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.

Philip La Croix

I have taken many risks in my lifetime. They are an inherent part of my day job which, oddly enough, is actually my Knight job. Fighting with real swords, jousting, jumping off horses at a full gallop. These are daily tasks for me. That being the case, it goes without saying that this profession has a shelf life. I’ve always known that I would need to find a new career eventually, and at one point, I thought the decision to leave the knight-life behind for a new adventure had been made for me. Read more>>

Shanavia Evans

Risks are apart of everyday life. Each day I feel like I’m taking a risk because each day we have to make decisions for our future. Moving to Saint Louis was one of the biggest risks I’ve ever taken. I moved here knowing no one, and with no source of income. I prayed a lot still do, because till this day Faith is what brought me through the trials and tribulations. Read more>>

Sarah Tapia

I had been working at a mortuary for a few years and while i enjoyed my job and loved the people I worked with, and it was usually pretty interesting, I found my anxiety was quickly getting worse. My daughter was in her late teen years (16-19) and was “difficult” in addition to being in a new marriage, I had a lot going on to say the least. I started obsessing over time. Not having enough time. Read more>>

Sarah O’Brien

If you want to go from a good artist to a great artist you will need to take a risk at some point. Currently I sit in a cubicle, drained of energy at 35 weeks pregnant, ready to quit my day job and take one of the biggest risks of my career: becoming a full-time artist and mother. Read more>>

Shayna Malhotra

I made the challenging decision to move to a new country, leaving behind my well-established studio in Delhi, India during COVID, in order to pursue my dreams. I have an urge for keep growing and pushing my boundaries. I often find putting myself in tough spots in order to discover my weakness and making them my strengths. Performing on stage gives me life, and teaching gives me purpose and stability. Read more>>

Kaylista Underwood

The first biggest risk I took was leaving my dream college of Ohio University after 2 years and transferring to The University of Toledo. I loved Athens, Ohio and it was there that I really shed my adolescence and stepped into a more mature and knowledgable version of myself. OU had told me I was going to be a 5 year student; the result of my indecisiveness when it came to choosing a major.  Read more>>

Kimberly Burton

One risk that I took in my business was joining a coaching program. Given that I started photography as a teen, there were many things that I learned along the way from simply not knowing better. I have had various mentors in the past; however, I wanted a consistent mentor who could help me and my business elevate to the level I always dreamed of. Read more>>

Garrett Brown

I have been a music producer and touring DJ for 10 years. I have always wanted to do something involving real estate and I saw the opportunity to create a glamping site that would be used for short term rentals. Slowing my music business down and retiring from touring was a big decision that alot of people thought I was crazy to do. Read more>>

Yajaira LaLuz

I took a significant leap by departing from a stable full-time job with union perks to pursue my dream of establishing a wellness business. This venture is dedicated to guiding individuals toward discovering their inner peace. In my upbringing within the South Bronx projects of NYC, the concept of inner well-being or wellness was foreign to me. Growing up in a traditional Latino household, expressing dissatisfaction or the need for something more was discouraged. It felt unattainable to strive for peace. Read more>>

Patricia Baldwin

Sold it all! That’s right-on a whim, as I’d call it looking back from this 10 years gone by vantage-selling my home, all possessions, car, packing my youngest son, husband, and I into two 50lb suitcases each and taking off for a two year life down under was complete whimsy! All this being decided and executed over a quick nine month time frame was a bit ludicrous. But stars align, trust ruled, and good work paid off. Read more>>

Lisa Lee

I always wanted to make a tasteful film depicting an exploration into the fetish, BDSM world of erotica. Read more>>

Cherell Butler

I was contacted by an individual provider to join an outpatient counseling service (private practice) for patients, who experience mental, behavioral health and life challenges. After planning my retirement of 30 years of service to Aiken County Public School District. Following several months of consideration, I accepted the offer and began providing individual counseling services to adolescents and young adults, who were experiencing anxiety, depression, bipolar disorder, schizophrenia, substance use disorder, grief, and mood disorders. Read more>>

