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.

Travis Singletary

One of the most significant risks I took was starting SkyRas Media, my full production company. Before taking the plunge, I was working steadily in the television industry as an editor, a role that, while creatively fulfilling, offered a predictable and stable career path. Read more>>

Dr. Bryanna Campbell

I believe that one of the biggest risks I have ever taken was the decision to open my open therapy practice. The road to that decision involved years of me learning to trust my developing understanding of myself and my discernment. Read more>>

Lena McCarthy

When I was 24, I started painting in the streets of Santiago, Chile. I had been living there for over a year, teaching English and then making art in a studio in someone’s house. Read more>>

Matthew Anderson

Looking back at my life now, I feel that the biggest, life-changing risk that I’ve taken was moving to Long Beach CA from Worthington MN when I was 21 years old. I knew no one in Long Beach. Read more>>

Onterio Cross

As a father, Published author, a podcaster, a full-time caregiver for my mother battling Alzheimer’s, and a current MBA student, I embody the essence of risk-taking. Read more>>

LEMARA

I have loved song writing since I was as young as I can remember. I have vivid memories of using my mother’s Motorola razor at the time to record songs I had written before I could even properly write. Read more>>

Justin Kerbo

Everyone told me how risky it is to start a business, how hard it would be, and how I wouldn’t have any security regarding income. I did something nobody recommends, I quit my dead-end job in January 2022 without a single backup plan in hopes I could bring enough pressure on myself to break out of the mold. Read more>>

Jenna Wright

When I graduated high school, I packed up my car and moved to Nashville on a whim. I knew I was all in on pursuing my dream of being an artist. After a year there, when I turned 19 I decided I wanted to move to LA. Read more>>

Paul Lorenz

Taking a risk is essential to growth and understanding. Art does not move forward if risks are not taken. I have never felt that a painting is finished unless and element of risk is involved. Read more>>

Lyndah Tello

In the late 1990’s I was living in NYC, single mom with three kids on a school teacher’s salary. We took a summer vacation, a low budget camping trip. Where ever we are in the world we went to church, and so that summer we ended up in a little church in Rocky Mount, NC. Read more>>

Michael Wavves

My entire pursuit of a music career has been a risk. The moment I made the choice to turn my music from a hobby and passion into a full-time career, is the moment I began dedicating so much time, money, and effort towards making this dream happen. Read more>>

Meghan Umlauf

Working in sales is a risk in itself – I don’t get paid for my work unless a client books their vacation with me AND they travel. So every choice made to build my current clientele and business has been a risk to some degree – from how much to spend on advertising and promotion to how much time to spend with each prospective client! Read more>>

Adrienne Leigh

Moving across the country & not knowing anyone. Scary right? Let’s add opening a business & building a clientele from the ground up to the mix. Oh! And don’t forget being smack dab in the middle of a pandemic. Read more>>

Dr. Remina Panjwani

I started from humble beginnings in an immigrant family where I broke tradition as the first to pursue higher education and a career in medicine. Amidst a backdrop of limited encouragement and resources, my journey began in an environment familiar with survival mode. Read more>>

Micaela Nauman

In 2011, fresh out of college and fueled by dreams, I set my sights on California to embark on what would become the adventure of a lifetime. With a mix of naivety and excitement, I start my own design business. Read more>>

Jonathan Chia

The first major risk I ever took caused the greatest consequences and placed my life directly into harm’s way. 9-11 took place right after I graduated high school. Already a father right out of high school, in 2006, I left my hometown of Cincinnati, Ohio, and enlisted into the U.S Army. Read more>>

Dr. DaShaunda Turner

First, let me preface my response with everyone takes a risk every day. It is critical to understand the importance of taking calculated risks. In other words, one shouldn’t cut corners when it relates to research and development. Read more>>

Isaac Edelman

The NCAA men’s basketball tournament is famous for its Cinderella stories. In 2023, Florida Atlantic University’s Owls wore the coveted glass slippers, going from complete unknowns to breaking the brackets and winning the hearts of many viewers. Read more>>

Jules Paymer

Throughout my career, I’ve learned that taking risks is the only way that you’re going to move forward. When I first started making music, I wanted my music to be consumable to large audiences, something digestible so that people wouldn’t have a chance to say no to. Read more>>

