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.

Mateo Messina

1995 was the year I realized I could possibly write a symphony without reading music. At the age of 22, I was recording music in our university’s studio when a student engineer introduced me to MIDI (Musical Instrument Digital Interface). Read more>>

Anne Bradfield

As it was for many small business owners in the events and service industries, the onset of the pandemic was pretty earth-rattling. My floral design business had focused primarily on weddings for the past 18 years. Read more>>

Geraldine Andre-Major

In the midst of the pandemic, when the world was filled with uncertainty, I found myself at a crossroads. As a Head Preschool Teacher, I was furloughed from my job, a role that had been a source of fulfillment and joy. Read more>>

Christopher Copelabnd

My story begins like many people in my current position: a freelance, multi-hyphenate creative working out of Los Angeles, California, after moving here from a small town in a flyover state, dreaming of pursuing big dreams in a big city. Read more>>

Reena Majithia

Going from the healthcare field to business owner was not an easy road. I started as a CNA right out of highschool. Worked as a CNA for 5-6 years doing homehealth and then transitoned to working in the hospital. Read more>>

Joanna Gragnani

About a year and a half ago my third child was born, and about a week later my partner and I became owners of an old pottery studio/gallery. Read more>>

Saloni Singh

Growing up, I guess I was a pretty artsy kid- my idea of leisure was sitting with a blank piece of paper and some crayons. I loved drawing silly cartoons and landscapes and later on, studies of paintings. Read more>>

Chelsea Horton

After receiving my Master’s Degree in Dance/Movement Therapy in 2017, I followed the traditional path of working full time in the mental health system. Read more>>

Matthew Sorensen

At the end of 2019, the company I had been the Director of Talent Acquisition at for four years was acquired, and I didn’t see it coming. I was out of a job, but couldn’t be more excited. Read more>>

McKendree Key

I’ve been lucky enough in my life to be able to take risks. For example, starting a new business with no guarantee that it would work out. My business partner and I started Betty’s Ceramics Club almost a year ago. Read more>>

Kat Ibasco

The biggest risk I ever took was the beginning of my journey into theatre. Raised in a STEM-focused environment, I was certain, all my life, I was headed for engineering school. Read more>>

Allison Owens

The biggest risk that I’ve made in my career was to stop pursuing a conventional career and looking for corporate design jobs. When it comes to my passions I am resolute. Read more>>

Martha Davidson

My leadership journey began after college, starting in the mailroom and progressing to managing keypunch operators. This foundational role taught me essential lessons in team leadership and risk-taking. Read more>>

Sarah Bishop

One of the biggest risks I’ve taken was stepping into full recovery from a life threatening eating disorder. One the surface, the risk would have been to stay stuck in the spiral of anorexia, a disease I struggled with on and off from ages 14 to 21. Read more>>

Veena Aragam

Taking the risk to become an artist “later in life” was huge for me. (I was 28, I wasn’t so old, but I think when it comes to how we are defined in society, it can be considered an older age to start being an artist…lucky for me, I don’t care about that stuff. Hahaha.) Read more>>

Jason Lai

Buying Out a Business Partner: A Journey to Independence and Growth In 2010, I embarked on a business venture with a partner, filled with optimism and entrepreneurial spirit. Read more>> 

Catrina Morbidelli

Taking risks in my work is something I’ve grown to embrace, though it hasn’t always been easy. A personal example comes from my fitness journey, particularly with yoga. Read more>>

Sonya Antoine

I knew on the journey to pursuing my last Master’s Degree in Clinical Mental Health Counseling that one day I would open my own private practice. It was always a dream of mine!! Read more>>

Gemma Farquhar

One of the most significant risks I’ve taken in my life was deciding not to go to college. I realized that I wanted to fully immerse myself in the world of film and the broader creative industry without delay, and gain life experience and training on my own terms. Read more>>

Jessica Chavira-Eubanks

The most significant risk I have taken was pivoting my business, Purple Couch Therapy. I began Purple Couch Therapy to serve Black/bodies of culture in my community. Read more>>

Melinda Martinez

A year ago I decided I wanted to start painting furniture. I desperately wanted to see the furniture in my own home take on a new life. I’ve always been a creative at heart. Read more>>

Holly Morris

About 20 years into mine and my husband’s professional careers, me as an entrepreneur and him as a hospital administrater, we felt called to take a dramatic risk and leave it all to help start a non-profit. Read more>>

