Tony Robbins says the #1 human need is certainty, but do you know what the second need is? It’s uncertainty. This tug of war between the competing needs of safety and risk are at the heart of so many dilemmas we face in life and for most folks the goal isn’t to eliminate risk – rather it’s to understand this core human need. In our view, the best way to understand or learn is through stories and so we’ve asked some very talented entrepreneurs and creatives to tell us the stories behind some of the risks they’ve taken.

Libby Smith

In 5th grade, I was told by many specialists that I had a very rare eye disease, and I was going blind. It was so rare at the time, they had no idea when — “2 weeks, 2 months, 2 years, 20 years…we don’t know”. Read more>>

Mee McCormick

The first significant risk I took was 15 years ago when I decided to heal the massive ulceration of the total circumference of my small intestines with food. Read more>>

Jennifer Debiaw

I’ve always been a very risk averse person. Throughout my life, I always made safe and easy choices. I went to Texas A&M. It was close to home, but not too close. Read more>>

Thane Zrongo

Every day of my life is loaded with risk just as everyone else’s is. I’m actively choosing to take this question in another direction because I think that it’s important. Read more>>

Chris Lauer

Against the backdrop of a very small (albeit famous) town, I was presented with an opportunity to move from a comfortable apartment into a warehouse that I had been using as a studio space. Read more>>

Katherine Valencia-Burleson

As a teenager and young adult I struggled (understatement) with IV opiate addiction. It was the dark night of my soul. I had tried all traditional rehab treatments until I had no hope left to give. Read more>>

Marissa Rose

Being in the creative industry means taking massive risks. When I was attending college was around the same time I began my modeling career. Read more>>

Hannah Lou Woods

I feel like as a musician or person on a more creative life path you’re always taking a risk, as it’s not always certain what will happen, and certainly there is also some financial risk as well. Read more>>

Claudio Olegario

I moved to Los Angeles in 2023 to further my studies in theater and cinema. Back in Brazil, I had an agent and understood how the Brazilian artistic market operated. Read more>>

John Chaos

Way back in 2006 I had the chance to go over to Europe to visit a friend of mine. I had planned to take my gear with me to perform because I figured it would be a working vacation. Read more>>

Kirby Slager

At the end of 2021, I took a risk interviewing for a position I wasn’t certain was in alignment with my values. A dear friend of mine came to me and mentioned how she felt I’d be a perfect fit for a newer start-up company teaching Breathwork. Read more>>

Crystal Moses

I decided to bet on myself June 2021. I quit my state job and took a leap of faith to start my own business. This has always been a dream of mine, I just didn’t know how it would manifest in my life. Read more>>

Annie Delre

I took a huge risk…it was investing in my future. When applying to colleges, my parents made it super clear they weren’t signing any loans & wouldn’t be able to pay for any of my college. Read more>>

Jennifer Sconyers

The biggest risk that I have ever taken was starting my business. I’ve always known that I wanted to run my own thing. From the age of 15, I dreamed of running an entity where I would sell clothes and shoes for extended sizes. Read more>>

Olivia Martini

Your life is defined by the risks you take. I think for most people the goal is to be comfortable. But I think the best way to be comfortable is to just continue taking risks. Read more>>

Michelle Velan

MV: Absolutely! I’ve taken my fair share of risks. From moving to London to pursuing an MBA, and transiting from one startup to another due to misalignment with the company culture. Read more>>

Nekisha Cosey

I was born in Milwaukee, Wisconsin. As a young child, while my peers desired to be police officers, doctors, and firemen or firewomen, I desired to be a writer. Read more>>

Aprill Williams

Taking risks is an inherent part of being an entrepreneur. It involves making decisions with uncertain outcomes in pursuit of business growth or innovation. Read more>>

Diana Burgess

A few years ago I quit my day job and started pursuing music full time. I had been dreaming of making my own schedule and setting aside quality time to write music, and my decision to prioritize my art felt like the only way forward. Read more>>

Dean Hall

In 2013, three years after the death of my wife, I was losing my battle with leukemia and lymphoma. In my mind, I had two choices: Read more>>

