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.

Quanaisha Stafford

The most significant risk I’ve ever taken was when I dropped out of school to pursue my art. I already received a degree in Interior Design but wanted to further my education and get a degree in Fine Arts. By the time I got into school, I was already emotionally drained by college. Then COVID happened, and going to school was hard. Between trying to keep my job and trying to attend classes, it was a lot. Read more>>

Jennifer Richardson

After serving as a news anchor for a fulfilling 15 years, my life took a new turn when I got married and started a family. Balancing a thriving career with the desire to be a dedicated and present mother became a constant tug-of-war within me. However, when the COVID-19 pandemic emerged, it presented a unique opportunity to take a leap of faith and embark on a new venture. Read more>>

Dr. KayLa N. Allen

The biggest I have ever taken was believing in myself. You see, while I have always known of my purpose and passion in helping others, I didn’t have an example or a place to turn to for all of the perfect answers to make things come to life. I wanted to do something that made me truly happy while sharing my experiences to help others. Everything that I have now started with doing something I love – writing. Read more>>

Kathleen Joy

As a seasoned advisor to senior leaders, I’ve always found joy in unlocking new perspectives and possibilities for individuals and teams. My career, centered around optimizing leadership and team performance, has been fulfilling. Yet, an inner calling for creative expression led me down an unconventional path. About 11 years ago,I began experimenting with interactive art installations. This wasn’t just a hobby; it was a quest to explore how different worldviews can aid in personal discovery and transformation. Read more>>

Tracy Green

I grew up in a southern city in Louisiana as a black female child and the victim of long-term sexual abuse. In my community, most people know the goings on in the neighborhood, but few addressed or confronted it. While I was repeatedly told and reminded that “we don’t talk about family business outside the home”, no one prepared me for the teasing and taunting of my peers in the school yard. The devastation and trauma of my existence seemed unending. My identity became what I felt about what was happening to me; shame, guilt, and anger. Read more>>

Autumn Fawn Carrillo Morrison

Risks are the foundation of success. I like to think of myself as a calculated Risk Taker. I remember a singer’s mom once asked me to coach her daughter on becoming successful as a singer. The first thing I told her is to get comfortable taking risks. Start small. When I was living in Toronto working at a corporate job in administration, a LONG way from my dreams in the arts and entertainment, I noticed that I was standing in the middle of the platform waiting for the subway. Read more>>

Brandy Ange

I decided to publish my first book a few years after I graduated from college. I had a full time 9-5 job and some other side gigs, just trying to pay down student loans. I was overworked and miserable since none of my jobs allowed me to really be creative. I realised that I had settled for plan B before ever even trying plan A. Read more>>

Steven Tummino

Our Biggest risk would be starting our business. I was a full-time college student at the time and David was a full time retail manager, we didn’t necessarily have an immense amount of free time but we had a love and passion for nature and ways to bring it into our home. We found ourselves spending all our free time perfecting our own space exploring the outdoors and bringing it into our design. Read more>>

Judy Benitez

Starting my small business was a risk that has changed my life tremendously for the better. The idea of being my own boss and seeing where and how far my business can take me did startle me to begin with, but the progress I’ve made since then has made me grateful for where I am now. In the beginning of it all, I was laid off of my previous job due to budget cuts during the pandemic in 2020. Read more>>

Gina Kitzmiller

Playing small. It’s something I’ve done for most of my life. It was a way to stay safe and not rock the boat. Read more>>

Stephanie Kirkland

I spent 10 years building a career in communications. As I moved up in my organization, my role became increasingly revered and more lucrative. And yet, something was missing. Most people might “stick it out” and finish the career they started, but I chose a different path. I took a risk and decided to take a step back from building that career, and instead I followed the path that my heart had always called me—art. Read more>>

