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.

 

Camila Coddou

Some, including myself, might say I run a bit anxious. I can be a bit risk averse, I’m scared of flying, I have a thing about expiration dates on food, I am pretty vigilant about my stepdaughter’s physical safety, and I am absolutely a helicopter dog parent. However, something that I have recently started to understand about myself is that I can be a high risk-high reward person. Read more>>

Lara Stolman

Making “Swim Team,” an independent documentary film, was the biggest professional risk I’ve ever taken. I had to practically pay for it myself, without any assurance that I would recoup the investment (which I ultimately did). It was indeed an investment in myself and throughout my attitude was this is happening, I will do this regardless of the naysayers and there were plenty. Read more>>

Jayla Eskridge

Some may call it a risk, I call it taking a leap faith. Starting my own business and putting my feet into the real estate world was the best move I could’ve possibly made.I knew I always wanted to do something alone the lines of owning property and interior design but I wasn’t where to start. I researched on how to start short term rental and started praying on that vision and listening to God when he told me to pursue my dream. Read more>>

Allyssa Halbert

If you really knew me personally, I believe the LAST thing someone would describe me as is a “Risk Taker.” I like predictable, I like results driven, I like playing it safe. I tend to worry a lot about things beyond my control and fear the unknown. That was, until I started to ask myself, “What’s the absolute WORST thing that could happen.” Read more>>

Eva Winter

During the pandemic in 2020 I made the decision to retire as a dental hygienist after 20 years and open my pastry shop to live out my dream and show the world what I can do. During the pandemic my husband and I redid the back storage room of our retail store (HVAC, installation, sales and service) to make it my pastry shop. When COVID was slowing the world down, we were able to provide work to my other employees as they also helped build my shop. Read more>>

Altesse Aurum

2023, a year of taking risk. It was January of 2023 and I asked my mentor (Geraldine Jones),”Do you think I could win Daytona Beach Continental?” I will never forget the look that came to her face as she told me “You’re doing alright, I think you should give it a shot. If you don’t win Continental, I’ll take you down to Miss Florida.” For the oldest Drag Queen in Florida who is 80 years old and has 50 years of experience to tell me that,I knew I had to give it my all. For those who don’t know Miss Continental is a pageant system dating back to 1981(Approx). Read more>>

Crystal Benitez

I am a Bronx native, and my upbringing instilled in me the values of hard work and perseverance as essential ingredients for success. During my undergraduate years, I committed to both full-time work and full-time studies to contribute towards my tuition and living expenses. Initially pursuing a bio major with aspirations in the medical field, I took an art course for enjoyment, and to my surprise, my professors recognized my passion for the arts.  Read more>>

Amy and Memory Baker

We opened our shop in 2020 when the rest of the world was shutting down. We sold our home in another town and packed up our belongings and fur-babies and moved 4 hours away to pursue our dream. We knew we were taking a huge risk opening the shop during the pandemic, but we were 100% devoted to our dream and did not want to wait any longer to make it happen. Read more>>

Kyle Clark

My decision to become an Artist, I would say, started with a rather large risk. Growing up around Flint Michigan, there weren’t that many creative outlets aside from a few theatres across the majority of the state. And I had spent eight years working as a Janitor to help pay for Undergrad as well as bartending/concession gigs at this theatre in town. And both of these jobs were helpful, but I couldn’t put away the feeling at night that something was missing or there was something else I should be doing–I just had a complete lack of fulfillment and content-ness in my life. Read more>>

Lilly Hampton

I believe this is something that all humans should take into consideration especially if it’s beneficial for your mental health. I took on this “risk” to quit my full time 9-5 desk job so that I could be my OWN boss and create my OWN schedules. Most importantly, I wanted to be home with my family. Family means everything to me. Growing up with 5 older siblings, you grow through many obstacles and challenges that prepare you for the real world. Read more>>

Tamara Kostianovsky

My entire career es based on risk-taking for choosing a subject that is controversial and often can be seen as violent and abject. I create sculptures and installations that depict or evoke severed trees and animal carcasses. These works were originally inspired by imagery I saw growing up in Argentina during the Military Junta, where the ubiquitous presence of carcasses in the markets of Buenos Aires became, in my mind, a surrogate for the State-sponsored violence dominant during that era. Read more>>

Debbie Gianini

It was December of 2017…..I had taken up running half marathons in my late forties and fully embraced the feeling of the “runners high”. As I completed my last Disney half, I noticed a pain in my neck and went to the orthopedic soon after returning home. It was not the news I wanted to hear. Two herniated disks in my neck and I was told to find something other than running! That set me on a journey of complete loss and thus put me in a negative mindset. Read more>>

Ginamarie Soto

Taking the greatest risk of my life was a journey fueled by my maternal instincts and a passion for making a lasting impact on the children in Midland, Texas. Recognizing the need for a nurturing environment like the Little Gym for my 2 1/2-year-old, I embarked on a venture that not only shaped his developmental growth but also revealed my potential when Unleashed Brands acquired the Little Gym franchises, I turned experience into opportunity. Read more>>

Leslie Tharp

One of the early and very risky projects was one of my first large public art projects when I was somewhat new to executing contracts and building to a large scale. This piece was for a local hospital, and the art committee commissioning the project knew of me and my work through several local channels and chose to take a chance on me. For both my reputation and technical abilities, this was a big opportunity to show what I could do. Read more>>

