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.
Juri Takeoka
I was born and raised in Japan and moved to the United States in June of 2024 after receiving my green card from my marriage to my husband, Cam. I used to work as an AuPair in the Bay Area back in 2021-2023, that’s when I met Cam and things went great. When I was looking for a photographer for our engagement photos, I realized it must be such a cool job. After a lot of research, I got my very first camera. I learned how to use it and how to edit photos on youtube. Once I started practicing, I was having so much fun! Read more>>
Tahani Roman
During the pandemic/lockdown I decided to host friends over at my apartment to ‘practice” and get comfortable performing in front of people. I had lots of time on my hands as did the rest of the world. I hated the job I had, and I made the decision to give this a try (DJ). I took a risk by leaving the corporate 9-5 job and decided to turn my passion into profit. It was a scary and risky step to take when the entire world was shut down. It was a huge risk to take, not getting a paycheck weekly, not getting health insurance, sick days, 401k. I believed in myself and it was a gamble that really is paying off! Read more>>
David Bell
Sometimes, you must jump out the window to get the desired results. Common sense tells you no. Your family and friends told you no, and looking in, they are right. You shouldn’t jump out of the window if you don’t want gravity to take action and send you flying to the ground at an alarming speed. In films, the fall is always shorter, or a soft bush outside catches our hero. Maybe they’re secretly good at parkour and flip from tree branch to tree branch. In my life, I like to think it is the perfect syncing of both; sure, gravity exists, but so do strangely soft bushes that could stop a 183-pound falling object from the 5th floor from breaking anything. Read more>>
Spen Schwab
Leaving the past behind to pursue my passions and dreams. For most of my life I followed what I thought was a stable path through life, I had a successful career building and troubleshooting complex computer systems. I worked hard and long hours constantly striving to make sure that all the humans on the other sides of the machines that I toiled to keep running as smooth as possible would provide a seamless experience. In 2019 I started to write and in 2020 I began to paint. My Neighbor Pat had gifted me some canvas. I found some of my sons Ikea tempura paint and began to apply to one of the canvases. One after another I would produce another work of art. Read more>>
Tim Kellams
Risk taking is a huge part of being an independent musician. I decided I wanted to pursue music full time when I was still a teenager. I quit my job as a retail manager. I built my own recording studio at home and started performing live within the same year. I am still pursuing music over a decade later. It’s my number one passion. I never chose a career or life outside of music. There have been many ups and downs during this musical journey. My grandfather lived with me for my entire life. He passed away in 2017. I had to perform a show just a few days later. Read more>>
Jody Rigsby
In 2015, my husband and I had the typical suburban lifestyle: brick home, yard, and two cars. We felt stuck and bored and asked each other what we each wanted out of life. He wanted to travel and I wanted an adventure. We decided that we would sell everything a trailer, a truck to haul it, and travel while working. Within three months, we left our friends, family, and familiar surroundings, to go on the road. Beginning this lifestyle was scary. We had no idea if we could sustain ourselves or if we’d like living in this new lifestyle. It was an adjustment from so many aspects, yet the biggest change was transforming how I paint. Read more>>
Nicole Pate
Up until I got married in my 40s, I had been an independent self-sufficient woman enjoying decades of travel and successful careers in 2 different industries. After I married, I made the decision to step back from my career and work part time assisting my husband with his company. The decision was made based on our adoption journey through the local foster care system. My husband and I knew it was not reasonable to both work 40-50 hours per week while welcoming children into our home who would need constant emotional support. There would also be lots of appointments while the state had legal guardianship over them. Fast forward a few years. We bought a new house for our growing family, finalized adoption of our two children and the marriage began to crumble under the weight of my husband’s alcoholism. Read more>>
Anna Kishlaly
As an artist, one of the biggest risks I’ve taken wasn’t about money or a career decision, but the emotional risk of choosing to fully accept and take responsibility for my identity as an artist before I even had actual art to represent. It’s a risk because, in the early stages, you’re essentially staking your sense of self and your future on something that doesn’t yet exist in physical form. Read more>>
