I didn’t have a clear passion or path. When I finally found my calling, I struggled to believe I was capable of pursuing it. Read more>>
Brittany Hall
Taking a risk? What does taking a risk mean to me? It All Started in 2024 when I was admitted to Full Sail University for Film in Media Productions, I am from Seaford Delaware, born and raised. I am used to the cold breeze when I step long along the lineless roads and thick sand running along my feet. Let’s just say that film School was a huge decision for me. Along this journey, I had to leave friends that I’ve had for years. I even had to leave my theater crew, which was so devastating for me. Most importantly my family, my nephew, everything was just too soon. “Are you sure this is the right decision?” “Will me, moving away cause conflict within my relationships?” “Is this a selfish decision to make?” All of those things swarmed around my head at those times in my life, and I had to think very deeply about what was next to come for me. These are the nights I prayed for an answer; I knew he would have the ultimate decision. Read more>>
Irene Wu
I’ve always dreamed very big and wanted to work in the entertainment industry. I remember I would drive down the 101 on the way 626 from the 818 on the weekends with my family and we would pass by the big Universal building and I remember I told my dad, “Dad, one day I’m going to work in that building.” I never thought it would be easy but that was the beginning of manifesting my career. I’ve always been very picky and dead set on the things that I wanted. I knew I couldn’t do anything but work in the entertainment industry… it was a feeling I had to follow. Read more>>
Murray Sawchuck
My whole family was in the Railway business or Forestry business so jumping into doing magic tricks for a living was like being the black sheep of the family, giving up a 401K, Pension plan for walking on stage nightly and hoping people would pay money to see me entertain them. I started at 7 years old and by my early teens I was doing 3 – 5 shows a weekend in Vancouver, British Columbia where I am from and I have never looked back! We just celebrated my 23rd year headlining on the Las Vegas Strip! The reason I took the risk is because I could always go back and get a corporate regular job, as they will always be there but to jump out and make a job for yourself with your dream is so much harder but the rewards are so much greater! Most people work 52 weeks a year and look forward to 2 weeks a year off but when you do something that is your passion you don’t work a day in your life… so you really take 52 weeks a year off like a vacation. Read more>>
Will Hudgins
Growing up, I was always one that’s been drawn to creative outlets and making things. When I was introduced to woodworking, I fell completely in love with the process and how it made me feel. It was something I knew I wanted to keep around in my life forever. As the passion grew, I couldn’t ignore my desire to design and build custom furniture as a career. I was also extremely attracted to the lifestyle folks had in Southern California after visiting a couple times. I wanted to create a life where I could have both of these everyday. Read more>>
Christine Kim
I left my hometown, Seoul, South Korea when I was 15, because I wanted to become an actress in Hollywood one day. I was a minor from a foreign country who didn’t know anyone in the industry, but I wanted to move to America to learn the language and culture while I was still young. And that is a BIG risk!!!! I attended a private Christian high school in Columbia, South Carolina, I attended SUNY Stony Brook where I earned my BA in Theater Arts, and I moved to Los Angeles, CA where I earned my Masters in Fine Arts. At the age of 25, I finally started working on the film sets. I made appearance in commercials, films, TV shows, and streaming services. Read more>>
Angela Fritz
One of the biggest risks I’ve taken actually has forever changed my career and my life for the better. I was born with sensorineural hearing loss and have worn hearing aids and been learning ASL throughout my life. As a kid, I was bullied for being different and spent most of my life feeling ashamed of my disability and wishing I was “normal”. Working with kids with disabilities and seeing all the strengths that come from it, as well as years of therapy, slowly changed this perspective, and put me on a road to acceptance and pride in my disability. When I shared publicly about my experience with hearing loss, I was terrified, worried I would again feel belittled and othered like I did as a kid. The response, however, was the exact opposite. It inspired others to open up about what makes them different as well, and I was met with tons of support and encouragement. Being vulnerable about my disability gave me opportunities to make important changes within my circles to create a culture of inclusion and belonging for all. It provided me a platform to spread awareness and advocate for change in very powerful ways. It also has opened up important avenues for connecting with patients and families in a really special way due to my personal experience with disability, which has led to powerful patient- and family-centered care within my professional spheres. Taking this risk taught me that when we are vulnerable, we are brave, and bravery changes the world! Read more>>
Bianca Foscht
I believe the creative industry is all about risk taking, because it is an industry that is in so many ways unpredictable. There is really not a right or wrong way to go about it, and that’s the beauty about this industry. Something that might have worked for someone else might not work for you and even though it can be daunting sometimes to not have one proven path that works for all, it also give the individual creative freedom to explore. I’m a huge believer in “fortune favors the brave” and I think as an actor specifically one has to climb out of their comfort zone and be vulnerable and brave. Most of my greatest breakthroughs and learning experiences were gained by me taking risks. I remember reaching out to one of my great role models in the industry without prior connection. An cold email that I thought would never be read. Out of surprise, the person I reached out to replied and started mentoring me not long time later. Read more>>
Smiely Khurana
One of the biggest risks I’ve taken was leaving my stable 9-to-5 job to pursue The Sustainable Act full-time. I walked away from security to grow a platform and business focused on amplifying underrepresented voices in sustainability—a space that’s already underfunded and often overlooked. It wasn’t an easy decision. But I felt a deep urgency to create something disruptive, a media platform that could inspire action and elevate voices often left out of the conversation. Read more>>
Robert Kay
