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.

Arifah Yusuf

When I graduated with my Bachelor of Social Work from Toronto Metropolitan University (formerly Ryerson) in 2005, I was at a crossroads. I had just completed my placement and was offered a job there. The catch? The pay was just above minimum wage. I had bills to pay, ambitions to pursue, and that offer didn’t feel like the “dream job” I had worked so hard for. Read more>>

Bao Nguyen

In the summer of 2021, I went to the Yale Norfolk Summer School of Art, a residency program for senior-raising students across the globe. The program happened in a beautiful estate in upstate Connecticut. Over the span of 6 weeks, a group of students live and work and make art together. In this estate, I created my first every series of one-on-one performances. I created a guided walking tour and performed the piece 30 times for each of the participants and faculty members in the residency. Over three days, I exhausted my body by performing almost for 10 hours everyday. The performances were an intense experience of focus and passion for me. I learn about my own drive and ambition through the process. Read more>>

Dylan Woodhouse

I was supposed to be a heavy diesel mechanic. That was the plan. Or at least, it was the plan others had for me. My parents wanted something “within my skill set” for me. In Zimbabwe, where I grew up, that made sense. You get a job, you work with your hands, you keep your head down. Practical. Predictable. Read more>>

Jayzel Alconis

One of the biggest risks I’ve taken was stepping out of my comfort zone to pursue a life and career abroad. I had been working as a nurse for 4 years in a prestigious hospital in the Philippines. I was comfortable and stable—but deep inside, I felt a longing for change, for growth, for something more. Read more>>

Javier Aponte

I took the risk of quitting an existing “secure” job I had to just pursue what I wanted to do since I was a little boy… Being a profesional musician. I had a good job as an art director in a big firm but the pressure was ridiculously inmense, so I said to myself: “You know what? If you are willing to take this amount of pressure and deal with it, do it for you!!” So I did! I devoted myself in that moment to be a full time musician instead of a part time “gig”.  Read more>>

Janessa Ruiz

The world often tells us that coloring inside the lines is the best way to make a pretty picture, but my most inspiring mentors and teachers taught me that exploring outside of them is what makes art. It’s a lesson that would guide me from career to career, showing me how to combine my experiences into a force for good. I was never afraid to be incompatible with the world around me, but I never knew that staying true to that different constitution would force me to forge a completely unconventional path of my own. Read more>>

Capri Richardson

When people ask, “What’s your why?” or “What brings your life meaning?” I used to think it was volleyball — playing it, coaching it, living it. I thought my purpose was to become a big-time collegiate coach. But I’ve come to realize: that was only part of the journey.

As a former collegiate and professional volleyball player, choosing a career in collegiate coaching felt like the natural next step. But there was always another side of me that was deeply curious — the side that loved psychology and the inner workings of the mind. To me, every person was a puzzle. Even if you got close to understanding one, you had to start fresh with the next. Read more>>

Crystal Young

For many years, I was in retail management, I later transitioned to Human Resources management with a concentration in talent acquisition and classification and compensation.

In October 2022, I lost my husband to suicide. It was probably single handedly the most devastating thing that I’ve ever experienced. Not just for me but our children. I took a few months off and fully expected to go back to work in those management roles. I went back. I tried. But my heart was not there anymore. The life event really put into perspective how important and fragile life is. Read more>>

Chad Hardy

I moved to Murfreesboro, TN to be with my now wife and bought into Guardian MMA a household gym that had been around nearly 20 years. The buisness was going under and I helped step in and save it turning it into one of the biggest mma gyms in Tennessee. Read more>>

Hillary Jones McCullough

After I graduated with my MFA I stayed in the same city for about a year. During that time I worked multiple odd jobs (part time restaurant work, house/petsitting, etc). A friend helped me get a full time corporate job (it wasn’t art-related, but it paid okay and came with benefits- something I’d ever had before). Read more>>

Lil Derik

Recently, I took the risk of taking on a new role that would take time away from me focusing on music 24/7. That risk was becoming a substitute teacher and basketball coach. Two things I wasn’t sure on but turned out to be perfect for me. I thought I wouldn’t have as much time to dedicate to my music but I was wrong. Coaching and teaching hasn’t stopped me from being an artist, it’s actually assisted me financially & I’ve been booked for more shows this year than my whole career. Working with the youth has given me a new sense of fulfillment as well. As an artist, I try to do things that fulfill me & keeps me motivated & in a positive mood. So this is one risk that has worked out for me perfectly. Read more>>

