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.

Bruce Checefsky

Creativity means working outside the box. Artists observe the world and respond. We see things differently and, as many would agree, with clarity and purpose, often at the expense of redundancy. We are not suitable for all jobs. An artist carves their own path in culture and society. We create our tools and develop a language to describe our work. Explaining what we do comes at a cost too great for many of us. But put a group of artists in a room and, unlike a corporate board meeting or politicians trying to heal by hurt, we get things done. It’s our nature to produce results. We solve problems creatively. Read more>>

Negin Niknejad

I wouldn’t even call it a risk. It was more about listening to my intuition. I was the head aesthetician at a well-known boutique health club and spa and things had been stale for a while. My aunt in Iran was diagnosed with terminal cancer and I dropped everything to go see her and visit my home country after 26 years. I quit my job and began to prepare for my trip. To make extra money for my long travel ahead, I thought to offer some facials in my kitchen to a few close friends. I had just purchased a massage table and I thought why not? Read more>>

Rashnide Aguy

Taking a risk can be terrifying, but it can also lead to life-changing growth. One of the biggest risks I ever took was deciding to study abroad on my own. Growing up, my family traveled often—my dad was constantly traveling from Haiti to the states, and my mom always planned our summer road trips. My travels always revolved around family and as I once I became a teen, I was going on more church youth trips, so I never experienced traveling alone. Read more>>

Wangari Njathi

Leaving my home in Nairobi, Kenya, to pursue a Ph.D. in North Carolina was a life-changing risk—one filled with uncertainty, challenges, and personal growth. At the time, I had always been deeply passionate about data-driven marketing and communication, but I knew that to truly make an impact, I needed to immerse myself in global perspectives, push beyond my comfort zone, and challenge myself academically and professionally. Read more>>

Glenny Medina

One of the biggest risks I took was starting my own boutique after losing my job at State Farm during the pandemic. I had worked there for over 10 years, and losing my job was a big shock. I didn’t know what to do next, but I always loved fashion and business.

Instead of finding another job, I decided to start an online boutique. It was scary because I had never run a business before, but I worked hard, learned new skills, and kept going. Read more>>

Ricardo Sanchez

The biggest risk I have ever taken was when I decided to move to Atlanta in 2023 to further pursue my career within music. With no job prospects and no certainty as to whether or not this would work, moving to Atlanta ended up turning into one of the greatest decisions I’ve ever made. I had two friends that I knew from college that had moved here a year prior and they wanted me to be their third roommate. They were also pursuing a career in the music industry and had told me about how driven the scene in Atlanta was. I had saved up about 2/3 months worth of rent and decided to pack my bags and make the drive from New York. While the road was definitely a bumpy one, I am thankful to see where I ended up. Fast forward two years and I now manage one of the biggest studios in Atlanta. Read more>>

Ali Lobo

The biggest risk I’ve taken was launching my own LLC as a holistic nutrition coach. At the time (2020), I had a stable job and a predictable income, but I felt this deep, almost nagging pull toward creating something of my own—something that aligned with my passion for helping people live healthier, more balanced lives. Read more>>

Bettina Ward

In December of 2018 I decided to go take a yoga class at a studio near my house. I had never been there before and my husband had signed up for a bowling league on Monday nights so I decided I didn’t want to sit around, and off I went. The teacher was great, the class was awesome, and the people in the studio were so kind and welcoming. I immediately bought a package and started going back almost every day. I had been practicing yoga for many years but this was different. It lit something up in side of me. Read more>>

Eryn Renee Young

I founded my ballet company, XAOC Contemporary Ballet, when I was just 19 years old. At the time, I didn’t think I was taking a risk – I just knew I wanted to make dance, and for that I needed dancers.

At the time, there were tons of small opportunities to show work and when you’re all young and hungry and in it for the dream, it’s easy to find artists willing to create with you for $50 bucks and the chance to be on stage. I was so fortunate to find dancers who were as passionate as I was and who were willing to join me on the journey, knowing that we were all young and broke and doing the best we could. We did close to 100 shows in just a few years. Read more>>

Jasmine Echols

One of the biggest risks I’ve taken was resigning from my retail job. Months prior, I had taken on a part-time role that I really enjoyed, but sometimes the hours clashed. At the same time, I was shifting my focus toward growing my business and dedicating more time to my writing.