A while back on one of the economic cycle downturns our company shrunk down to myself and one other person. As an engineer I had as yet failed to understand why marketing should have been my #1 priority ahead of thinking about technology. At that time we had very little cash but had already signed up to have a booth at a local trade show. The two of us went and damn if the show wasn’t dead. The economy was bad all over. We skipped out of the booth on the last day to have lunch and try to de-stress. When we returned the folks in the booth next to us said a fellow had come by looking for us. Read more>>
Sheryl Coughlan
Taking risks has been a recurring theme in my life, but the greatest one by far was opening a business with every last dime in my bank account. In 2015, after years of recovering from a major health scare, I decided to follow my passion for buying and selling antiques and vintage treasures. I poured my heart and soul into this venture, pushing myself into uncharted territory. That leap of faith led to the creation of Antiques on Magnolia, my small storefront in Burbank, California. What started as a modest beginning grew beyond my wildest dreams. The business has blossomed into the thriving company it is today—proof that taking a chance on your passion can truly be worth the reward.. Read more>>
Vanessa Drew
In 2005, I took a big risk by opening my first colon hydrotherapy clinic in a basement under the health food store where I worked in Brooklyn. I ran the business alongside my ex-boyfriend, and as the business grew, we grew apart. By 2008, I made the difficult decision to leave him, move back to my family, and start over. At that time, I wasn’t sure if I could run the business on my own, but I pushed forward and launched my own studio, Cleansing Concepts. Nearly 20 years later, I now have four locations and a successful online business selling detox clay products. It was a risk because I had no formal business training, but my passion for helping people drove me—and that’s exactly what I’ve been doing ever since. Read more>>
Emily Sealy
For the past 10 years or so, I have had multiple part time jobs instead of one full time job and enjoyed the variety. After graduating from acupuncture school, I was hesitant to start a private practice and go full force on it- instead I worked at a few different clinics to get experience, and started my practice as a very small side business. I was able to sublet a treatment space from a previous classmate for one day per week, and found it to be quite fulfilling to see clients there, doing my own thing, and taking time with each client. I liked it but I was also scared of putting “all of my eggs in one basket” by taking on more days or responsibility. Read more>>
Fabiola Angelí
I believe that pursuing our creative ideas and daring to create from our heart and soul is one of the biggest risks we can take. So as creatives we basically live taking risks! It not only involves the risks of finances, stability, and job security, but more than anything it involves the risk of vulnerability and being seen. When we create from our hearts and souls we are opening ourselves up and exposing our humanity to the world. In that journey, we are allowing our authenticity and all that we are to birth our ideas. As we water those ideas, they grow into art, services, programs, and more. With that in mind, I see my entire journey of being a creative entrepreneur as taking a risk. Read more>>
Maria Wolford
About four years ago, I knew that I was needing a change. I was working a corporate job, driving in lots of traffic, doing the same job day-in and day-out. Working a job that was bringing someone else their dream life while I felt stuck in a rut that was getting deeper and deeper. After years of this, I knew that I would need to make a big change to achieve the life that I wanted and needed. So I talked with my husband and a few close family and friends about how I was going to make the move necessary to give me the life I desired and dreamed of. Yes, this meant leaving my stable, comfortable, and consistent job that provided me benefits plus a reliable, steady paycheck. Leaving what was known and predictable was not a decision that I made lightly. Read more>>
Samantha Henderson
In 2022, I sold everything and moved across the country from Connecticut to LA with no job, car, or apartment set up in order to chase my dream of being an actor; even though I had no experience or training in acting. I had wanted to be an actor my entire life, but began to increasingly feel like I could not get the idea out of my head. I was feeling extremely unfulfilled and depressed. Every time I watched a show or movie, I felt an immense heartache that I was supposed to be involved in something bigger. So, when I lost my job, my car, and my apartment all at once, I knew it was a sign from the universe to pursue my dream. I found a random sublet in Venice Beach on Facebook to live in while I searched for a job and an apartment, sold everything I owned, and bought a plane ticket. Read more>>
Erskin Anavitarte
When we moved to Nashville almost 12 yrs ago… we had little to commend itself to the start of a fantastic music career. In fact, we had a strong desire and a few songs on my guitar. I was however willing to step into risky bars and clubs to grow in my craft. I think this season of risk prepared the way for other great moments in my families life, because once i saw the faithfulness of God in those early years it gave me hope to trust him for greater things later. Read more>>
林 Vincent 松諺 Lin
I mean,doing an art work is totally taking a risk ,it is basically walking in a pure darkness , the only ” sensory organ” you can rely on is your heart. You must dig in deeper and deeper until you find the main core , and after all , creating light step by step, one by one by your own , then finally mesmerizing into the light you create for yourself , live in your own infinity creation forever. It’s a trip , an adventure with chaos essence always surrounding you , sometimes you may got lost , sometimes you may feel frustrating , sometimes you may confuse . There’s always upcoming new challenge , but once you get on your own path , whether doing art or any other things else , facing your’s own heart is the only path which can lead to the door of non- duality , and truly live free in every present . Read more>>
Kay Louis
The year was late 2020, and like so many others, I found myself at a crossroads. I was working full-time, clocking in and out of a job that felt uninspired and unfulfilling. I had become disconnected from the very reason I pursued massage therapy in the first place: my love for helping people heal, recharge, and reconnect with themselves. Despite my passion, I felt undervalued, unmotivated, and creatively stifled in a role that didn’t reflect my vision or potential. Read more>>