Alizée Rémond
For most of my life I thought that taking a life changing risk was too unsafe and risky. I was a stressed, introverted and control freak person so everything too big, challenging or out of the box was terrifying. I was full of fears and it felt comfort, at least for a while, not to try to change that “safe” life. But in the back of my mind, I couldn’t stop dreaming bigger. I wanted to be more brave and bold, I wanted so badly to do something on my own in the self-development field but it wasn’t that simple. I thought “it’s impossible to be achieved, it’s too risky, are you crazy?”. I was trying to find excuses, more than this, I was creating my own excuses not to start. Read more>>
Kevin Sommers
Good morning My name is Kevin Sommers I am a veteran of the United States Army of Thirteen Years. In 2019 I was deployed to Africa. While gone I had plenty of dreams & aspirations becoming an actor & starting my clothing line was amongst a few of them. Little did i know that when i arrived home in 2020 that the wasn’t quite the same as I left it. I arrived home from war into a real war COVID 19. Read more>>
Jolie Davenport
One of the biggest risks I’ve taken was waiting to pursue my music journey as an artist. Music has always been a passion of mine, but I made the conscious decision to focus on building my company first. My goal was to create financial stability and establish a foundation that would allow me to enter the music industry on my terms. I wanted to have the resources to work with talented producers, secure collaborations, and present myself as a serious artist ready to grow in the industry. Read more>>
Pamela King
When I decided to leave teaching after 15 years, I was equal parts terrified and exhilarated. Teaching had been my comfort zone, my identity, and honestly, my safety net. But I reached a point where I couldn’t ignore the nagging feeling that I wanted something… more. I didn’t know what “more” was, but I knew it wasn’t in my classroom. So, I took the leap. No job lined up. No business plan. Just a lot of faith in myself, a good dose of curiosity, and a side order of panic. At first, I convinced myself it was temporary. “I’ll just do some ‘helping’ projects while I wait for my big idea to show up,” I thought. Read more>>
Mary Leveridge
Everything in life comes with risk, but choosing to be an artist was one of the most life changing risks I’ve ever taken. I was in college in England studying Equine Science. I had wanted to ride and train horses for the rest of my life. I thought it was what I was supposed to do, having done it for over a decade at that point. There was, however, this small part of me that loved the theatre, loved watching stories come to life, but was always too shy to ever do anything about it. It all came to a head in college and I knew I had to go home and at least give it a try and take a class or I would never be able to forgive myself. So, I enrolled at the local community college, undeclared, took my first class doing monologues and scenes and was immediately hooked. I knew that horses would always be a part of my life, but that acting and storytelling is what my purpose truly is. Read more>>
Jean Desant
I was five years into my corporate job when things started to unravel. The company was going through significant changes, and I was faced with a tough decision: relocate to another state to keep my job or risk losing it altogether. The uncertainty and instability were overwhelming, and it started to take a toll on my mental health. Although I was spared during a massive round of layoffs, the constant anxiety of not knowing if I’d still have a job the next day was draining. Read more>>
Sanya` Hudson
In 2004, I took a huge risk and relocated from Brooklyn, New York to Pensacola, Florida. Although I took a significant pay cut, the move was essential to providing my daughter with a quality education as well as improving our quality of life. We were both happy until our happiness abruptly ended after a few short weeks when we were affected by Hurricane Ivan. Read more>>
Nicole Ohr
In 2013, the dance company that I had been performing with for 5 years, Undertoe Dance Project, was discontinuing, along with the outdoor dance festival, Astoria Dance Festival, that was founded by the company. I felt that this event was worth furthering, and as a result, took on the position of co-producer, renaming the festival Dance Astoria. I had no previous experience as a producer, however, this event I felt was one of a kind. Bringing dance to the public, to both bring more visibility to the arts, and to support local businesses, in my mind, was a way to create great community. My former choreographer provided me with the contacts at Bohemian Hall & Beer Garden, and from there we booked the space, and found local businesses to help sponsor the event. Read more>>
Leah Norris