Jorge Bueno Jr

From an idea, Creating my own clothing to taking business trips for technical training to Florida on embroidery machines to building an embroidery business from scratch, It has become a passion. Digitizing logos, embroidering on garments, witnessing day to day happy family and friends receiving their custom order. Doubts flooded the area, an idea has come about changing the game on creating clothing. Read more>>

Dr. Sy’Quon Shaw

I embody the role of the first domino, understanding that to embrace risk, one must be prepared for that first fall. I like to think that my life to a book often judged solely by its cover. However, as one delves into its pages, one discovers layers beyond what meets the eye. My venture into risk-taking commenced when I commenced therapy in 2014. Read more>>

Daniela Tabares

Back in 2019, when COVID-19 hit, life got real interesting. I was juggling a full-time corporate position and building my brand, living with my parents, and chasing around a two-year-old toddler. The uncertainty of the times made me realize that my job might not be secure, and the idea of being sent home or layed off was frightening at first. Read more>>

Joshua Alvarez

taking a leap into the art world without any education in art was a risk in itself and somewhat intimidating. Once I was able to put that aside and just jump in headfirst and create work that was an extension of myself, I felt I was doing what I am meant to do and create what is true to me. Read more>>

LeeAnn Webster

wo and a half years ago someone asked me a question that completely changed my life. The question itself (“what are you doing for fun?”) was not revolutionary, yet it set me on a path to taking one of the greatest risks of my life – creating a one woman show. I don’t have a theater background and I’m not an actress, so the very idea was scary. Read more>>

Kassey Rich

This past year, I made a subtle yet significant pivot in my styling business by exploring the idea of offering personal styling services. I’ve had a handful of personal clients throughout the years but never spent much time planning out what it could look like as a real business. So, while the entertainment industry was slow because of the strikes, I began taking time to create packages.Read more>>

ET DEAUX

It all started with the spread of COVID. I was running a restaurant as part owner and spending 16 hours a day on location. When the spread of COVID shut us and many other businesses down I had an option to either find new work or take the risk and start doing what I love. Read more>>

Boston FoodDudes

Joining an already crowded field of Social Media Food Influencers was a bit scary at first. Many other influencers had years of experience and major followings. We wanted to do something different to help us stand out, and in doing so we took a risk of betting on ourselves and doing something very out of the norm on Foodie Instagram. Read more>>

Rachel Freiman

When I first started my company, I will was full time teacher. I absolutely loved teaching and had no plans to leave, but the more I learned about the health and fitness industry from my own journey, the more flabbergasted I was at how much BS was in the market. The teacher in my was determined to do something different–in a world full of point systems and shakes, I was going to educate. Read more>>

Katy Marie

I had finally hit my limit. I couldn’t deny that strong and uneasy feeling inside myself any longer, the knowing, that I had to make some big life changes. I wasn’t on my life path. Leaving my current life circumstances felt scary yet staying felt more wrong. Read more>>

Sabrina Rios

I feel like life is all about taking smart and educated risks. It’s how we grow as individuals, and find out what we are truly capable of. Starting my art business was definitely “taking a risk” in my eyes. I had many irrational fears pop into my mind like, “What will others think?”, “What makes ME special enough to try to sell my artwork to others?”, and “What if no one likes my stuff or says something mean?”. Read more>>

Mariela Ayala

Sometimes risks are unexpected gifts from you; just loving yourself how you deserve. It was December 20, 2019. As usual, I opened my letter from the social security disability that I have been receiving for the past 20 years, and my soul left my body. The top of the letter reads ” Social Security Notice of Case Closure.” I sat there in disbelief, uttering, ” I am free. ” Read more>>