Renadda Wiggins

Driving from Memphis, Tennessee to Los Angeles, California in one day with no job or place to stay was a daring move, especially after touring with Ebony Fashion Fair, one of the largest African-American tour troops. The journey was a convergence of passion, determination, and the pursuit of a dream. Read more>>

Derek Delson

Filmmaking means constantly taking risks. Merely deciding to become a filmmaker professionally is a great risk. But when there is great risk, there is also great gain. Read more>>

Chris Parvin

In every venture, scaling is a major risk. When we first opened White Rhino Coffee, we were very successful with one location, but I had a strong desire to see us expand. Read more>>

Tyler Peck

When I was 7, I saw an image of “Falling Water” by Frank Lloyd Wright, and decided then and there I would be an architect when I grew up. I stayed the course and pursued it quite vigorously all through high school, and ended up at a very fancy architecture school in New York for college. Read more>>

Frederick Trust

Being the collector of the Wizard of Oz memorabilia for the past 35 years, it was a dream to open the museum one day. My background in software development lacks the necessary skills to open and run the museum. Read more>>

Harrison Noble

I was speaking to my mum recently about how far I had come in regard to my anxiety and mental health and she reminded me of something. When I was young I was experiencing anxiety and was taken to see a therapist, she told me I was so shy I hid behind the chair I was supposed to sit in, too scared to even face the therapist. Read more>>

Destiny Humrich

My career as a tattooer was not something I initially sought out, and I absolutely took a huge chance in pursuing it. When I had graduated college, I was working for a small business as a paint and sip instructor/ bartender, and it seemed to be the perfect post-school plan since it was in a creative field without being too “new” and intimidating. Read more>>

Kari Mirabal

Left corporate American in 2000 to launch an IT Recruiting company. I was pregnant and decided to be a stay home Mom to raise my son. I have been a business owner/consultant ever since. Read more>>

Adrian Taylor

A huge risk I can recall was the decision to pursue a career in Music full-time. Coming from a small college town in South Bend, Indiana, there isn’t much to do when it comes to pursuing music so I had to work various jobs to support my career in music. Read more>>

Thomas Araujo

I started off my adulthood with a truck full of weed, I was your average dealer driving up and down the state transporting. I did this for years until one day I found something called Instagram….and it was there I found the Cannabis Community. Read more>>

Katharine Donovan Kane

There is a book in me, I used to say. But I kept this secret to myself when I was younger. For some reason the idea of wanting to write a book felt scary, impossible to do. Read more>>

Abby Herman

My biggest risk has been starting my own business. And maybe not even starting it, but leaving a very secure (though low-paying) teaching career to grow it full time. Read more>>

Jennie Pyfferoen

I had spent 7 years building my business. I was a busy and well booked newborn and family photographer in Nashville. One day, I saw a family film by Courtney Holmes and it changed everything. Read more>>

Jonathan Rosell

Embarking on a solo career in the music industry was undoubtedly one of the most exhilarating risks I’ve taken. Back in 2014, when my band disbanded, I found myself at a crossroads. Read more>>

Dr. Shawna Eischens

Danceline Moving to AZ for med school Starting my own practice Come back to this Read more>>

William Baker

I really hoped one day to create content on social media that taught people filmmaking. For the longest time, I saw making content on social media as not being a practical way to make money. Read more>>

Sonay Williams

My biggest risk to date is quitting my 9-5 and going all in on my business, Sonay & Co. If you had asked me before if I foresaw myself as an entrepreneur, my answer would have been no. Yet, I quit my consistent and pretty steady job just two months shy of 8 years. Read more>>

Dr. K

It was 2016. We already were producing a village at high times called “Vader village” under the name “the conglomerate”. We had crated brands like: “Paris Og, Vader Extracts, Loudpack, King Pen with the team together. Read more>>

Teddy Tedholm

As an artist, I think it’s all risk. You have to take risks to find ways to put your work out there and you need to take a chance to believe in yourself enough to make it happen. Read more>>

Harmony Montoya

The biggest risk I took in my life was when I decided to resign from the corporate job that I had held for 13 years. I took a leap of faith and jumped right into becoming a full-time entrepreneur, business owner, and Photographer. Read more>>

Andrea Emerson

When I found out I was pregnant with my second child I noticed the impending change in my family life was mirrored by a desire to make a change in my professional life. Read more>>