My career has been full of risks since the beginning. Which is funny thinking about it now since I initially enrolled in beauty school because my dad offered to pay for me to go. My original life plan was to go to beauty school right after graduating high school and learn the trade. Then work in some chain salon for a stable income while resuming my studies for a BA or higher in music education. Obviously things did not go as planned. I ended up really loving hair and how it sparked my creativity more than music ever did. It also allowed me the opportunity to connect with people, which is something I’ve struggled with my entire life until I started my cosmetology career. Another thing that didn’t go as planned was I unfortunately didn’t have my tuition paid for after all. I paid my own way with savings and working retail on my non-school days. Read more>>
Jasmin Peters
The biggest risk I have taken was coming to LA for 9 months to be mentored by Stargate (Rihanna, Katy Perry, Ne-Yo). I got on a flight from London with 5 nights booked in an airbnb with a girl I’d never met before (who is now one of my closest friends) while we looked for an apartment. We spent the first week of the mentorship program bouncing between couches and airbnbs, leaving most of our belongings locked in the studio every night while we found and finalised our place. I’d never even been to LA before so it was objectively terrifying, but definitely a huge character building and bonding experience, and most importantly it allowed me to be here, fully immersed in my craft, learning and creating with grammy award winners. Read more>>
Michelle Thompson
Being an artist is a risk. Working so hard at something that may or may not get selected or reviewed or observed or provide positive financial outcomes can be heart breaking, but at the same time if you don’t try then you will never know or experience the joys that art can bring to people and yourself. I feel that I was born to be an artist, and each day as an artist is a gift and an immense lesson. I am a creative risk taker who loves collaboration. I challenge myself with cross discipline works that bring many innovative minds together. I work with composers, musicians, playwrights, actors, visual artists, poets, fashion designers, museums, unique spaces, filmmakers, and more. Read more>>
Lauren White Davis
Entrepreneurship is a risk by definition. Being an individual constantly brimming with new and exciting ideas, I am not a stranger to taking risks. The lesson learned over the years is how to focus those ideas into action to make calculated risks, worthy of positive payoffs. When we were approached by our business partner to assist him in expanding Chivo Coffee Co, we were already running our own small business, Lemonseed Botany Bodega. The previous year, we took the kids out to a farm and test drove a 1980’s county school bus. We bought it on the spot with plans of turning it into our mobile plant shop: our botany bodega. Read more>>
Rachael Harms Mahlandt
A risk I’ve taken was to install a space in my yard for passersby to enjoy. I started by adding a Dinosaur Diorama (called a Dinorama) and then added the Dino Exchange followed by a book swap for itty bitty books. Later I added an even smaller book exchange, another two dioramas, an informational stand all about bees and an exchange for mugs. When I share about these installations I often hear ‘Aren’t you worried about your spot being damaged?’ or ‘I could never do that here, someone would just take it all.’ That was definitely a hesitation of mine but I’m so glad I didn’t let it hold me back. My installations and working with a friend to make a map to places like this in our city of Portland, Oregon has lead to some incredible life experiences. I’ve met so many unbelievably kind and creative people, had folks visit from all over the world, and now know that many more spaces like this exist because people were inspired by the movement here in Portland. Read more>>
Paul Yerian
Do you remember a time that you drew a picture or made a slide show, maybe you wrote a poem or maybe struck a few chords on a piano? That one time that you created something from nothing and you wanted to show someone, people, the world must see this creation! But not everyone will like this right? So what about the people that dont like it? What if its not just a person but maybe a couple people. I mean just because I made something doesnt mean its cool or people are going to like it. Im not the best but do I have to be? Can my imperfect growth outimpress my imperfections? What if its not good enough, like im not good enough. Read more>>
Shayla Gordon-jesse
I had been asking God for direction on my calling. I knew He wanted me to share my faith, but I had no idea in what way. I also knew I was hindering Him with my lack of faith because I struggled believing I was good enough for Him to use. I was allowing my personal struggles to steal my focus from God. I was also allowing it to chip away at my self-worth and my joy. I had been tying my identity to the emotions from a personal struggle I was dealing with instead of my relationship with God. I had fallen into the habit of making prayer time a one way conversation with God as I was doing all of the talking. It’s not that I had forgotten the importance of listening for God’s direction, but reflecting back, I think I had decided I didn’t want to hear what I knew He wanted to tell me. Read more>>