Tyler Ross

I worked at a Chicago public school for almost 10 years and have been providing for myself exclusively from the money made in comedy and my event hosting business. Read more>>

Lady Vasiliki Mitchell

I have taken a risk of becoming a full-time contemporary artist. Stepping out on faith to see my art through. Allowing all of my emotions, good, bad, right, wrong , and indifferent to pour out and create some memorable pieces. Read more>> 

Cortney Bolek

There’s a story within “Discipline is Destiny” by Ryan Holiday that struck a chord deep within me—the tale of Hercules standing at a crossroads, offered the choice between a life of vice or virtue. Arete, Greek for virtue, resonates profoundly in this narrative. A little over a year ago, I dared to step away from my safety net, embarking on a path of literal Areté. Yet, a year into this journey, I found myself once more at a crossroads—swirling in uncertainty. On December 1st, I received some unexpected news: my role was being restructured, and my time there abruptly ended. Read more>>

Sherine Aubert

I sometimes feel like my entire career path can be thought of as “risky”, but starting a private practice and co founding a suppository wellness company while expanding my family all in about a year feels like the risk-est (and wildest) ride. Here’s the longer version of the story- I have always been fascinated by the pelvis, whether I was shaking my pelvis in dance class as a kid, amazed by the complex anatomy in undergrad and grad school and personally experiencing the pleasure and confidence a happy pelvis can yield. Read more>>

Elizabeth Akmal

When I learned about 3D Printing, I was intrigued by the technology, but worried I wouldn’t be able to put in the time and energy it takes to learn a new skill. Since I am also a mother and a caretaker, it leaves me with limited extra time. I started by researching everything I could about 3D printing, the process, the practicality, and how it could be used in my life. Soon after I stared my research, I was fortunate to use a 3D Printer thanks to a friend.  Read more>>

Anthlone Wade

Since the day I started working , I knew nothing but cooking. I was a chef for 10 years. My life took a turn in my early 20s when I found out I was going to be a father. Being a father was a blessing for me but I also took on the responsibility of bearing all the stress and pressure of being the best that I could be for my son. Everything was great until one day, I went to the doctor for a check up but also I noticed abnormal lump in my neck. Read more>>

Carlo Valentino

Pursuing a career in a creative industry poses certain challenges. Freelancing, working for an agency, or a corporation, there are many avenues that creatives can follow, but which is the right one? I believe there is no right decision as this is the beauty of being a creative. We can navigate different opportunities according to our interests & skillsets and pivot if necessary. Read more>>

John Tucker

My biggest risk in life is just chasing my dreams and never giving up on myself . Everyday is a risk for me because I chose a lifestyle that is not promised meaning I dont have a forsure paycheck I have to get out there and find my clients in my early days I used to take a lot of risks and I still do by just picking up that camera doing what I love everyday, I have being homeless , starving , lonely just to chase a dream no one can see so I think me following my dreams was my biggest risk. Read more>>

Trystin Kier Francis

In 2018 while on holiday in Southern, Northern, and Eastern Africa I was inspired to design a plate collection. I recall sitting on “Macaneta” beach in northern Mozambique as the waves of the Indian Ocean crashed and suspended onto the sand. This was the moment I began to see the images of this collection. I originally thought about designing a full dinner service collection. However, I quickly realized it would be best to keep it simple and take a thematic approach centered around everyone’s favorite course, dessert. Read more>>

Nate Bright

I love this question! Excuse me while I get up on my soapbox: We’ve been lied to our entire lives. By our parents, by our teachers, by society in general. We’ve been conditioned to believe that we have ‘failed’ if we don’t do something correctly the first time. And failure is to be avoided at all costs! If you don’t get straight A’s in math, you’re not good at math. If you miss a note and sing off key, you can’t sing. If your new business doesn’t make you a millionaire in the first year, what’s the point?  Read more>>

Brittany Allen

The first risk I took was starting my business! Like many people, I didn’t have a huge savings put back nor have I inherited a lot of money. My parents don’t help me financially. So starting a business as a single mom in my 20s, was very intimidating. It’ll probably always will be but my love for what I do trumps the fear. I had been working for Wag/Amazon in 2018! When I was finally to the point to take the leap, I couldn’t stand it any longer. Read more>>

Tink/Sam Rainbow/Falzone

Both Sam and I were teachers prior to starting this business. We walked away from benefits, a pension, and the security of a salary. We invested all of our time and money in this and wouldn’t be where we are if we didn’t. Sometimes you just need to jump! We are the kind of people that go all-in; in our eyes there is no other way. Neither of us came from money or financial security, but it’s what we both so badly wanted that for ourselves. We decided to leave teaching and go all-in together. Prior to Sam joining this, I (Tink) worked part time as a Professional Organizer and started a small company, Clean House. Read more>>

Cory Dueger

When I was 19 years old I was studying at the College of Charleston. I noticed an advertisement that there was a local audition for a modeling and talent expo in Atlanta, GA called Model Search America. There were top agents attending that were looking for new faces. I went to the audition and was accepted to the event. There was a cost to attend, but I made sure I saved up enough to take part in this opportunity. Read more>>