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.

Ashley Canevari

Prior to starting my business as a wedding planner, I worked a steady corporate job for a large financial technology company. I moved up quite a bit within the company, and was comfortable with how things were going. I always had a check coming in, had a significant amount of vacation/sick/holiday time off and wasn’t interested in changing anything about my situation. Read more>>

Jalen Fauntleroy

Two of the biggest risks I’ve taken were having graduated from college and moving to California during the middle of the pandemic in 2020. In both cases I’d say the biggest risk was allowing myself to go through the fire of the unknown, and getting to the other side of any fears I had. Read more>>

Maddison Fortuna

I have spent my entire life dreaming of being a nurse. From watching, trauma life in the er, as a child, to not even batting an eye while getting shots, I knew the medical field was for me. Although I accomplished all my nursing goals, once I finally started working as a nurse my glamorized perception of this role was quickly crushed. Read more>>

January Riggin

I never thought in a million years. I would be the founder of a nonprofit. I am a survivor of trafficking and exploitation, domestic violence, addiction, and the criminal justice system as well as a lifetime of trauma. I am the founder of Soap2Hope nonprofit organization. Read more>>

Adrian Troublefield

Standing there still as a tree in complete shock, my shoes were wet like that of a sponge, the strong smell of chicken loomed in my clothing. As I watched hundreds of dishes piled up in the sink, outside the window was my co- worker taking long cigarette breaks, as usual, slow as a sloth. Read more>>

Sara Webb

In 2019, I got sober, got a divorce, and came out of the closet — not necessarily in that order. That sentence rolls off the proverbial tongue easily, but it was one of the most challenging times of my whole life in so many ways. Read more>>

Audra Morgan

One of the first greatest risks I took early on in life was moving from Colorado to California to pursue an acting career at 18 years old. I knew from the time I was a freshman in high school that I wanted to be an actress. Read more>>

Rossana Jeran

Risk involves pushing boundaries and trying new things that can lead to novel ideas and groundbreaking solutions. Whether it’s technology, business, science, medicine or the arts, all innovation and breakthrough comes from taking risks. Without it, potentiality and progress would stagnate. Read more>>

Erin Armstrong

Pursuing a creative job is already a big risk. Pursuing one that has stigma attached to it, male dominated, and very competitive is another. Reaching out to the ad on Craigslist for a tattoo apprenticeship was the best risk I have ever taken. The second was when I was able to quit my two jobs and support myself full time as an artist. Read more>>

Shin Yu Liu

Anyone who’s ever travelled anywhere will tell you that learning about the cultures of neighbouring countries is an entire journey in and of itself; much less, having to adjust to one that’s all the way on the other side of our big, beautiful globe. Read more>>

Kä Neunhoffer

During the pandemic, I was at home to my family ranch in Texas. The entertainment world had ground to a halt and we weren’t sure when we would go back to work. While at home, I wound up spending a lot of time with my childhood friend, a choreographer named Libbie. Read more>>

Keira Henninger

In 2009 when I first started my exploration and interest in my profession I was pretty much the one and only female doing it. Most event producers and race directors were non profits, and not looking to do it as a job and profession. I wanted to change that, and I did. Read more>>

Alexis Huerta

I started off as a dancer (at the age of 5 til 18) and a dance instructor traveled to china on a two month dancing tour and when I came back to the states I got pregnant with my first child and I was tired of working in a clothing store not bringing much home . Read more>>

Jake Thompson

The year is 2008 and I’m a 19-year-old junior in college building my own film studies degree at the University of Minnesota. The opportunities in the midwest are far and fickle between, so you can imagine my wonder/wanderlust when visiting my parents in San Diego and discovering my cousin’s husband grew up with one of the iconic series ‘Ugly Betty”s TV writers. Read more>>

Alicia Powers

Back in 2019 after working in 2 toxic environments for well over a decade I decided to take a risk and pursue salon ownership. I left the familiar behind, I embraced the uncertainty. I faced challenges head-on, and discovered a world of new opportunities for growth. Read more>>

Cait Devin

I feel that the best careers come from a series of calculated risks. Additionally, I have always thought that if one is afraid to fail in the public eye, they aren’t truly ready to succeed either. Read more>>

Colleen RJC Bratton

In the winter of 2022, I felt a strong push to explore a completely new form of making, one that implemented a serious devotion to a more sustainable practice. At the same time as this inclination, I was learning more about green burial options like human composting. Read more>>

Dr Lynn Anderson

Taking a risk is something we all do every day simply by getting out of bed and facing the world, but some of us take a more significant risk in hopes of finding our purpose and the meaning of life. Living in a small town in Maine, my parents taught me to follow the status quo and not take risks. Read more>>

Celtic Honey

I have always been in love with art. All forms of it. From martial arts, cosplay, makeup, singing, painting and into performing. It never occurred to me that I would be where I am today. I’ve been attending cons for over 25 years but I’ve only started guesting this past year. Read more>>

Raven Ross

In my junior year of college, I decided I wanted to be a chef with no prior experience and I wanted to start a business to go along with it. I was 1 year from finishing my Bachelor’s in Allied Health with plans to go to Physical Therapy school, but 2018 came around and I realized that I had no passion for it at all. Read more>>

Keyuna Jones

The risk I have taken has been something I never imaged being so prolonged that I would constantly have to start over! The hair industry full of competitors and unlicensed to self taught hair stylist that are actually better than those who have had licenses for years. Read more>>

Ron Laboray

Thank you for asking me to be interviewed. I appreciate the opportunity to share my experience with risk taking because risk taking is an important topic for creatives. Risk taking moves a creative out of their comfort zone and into fertile ground for new discoveries. Read more>>