Joe Nicastro
As an accident lawyer, every case is a calculated risk. It’s a profession that demands standing up for people from all walks of life, investing resources into the fight, and taking on powerful insurance companies and corporations. Of all the cases we’ve handled, one case stands out—a high-stakes battle against one of the most recognizable names in the industry: Domino’s Pizza. In 2019, a Domino’s Pizza delivery driver, under pressure to meet delivery deadlines, was speeding and driving recklessly. The urgency to deliver pizza on time came at a dangerous cost. The driver crashed into our client’s car with such force that her vehicle was pushed off the road and into a fire hydrant, completely dislodging it. It was clear that the driver’s actions—fueled by corporate demands—were directly responsible for the crash and our client’s injuries. Read more>>
Sarah Grote
I worked in corporate and nonprofit companies for 20 years. In 2012, after managing a development group and direct mail fundraising programs for 12 years, I was laid off. It wasn’t the end of the world, but certainly an adjustment from an intense work and commuting schedule. I started on my job search and had interviews. I remember I was one question away from certification in a totally different industry. I had a nagging voice in my head, and too much anxiety to ignore the fact that it wasn’t the direction I needed to go. After a few months, my husband saw the frustration on my face and told me that I was always there to support his career and transitions and that I should try my creative journey and embark on doing photography full-time. And we’d regroup in six months – if it took off, great! If not, we should see what’s best. Read more>>
Andrew Bernett
My journey to developing Bee Well Therapeutics has been paved with calculated risks. From pursuing a chemistry degree to working in industries ranging from cardiac research, pharmaceuticals to jet engine assembly, I’ve consistently pushed beyond my comfort zone. These experiences, while varied, provided invaluable training in areas like clinical trials, waste reduction, electrical systems, and driving measurable results. This diverse background, built on a foundation of risk-taking, ultimately prepared me to take the biggest risk of all: launching my own business and bringing this life-changing medical device to market. I wouldn’t be where I am today without embracing those earlier challenges. Read more>>
Caitlyn Boardman
Getting sober was the best risk I’ve ever taken. I say risk because I was scared to take that full leap for the longest time. I kept trying sobriety out and I kept running back to alcohol a month later… I was just too scared to leave that version of myself behind but I knew that in order to grow, heal and become the person I needed to be then I needed to get sober. So I kept trying and eventually I hit 1 month, then 2 months and now I’m a little over 3 years sober. My life has truly changed for the better and I couldn’t have gotten this far without sobriety. Read more>>
Wilmarie Hernandez
From a young age I noticed how taking calculated risks always led to growth and aligned experiences. While in college I took the risk of switching majors from engineering to, what it seemed at the time, a way less lucrative career choice but one that felt more aligned with my desires, interests, and values. It ended up being a very fulfilling career that even allowed me to achieve a comfortable level of financial freedom. In the first half of my twenties I took the risk of using dating apps, when it was still a new thing and pretty taboo among my peers. I took the risk of meeting people through these apps, people from different social and cultural backgrounds that allowed me to widen my perspective and knowing myself better. Read more>>
Katina Inger
We all take risks everyday. I think risk taking means we are traveling along our growth edge. It’s not sustainable as a day to day way of living but more as a marker that we are moving toward something in life. One of the biggest risks I’ve ever taken was stepping away from a conventional life that, on the surface, seemed stable and secure. I gave up a long-term relationship, left a family home where I had lived for eight years, and moved from the East Coast to the West Coast. It wasn’t just about relocating—it was about choosing to embrace art as my full-time passion and life path. Read more>>
Esther Alvarez
My mom always tells others how I would substitute a barbie for makeup when I was little. When I reached my pre-teens, my mom taught me how to take care of my skin. That is how my love towards skincare started. I had something in common that I could share with my mom. As I grew older, my love for makeup became evident and started offering makeup for free to those who could not afford it. I found so much joy seeing how their confidence grew when they saw themselves in the mirror. I became a middle school teacher, but I never stopped doing freelance makeup. Read more>>