Tiffany Jeffers

A few years ago, I took a risk that didn’t make much sense on paper. I left a steady job with great benefits and a reliable paycheck to follow a vision I couldn’t shake. It wasn’t polished. It wasn’t perfect. But it was persistent. I didn’t have a big grant or a fancy launch plan. What I had was a deep sense that our community needed something more. And I believed, even with trembling hands, that I was being called to help build it. Read more>>

David Mammano

In my late teens and early twenties, I dove headfirst into the world of stand-up comedy. I even moved to Chicago, the comedy mecca of the Midwest, to give it a real shot. I hit the open mics, hustled the clubs, and soaked in every lesson I could from the legends and lunatics alike. It was a thrilling ride, but after about a year, I came to a realization: while I loved making people laugh, I didn’t want to turn comedy into a full-time career. Read more>>

Maya Shaw

The biggest risk I’ve ever taken was giving up everything I knew — my family, my friends, my hometown, the love of my life and moving to New York City, a place where I didn’t know a single soul, just to follow the music burning inside me.

I knew it was a risk. Of course I knew. But the fire in me was stronger than the fear. I felt like nothing could stop me anymore. Read more>>

Ziyan Bai

Leaving my nursing career to pursue art felt like jumping into the unknown without a parachute. I had spent years training to become a nurse in Beijing, My life was “secure.” But deep down, I felt like I was watching my life unfold from outside my own body. I was caring for others, but forgetting how to care for myself.

The decision to walk away from nursing wasn’t immediate or clean. It meant disappointing expectations, letting go of stability, and starting over in a completely different country, culture, and language. But it also meant reclaiming my agency, my voice, and my time. Read more>>

Sophia Perlee

I went to the University of Georgia and received a degree in marketing. It was Athens, GA, that exposed me to the exciting opportunities of being a marketer for musicians, venues, and artists. I got a taste of every aspect of marketing for the arts – social media management, website design, promotional events, and traditional advertising methods. I came out of school with a well-rounded idea of how to do the most good with digital tools available to those with a limited budget and a wide bandwidth for creative expression. Read more>>

Asia “Ashton” Morgan

Every day I wake up, I’m taking a risk with this DJ life. DJs don’t just play music, we put ourselves on display, vulnerable to every eye and ear, whether we’re on some of the world’s largest stages or the smallest, most intimate ones. This life can take a lot out of you, the late nights, sometimes the early mornings, and the constant pressure to please everyone, even when you know you can’t. It takes guts to be seen, to be judged, and still give it everything, all while making sure you’re not just doing the same thing over and over again. But we do it, because we love it. I do it because I love the music. I love the people. I love the lights. Read more>>

Ciara Bogdanovic

One of the biggest risks I’ve taken was hiring employees for my practice. As a therapist, I had some challenging experiences during my training years, and I always knew I wanted to create a different kind of environment for associate clinicians, one that was supportive, collaborative, and grounded in both compassion and structure. Read more>>

Danielle Harper

Well, when I got married I decided to completely leave the business to have kids. I took 5years off completely stepped out of the entertainment industry lost all contacts everything. About a year and half ago I took a. Huge risk coming back into the industry without any help or real knowledge of what had happened for 5 years. It was a huge risk. But it has been a wild ride since. I may still hold a full time job to keep financial stability for my family but the work is coming and my career is building again. It has been something. Read more>>

Kelly McDowell

I’ve been building events since I was a teenager. The first one I ever ran was a Battle of the Bands at a local fair — and somehow, from that moment on, organizing creative things just kept showing up in my life.

I studied business communications and public relations in school, but I cut my teeth in the event world working with major organizations like Molson Indy and Snow Jam, flying across Canada and the U.S., and later helping the (then tiny) Whistler Arts Council grow a small in-school event into a major arts and tourism draw. Read more>>

Renez

The biggest risk I’ve taken was leaving my cozy, high-paying corporate tech job and my 12-year relationship within the same month. I was a nerdy tech program management professional for 20 years and established a very nice nest egg while working for some of the top Tech companies in Silicon Valley (LinkedIn, Google, PayPal, Meta, Virgin America, Ebay). I had a spiritual awakening around 2014 and that forever changed my life as well. I was working at LinkedIn at the time and I just hit a wall. None of the work I was doing made sense to me anymore. I tried looking or a different position within LinkedIn and asked my boss for help, but that ultimately led me to getting pushed out because my boss did not like the fact that I didn’t want to work in his team anymore. Read more>>

Olivia Rachel Austin

The most significant risk I’ve taken as an artist has been committing to a voice that doesn’t fully belong anywhere.