Letting go of the stability of a guaranteed paycheck wasn’t easy—I definitely could have used the income. But I knew deep down that it was time to take the leap, even though I didn’t have everything “set in place.” Read more>>

Benjamin Phan

I didn’t come from a dance or entertainment background, so my parents were reluctant to support my decision to pursue a career in dance. They weren’t wrong to be skeptical—I had only taken up Hip Hop dance shortly after high school, and I had just completely bombed a recent audition. At that point, I planned to return to college. But then, something in me refused to quit. I had no one to prove anything to but myself, and I’m glad I took that bet—because shortly after, my life changed. Read more>>

Zoie Stout

Taking a risk is a big deal to many individuals. My personal outlook on risk taking is simple, yet so complex. I believe taking a risk can play a part in the foundation of ones life. I, Zoie Stout, took a risk on creating a business as a young adult. At the early age of 15, I started EZModeling with an amazing photographer. Said photographer became very busy with his work, so we decided it was best to part ways as far as the business standpoint. I then branched out to work with another talented photographer! This individual was with me for almost four years. Just before 2024, I wanted to take a huge risk. I wanted to start signing models. Johnson City Modeling was a business in which we worked to host non-profit fashion shows. Read more>>

Hafu Go

Straight out of college, I had a comfortable marketing job—20 hours a week, living with my parents, no real expenses. But even though it didn’t take much time, it took up my mind. I was constantly checking emails, thinking about work, and I knew I wasn’t giving my content everything I had. Read more>>

Jonathan Heuer

When I was 30 I left my career in architecture and moved from the SF Bay area to Los Angeles to pursue music professionally. It began with 1 year studying at the Musician’s Institute in Hollywood, where I would meet some amazing teachers and players and give me the opportunity to really focus on my guitar. (My father was already living in Los Angeles after moving there to pursue his dream of acting years before, so the move was easier than it might have been otherwise. I’m not sure I would have had the courage to start over like that if it were not for him having done something similar already). Read more>>

Stephanie Rucker

Launching a catering business without a clear roadmap was a risk and not knowing if my community would support and embrace me.

However, my eldest daughter, JeRae’, encouraged me with a simple yet powerful question: If not now, then when? That push led to the birth of Tweety’s—starting with nothing more than a name and a dream. Read more>>

Reatta Hall

Taking the leap to become the franchise owner of Slutty Vegan Birmingham was one of the most significant and life-changing risks I’ve ever taken. Here’s the story:

In early 2020, I was working a stable job in the corporate world, but something was missing. I had a growing passion for the food industry and an unshakable desire to make a difference in my community. Slutty Vegan, founded by Pinky Cole, had already made waves in Atlanta, and I was inspired by her vision and the impact she was making. The idea of bringing that same vibrant energy and delicious, bold flavors to Birmingham started to take root in my mind. Read more>>

Dana Aronson

The risk that I am about to share was really the risk that set me on the path to clinical herbalism. I just had moved to Oakland, CA from my home town, I was going to school for American Sign Language, and working in a yoga studio. Two weeks into that job (the first job I obtained and had to keep to pay the bills), fired me. I was devastated. I was never fired from a job before and it broke my little 20-something year old heart. On a day that class got out early, I was walking around and checking out Berkeley. I walked into an herb shop and the sweetest woman greeted me. I was immediately drawn to all the herbs on the walls and it sparked my curiosity. Read more>>

Jessie Joslin

I have always played it safe and followed the traditional path that I thought I was supposed to walk. I dreamt of working in Marketing so I went to college and then got my MBA in Marketing Management, I worked hard in my career to climb the corporate ladder to achieve the success of different titles and promotions. I built teams and led big projects and had the corner office with a view. I had everything but flexibility and something that was just mine. I started to wonder what else was possible. I wanted to be available when my middle school kids got home from school. I didn’t want to be on calls with people late into the night and during my kids sports games. I felt like I wanted to build something that was just mine and see what I was capable of however I didn’t know exactly what I wanted to build. Read more>>

Omar Nunez

One of the biggest risks I have taken is quitting the day job. It was around 2015 after buying our first home that I decided to take the leap and say goodbye to the day job and pursue DJing full time. I started DJing when I was in high school and throughout the years I had built a brand around my name and built a business around it. From rocking bars and clubs to DJing for high-end events and weddings, I was getting booked more and more. At this point, the day job was more of a security plan and I had already been thinking of taking the leap. The catalyst for me saying good bye to the day job was the fact that I needed a particular day off to DJ an event. Read more>>

Evelien Kong

First, thank you for having me back! I really appreciate the support Canvas Rebel has given me.

One big risk I took was deciding, in college, to seriously pursue a career in entertainment.

