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.

Agustina Rodriguez

The biggest risk I’ve taken is allowing myself to pursue public art full-time. I studied studio art as an undergrad and worked in mixed media. In my early 20’s I got into glass-blowing, leading me to 3 years living in Italy. During that time I became interested in better understanding the built environment and looked for ways to blend my visual art skills with site specific installations. In Italy I had the opportunity to participate in my first group art exhibition with a large-scale installation – I was hooked, later realizing that the pull was in creative placemaking. This new found interest led me to a 4 year Master of Architecture where I peripherally maintained my interest in installation art, often attempting to merge the disciplines of site specific art and architecture. Read more>>

Amy Heasman

Introduction: In 2011, I made a life-altering decision to leave my hometown of London and fly to Australia with the intention of starting a new life. This wasn’t just a trip; it was a conscious choice to find a new place to call home and set roots. I left behind my entire family, an incredible tribe of friends, my career in marketing, and my passion for music. It was a terrifying decision, but one I knew I had to make. After two years in Australia, I moved to Canada, where I traveled through Alberta and British Columbia for three years before settling in the Kootenays in 2016. I pursued my yoga teacher training that same year and began building a yoga-based business. I once dreamed of creating a yoga festival but had little belief it could ever become a reality. Read more>>

Andrea Kucharczyk

Life is undeniably a tapestry woven from the threads of risk and reward, yet only a few truly grasp the importance of seizing the opportunities that arise. In a world that often promotes safe choices and adhering to the lines drawn by societal expectations, it takes extraordinary courage to step outside of the familiar. Those fearless individuals who dare to play by their own rules often leave indelible marks on history. They remind us that greatness comes not from playing it safe but from the audacity to dream and act with conviction. Read more>>

Ashley Rose Ramirez

As an entrepreneur and creative, you are prone to walk astray from the typical path. This all takes courage, an inclination towards risk, with a dash of healthy delusion. Coming out from the pandemic I felt stripped of time. It was a complete halt of momentum that left me feeling stifled with an innate yearning for growth. As restrictions of lock down were lifted, I felt an unavoidable pull to take a risk that would lead me so far away from my comfort zone; this is after all, the only way to grow. Read more>>

Augie Ray

Im taking a risk right now! Currently, I own a creative space ( subscription based) in the San Fernando Valley and I took a leap of faith, after 8 years of running what was once a recording space I decided to follow my passion’s in transitioning Hypes Studios LA in to an all in one for creatives. A place where artist, videographer, producers could have a space to develop themselves as I did when I was coming up in the music industry. We re starting new and fresh . Read more>>

Cathy Laffan

I received a call that no one ever wants to receive, my Dad had been in an accident and broken his leg in three places requiring emergency surgery. At the time, my Dad was about 80 years old and living alone in Texas. I was living in Massachusetts, my two sisters were in Massachusetts, and my brother was living in Florida. We worked together and decided that two of us would fly to Texas for Dad’s surgery and in-patient rehab. We took turns flying in and out of Texas to support my Dad. When I was with Dad, I asked him what he would do if he couldn’t care for himself. It became clear that he didn’t have a plan, wasn’t going to create one, and certainly wasn’t willing to relocate to Massachusetts or Florida. Read more>>

Cynthia Gonzalez

At age 50 I decided to retire early after 15 years of service in the Federal Government. I still have to wait til age 62 to collect my pension. But that’s OK, After embarking in entrepreneurship by founding in October 2021 the 1st Puerto Rico Cigar Festival after 147 yrs of the last one held in 1883, certifying myself not only BarSmarts by Pernod Ricard, but also as a Cigar Sommelier Tobacconist CCST with SGM (Sotl Global Movement). I decided to start a second career in the aviation industry and graduated as a Flight Attendant in June 9th 2023 with one of the top legacy airlines in the United States. Read more>>