ALICIA DUGAR STEPHENSON

Climbing the corporate ladder after college got real scary when I realized I no longer felt inspired. I had pushed through the daily struggles of being diagnosed with lupus, just to make other people happy. I was NOT happy with my life, even though I had liquidity and a benefits package. Every day I would have a fight with snooze until I couldn’t fight it any more. I realized I needed to help people like yoga helped me. Read more>>

Elisabetta Marzetti

In my life, I haven’t always been a photographer. Initially, I was a high school teacher of Spanish language and culture. However, alongside my teaching career, I discovered a passion for photography. After five years, I made a pivotal decision: photography would be my life. This meant leaving my permanent teaching position and opening my own business with zero clients. I sold my car and used the money to buy my first camera. Read more>>

Tyler Bradley

Taking the biggest risk of my life, I quit my job to travel internationally. I’d reached a point where I equated my self-worth with my job, and it wasn’t bringing me authentic joy. I knew that I had to do something big to break me out of this cycle. However, it wasn’t any easy decision and took me about 1.5 years to decide to actually do it. While contemplating taking the risk, I spent various therapy sessions discussing my fears which included: Read more>>

Federika Cariati

After living abroad in Mexico for over a year, I returned to Arizona at the end of a work contract. I found myself staring into what felt like a vast open space, unsure of the direction I should take in my life. I had been feeling the call to pursue ceramics more seriously but was grappling with daunting limiting beliefs, particularly imposter syndrome and fear of failure. Read more>>

Voodo Fé

I love the ball in my hands with 3 seconds on the clock. The won’t always go in, yet I’ll never be afraid to take the shot. I’ve taken huge risk in business, relationships and personal decisions, yet the one that most important risk I’ve taken was deciding to quit drinking 10 years ago. I had my first drink at 12 and turned into a serious problem. It was connected to a fake confidence, fake self and fake version of me. Read more>>

Tatiana Johnson

Generally I’m not a huge “risk taker” but right after graduating from Hampton University, I took a bold step by moving to Los Angeles to pursue my dreams within the entertainment industry. At that time, I was working as a Pharmacy Technician—a stable job but not aligned with my passion. Heading to LA felt like a risk, driven by the belief that I’d dive into the industry alongside my aunt on a film project. However, when that plan fell through, reality hit hard. As I chased my entertainment dreams, my student loans chased me for payments. Read more>>

Gary Watkins

I was bouncing job to job to find a stable enough income that can maintain my lifestyle and responsibilities as a young adult. Eventually I found a job that paid good for where I was in my life at the time. But it wasn’t something I wanted to do long term. I started my brand/ business after I finish school, while I was still working at the job. Read more>>

Ryan Brown

Starting a new music project at 40 years old is pretty scary. I could share about that and my experience as an older artist just starting out on a new project. Read more>>

Rahkii

Embarking on this musical journey as a black female artist and mom has been a profound risk, but one that I embrace. Being a mom is my greatest joy, and it’s a huge part of my identity that I’ll never compromise. Stepping into the world of music, an industry known for its challenges, means facing potential scrutiny and breaking through preconceived notions. Juggling late-night studio sessions with early mornings tending to my family, I’ve learned to navigate the balance between pursuing my passion and fulfilling my role as a mom. Read more>>

Serotonin

Being an independent artist, alone makes your whole career a risk, everything you create, distribute, and market is all up to your strength, resilience, and belief in your material. Not having a budget, a label, a “team” could have discouraged me but the right one will come, I’m sure of it.. for now I realized I have my own path to pave and there’s nothing wrong with flying solo for a while, there’s actually a freedom in creative direction which is the most important aspect to me in this career next to the completion of material and the ability to eat after a release and an appearance ya know. Luckily my family has been great support, and always motivates me to commit to and continue my journey… Read more>>

BARBARA SHARPE

In my opinion the decision to become an entrepreneur is one of the biggest risks anyone can decide to undertake. For me the decision to transition from a full-time position to one involving the navigation of a landscape of uncertainty is truly a risk. One that not many people are willing to take. Read more>>

