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.
Benjamin Jones
Five years ago, almost to the day, I decided to leave a six-figure income in the field of brand management to pursue ministry. At the time, I had no idea what that was going to look like, but I felt compelled to pursue what had become my passion. Ever since I was in college, I discovered and developed a serious faith that began to shape my whole world. It determined my values, how I approached relationships and which career to pursue. This led me to working for a couple of years as a campus minister in Nashville where I happened to meet my wife. Read more>>
Shelby Baldock
I’m sure this story is familiar to a lot of people: It’s right before the pandemic and things are looking up. Suddenly, the world comes to quick stop and you lose all of your clients and your money. So, you take a corporate job to get out of the hole, and by doing so realize that you don’t want to spend the rest of your life doing that kind of work. After (very fortunately) getting out of the pandemic-induced financial hole, I quit my full time job and jumped back into the freelance world with hopes of really reorienting my career towards more-meaningful projects (and also haphazardly attempting a work/life balance.) Since then, I’ve been lucky to edit a lot of documentary projects, whether they be passion projects with little to no pay, or branded/sponsored projects with good people. I haven’t totally figured it all out yet, but I’m thankful to have had the work, which provided an opportunity to take a big career risk. Read more>>
Brittany M. Reid
I’m a bit of an obsessive planner, but when it comes to my creative practice this can actually hinder me. Since I work across several mediums, taking risks is part of what helps me grow as an artist. I started collaging about 3.5 years ago and when I started sharing my work with others that felt vulnerable and scary. I had this fear of being perceived, but it allowed me to connect with so many other talented collagists and learn from them. Learn about their experiences, their techniques, their styles, their struggles. An important turning point for me was when I began integrating resin and spray paint into my practice. Read more>>
Frankie Siragusa
I’ve been music obsessed before I even spoke my first word. My mother would play music in the house and anytime she did I would stop crying and immediately stare in the direction these sounds were coming from totally transfixed. And though I came from a family of musicians, I didn’t know anyone in the music business growing up at all. I moved to LA by myself after going to school for recording/engineering and started from scratch integrating myself into this very crowded industry of professionals. To me that was a big risk. LA is expensive and though the infrastructure is here for the music business, it was a very vague and unclear path ahead of me. In a lot of ways that hasn’t changed. Read more>>
Crista Reid
My first year of self-employment initiated me with unpredicted risks, and some of the most incredible rewards. On January 1st, 2020, I took the biggest risk yet. I left my stable day-job of seven years to give my heart and soul to the dance troupe that changed my life. I had joined Boulder Burlesque, a performance art dance troupe based in Boulder, CO, in 2015 when it was under the direction of the founder, Madame Merci. Being park of this remarkable group of sexually empowered women who were unafraid to love their bodies showed me how to love my own body and embrace sexuality for the first time in my life. I knew I wanted to pay this incredible gift forward by carrying the torch for Madame Merci. Read more>>
Valerie Burke
Starting my own photography business was a risk. I went to school for photography and have always wanted to pursue it, and after graduating I was able to find photography jobs that I enjoyed doing and allowed me to travel. There was always work going on and I was constantly on the move. It was crazy and busy but it worked for me and I liked it. Fast forward several years to 2019 when Covid hit and like most people, my world was flipped upside down. My work immediately stopped and I had nothing to do. At that time, most of the work I was doing was event based and usually had groups of 50-100+ guests. Obviously that didn’t bode well for a global pandemic. I was nervous that in a blink of an eye all my work immediately shut down and was going to be gone for the unforeseeable future. Read more>>
Tony Martignetti
The biggest risk I ever took was deciding to leave the corporate world to start my business. There came a day when I found myself sitting in yet another business meeting, looking around at a room of people who I knew were doing work that they had lost passion for and held no meaning to them. I knew because I had no passion for it either. I sat there, listening to a few executives argue about an insignificant issue. It was clear that they were fighting to save “face” and preserve their image. Meanwhile, I noticed how many people in the room were on their phones, totally checked out, and disinterested. Read more>>
