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.

Audrey Payne

About 10 years ago, I seriously injured my spine during a group exercise class at the gym. I had always been an active person, but this injury swept the rug out from under me and forced me to slow way down. I had to quit running cold turkey, which was my daily meditation, as even the most mundane, low-impact activities caused tremendous pain. Healing took years and included various medications, physical therapy, a spinal fusion, and a whole lot of waiting. Read more>>

Amanda Jennings

When I decided to leave my full-time job to pursue real estate full-time, it was one of the most significant risks I’ve ever taken. I had a stable career, a steady income, and the comfort of knowing exactly what to expect each day. But deep down, I knew I wasn’t completely fulfilled. Real estate had always been a passion of mine, something I’d dabbled in on the side, but I felt the pull to make it my main focus. Read more>>

Alex Ricciardelli

My biggest risk, walking down the street with gallon of Orange Juice! Ha! Just kidding. Rewind to a time when being surrounded with your family or friends was a “risk”. I was laid off from my job and it took me years to get that job as a I.T Consultant so I was very discouraged because it was going to be impossible to get another job especially during the pandemic. I ended up doing what I do best, fixing computers and buying them off the internet then reselling them online and locally. I realized stores would open back up soon and knew it would be a lot harder to survive off of this. I started doing website design for local landscapers and start up companies.  Read more>>

Joseph D. Mcqueen

With anything in life, you have to take risks. Whatever path you’re on, at some point or another, you will be presented with an unkind decision to make. In my life, I have been presented with too many crossroads to count. Life-changing choices that would ultimately alter the course of my career and vision for my life. When looking back at the gambles I’ve taken, perhaps the most obvious one would be choosing to study in the US over the UK. After spending my entire upbringing and life in England, I never really considered the possibility of branching out beyond the areas I’ve always known. Read more>>

Vicki Bartel

For a decade, I was deep in the world of wedding photography, capturing those unforgettable moments and thriving with a steady stream of clients. The income was fantastic, and I had established a solid reputation. But then, I dipped my toes into lifestyle brand photography and felt a spark. Helping female entrepreneurs tell their stories? That lit me up like nothing else. Weddings started feeling too stressful, and I craved flexibility, more family time, and honestly? A new challenge. Read more>>

Cherylyn Lavagnino

Being an artist always involves risk taking. One is constantly putting oneself on the line. In order to make interesting work an artist must be vulnerable and willing to share aspects of themselves that are deeply personal. Our work is constantly evaluated by others – sometimes appreciative and sometimes otherwise. As a result the goal for me has been to stay deeply involved in my creative process and to try to push myself past comfort into unknown and often places that cause me to feel insecure. I am willing to do this in order to make a work that I value and is hopefully fresh and compelling to others. Read more>>

Dejah Gomez

At the age of 5, I took the risk to use my voice to sing. I knew from the moment I witnessed a mother daughter duo singing at church, that I too, would one day be brave enough to sing my heart out for all to hear and feel. Read more>>

Johnny Bermudez

From Wall Street to NFL Agent to Hollywood and Beyond Reflecting on the pivotal moments in my life, transitioning from Wall Street to becoming an NFL agent, and eventually an actor and producer, stands out as a defining chapter. This journey also included a significant move from Brooklyn, New York, to Northern Portugal. My career began in the fast-paced world of Wall Street, but I soon felt a pull towards something different. Driven by a passion for sports, I became an NFL agent, initially working for a big agency before striking out on my own with Clint Hart, the Free Safety for the San Diego Chargers—very much like Jerry Maguire(ish). Read more>>

Kai Watson

Risk #1 I’ve worked in corporate america as an Executive Assistant for Fortune 500 companies for 20+ years, while fighting my passion for the beauty industry to do what was deemed “safe” amongst my family. At the age of 42, I took a leap and decided to go to cosmetology school. I did this part time in the evenings after my shift was over at my full time job in corporate. Scared and feeling alone, because out of the entire school there were two other women in my age bracket and one of them did not continue. Most of the people there were fresh out of high school and most in their 20’s. Read more>>

Sabrina Campa

A significant risk I took was the decision to pivot from being a mixed media artist to diving into the world of esthetics and eventually opening my own business, Dark Joy. My artistic journey started with various forms of creative expression, from painting to aerial dancing. Each medium allowed me to explore and expand my creative boundaries. However, I found myself seeking a new outlet, something that would allow me to blend my love for art with a more personal and transformative experience. Read more>>

Kindle Thompson

I have taken many risks in my career. One of the biggest I’ve made this year is booking myself for three fashion shows in one month, Oklahoma, KC, and New York. I will be beyond busy, but that’s a sign I’m going somewhere as a model. Read more>>

Layla Mayeline

Taking the leap to leave a stable job in retail and pursuing something uncertain was one of the most significant risks I’ve ever taken. For years, I had a secure 9-to-5 job working at a retail store. It was comfortable, familiar, and provided me with a steady income. But deep down, I knew I wanted more. I had a growing passion for graphic design and content creation, and I realized that if I didn’t take the plunge, I might never have the chance to build something of my own. Read more>>

Charente Carr

So, I’ve always been passionate about writing and connecting with people. When I was just 14, I started a YouTube channel to share my thoughts and find a community. It was a way to escape reality during a tough time when I was in and out of the hospital. Unfortunately, life got in the way, and I had to put my channel on hold to focus on school and career. Fast forward to 2020, the pandemic hit, and I lost my best friend/sister. It was a huge wake-up call. I realized life is short, and I needed to chase my dreams. Read more>>