Porchel Threadgill

Leaving the stability of my 9-5 job was a pivotal risk in my entrepreneurial journey. Fueled by a compelling vision, I envisioned a venture that aligned more closely with my passions and aspirations. The decision stemmed from a desire for freedom and the pursuit of a greater purpose. It involved meticulous planning, weighing potential challenges, and crafting a strategy to transform my vision into a reality. Read more>>

Gina Luker

I hired a biz coach a few years ago that convinced me I’d never be truly successful unless I leveled up my life in every way. Read more>>

Jennifer Butler

It's intriguing to contemplate this question as I reflect on the numerous risks I've taken in my life. Some of these risks have proven successful, while others haven't panned out as well. Read more>>

Chonies

My life changed in 2020 along with the rest of the world. Read more>>

Rebecca Chiara Marano

I honestly think I’ve lost track of the number of risks I’ve had to take over the course of my career, but I think that just goes to show how important it is to be a sensible risk-taker when it comes to pursuing a creative career. In fact, I’d say my biggest risk was just deciding to pursue my career at all! Even though I’d been a performer from a young age (musical theater, film, dance, circus arts, etc.), my family always wanted me to go to medical school and become a doctor. Read more>>

John Maisano

I’ve designed Museum exhibits for the past 34 years for Yale Universities Peabody Museum, The Texas Memorial Museum at the University of Texas, and the Jackson School of Geology at the University of Texas. I’ve always worked day jobs even through college. Read more>>

DeAndre Cooley

Backstory; Read more>>

Bamboo Hu

My whole life is a risk, every step that I chose to walk was unusual, compared to the other peers. Learned piano and violin when I was just a little kid, and then became a hard-working student again, tried to go to the best film school in China but failed, decided to work very early then quit when I had a good chance to promote, and became a hard-working student again. It’s kind of like fate that all the decisions that I make unconsciously influence my life path, and I never regret it. Read more>>

J Luis SF

A couple of years ago, I took a giant leap: I immigrated to the United States without knowing English very well. In Lima, Peru, I already had my own space as a tattoo artist, with loyal clients and a studio that felt like home. But I felt the need for a change and to challenge myself. Read more>>

Raul Rodriguez

I don’t know what my life would have been like if I didn’t take the risk. To me, the risk was leaving my job and betting on myself. Luckily for me, I had sort of a plan. In hindsight, my plan was weak at best. We all would love to leave a job for a career but if you are not ready to sacrifice and put it all on the line I suggest finding people who have made the transition successfully and even those who have failed and learn as much as possible and let them be your mentors. Read more>>

Jinny Wong

As an actor and performer—We take risks every day. Every time we make choices in an audition, everytime we choose to reach out to a casting director or agent, we risk rejection and being misunderstood. The key is to not think of it as taking a “risk” but to see it taking a leap of faith. Read more>>

La’Tara Jackson

Something about working for others has never felt right to me. It wasn’t that I wasn’t a good employee, rather I always seemed to be the little trouble maker. This was no different, but only this time I was working for myself under the leadership of someone else by way of network marketing. The thing with network marketing is, you want to find your people, your distinct soul tribe. Read more>>

Rashad

People don’t understand the true dedication it takes to stay in the game. I’ve taken risk beyond my financial bracket and even beyond the tolerance that others have for me while watching me take them. To be creative is risky within itself because there is no guarantee that those you present your creativity to would approve of it or not. The biggest risk so far is still going after what I want after seeing so many lose faith in me. Read more>>

Lori Allen

The largest risk I have taken in my career is leaving my position at Wolfson Children’s Hospital to open a private practice. I was the clinical lead for speech-language pathology for outpatient pediatrics, an Epic credential trainer with Baptist, and a well-established clinician with Wolfson Children’s outpatient rehabilitation for almost ten years. I had created a solid position with steady clientele and was highly valued. Read more>>

Laura Pierpont

I took a pretty big risk putting together a weekend workshop for my passion project turned company. And it was not easy. Read more>>