Katie Duda
I grew up in the midwest where it is really uncommon to see people move away from their hometown. I knew in my early twenties that I wanted to make a dramatic change in my life — the life I was living based on society’s standards was a life I wanted no part of. I was in a career that felt completely out of alignment with my true self, and I felt called to experience a different part of the country where I felt inspired, energized, and restored. Though it didn’t make sense to anyone in my community at the time, I quit my comfortable job, sold the condo I owned for only a few years, and moved across the country to San Francisco sight unseen (and without a job) with my fiance at the time. I felt such a strong conviction deep in my core that it was the right thing and what I needed to do, despite it logically not making sense on paper. Read more>>
Renata Rodrigues
I think everyone sees risk differently. I strive for what I want and I take the necessary measures to get to where I want to be, which involves, most of the time, being out of my comfort zone. I moved from Brazil to Australia when I was 21 years old. My English was very poor and I also didn’t have a lot of money or parents that could support me financially. I was working as a graphic designer in Sao Paulo in a multinational company. Due to long working hours doing digital photo restoration, I developed tendinitis on my wrist, elbow and shoulder, what put me off work. So I saw my opportunity and I left my job, sold my car, cleaned my bank account and travelled to Sydney with enough money for 3 months of English school. I studied hard, I worked hard in whatever job I could get and I never went back. That was the beginning of many years of travels, challenges, different jobs, friendships and life experiences. I am so glad I did it. It allowed me to experience many cultures, be independent and to get to know my worth and what I bring to the table. Read more>>
TJ Burrowes
I think, funny enough, my life is ran off of risk taking. It’s nothing that I have achieved thus far, without taking some type of risk to get whatever it was I wanted. Read more>>
Brian Keith
The age of thirty-three is usually when people finally start settling into the rhythms of adulthood, gaining confidence in the routines of their family life or their careers, the metaphorical crossroads of decision receding into the distance behind them. But for me, the age of thirty-three found me standing on the edge of a precipice between my current career and an entirely different one, about to take a step of faith in a direction that would change the rest of my life. Behind the scenes, God had already been at work, using challenging circumstances for me and my wife as the catalyst for a long season of introspection and contemplation. On the verge of adopting our first child, I started thinking about stepping away from my full-time job in ministry to explore my artistic passion in the form of a new calling in fine art. Read more>>
Mason Aksamit
I am currently in production of my first feature film “Drepper | The Happiest Man on Earth” this is without a budget so I have been filming in 1 minute segments with minimal cast and crew to post as reels for social media. I am now getting streaming on prime and tubi so I’ll continue to build the film as short episodes on there. This industry has shown to promote fame over talent so as I build this film I’m working to build my social following to over 1 million followers. Feel free to message me with ideas. I’m willing to experiment. Read more>>
Cassie L. Jones
Thank you for the opportunity to share a story about taking a risk! When we look at what kinds of risks we are willing to take in our lives, we have to begin with the end in mind. We have to dig deeper and know our “big why” for doing what we are doing. I love to pose this statement to my clients…If I finally had (blank) then I could finally be who I am and do what I want. Or if we time travel to your 80th birthday party, what is your life story going to feel, sound, be like?? We always have to see a bigger picture, so we have a foundation for why we are willing to take the risk. Read more>>
Steve Kesoglides
As a graffiti artist, there was always a huge risk involved. When we first started in the late 60’s, graffiti was not only highly frowned upon, but illegal as well. We started painting designs and murals on train cars that were parked in the yard, and we had to avoid the security and conductors that were canvassing the yards. They would wave their flashlights from a distance, but we never saw actual faces. Trains were seemingly starting up by themselves and shadows and fog engulfed the tracks. As kids, we coined it the ghost yard. Read more>>