Dale Edward Chung

I think the biggest risk I’ve taken was quitting my 9-5 job to pursue a career in music with no real plan. Thanks to the encouragement of my mom, I took a leap of faith. That was over 20 years ago and here’s how I get to that point.Back in the late 90s, I was with a group that was two degrees from Digital Underground. I thought that group was my last chance to finally “make it” in music. Unfortunately, we imploded and I left to the group to figure out how I wanted my future to look. Fast forward to the early 2000s, I was working at a corporate job, producing music in my apartment and doing nothing with it. I think I had released a CD of my own of songs that were just sitting on my computer doing nothing.  Read more>>

Danny Jordan

For many people, my whole career could be considered one big risk that I’ve taken. Choosing to pursue any creative field is difficult at the best of times, and doing so has been the biggest and most rewarding risk I’ve ever taken. Growing up, I was really interested in math and science and, until I started playing viola, I had always imagined working as a scientist in some kind of lab. But, when I started learning my instrument, I was taken by classical music in a way that I had never experienced before. Read more>>

Dearice Spencer- Shackleford

Allow me to share with you a story—not just of survival, but of thriving against all odds. It’s a story that began not in celebration, but in the shadow of unimaginable loss. Within a single month, I faced the earth-shattering pain of losing both my husband and my father. The impact of this double tragedy was nothing short of devastating, plunging me into a deep, spiraling depression. I found myself teetering on the edge of despair, questioning my will to continue, struggling to find the strength to raise my children as a single mother. Read more>>

Dr Rhiannon Dubois

In April 2017, I resigned from my private practice job as a Clinical Psychologist. It had been my first job after college, and in the nine years there, I had seen thousands of clients, supervised student interns and psychologists, and served as Acting Clinical Director. The clinic was located one block from the beach, in one of Australia’s most loved tourist destinations. It was a great gig, but a comfortable one. I needed change. Five years earlier, my ex-husband had unexpectedly walked out on our marriage with no explanation. It’s not something that any 29-year-old woman anticipates after just 2.5 years of marriage. Read more>>

Ebonee B

I started out as self taught with my skills prior to adding more knowledge from different sources. I took a risk when starting my business which included crochet, and custom gifts. I wasn’t sure how things would go and if I’d really make money from it. I still bet on myself and went for it, along the way there were challenges and even times when money may not have been what I wanted but as with anything the rewards aren’t always right away. You have to put in time, effort, and even sweat and tears. I started doing yoga 10 years ago self taught at home, I hadn’t even thought of taking up teacher training until I had been asked my a few friends who were interested in me teaching them. Read more>>

Edward Gelhaus

Artistry is a double edge sword. When one considers pursuing a career in acting, that decision itself is a risk. It can bring the happiest moments of life, while also bringing moments in which one doubts every decision they’ve made along the way. One can follow their passion, work hard and strive for excellence and yet still there is never a guarantee of success. The majority of the days aren’t the glitz and glam of Hollywood as seen in magazines or on social media – but rather an endless grind and hustle. Most times the public doesn’t see the artist’s true journey, rather they see the façade that everyone paints. Read more>>

Flora Sinha

Three years after being diagnosed with secondary infertility, working on the medical front lines during the Covid-19 pandemic, and reaching the point of burnout multiple times, I decided to take a step back from medicine and start my own 1:1 mindset coaching practice. For most people, this does not seem out of the normal. For those in the medicine field, especially physicians, this is a big deal. I had spent my entire 20s and a bit of my 30s devoted towards working towards becoming a doctor. My identity was tied to being the best physician I could be, relating to patients, and bringing a sense of comfort to them. Read more>>

Franky Fade

A huge risk that I took that was most important for my future and development, was quitting my full-time job in my early 20’s so that I could have more time to pursue a “career” as a songwriter/record producer. This was a big risk in multiple ways. I was risking being kicked out of my parents house because I was doing something unfavorable and seemingly unproductive to most people. I was trying to create a living in a space that is unpredictable, and probably 90% of people who try at it make very little to money at all, even over the course of many years. Despite all of this risk, my choice would eventually shape me into a well experienced, and competent entrepreneur with many skills who’s good at thinking on his feet to create and attract opportunities that keep lights on, and to retain a strong network of competent individuals in the same field, and beyond. Read more>>