Darryl Jones
I’ve been working as a film producer for the past 8 years, and I can tell you that the entire profession is a risk. If you’ve been paying attention for the last few years, you can imagine why: Covid, recessions, corporate consolidation, strikes, AI and even climate change, like the January 2025 firestorms in Los Angeles or Hurricane Helene here in NC. Freelancing has never been a stable path, but in my experience things have become even more uncertain than when I first started. I love film producing, but the film business is in an existential crisis. I feel this, as do many others, but paradoxically I’ve never had more hope about the future. Read more>>
Jenna Nelson
This business has been my biggest and most rewarding risk. I was doing pet sitting on the side up until 2021 and working in the restaurant service industry. During COVID I reflected a lot about where I wanted to go in life and decided I wanted to break free from the job I had whenever the world decided to open back up. I took the time to build a website, became certified and obtained pet insurance. I let my side gig clients know I was going full time and got the momentum going quickly. The first two years were slow and had months where I did not know if i’d make it but had continuous support and have persisted. Its opened me up to other avenues of marketing, customer service and really shown me what it means to be a small business owner. I’ve kicked off the training wheels this past year and this year plan to grow as far as more walking clients, my understanding of the financial structure and stability, and community involvement. Read more>>
Germán Augusto Rodriguez Laverde
The most important risk was pursuing my dreams, and I believe the key moment for every artist is hearing the NOs—they define your path and career. Read more>>
Nicholas Lewert
Hi. I don’t know if I knew this scenario would be considered a “risk” at the time. In 2017, I began my first semester at a university in south Florida. I was involved in their music performance program at the college for the duration of the semester. Admittedly, there was never a time where I felt settled and in the “right place” while in this program. Not to overplay the “I never fit in” stereotype, but I truly didn’t align with the curriculum they were offering. At the time, I felt I had already experienced an atmosphere of belonging in other programs, such as my time during the Berklee five week program, and even my high school marching band. Read more>>
Uziel Gomez
The biggest risk I’ve ever taken was launching my firm, Primeros Financial. As the first in my family to graduate college, I started earning a salary that was more than my family had ever seen. Leaving that stability behind to start from scratch wasn’t easy. But I knew if I didn’t take the leap now or I might never do it. I grew up in a low-income household where money was tight, but we always managed to get by. My dad has working since he was 12, doing intense, physically demanding jobs. My mom worked at a factory until the ‘08 recession, when she was laid off. Growing up, “getting by” meant there was no extra money to save for things like retirement. Read more>>
Zoe Miles
I left all that I knew behind just over a year ago, and relocated to Dorset with my partner. I quit my full time job – and I set up my own business again, ploughing all of my savings into it. But this time without the support network of friends or family around to build it has been 10 times harder and brand awareness has been a key task for me to try and achieve. So I’m trying new things like attending networking events and entering national awards, which doesn’t come all too naturally to me…. But I keep feeling the fear and doing it anyway! Read more>>
Kelly Schuermann
In late summer of 2020, a warehouse artist’s studio became available in Reno, Nevada. At the time, I was working as the workshop manager at Atelier Truckee. Unfortunately, in March of 2020, our owners had to make a very hard decision and we’re forced to close with no reopening date. There was no gatherings beyond two people outside for our small town. As a workshop space for adults Atelier could not function. Read more>>
Danny Stanley
I have learned that we should not have fear when we are faced with taking leaps in life, but to fear the consequences of not doing so. It’s best to take the leap (the risk) and trust that the net will appear…because it does! In 2020, during covid lock down, a lot of us were sent home to work. During that time I was one of the many sent to work from home and I was working a corporate job that I absolutely hated. As I was at my desk typing away on an insurance claim, my artist desk with all of my half finished work was across the room calling out to me. As I stared across the room peering at the desk I truly wanted to be working at, but noticing the one I felt chained to against my will, I broke down crying. Read more>>