As the only child of immigrant parents from Hong Kong, there was a cultural expectation for me to have a stable, practical career—like being a doctor, lawyer, or working in finance. And since I was their only hope, all bets were on me, so the pressure was on! My parents, of course, also wanted the best for me, and I certainly didn’t want to be unemployed after college, so I started as an accounting major. Read more>>

Kristiina Soulmaster

Taking the Leap: How a Bold Risk Led to the Creation of Soulmaster Studio

Life is full of moments where we stand at a crossroads, faced with a decision that could change everything. For me, that moment came when I decided to leave behind the familiar and step into the unknown. Moving from Europe toward the United States to expand Soulmaster Studio and bring my vision to life on a larger scale. Read more>>

Marta Riva

The biggest risk I took in my life was completely changing the nature of my career. I transitioned from a scientific career to an artistic one.

I have a background as a marine biologist and grew up as a self-taught artist. I hold a bachelor’s degree in biology and a master’s degree in marine sciences.

After my university years, I decided to take a year off to focus on making art and to recharge after years of intense academic commitment. Read more>>

Akuyoe Graham

Writing my one-woman play and then performing it around the country. 30 years ago, I wrote Spirit Awakening; a one-woman play chronicling my life’s journey from Ghana, to London to the United States. In the piece, I penned some of the most traumatic experiences that I’d had as a child- leaving the comfort of my Ghanaian home- a tribal princess- joining my mother in London- and consequently becoming “a mere speck of pepper in a sea of salt…” It was also in London where I was sexually assaulted at the tender age of 8; where my beautiful, courageous single mother worked tirelessly to make sure I received a good education and traveled throughout Europe. Read more>>

Chizoba Okeke

Immediately after graduating from college, I found myself at a crossroads. It was the height of COVID, and like many others, I was trying to navigate an uncertain future. As I prepared to drop my graduation photos, I began crafting a caption that highlighted my accomplishments. But as I sat there, trying to list what I had achieved, I was hit with an unexpected realization—I didn’t feel accomplished. Read more>>

Kimberly Gillett

I’ve decided to take a risk in my career by merging my past and current professions to provide a service to people that I’m truly passionate about, helping people move better to feel better. It meant challenging the way we currently look at and treat musculoskeletal health and fitness and not following the restrictions dictated by health insurance. Read more>>

Stasha Washburn

I have endometriosis, one of the most painful conditions in the world. Unfortunately, when it comes to working, it didn’t work out. Every month I would be in so much pain I’d pass out, or have to run to the bathroom to throw up, neither are things bosses like. I couldn’t hold a job for more than a year because of it. So one day I realized if I want a chance of stability I’d have to work for myself – and I’d have to do it around my cycle. Because the medical system had nothing for me, I had spent 20 years looking into holistic health around the world. Read more>>

Jessica Husted

Last year, around this time, I launched a new website for my photography business. I was working with my business coach, Molly McCauley of Make Pretty Workshop, and we were doing what she refers to as an “overhaul”. It’s where she comes in and truly makes everything pretty again. While my old website was beautiful, it just didn’t feel like me and I wanted to step more outside of the creative box I’ve been in for so long. So, Molly found templates that she thought would work best with the direction I was going in and from there I chose one and then she implemented the imagery from my galleries. I worked with a copywriter, Kaitlyn Parker, from Copy Uncorked as well as an SEO specialist, Sara from Sara does SEO. Read more>>

Carli Baldwin

The Covid-19 Pandemic was a turning point; for our world, society and for many individuals confronting the rapid unravelling of how life “used to be” and “should” become. For me, it was a moment of reckoning, one that led me take the leap and ditch my desk job and to build my own business as a yoga teacher. I chose risk and authenticity over safe and “should”. Read more>>

Jason Rodriguez

For my family and me, this was a big risk. I wanted to start small by bringing just one product from Camden, New Jersey, hoping to introduce something special. Our goal was to bring joy to the South Jersey community and encourage more people to try our food. However, we took the risk without knowing whether those outside our community would be open to something new. Read more>>

Octavia Landix

Up until about a year ago, I have gotten very use to being in the background in my line of work. Much of my energy came from a place of investing and supporting others in there musical careers. I love what I do and enjoy being apart of great art. I found myself in so many situations where people were amazed at my talents and skills implying I be more in the forefront. I would occasionally but then find myself reverting back to where it felt comfortable. Like a yoyo effect, I wasn’t quite ready yet. Now have I made a decision to bet on myself. I understand now that If I am not willing to take a risk on myself, why should I expect anyone else to. No risk, no reward. Read more>>