Gabriel Shaffer

One of the most significant risks ive ever taken, happened on Halloween night nine years ago when I decided to move to New Orleans. I had a solo exhibition with the notorious Red Truck Gallery, which was to put it kindly in disarray. The owner convinced me to come work for Red Truck, which although at that moment posed a big challenge it also seemed like an opportunity and I adore New Orleans. I had been living and working as a full time artist in Asheville,NC for the better part of a decade at that time and felt stagnant. Red Truck had been around for about 5-6 years at that point and was connected to a number of artists and venues I admired in the Low brow and Pop Surrealist genres. I saw a chance for growth. Read more>>

Heather Carpenter

I think starting your own business is a massive risk in itself. You’re giving up a steady income with benefits and hoping you can build enough clientele to make a living off of. Until I started this business, I never had a job outside of babysitting gigs here and there in college because I focused heavily on school. I remember thinking I had NO clue what I was doing and asking everyone I knew who ran a business in the music industry where to begin. I prayed a lot about it and felt like this was what God was calling me to do, and I haven’t looked back since. Looking back now that I’m five years in, I’m so glad I did it. Read more>>

Jackson Williams

The biggest risk I have taken in my career was my move down to Los Angeles in August 2023. Up until that point in my creative career I had played it generally safe. My job out of college was at a production company that focused in Real Estate marketing solutions in the San Francisco Bay Area. Towards the beginning of my 3rd year with the company I really started to realize that I was stuck in this comfort zone of having this stable job and living at home. The company had grown a lot and I became super disappointed that the years had been going by and I hadn’t really been going anywhere. I felt like I was spending my time building somebody else’s dream. This discomfort ultimately started to show in my work and in my attitude and eventually, I was fired. Read more>>

Jen Dayton

Taking a significant risk often involves stepping out of a familiar and secure environment into the unknown. For me, this journey began when I decided to leave my 20-year full-time position as an emergency medicine physician assistant to pursue my dream of becoming a full-time artist. From a young age, I aspired to be an artist, but my confidence was shattered during my first year of art school when I was advised to pursue a different path. This advice led me to abandon art for a decade. It wasn’t until after graduating from PA school that I started creating again, thanks to a thoughtful gift from my husband: an easel, a canvas, paint, and brushes. Initially, I painted only for myself, never taking it seriously, hindered by insecurity and the belief that I wasn’t good enough. Read more>>

Jenny Lyric

Two weeks after graduating from college with a degree in psychology, I took a leap of faith and moved to Los Angeles with only $400 in my pocket and a dream in my heart. But how did I end up making such a bold move? It all started with a group I founded called Coco Avenue. In 2016, we gained recognition as the first Black Kpop group after our Kpop cover videos went viral. The group was made up of young women from across the country, most of whom I met through YouTube. Initially, there were six of us, and we did our best to create content by compiling videos and audio from our various locations. However, we soon realized that to truly succeed, we needed to be in the same place. Read more>>

Jessica Vandenbush

Any art is a risk. Our lives are art. Love is art. The work we do or how we approach that work is art. The way we solve the problems of our lives, that’s art. If this art of ours, whatever it is, doesn’t feel dangerous then we are doing ourselves and the world a disservice. We were all put here to make beautiful art of our lives. The greatest risk I’ve taken is daring to be authentically me, even after I’ve failed, even after I’ve been criticized, even after I have a pile of reasons to convince me that I am a fool. I’ve started a running podcast when there was no other women in the space and I didn’t know what the hell I was doing. I barely had just started running and had never recorded anything before. Absolutely no background in journalism or broadcasting. I had ran a few 5ks as a thirty something year old. I was a mom in Ohio that had something burning inside of me wanting to get out. Something I couldn’t ignore.  Read more>>