Mar Gimenez

I left my home in Spain to chase a dream. Music has been my guide and the driving force behind my struggle ever since. In 2020, I received the incredible news that I had been awarded a full scholarship to study at Berklee College of Music, one of the world’s premier music institutions. Read more>>

Tammy Hua

I actually didn’t consider pursuing film and photography until my second year of college. I had initially gotten into college as a business major, and was fairly certain I was gonna stick with that. I struggled a lot my first few years of undergrad. Read more>>

Karina Gaynutdinova

Arriving in The United States in 2005 with only $300, I faced the daunting challenge of starting a new life. Despite not speaking any English, I held onto the belief that I would find a fighting chance in the Land of Opportunities compared to my native home of Russia. Read more>>

Anthony Gregg

Diving headfirst into Gregg Design Company was the riskiest move of my life, both professionally and personally. But let’s set our time machine back about 30 years to a small farming town in NW Ohio. My family has owned John’s Sons Donut Shop for over four decades, a place where the sweet scent of Bavarian cream and apple fritters hung thick in the air! Read more>>

Christina Jung

My life changed the moment I found out I was pregnant, and then again when I consciously decided to become a single parent. I was 23 years old, fresh out of college, still reeling from the pandemic, and had zero idea of what I wanted to do with my life. But when I took that pregnancy test and it showed two clear lines, I knew what my decision would be. Read more>>

Liz Labelle

I’m a Canadian singer songwriter, artist and musician from Montreal. I was raised by Polish parents in a very traditional manner: go to school, work hard, get a degree and land a high paying job. Well I took the hard work notion and applied it to my passion: making music. Read more>>

Anthony Caulkins

Success in music, the arts, and really any work where you are your own boss is all about risk. Failure is pretty much guaranteed to happen, and happen again, and again, and then one more time on your path to success or even just eking out a living. Read more>>

Acacia Williams

First thing first. Risk excite me. The unknown territory of what could be, or not be is a thrill in itself and a lesson to be learned. The biggest risk I have taken as a Woman and Entrepreneur is believing in myself, along with my widespread, versatile vision. Read more>>

Rebeca Sanchez Montero

Being an artist is all about taking a risk. I feel like I’m an expert on this subject since I grew up as a child of immigrants. My parents came to this country taking a risk in their lives. Taking a risk to start a family. Read more>>

Dru Snider

If I’m being honest, I started putting out music because it’s part of my “bucket list”. I had a health scare while visiting family in Austin, TX. I woke up one day and my right leg stopped functioning correctly. It would buckle on itself whenever I put any weight on it. Read more>>

Christopher Coots

Early in our business, in 2019, we decided to take a leap and invest in industrial sewing and embroidery machines. For those of you who aren’t familiar with these sorts of machines, they can be very expensive (and expansive), and we were unsure of just how well they would impact our business. Read more>>

Rosalie Prendergast

As a child growing up in a small town in New England, I was not known for taking risks or pioneering new paths. My activities consisted of playing sports, riding horses, making pottery, and attending school. Read more>>

Jason Flame

At 19 years old, I decided that I was going to start my own martial arts school. With no start up capital, no college degree and no back up plan,, I decided that I was going to turn my passion into my profession. Read more>>

Jessica Jones

Taking the risk at 20 years old to quit my job and start my lash business was frightening to say the least. My parents had always worked in the corporate field, and I had no friends or family that owned their own business to ask for advice. Read more>>

Vonni Starks

Doing music is taking a huge risk your putting yourself out there to complete strangers in hopes they will like what you have to offer, getting over that feeling the initial fear everything gets easy Read more>>

Jasbir Saggu

I’ve always had a creative inclination, starting from my early days of painting and sketching to designing go-karts, race circuits, event concepts, and even hostel spaces. The inspiration to think outside the box often came during my biking adventures across the mountains. Read more>>

Adelia Johnson

I host an amazing event called the #SisterHypeSquad Celebration. During this celebration, I bring women together to connect, be encouraged/motivated, and celebrate one another’s wins. When God gave me the vision for it, my first question was how am I supposed to pay for this? God told me that if he gave me the vision, the provision would follow. Read more>>

Yuan Escusa

Starting a business at a younger age is always a risk. Growing up with traditional Filipino parents, they always told me that I had to go to school and become a nurse, typical filipino thing to do. While going to school, studying and volunteering in nursing school, I realized that this was not my passion. Read more>>

Zara Kand

As they say, choosing a career as an artist can be risky business. There is never a guarantee of where exactly it will lead, in terms of financial stability, representation, exposure, and all the other facets necessary for a successful path. Read more>>

Melanie Bowles

Way back in the early 90s, I wanted to open a sanctuary for at-risk horses. Horses who had been abused, neglected, confiscated by law enforcement from bad situations. The problem? Aside from the fact that horses need a lot of land and they require a lot care (translation: they require a lot of money). Read more>>

AJ Negron

In 2018 I decided to blindly move to Europe to pursue freedom within my craft as a professional ballet dancer. I wanted the ability to choose who I could work with after years of having no say in how things were done. I wanted a broader community, more diversity in my work, and interesting influences outside the world I had in company life. Read more>>

Sarah Welch

Starting Inkdrop Lit in 2017 was the biggest—and best—risk I’ve ever taken. There’s a lot to appreciate about a “real job”: the steady paycheck, the PTO, the better health insurance, the predictability… But, despite the challenges, being my own boss has come with far more benefits than I could have imagined. Read more>>

Kate Eliza

I think anytime an artist shows their art, it can feel risky. Will it be perceived the way it was intended? Will people like it? Will it sell? I have taken a break from showing my paintings for the past few years while I have built up my other business; making handmade art supplies for other artists. Read more>>