Miguel Berlingeri
I am fifty-four years old and just graduated from Full Sail University with a Bachelors of Science in Film Production. I left a six figure job as a construction project manager to pursue this desire to make movies that has lived within me for forty-eight years. Acting is now my passion and am moving from Florida to Los Angeles in order to further that pursuit. In the midst of the strikes and economy in California, and the nation, I’m going there like countless others have gone with the same desire- usually much younger. Read more>>
Gita Bhargava
My journey began 43 years ago in a small town in India where I became the first young female to run a business after my father’s death. After the passing of my father I ran the family pharmacy store for 6 years till I got married and immigrated to the USA. I immigrated 5 dollars in my pocket and not knowing English and had to fight through language and gender barriers to make a life for me and my family. I went on to found a successful company, Global Upside, in 1999. Read more>>
Jeff Williamson
For many of us, the Covid season was / is trying. Our routines and what was considered normal became abnormal. In August 2020, my wife was hospitalized with the virus and was touch and go for about two weeks. I’m thankful that God healed her and help make her whole. A lot of times, there are “Hail Mary” prayers and wishes that happen when we are tested and have our backs against the way. This wasn’t the case for me directly but I did want to live my life more intentionally, gain more training to help others and serve in a larger capacity than I was prior to that moment. My wife’s Covid experience was the wake up call that I used to live far more intentionally. Read more>>
Sonovia Washington
Sonovia’s journey began in San Diego, where she led a comfortable life with a stable job and routine. However, deep down, she had an unwavering passion for creative directing and styling, which she had been nurturing as a side project for years. The desire to pursue her true calling became too strong to ignore, and she knew it was time to take a leap of faith. Dropping everything she had in San Diego, Sonovia made the bold decision to move to Los Angeles, the heart of the entertainment and fashion industry. Read more>>
Zurisaday Decker
From a young age, I knew I was put on this earth to accomplish the unimaginable. I knew my God had placed me on this earth to advocate for exceptional learners shortly after my nephew was born with Down Syndrome and was diagnosed Hard of Hearing. At that time, the path set for me involved going to work in the family business, getting married, and having children. My goal and purpose was to pursue a career in Interdisciplinary Early Childhood Education. I enrolled in my local community college and dropped out a year later. Read more>>
Jamie Ratowski
In thinking about the biggest risk(s) I have taken, it can be broken down into two parts that lead to the same wonderful result. In 2014, I decided to move alone from my hometown in Pennsylvania to attend graduate school in South Florida to study and become a marriage and family therapist. Now, this in itself does not necessarily seem like a huge risk, but I was only 22, my whole family and all of my friends lived in PA…and I was traveling alone to a new state for the first time in my life! Navigating living without your support system for the first time at a young age can be scary and I definitely went through a wide range of emotions for the first few years. I was able to eventually find my footing, meeting friends, classmates, and landing a job in the field to learn more about therapy and the business side of mental health. Read more>>
Thomas Ernst
Have you ever wondered what its like to move to another country and starting all over again and the struggle that comes with it? I’ve been working as an Actor in Denmark since I was 11 years old and made it all the way to the top and my dreams come true. I accomplished everytung I ever dreamed of. When I bacame aorund 25 years old I started to hit a limbo. I was not a teenager anymore but I still wasent a dad. During my acting career in Denmark I made alot of connections in Los Angeles and people wanted to work with me. I decided to take a rask and move to Amercica to persue and international career until I could play dad roles. All by myself. Read more>>
Stephanie McIntyre
The biggest risk that I decided to take was to work in the film industry. It is ever changing and yet I thrive on the spontaneity. It was the best decision for me. Read more>>
Sophia Rabinovitz
A couple of years back I decided to take the full plunge into artistic work and quit all of my other part-time jobs in order to pursue growing my company. There were a very scary few weeks there were nothing happened, but then the connections and partnerships started to come in and eventually flourish. It taught me that you need to make space in your life for new things to happen and be patient. Read more>>