B2b With Ross And Bella
Over the past few years we found ourselves constantly diving into deep and hilarious conversations about the dance music industry- a space we both love and are connected to. We’d talk for hours about the stories and personalities behind the scenes—the kind of things we knew people would find fascinating but rarely get to hear. That’s when the idea for our podcast, B2B, was born. But the thought of starting a podcast felt like stepping into a completely new world. Neither of us had experience in podcasting, and the idea of putting ourselves out there—vulnerable to the opinions of friends, strangers, and the internet—was terrifying. Read more>>
Nicole Burbank
The biggest risk I’ve ever taken was quite literally walking away from everything to start over. In 2019, I had a profound breathwork and somatic experience that catapulted me onto a path of self-discovery. Up until that point, I thought I knew myself, but in reality, I only knew the version of me that “society” and “culture” had molded. The truth was, I had no idea who I really was at my core. Read more>>
Alejandra Lievano
As a restless, left-handed Sagittarius, I’ve come to believe that taking risks is woven into the fabric of my soul. To me, it’s a practice, a creative process, a portal that opens up opportunities for me to experience life fully. Every leap, every decision that has sent me falling (sometimes literally) into the unknown has been both a lesson and a reminder that my soul craves expansion. Read more>>
Alycia Shiann
The biggest risk I took was pursuing art full time. When I was applying for colleges, I was excited to tell people that I was planning to major in art after high school. However, when I told people this, it was often followed with disapproving faces or questions on how I was going to make a living. Even though I followed through with my plan to major in art in college, it was still upsetting to not be understood or supported. Throughout college, my end goal was to get a 9-5 graphic design job once I graduated, even though my true passion was for drawing and painting. Read more>>
Maggie Rose Macar
The biggest risk I’ve ever taken was founding zant. I gave up everything to start and grow this company including my savings, my career stability, and countless personal moments. When I made the decision to go all in, I left a secure job to dedicate every ounce of my time and energy to building zant. I sacrificed financial security, depleted my savings, and faced the uncertainty that comes with putting everything on the line for a dream. More than that, I gave up time with family and friends to seize every opportunity and ensure no moment was wasted in the pursuit of zant’s mission. Read more>>
Francesca Delisle
Entrepreneurship is one of the greatest risks you can take. It demands everything—your time, energy, and resources. While we’re no longer hunting and gathering for survival, we are now building businesses and creating opportunities. In today’s world, the “dragons” we face are the challenges of entrepreneurship, and this has been the greatest dragon I’ve ever tamed. Read more>>
Gracy Darlin
In August 2024, I took a risk by going across the world from London to LA. This was such a huge risk filled with thrill and excitement. As a solo traveller and independent artist I didn’t know what to expect, I took a risk to get myself heard ,seen and to promote my music. After trying all avenues in my hometown. By taking this risk , I got experience a different culture a different life. I got to meet loads of people from all walks in life. I got to perform my music and meet other artist who also do music. I got to party and enjoy different foods. Read more>>
Richard Blades
When it comes to being an artist, risk-taking is an integral part of the process. There are the risks we must take with our work, constantly exploring different approaches to expressing ourselves. Then there are the bigger risks that must be taken to develop our careers. There are many along the way, some work out whereas others don’t. Regardless of the outcome, embracing these risks will aid in our creative and professional development. Read more>>
Danny Augustine
I’m not much of a risk taker, but I would say I do know when to take a step forward. I believe everyone’s life path has opportunities laid before them to better themselves. Sometimes these opportunities are passed up due to the inability to see past insecurities and a self-defeating mindset. My biggest move forward, in life, was moving to Chicago to finish my art degree at The School of the Art Institute of Chicago. I moved to the city with two months’ rent and a dream. When looking back, I was more gutsy back then. If I made the same move today, I would be overly prepared and things would be less exciting than the unknown adventure of the past. Slowly like a stream to a river, I found my roots starting to settle into the city I felt was so overwhelming and busy, to the current day where I feel I’ve outgrown the 2nd City. Read more>>