Rhea Adkins

The biggest risk to this date was taking a leap of faith and putting my all into my business. I had my Son at age 15 and by age 17 he was diagnosed with Cerebral Palsy. It’s hard to believe that was almost 20 years ago, wow!!! Something I’ve learned that often goes unnoticed is when you spend time focused on others it’s hard to see who you are at your core…This is my core defining moment of taking a risk… Read more>>

Jenifer Ezell

As a curious explorer of life, taking risks along the way has been a huge part of the journey. I took a risk falling into and following love, a relationship that was the catalyst to changing my trajectory in a way I could have never imagined. Read more>>

Ed Moreno

A life pursuing the arts as a career is a risk. There is no sense of stability for (there may be exceptions but they are rare). For myself it was a gamble that was ignited by the romanticization of a career as an artist. I grew up in public housing and the only real want my mom had of me was to make sure I stood of the street and didn’t become a parent at a young age. Read more>>

Jerniqua Harris

Hello. September, 1985, I was born with many complications. I had seizures, I was not holding down my food, I had to be tube fed, I had breathing problems, I had to be placed in an incubator. I was not expected to live. By the grace of God and many prayers, I pulled through. October, 1985, I was sent home with seizure medication. Read more>>

Kayy Finn

In a pre COVID-19 world I was a tenured New York City special education teacher, followed by tenured School Counselor, who had just completed her Educational Leadership degree from Fordham University working towards writing School Counseling curriculums. I was on a strategic pathway towards becoming an educational administrator and had big dreams of working at the Superintendent level implementing social, emotional learning supports in school districts. Read more>>

Luke McDonald

The biggest risk I’ve taken would be my decision to pursue photography. Back in 2019, I was a computer science student, with a semester left before graduation. I was unhappy in school and my performance. I knew deep down that I didn’t want to become a software engineer. At the time, I was a hobbyist photographer, shooting mainly on my phone. I knew that I wanted to push my art, but for years I had been terrified of failing. Read more>>

Shannon Whalen

I have always been one to go against the norm so to speak. I never wanted to climb the ladder of a corporation or build someone else’s dream. And the journey to create your own path, and build your own dream requires the courage to take risks big and small over and over again. So here is the story of risks I’ve taken along my journey, up til the biggest scariest risk of all… pursuing my purpose. Read more>>

Jess McKay

In Los Angeles, I found my calling as a puppeteer and puppet builder. Working at The Jim Henson Company, a name synonymous with puppetry, was more than a job; it was a realization of a dream. However, beneath the surface of this dream, there lay an unsettling truth that would soon challenge my principles and career. Read more>>

Doudgy Charmant

Doudgy Charmant: A Journey from Haiti to Artistic Triumph, The artist with the Million Dollar art Introduction: In the world of art, few stories are as compelling and inspiring as that of Doudgy Charmant, a talented artist with a remarkable background. Descended from the lineage of the renowned Haitian general Jean-Jack Desaline, Doudgy inherited not just a rich cultural heritage but also a burning passion for art. Read more>>

Mir Johnson

I was once told that “If you have a dream and you don’t act on it, it’s just a fantasy.” My biggest risk in life so far was definitely taking a leap of faith moving to LA in the beginning of 2020 (pre-pandemic). It was an interesting time and experience to go through “surviving” in a new city in the state that the world was in at the time but I knew LA was where I need to be at the time so I had to stick it out and because of that I’ve been prospering throughout the years. Read more>>

Ben Rogers

The biggest risk that I ever took was starting my company. It was 2020, right in the midst of the covid pandemic. We had recently had our first kid, she was only about 4 months old. I left a very stable job. We worked great hours, they paid me a very fair wage, I had a company truck to drive home, and my bosses were all top notch. I wanted something more. I’d been in the HVAC profession here in my hometown for 14 years at that point. I’d worked for many of the local companies and I knew first hand that I had what it takes out perform them. 3 months into business, with the before mentioned brand new child and I found myself with $86 in my bank account. Read more>>