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.

Jarrett Arnold

To me, making art, is taking a risk, every time I approach my work, it is a new experiment. I begin each day making art which is a ritual I have continued now for about thirty years. The most important risk an artist takes however is the risk to make bad art. When I make art, I try to take as many risks as I possibly can. It wasn’t always like this though. When I first started taking myself seriously as an artist, I felt that my work should be understood as I intended it, I used symbolism and I was often trying to express my own emotional state to the viewer. I focused on the skills needed to draw and paint realistically from observation and I venerated work that was realistic. Read more>>

Jessa Gilbert

Before I began working as a professional Artist or a Backcountry Guide I held down a full time job in Canada at MEC (think REI, but Canada). It was a good job – good benefits, predictable hours, great staff – but it was unfulfilling. One winter I found myself as a guest at Baldface Lodge, a Cat Ski lodge in Nelson, British Columbia pitching an Artist Residency to the owner, Jeff Pensiero. He told me no… but then said “why don’t you come guide for me instead?”. I had never thought of a career as a backcountry guide, didn’t know what the certification process would be, and had no idea what I would be saying yes to… but it seemed like too special and rare an opportunity to pass up. Read more>>

Joshua Foster

The biggest risk I took in my business was starting it. Although I genuinely enjoyed what I did and where I worked at the time, I felt that in my current position, there was a ceiling to the impact that I knew I could make in the building of up of communities. So I made the decision to leave my job and start my business, JAF. Over the course 90 days, I launched my LLC with the state, opened a business bank account, hired an accountant, designed my logo and website, created a client pitch deck, and took the leap. For me, ripping the band-aid off and diving in head first allowed me to hit the ground running with an intentional urgency to make this work. Read more>>

Mars Rodriguez

“Take the chance to make a choice to make a change”- I like to remember that on a daily basis, how to be more courageous, curious about things. I think naturally, as an artist I gravitate towards things that are new, fresh, freaky… and in order to find those things, you need to keep changing and trying this and that. I know is good sign to feel a lil scared to do something big because that’s the only way to evolve . Read more>>

Victoria Marie Malone

Speaking up for and advocating for those who struggle. Mental Well-being has been viewed in our society as a “disease”. We know that when there is an uneasiness in our system it rears itself physically, emotionally or mentally. Growing up, living and raising my sons in a small town was wonderful, but also put many limits on how you share your truth. Many communities foster the sense of community participation and support, but with limits that it all looks and feels good and happy. It was not until Covid and the magnifying glass that was put upon the collective health and wellness of our society did the conversation become real. Read more>>

Taylor Bosworth

I think first, moving to LA from the east coast with no real direction of work or how I would support myself was one of my biggest risks in life and during covid I might add. Then being presented with an opportunity to open a gallery with no prior experience was the other biggest risk I ever took. Being able to find the strength and confidence to believe in myself, all while at times feeling like I have no idea what the f*ck I am doing. To dare to fail and so publicly, because I would rather risk it all than not try at all. These two experiences have proven to me that I am much stronger than I think I am. Read more>>

Liv James

Oh, man…risk taking can be so scary, but when you’re being called to step out, you have to follow that prompting. For me, that came in 2019 after a major surgery that had me totally bedridden for over 3 months with another 9 months of recovery to follow. I took those few months to truly seek the Lord on what to do next with my life. I had been working as a Social Media Marketing Manager (plus the other 5+ hats you wear when you work in Social) since 2014 and I felt like there was more, but I didn’t know what that was. That period of time where I was totally out of commission was used to grow me in ways I never could have imagined and that’s when I felt God calling me to start the podcast. Read more>>

Fannie Brett

I just wrote a long story and your software didn’t keep it. I will relate in details how difficult it was to switch from being in a big Stsudio to having my small remote dubbing Cie. Read more>>

Esabalu

As a relatively new, full-time freelancer, I have taken my fair share of risks. Living in a world where we expect instant gratification and have very short attention spans, it’s hard to know whether you’re taking the right chances because seeing results takes time. One of my first big risks was moving from New York (a city where I had lived and built up my career for ten years) to LA in October of 2020—during the height of a global pandemic. Because of the almost overnight progress made on remote collaboration, the re-location worked out well and allowed me to explore a new city but I had no idea how it would pan out, aside from making sure I had a roof over my head. Read more>>