Adele Sypesteyn

After 20 years of selling my paintings through galleries, which was what I depended on for my living, I saw that the galleries were becoming less dependable financially. Read more>>

Kayla Shaw

As I reflect on my journey, I have always had a passion for modeling just as brightly as my dedication to healthcare. Balancing these two seemingly disparate worlds has been a challenge, but one that I was determined to navigate. Read more>>

AMN x DAS

After graduating high school I didn’t go to college like the rest of my peers , I left my hometown of Charlotte NC and moved to New York City to build my foundation and chase my dreams. Read more>>

Reginald Reed Jr.

Writing this memoir about the brutal murder of my mother. Later (30+ years)finding out that my father (who raised me) was involved in the crime. I work in corporate America and sharing a story of this magnitude could potentially come with risk and how people view you going forward. Read more>>

Sergio Cazares & Blanca  Ocegueda

We feel like life is all about taking risks. Some are bigger risks than others. When we decided to launch our business we took a very large risk with very little time to prepare. Read more>>

Meryl Binder

In 2012 I moved across the country to the middle of nowhere to be with my then boyfriend (now husband: spoiler alert). I had spent the previous 4.5 years working in professional sports in Philadelphia. Read more>>

Rose Mercado

One of the most significant risks I’ve taken in my career was transitioning from a successful solo business owner in the independent music space to becoming the COO of Little Engine Media. Read more>>

Damien Rider

I’ve built himself to become one of the world’s fittest extreme adventure athletes, with performance feats that defy logic and a devotion to inspire people around the world. Read more>>

Constance Nevels

Taking the Leap: The Birth of TheHairXP For ten years, I had honed my craft as a stylist. The dream of owning my own salon, however, remained just that – a dream. I’d dabbled in salon suites and rentals, but true independence beckoned. Read more>>

Alaina Marie

Being a twenty-year-old female, there are a lot of circumstances and expectations that are just beginning to unravel. Circumstances such as which career choices are deemed acceptable, how to respond to unforeseen challenges responsibly, and defining an identity that rings true to who somebody is at their core. Read more>>

Jennifer Smith

In the midst of COVID in mid-2020, I made a big decision to step away from my role as a public school teacher and shift my focus to fundraising for a local nonprofit organization where I had been a member for over a decade. Read more>>

Carolyn Sawyer

In July of 2008, The State of Colorado opened sealed adoption records for babies born and given up for adoption from 1950 to 1970. I requested and was given the sealed original documents that would provide the details of my adoption, such as my original birth certificate which would include my biological parents’ names, birthdates, and race as well as the parents that chose me to become a part of their family. Read more>>

Lily Jousson

I previously worked in a very different field: finance. The moment I decided to be brave, to quit and to invest fully into my art instead was the toughest, boldest and most joyful risk that I ever took in my life. It felt like a gamble. It felt terribly foolish. Read more>>

Aisha Saintiche

I would have to say the BIGGEST I have taken to date is the starting my business and becoming an entrepreneur. Truthfully, if someone would have asked me 10 years ago “Aisha would you ever consider entrepreneurship?” I would have laughed and said no way. Read more>>

Doug Guthrie

I had a few coaching clients while I was still in fulltime sales. My daughter convinced me to get Certified through USA Triathlon to more legitimize my coaching business. Read more>>

Barbara McCulloch

The biggest risk I ever took was leaving a successful art career at 55 in my own studio/gallery in order to chase a dream. It was a terrifying, but exhilarating leap into the unknown after a lifetime of using my skills to create income. Read more>>

Dana Lauren Castro

As I sat down in the dimly lit local gastropub with my laptop open, I never could have imagined the whirlwind of events that would soon follow. It all started when I was hired to do some light social media work for an African American conservative female candidate running for office. Read more>>

Derek Lawler

In 2011, after almost 8 years as a copywriter at two different advertising agencies, I made the decision to throw caution to the wind and venture out on my own as a freelancer. I said goodbye to the steady paycheck. Read more>>

Tanya Manuel

One thing I learned early on is that everything in life involves risk. The key is knowing when to walk away. When I started Beyond Flavor, I knew it was going to be a gamble, especially since I quit my $70,000-a-year job to run my business full-time. Read more>>