Mark Mcclurkan

I’ve worked a lot of different jobs over the years. I have done everything from cowboy to IT to being an executive at a company with hundreds of billions in their portfolio. Out of all the skills I picked up and years of experience I learned one unavoidable truth. We’re all expendable. As soon as the political winds change, you can go from being a “critical asset” to “no longer necessary” in a matter of days. Read more>>

Cliff Chen

The biggest risk I’ve ever taken was moving to the United States as a 19-year-old without a safety net. I’m originally from Malaysia and it was my first time being in college and living on my own. It was a little scary at the time but I knew the big change was necessary for me to chase my dreams. Read more>>

Wonhee Kim

Hi, I’m Wonhee Kim! I’m originally from South Korea, but now I’m based in Brooklyn, NYC. I always start by sharing where I’m from and where I am now because the biggest risk I’ve ever taken was moving to the U.S.
I came here in 2015, I can’t believe it’s been almost ten years!, though I had to return to Korea for two years during the pandemic.I never imagined I’d stay this long. Read more>>

Christian Thew

When I started Christian’s Custom Figures, most of my business was through craft shows or consignment at shops. Once COVID hit, I had to learn how to operate my business online. I started selling on Etsy and for a while that worked pretty well. Eventually, I ran into problems with Etsy’s poorly handled copyright & trademark system. I had to start from the bottom up with Shopify and completely relearn how to run my online business without the luxury of SEO being handled by a separate party. Since I started selling on Shopify last year, things have been good and are steadily rising! Read more>>

Lea Bodea

In 2016, I packed up from a life I knew for nearly twenty years in Charlottesville, Virginia and moved to Baltimore, Maryland to make visual art full time. I was forty-five years old.

I had spent most of the early 2000s working with children with Autism or families in traumatic circumstances. While working full time in challenging vocations, I spent my time at home drawing, painting with watercolor, playing guitar and singing, playing drums in local bands. Read more>>

Emily Swan

In my experience, there is no way to navigate this life as an artist without constantly taking risks, whether in applying a single stroke of paint or leaving a job to pursue freelance full-time. For me, that big risk was the latter. At the start of 2019, I decided to leave my full-time office/design job and work freelance primarily. I had attended comic-cons as an artist since 2011, but this would be the first time I would be able to focus all my energies towards that, without juggling full-time employment! I was optimistic and full of reignited excitement at the prospect of being my own boss. Read more>>

Haley Tilton

I’ve been making jewelry since I was 14 with my mom, I am now 29. My dad supported me by helping me purchase materials and display my jewelry in commission stores around town.
When I had my daughter in 2023, it took me a few months after being back at work to realize that I needed to go part-time from working 4 days a week to 3 days a week. I wasn’t sure how my husband and I would manage without that extra income, but I knew I could make it back if I just had that extra day a week to work on my jewelry business. My main reason for this is because being a mom is really hard and working full-time job at the same time feels impossible. Read more>>

Mili June

Taking risks….I always tell myself, there’s nothing to lose and everything to win. If something doesn’t work out, at least I’ve tried and I’ll have learned something along the way.

One of the biggest risks I’ve ever taken was stepping away from a stable career as a primary school teacher to fully pursue my passion for acting. Growing up in a small village in Switzerland, I was raised with a deep appreciation for stability, which led me to study education and become a teacher. While I truly love teaching, acting has always been my greatest passion. No matter what, I kept finding ways to be on stage or in front of the camera. Eventually, I asked myself: If not now, then when? Read more>>

Tierra Hensley

When I stepped into the world of real estate, I didn’t have the safety net that so many agents start with. I wasn’t from a family of realtors, I didn’t have a built-in network handing me referrals, and I certainly didn’t have the luxury of waiting around for business to magically appear. I was stepping into an industry where success often depends on who you know, and I knew… almost no one. Read more>>

Tab Howell

Our “business” is a non-profit called Noah’s Ministry and starting a non-profit was a big risk. We rely 100% on donations from individuals, businesses or churches. I have a special needs son and it is certainly a challenge to be a special needs parent, we have overcome many obstacles with him. While I was working for Fellowship of Christian Athletes, a well-established and successful nonprofit my wife and I started feeling called to start our non-profit to help support special needs families and to help churches develop special needs programs. We could see a lack of support because we experienced it personally and other families would share the same struggles with us. Read more>>

Daniel Hilles

After three years of starting as an intern at my first marketing job and steadily advancing, I immersed myself in every aspect of video production, photography, social media, and more. However, I eventually realized that I wasn’t where I truly wanted to be—and more importantly, that clients deserved a higher standard of service from their marketing partners. Read more>>