Kyree Fleming

Going to college for music production and audio engineering was a big risk for me because I would have a huge workload. I enrolled at a time where I was figuring out who I was and I was unsure of my future. A lot of people doubted me and suggested I get a job or take up something more stable. I’m glad I didn’t listen and I appreciate those tough experiences because they made me into something stronger. Read more>>

Kassandra Timothe

During the global pandemic, while everything was moving slow, and there wasnt much to do, I had one of the busiest year ever. The pandemic led me take one of the biggest risk ever… I left my job, in the midst of pandemic, when many were losing their jobs… to invest in myself. by running for office… The money I saved to buy a house, I ended using it all, over 20k to invest in my campaign for North Miami City Council. And on June 1, 2021, I fufilled my dream, of running for office by being elected as the first black, the first of Haitian descent and the youngest person elected to serve in North Miami’s District 2. Read more>>

Tiffany Jeans

When I made the decision to leave my 15-year marriage, it was a risk I only realized the magnitude of with hindsight. I married at the age of sixteen and up to this point my qualifications extended only to a GED, and my income was limited to part-time work as a massage therapist. My family couldn’t fathom why I would take such a risk, given my limited financial footing and the responsibilities I had as a mother of three. Read more>>

Meg Flint

The last year or so of my life has been full of opportunities for me (and my family) to take risks. But the biggest for me personally is naturally related to my blog. In September of 2022 I moved to Charlotte, North Carolina along with my husband and two kids. We moved from the Eastern Shore of Maryland. Maryland had been my home for 35 years, and my husband had never lived anywhere else either. Read more>>

Nicole & Marcus Johnson

When Marcus & I decided that real estate was going to be our path to financial freedom, we promised each other we would be willing to do what it took to make our goals happen. One of our first risks was leaving Cincinnati, OH and moving to Colorado in late 2011. Shortly after that we bought our first flip, even though we had virtually no experience in real estate or house flipping. We did nearly everything wrong! But we learned a lot and kept going. We had so many roadblocks those first several years that almost left us financially ruined. Read more>>

Mario Fernandez

There was a moment in my life when I stood at a crossroads, faced with a decision that would define my future. Initially, I had set my sights on technology and business. From the get-go, that was the plan. College, a degree, and a steady blue-collar life were all laid out in front of me. But deep inside, there was this burning desire, a voice whispering that I was meant for something more impactful. Read more>>

Carol Muleta

After an unexpected, and animated, conversation with God, I declared, “I’m taking a nap!”. My plan that day was to get my twin sons off to school and begin work on an upcoming parent workshop.  I could not do that because I was too restless.  Almost 13 years prior to that day, God had given me a vision that I would teach parents, near and far, essential skills for raising children who are confident, courageous, and capable of living up to their full potential. I suppose he thought I would be up to the task as I had been navigating a challenging terrain with one of my sons who had been diagnosed with developmental delays. I had my doubts. God met my skepticism with assurance that not only would people want to hear me speak; they would pay to hear me speak. Read more>>

Stuart Pearson

Being a musician, risk is one of your instruments. It’s like oxygen (and oxygen burns. Science!) When I was 20, I was writing songs with the now legendary Ken Cro-ken (a environmental painter who sadly passed a few years ago.) He was staying with his grandmother in her trailer in Fremont, CA and I was at home with my parents in Long Island. We wrote using actual mail (that sounds so old) and phone calls. I adored Ken as a brother and still do. Ken was one of those guys who always talked. He. Could. Not. Stop. Talking. One day he called me and said “you have to come out to California IMMEDIATELY!” He met a girl who was engaged to Donny Osmond, who at the time was hot hot hot in America (I guess I AM old). Read more>>

Curnesia Bogans

The journey towards becoming a licensed psychotherapist began while working a demanding corporate job. While working this corporate job, I noticed how the environment began to affect my mental and physical health. I could not continue to encourage my clients to live meaningful, healthy lives while I continued to operate within a toxic environment. It was time for me to practice what I preached. Read more>>

Pete Segar

I loved my career in engineering and product development, and over the years, rose to being the CEO of a global company that made computer ergonomic devices- something to be proud of. And as CEO, of course compensation was very good. The job had recently become very stressful, and I had planned to retire in three years, but after a surprise return of cancer, I decided that I was going to take that as a sign, and quit immediately to pursue my passion- making metal sculptures. Read more>>