Olivia Thorn

Being a senior at the University of Cincinnati in Spring 2022, I always knew I was passionate about utilizing and developing social media platforms. Read more>>

Kari Lebby

I am a chronic risk-taker. I started graduate school about a month after my father passed away suddenly in late July of 2019. Read more>>

Cassandra Schorn

Oh, I was a shy child. Probably a lot to do with my home life and not wanting to incite anyone’s anger. I don’t know. I was definitely afraid to assert myself. Read more>>

Erica Briganti

I have always had a strong work ethic, but would say risks aren’t something I typically take. During high school, I balanced three jobs while intensely studying ballet six days a week. Read more>>

Jessica Coté

I tried to make the announcement as if it were a completely normal thing to say on a Monday morning. “I’m going to buy two thousand pounds of rocks.” Read more>>

Janae Henebury- DeMello

I knew from a young age I was different. I didn’t make straight A’s like my siblings, I didn’t think of things as simply as others did and I certainly did not know how to sit still or be quiet.. Read more>>

A’lon

Taking risks in anything in life can be considered illogical. But, as for myself. I have something called faith. My faith triumphs logic, and this is because time and time again when I make risky faith-based decisions. Read more>>

Evelyn Jones Reed

The path toward achieving our aspirations can be arduous and filled with obstacles, but I am content with my decision to take risks in pursuit of my dreams. Read more>>

Jeffrey Gomez

My biggest risk was leaving the traditional workforce and a steady paycheck and starting my own business. It was difficult to leave a job where I had health benefits and a paycheck I could count on. Read more>>

Frances Echeverria Logan

Life since 2019 has been about taking risks and betting on myself and my ability to be successful in spaces where I have felt like I was forging my own path. Read more>>

Alisha Spangler

Taking a risk: Without risk there’s no growth. It’s kind of like a cascading effect, or at least that’s how I look at it. My risk is becoming a salon owner which has seen many ups and downs. Read more>>

Steven Schmidt

Taking risks has been a fundamental part of my journey, both personally and professionally. Moving from Michigan to New York City, and then to Los Angeles, were significant risks that involved stepping into the unknown, embracing new communities, and navigating the complexities of the acting world in these vibrant but competitive cities. Read more>>

Jacqueline Duncan

The risk that I took was when I left my 9 to 5 in March 2020 right at the beginning of COVID. I stepped out on faith to do what I felt was my purpose to do here on earth. Read more>>

Selina Li Bi

Since I was a child, stories and writing have been my way of connecting to the world around me. Writing has been a means of expressing myself, a safe place to explore the deep sea of my emotions. Read more>>

Desirée Maultsby

On a hot and humid afternoon in Tucson, amidst the monsoon season’s unexpected moisture, I found myself at a community college gym. Read more>>

Mac Cummings

When I transitioned from Secular music to Christian/Gospel, it was a big risk when it came to making a desirable income. I saw many DJs go back spinning Secular,, or play a variety because of the pay in one genre. Read more>>

Deb Marcelino

I was born in Fall River, a small booming mill city in Massachusetts to immigrant parents from the Azores. I remember how I had to go to a Portuguese bilingual school because I could barely speak a lick of English, Read more>>

Meera Sharma

I’m a firm believer in no risk, no reward. It’s how you view the term risk – a lot of the time it has some negative connotations around it but I believe life is all about making those risky decisions and pushing yourself out of your comfort zone. Read more>>

Nathaniel Alphonse Joseph Landry

I was teaching Middle School Art and two Art classes at southern University as an Adjunct Professor in the Fine Arts department when the Pandemic hit back in 2021. Read more>>

Giavonna Taylor

I decided to start The G’s Knees in 2022 with a rebrand in 2023. While the initial start was a risk in itself, it was the rebrand which made me take risks beyond my expectations. Read more>>

Erin Mavian

After nearly a decade in New York City, I found myself burned out, questioning the industry I was in and unclear on how to grow my salary while achieving greater flexibility throughout the day during my work week. Read more>>

Kanso Ogbolu

I studied Architecture in college because my Dad wanted me to. I had told him I wanted to become an artist and he said, “Artists don’t make money.” And so I decided to become an Architect. Read more>>