My work deals with hierarchy, agency, gender, poverty, and belief systems—often through the lens of growing up in the rural South. For years, I tried to make work that looked “neutral,” trying to process the complexity of my environment without putting myself at the center. But once I allowed my personal experience to guide the work—my femininity, my Southernness, my disillusionment with systems that shaped me—that’s when everything changed. Read more>>

Wayne Adams

A few years ago, I had the opportunity to propose an art exhibition at my alma mater, Calvin College (now Calvin University). I had wanted to scale up my projects, doing more ambitious works and exhibitions and had never had a solo exhibition at Calvin since graduating. I ended up sending about ten options for the director to choose from and he selected an installation of aluminum foil to cover their long, fifty-six foot wall. I had never made a piece that large and was working in a makeshift studio in a tiny room in our house, which I still work from. It was a daunting project, but if I could pull it off, I thought it would be amazing. Read more>>

Jiya Sultania

I think as people, we take risks every day. Every day, I find myself questioning something or the other, taking some kind of risk, sometimes small, sometimes big. But somehow, over time, I’ve learned to just try my best, keep good intentions, and leave the rest up to fate. That’s probably the biggest lesson I’ve taken away from the past four years of my life. And four years ago is when I took the biggest risk of all — moving to New York City for college, just to study something I’m passionate about. Everyone back home warned me it wouldn’t lead to a stable career. I was moving to a country I’d never been to before, where I didn’t know a single person, and I couldn’t see my family and friends whenever I wanted. But it was a risk I was willing to take and I’ve never regretted it. Read more>>

Tara Johnson

I took a risk by trying to break into a market not typically owned by women over 50. I set out to make a place for myself in the beauty and wellness niche on social media. I went from zero sales to being a high seller for many cosmetic products a place, not typically held by women, my age. Read more>>

Craig Kitto

Absolutely – starting Kitme was one of the biggest risks I’ve ever taken. I left a stable path to pursue a vision that didn’t have a guaranteed outcome. I believed in the idea of transforming how people engage with their owned items and/or past purchase history, but building something from scratch, especially a consumer app, meant an incredible amount of uncertainty. I’ve had to invest all of my time, money, and energy without knowing for certain what the result will be. However, I do know that making the necessary sacrifices and persevering through everything gets you closer to the end goal, day by day. Taking the leap in working full time on a startup taught me to trust my instincts. Resilience is everything, and conviction is of the uppermost importance. Read more>>

Sarah Harrison

In 2016, I started an office job at a warehouse. It was stable, it was safe, and it paid the bills. All the while, photography had always been my side hustle since 2014 — something I loved deeply, but considered “part-time.” I never quite imagined it could become my full-time career… until the world changed. Read more>>

Ana Roman

Back in 2006, I made the bold decision to leave my full-time job and pursue entrepreneurship with my boyfriend at the time. We set out to open a tattoo and punk rock apparel shop, driven by passion but limited by experience. Unfortunately, due to licensing and zoning issues, we couldn’t sustain the business for more than a year. I found myself back home, unemployed and unsure of what was next. Read more>>

Kara Batey Bertin

In late 2020 I took a new job as in-house counsel at a local real estate company. Prior to that, I worked at the same law firm for 13 years. I was a partner, board certified in my legal specialty and had developed client relationships. Because of my tenure at the law firm, I gave considerable thought to making a career change. I ultimately accepted the new job because it aligned with my long-term career goals at the time. Read more>>

Megan Murdock

I had graduated high school in 2008, and the economy was in recession. The advice to young graduates at the time was to study something stable. Don’t waste your time and money on a degree that would be useless. I felt so discouraged, I was always a creative person but knew a job in the arts was not an option. I had a hard time finding my footing over the next few years. I took time off from school to work as an Administrative Assistant in manufacturing. I finally had a little money and I was able to travel to places like Paris, and be inspired by the world around me. Read more>>

Burton Durand

One of the biggest risks a creative can take on is taking the leap from a stable agency job to being full-time freelance.