Audrey Collins
I have learned that risk taking is part of everyone’s life regardless of their profession, relationships, or health in general. Doing something about a situation is taking a risk just as much as not doing something. I believe we only handle making these “risky decisions” best when we come from an authentic place in our own sense of being. Without knowing we you are, which is an ever evolving thing in ways, we make choices that ultimately don’t serve our bigger purpose. I could banter this topic for a while cause it is much easier said than done haha Read more>>
Cassandra Vargas
When it comes to taking risks, I think to myself “the greater the risk, the greater the reward”. I knew this would be true of embarking on my journey to not only become a licensed esthetician and start my career in the beauty industry, but to then create my own brand and run a business that was solely mine. At 19 years old, I stopped to think about what made me happy in life. I knew that makeup artistry was my passion, but was I ready to ditch my stable 9-5 to pursue that dream? In the height of a global pandemic, was this realistic of me to consider? I decided that it was worth a try! In June of 2020, I reached out to a local makeup artist, Kristina Stuller, and became her apprentice. Read more>>
Sonia Pal
Working full time as a successful professional for many years, getting completely burnt out in the process, left me no choice but to take a break. I was working long hours, across different time zones, traveling away from family frequently and just exhausted. Within two weeks of this self-imposed sabbatical of sorts, I was bored. I realized, I had no hobby, I had no friends outside of the immediate circle around me. I had nothing to talk about other than work! Read more>>
Amy Impellizzeri
On June 1, 2009, in the middle of the most tumultuous economic period I had experienced in my professional life, I did something that many might consider very strange. I voluntarily left a very good, very lucrative, very coveted . . . job. Actually, I left my career. As a corporate litigator. For more than 13 years, I had been immersed in depositions, trials, motions in limine, and summary judgment arguments. Read more>>
Shaine Schroeder
In 2001 I was at Barnes & Noble thumbing through art magazines and I found one called “Juxtapoz.” It featured artists H.R. Giger, Derek Hess, Ed Templeton, and Glenn Barr. I recognized Giger as the one responsible for creating the aesthetic in the “Alien” film franchise. Templeton I knew from my days attempting to pass as a skateboarder. But when I dug into the issue and found Barr and Hess’s work, it changed everything. I felt like the kid at the record store who finds that rare Japanese import nobody else knew existed from a live show of his favorite band. One artist painted subjects I’d never seen in fine art before- robots, motorcycles, crowded bars with scantily clad angels- in a very tight, defined, meticulous style. Read more>>
Dr. Carl Truesdale
When I was in my facial plastic surgery fellowship, I had a big decision to make. I already knew I wanted to go immediately into private practice. The question was – where? Did I want to be a big fish in a small pond and move to a city where there weren’t many facial plastic surgeons? Or did I want to risk being a small fish in a big pond and stay in Beverly Hills, a city that is world-famous for facial plastic surgery, with surgeons on almost every block? I choose to aim to be a big fish in a big pond, set up a practice in one of the most competitive markets in the world and make a name for myself. Read more>>
Connie Morgan
The biggest risk came with the biggest upheaval of my life. My husband of 22 years abandoned me and our two boys six years ago and I went into fight or flight mode and I ended up doing a bit of both while I figured out my next steps. At the time I owned my own house cleaning business and I clung to those jobs as though my life depended on it…because it did and those of my children. In January of 2020 my body started sending me signals that it was time to make a change. I suffered a heart attack, a bulging disc, and gout in my foot which then turned to arthritis. Read more>>
Zoe Sakoutis
My first business, BluePrint Cleanse was a major success — I bootstrapped, scaled and sold it within 5 years. We were category leaders and creators. It was a huge success by every measure! It wasn’t easy by any stretch, but it ended very well, so, I kind of got the impression that every entrepreneurial endeavor would be just like that on, and maybe even better. I was wrong. My second business attempt did not end well. After about a year and a half, of pushing a bolder up a hill, we realized that there really wasn’t a strong enough need in the market for what we had created, and in order to scale it properly, we’d need to raise a ridiculous amount of money. So, we called it quits and humbly ate the loss. Read more>>