Qicheng Wu

I used to work full-time at an eco-friendly fashion company in Shanghai, China. The income was decent, and I generally enjoyed the work. However, after the terrifying COVID-19 lockdown in Shanghai, I decided to quit my job. The reason was pretty straightforward, even a bit naive: I needed to find my own sense of self-worth, and I believed that creating something I truly cared about was the best way to achieve that. Read more>>

Tina Padilla

I am a system impacted individual, and when I returned home, I saw things different. My Life was different, my community was different. I knew I would struggle to find work because I now had a record. I took a huge interest in my community and saw they were hurting, and lacking hope and resources. I then went into action, not even caring if I would ever get paid for helping my community, I just wanted to help, in any way possible . Read more>>

Tai Woodville

A few years back, I was invited by a fellow Portland artist, drummer & songwriter, José Medeles (the Breeders, 1939 Ensemble), to perform at an experimental art event, “Deep Happening.” He asked me to read poetry and dance. While I have a background in poetry, dancing was a risk. I have no dance training, just a later-in-life fascination with movement. Read more>>

Dilleen Marsh

WHY I SAID YES TO DOING A GRAPHIC NOVEL: In October of 2016 I drove from Utah to Barnstead, New Hampshire with my daughter and a friend. My daughter had auditioned and been accepted into a theatre group that was run by Kati Preston and her family. For only a brief moment, on the day that we dropped off my daughter, I met Kati Preston in person. Sometime during 2017 she called me. My daughter had acquainted her with my Instagram and the conversation ran something like this: Read more>>

Mariah Eaves

My husband and I started the very first escape room on the Central coast of Ca in 2015 a few months after we got married. At the time not many people had heard of escape rooms and we went to one in LA. On the way home my husband said “I bet we could make one of these.” To which I responded, “I bet you can!” After 6 months of building and self funding on our personal credit card we opened our doors and it was a huge success! We built a total of 4 rooms in 2 locations and happily sold it at the end of 2017. We’re happy to report it’s going strong and still known as the best escape room around! Read more>>

Kelly Poquiz Burke

I never expected to become an entrepreneur. Being raised by immigrant Filipino parents, having a stable job and prestigious title was the quintessential ‘American Dream’. By those standards, I had “made it”. I had an MBA from a top 20 business school. I was a Director of Brand Marketing. I was the primary provider, and my husband, Michael, and I had just built a brand new home for our growing family. However, there was one problem. I was chasing the wrong dream. Read more>>

Dj Hustle

Juggling three jobs and heading to auditions was my way of life for years, It was the life of a striving actor. Driving across town to call backs on my supposedly lunch break that rarely got me back to work in an hour. I started booking commercials that place me at a crossroad. One choice was to continue this hectic lifestyle and the other choice was to take a leap of faith to dedicate my life to acting. I chose the latter. So I quit my job and focused on acting full time. Read more>>

Amy Pusakulich

From the time I was a young child, I knew that I would grow up to work with children and families in need. I was the child who sat with the bullied kids, stood up for them, and lifted them up until they could stand up for themselves. On my first day of kindergarten, I was featured in our local newspaper because another child, who was terrified of starting school, stood frozen on the sidewalk sobbing. I had already bounded up the steps with a “Let’s do this!” attitude, but quickly pivoted and returned to take the crying child by the hand, told them things would be fine, and guided him into the school. Read more>>

Antonia Gambrell

For 19 and a half years I owned a beauty salon name Antonia’s Full Glamour Salon in east memphis, where I created a place of booth rental employment for over 35 individuals in that time span. I always wanted a Salon/Spa where you could get a variety of beauty services all under one roof so in 2016 I took a leap of faith and opened up SUGAR’S Hair Gallery and Spa in Collierville TN. I sold my old beauty salon(Antonia’s Full Glamour Salon) with 6 booth renters and opened up SUGAR’S. Read more>>

Marco Yanez

The biggest risk I’ve taken was my decision to pursue the sports creative industry. I didn’t grow up knowing I wanted to be a videographer for a soccer team my whole life. I truly stumbled upon the sports creative industry later on in my life than others. For me, I would say if I hadn’t had taken a risk on myself to take that first opportunity to put my foot in the door then I would have very much have regretted it. Read more>>

Lacie Doll

When I was in my twenties I served in the U.S. Navy. I had a very serious job, one that left me depleted at the end of the day and didn’t add to my quality of life. Even though i knew the work I was doing was important i wasn’t very fulfilled. I made the decision to transition back to civilian life, when given the chance to pursue happiness and figure out what my dream really was. Since then I have found my passion and it’s story telling. I have produced over a dozen shows and movies, written three books, launched my own production company and audiobook distribution company. It took almost a decade to complete all of my goals but I have found my quality of life. Read more>>

Madison Grissom

Madison’s Journey: Embracing Risks and Growth My name is Madison Grissom, and I’m 25 years old, born and raised in the District of Columbia area. My story is one of taking risks and embracing growth, starting from my early modeling days. The Beginning: SYEP Program I began modeling when I was 15, through the Summer Youth Employment Program (SYEP). This experience ignited my passion for the industry and gave me a taste of what could be possible. The Big Move: New York City The most significant risk I took came when I was 18. Fresh out of high school, my mom, who has always been my biggest supporter, told me to pack my bags one summer day. Read more>>