Hakeem Henderson

I began to wonder about my career and the life ahead of me after graduating from college. After my time in England, I reflected on how many people commented on the length of my journey, my skills, and the impact I might have on opera or music I was pursuing in an evolving culture. Read more>>

Christine Obiamalu

Last year in November, I found myself at a crossroads when I was laid off from my corporate job. This wasn’t the first time I had felt out of place in the corporate world; Read more>>

Patricia Robalino

At the age of 19, I left the boutique I opened in Ecuador. My grandfather created Joyeria Valencia and we had 14 family stores and mine was number 15. Since a little girl of 4, when I used to go with my grandfather to work, I would play with the loose stones and pretend to be a jewelry designer. Read more>>

Caleb Swindell

I think one of the biggest risks I’ve ever taken is following my dream of being an actor. I do not come from a family with a lot of resources so I knew that deciding to follow my passion and get into acting was something I would have to do on my own. Read more>>

Ashley Nader

Starting fini was, without a doubt, the biggest risk I’ve ever taken. Diving headfirst into the uncertain waters of entrepreneurship was both exhilarating and terrifying. Read more>>

Katherine Flynn

Four years ago I decided to take a leap of faith and begin a journey of self discovery and turn my life in a new direction. I always knew I would begin supporting clients on their life journey at some point in my life through channeling, but I wasn’t sure when and how it would come together. Read more>>

Tabitha Kit

Prior to starting my company in 2017, I worked as a spokesperson and model for various brands. During that time, people often approached me seeking advice on how to enter the industry and requested my assistance to obtain work. Read more>>

Brenton Thomas

When I started my first full-time job, my dream was to become a Chief Marketing Officer. I meticulously mapped out my entire career on my iPhone, detailing every step I needed to take from age 23 to 60 to reach my goal. Read more>>

Michael Cerqueira Da Costa

I’m not originally from America, and English is not my native language, but I still decided to come here to pursue my acting career. This decision was a significant risk for me, both personally and professionally. Read more>>

Andrea Lledo

Embarking on my journey in the art world was a leap of faith, one that required both courage and resilience. Coming from a family with no background in art, I knew I was stepping into uncharted territory. Read more>>

Matt Sofo

From an outside perspective, my entire career in the music industry has been a series of risks. From quitting my first job to pursue music, to sending my music to record labels and composers. Read more>>

Kelly Rocklein

Back in 2015 I made the difficult decision to drop out of college and pursue my passion for content creation and video editing. Looking back, I am so grateful for the courage I collected to take the leap, because I wouldn’t be where I am today had I not made the decisions I had. Read more>>

Jasmine Berame

2017 was a pivotal time in my life with so many signs that a massive change was about to take place. I resisted this change for a while, still unaware of what it entailed. Read more>>

Nicole Casadei

My name is Nicole and I’ve dreamt of being a hairstylist since I was 15 years old. I grew up in a town with less than 4,000 people in it and didn’t know where I’d end up- but I didn’t want to stay in my small town. Read more>>

Lilli Passero

During the pandemic I was approached by a coaching company about vocal coaching for them. I thought it was bizarre and hilarious that anyone would reach out to me about that. My “Imposter Syndrome” was through the roof. Read more>>

Gerald Dixon II

Let me preface this with, I would want you to read this as if I’m having a conversation with you. So with that being said, thank you for taking to the time to read and being open enough to know more about me. Read more>>

Arch Events

Opening the company WAS the risk – we were unemployed in the middle of a pandemic, and really had no sense of what the future held for us professionally or personally. Read more>>

Lauren Wells

After graduating from college with a degree in English in 2012, I spent a few years working for a life insurance company in Manhattan. I had a decent salary, full health insurance benefits, and regular raises. I had stability. Read more>>

Susan Vishmid

Choosing to be in a creative field is a risk in and of itself. The passion and drive one has for their craft often exceeds the drive for pursuing financial gains. Read more>>

Kenzie Travers

A turning point moment for me that felt like a big risk was quitting my full-time corporate job, selling all of my stuff and moving to another country while transitioning my in- person community to an online platform for feminine physiology based living. Read more>>

Marshall Parks

I’ve always been one to take a leap of faith and commit to big changes; the best rewards always have a lot of risk on the other side. I had spent the majority of the early 2020’s living in Indiana for work, and while the money was great I didn’t see much room for growth in my music career. Read more>>