Sky Ariella
After graduating from college, I was positive that I’d walk the secure, stable path of law school and end up with a guaranteed career. It felt safe and smart. Before I could dive into another few years of rigorous schooling, though, I decided to take a little trip — a solo backpacking adventure for six months through Asia. I’d never left the country before and I was ready to dive into the deep end. About halfway through the trip, a gnawing realization burrowed into my psyche. I didn’t want to go home, I didn’t want to go to law school, I didn’t want to sit around in rooms all day under pressure. I wanted a career that would make me feel free and let me do something I loved. Read more>>
Dominique Owen
As a creative I believe taking risks is essential. It’s how you learn, grow, evolve, and advance in your career and get closer to your dreams. I remember one of my first risks was when I was a teenager and hopped on a Megabus down south to be an extra in Ice Cube’s “Fist Fight” I was so nervous but learned so much, being there taught me set etiquette and it’s where I fell in love with working in film. Years later I was working a job that I hated, the pay was good but the position was taking a tole on my mental health I’d get cursed out all day by old people on the phone and even racially harassed at times. Read more>>
Khin aka Priscilla Rode
Taking a risk has never been a challenge for me. Ever since I could remember, making a profit from either bought goods or making crafts to sell such as beaded rings or necklaces. Investing in yourself is a risk most people don’t take, but that’s not the case for me. I have had four businesses in total which two of them are still running smoothly. Read more>>
Cassandra Miles
As the Executive Director of a start-up nonprofit endeavoring to build trust, and raise a lot of money, from the communities of Central Minnesota, I am constantly measuring, explaining, and embracing risk. In the private sector, it isn’t uncommon for companies to launch with a lot of debt and/or investor dollars that demand a return. The risk of failure is high. While the traditional financing approaches utilized by for profit start-ups aren’t available to a start-up nonprofit, the risks remain — except the risk of failure comes with the added weight of letting donors, volunteers, advocates and entire communities down. For this and a million other mission motivated reasons, the risk of starting a large scale nonprofit had to be carefully and thoughtfully measured. Read more>>
Artist Rico Edwards
Peace, Truthfully taking a risk can be applied to not only business, but anything someone wants out of life there’s going to be a risk. I truly believe there no is great reward without taking a risk, taking a leap of faith towards a sense of achievement. There is a certain beauty in the struggle, there’s so many lessons in the ugly / beginning stages of anything that’s worth pursing. Each person needs to have a certain type of passion and dedication before taking any risk. There is a certain mentally that one must possess before trying to achieve anything, it’s honestly a “risk it all” mentally. Read more>>
Maceo Bishop
Becoming a part of the film industry was the first risk I took. No one in my family had any experience working in the film business and so it was pretty much a mystery to me and my parents. The second risk I took was when I gave up a stable and well paid career as a camera assistant (with a pregnant wife) to become to Steadicam operator, with which I had a no experience. The next risk was leaving a very successful Stedicam career to become a cinematographer. Again I was leaving behind the known for the unknown, I managed all these transitions successfully. Read more>>
Mai Vang
In 2020, I embarked on a weight loss journey and managed to shed 50lbs by 2022. As my confidence grew, I made a courageous decision to confront my fears and not allow them to hinder my progress. I realized that I wanted to pursue a career in modeling because, for too long, I had allowed others’ opinions of me to define who I was. Throughout my life, I had been labeled as the “fat” sister, cousin, friend, and daughter, constantly hearing that I would be considered beautiful if I were smaller. Read more>>
Alex Allen
The biggest risk I took was the one that led me to the journey I’m on today. About 5 years ago I was working factory jobs to save money to create art full time. One day, I left. Earlier than I planned and I was scared out of mind. I felt this way for months but somehow pushed through. That summer I was offered a mural gig, my first public art project. I never considered doing murals at the time, I was solely a canvas painter. It was that week when my whole life changed, I knew it and I felt it. I was hooked. Read more>>