I worked in Advertising for about 15 years before I fully changed direction. Moving up the ad agency ladder from Junior Designer to Senior Art Director, and then Creative Director at a merch design shop, I found myself taking on more and more freelance projects to fill a creative need. It got to the point where I was essentially working two jobs, 7 days-and-nights a week. Read more>>

Megan Ihnen

Perhaps we’re all familiar with the Anäis Nin quote, “Life shrinks or expands in proportion to one’s courage.” Or, the misattributed Nin quote (which, more accurately, seems to be from Elizabeth Appell), “…and then the day came when the risk to remain tight, in a bud, became more painful than the risk it took to blossom…” Both of these sentiments ring out in my mind when I think about the summer of 2018. Read more>>

Chele Sellman

“The biggest risk I ever took wasn’t leaving a job or launching a business. It was finally deciding to believe in myself without needing anyone else’s permission.”

All my life, I lived for someone else’s dream. You could say I didn’t know how to dream for myself. At the age of 38, I had no dreams. After a failed partnership and launch of a children’s animation series, I found myself sitting at my desk in my living room, staring at my monitor and Facebook. I came across an indie “fashion” magazine that appeared to be thriving made by someone I had known through Facebook. Read more>>

Tue Hoe

Taking risks has been central to my journey as an actor. One of the biggest was moving from Denmark to New York to attend the renowned William Esper Studio. It’s a prestigious acting school known for its focus on the Meisner technique. I took this leap knowing I wouldn’t have the financial safety net I was used to. With a student visa, I couldn’t work, and New York isn’t cheap. The uncertainty was terrifying—but the pull of the city, and my passion for acting, was impossible to ignore. Read more>>

Arthur Bolden III

In 2021, I took one of the biggest risks of my life. I made the decision to sell my home in Texas and move to Los Angeles to pursue an artist lifestyle full-time. It wasn’t a move I made lightly—on paper, I had stability: a well-paying 9–5 job with benefits and the comfort of working from home. But deep down, I knew I was stuck. I had grown comfortable, but not fulfilled. I needed more. Read more>>

Michelle Burke

That moment in 2012 was the first time I truly bet on myself. It wasn’t the last.

I had the life I was supposed to want, a great job, a beautiful condo, financial stability. But inside, I was falling apart. I didn’t want to get out of bed. I cried more mornings than not. My personal trainer could take one look at me and know I was barely holding it together. By November, I was already done with a school year which had only just begun. By March, I was blasting Kundalini mantras on my way to work, just trying to get through the day, and crying on my way home. By April, I had made up my mind, I was leaving. I was moving to the beach. And I didn’t care who knew. Read more>>

Beverly Todd

This is such a great question, and it really hits home for me! If there’s one thing I’ve learned in life and art, it’s that taking a risk can be the most rewarding leap you ever make. Let me tell you a story about a big one I took. Read more>>

Debra Hoyt

We were living in Austin, MN and driving two hours one way to attend church in the Minneapolis area. The Lord had been teaching us to go deeper in His Word and live by faith in every area of our lives. Midway through my sixth year teaching in the local high school I felt the Lord tell me it was time to step into the next part of our journey. After my husband and I prayed we felt the release and I put in my resignation for the school even though I didn’t have a new position yet. Read more>>

Nikki Rice

The biggest risk I’ve ever taken was deciding to leave my career with no plan. Though I would absolutely not suggest this, three years ago I was at a point in my life where I was not living authentic to my values and my health both mentally and physically was suffering for it. Though there were many skeptics who challenged my decision, making the shift to become a yoga teacher and start my business, Cedar & Sage was the best decision I have ever made. Read more>>

Lauren Broomall

Growing up, I don’t remember being super interested in traveling or living anywhere different. In a weird kinda way I didn’t really know how one would actually go about moving, so I never really even thought about it. I was always kind of a “follow the path I was told to follow” kind of person. Read more>>

Rashmi Rao

In 2023, amidst a world reeling from polycrises—ranging from geopolitical conflict and the destabilizing onset of AI, to inflation and sweeping layoffs—I took one of the biggest risks of my professional life: I launched HLWF® Alliance, a nonprofit committed to transforming women’s roles across the entire spectrum of healthcare, healthtech, life sciences, wellness, and fitness. Read more>>