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.

Myesha Thompson

I finished my master’s program in Spring of 2019. I searched for months for a job in my field, ideally a Wellness Coordinator or some type of Health Coach for a company. When I finally started getting interviews none of them worked out. At the time I was at a job where I was unhappy, underpaid, and not even working in my field, I was fed up! Read more>>

Michael Torres Jaimes

I moved to LA to follow my passion to become a personal growth spiritual leader. I struggled with finding jobs to make ends meet. I’ll be teaching personal empowerment classes for free. I drove Uber and saved my money because I wanted to take more advanced trainings. When I had saved up enough money to take the trainings I crashed my car at the same time was asked to leave the place I was staying in. Read more>>

Shannon Beshears

I knew I wanted to pursue a career in a creative/artistic way since I was very young. However, being from a small town in Illinois, I was surrounded by people who told me my dreams were impossible and even delusional. Quick cut to me being nominated for an Emmy this year for my stunt work on Stranger Things Season 4. Read more>>

Danielle Connolly

Becoming a content creator and posting publicly online felt like a risk for me because I was never actually a social media person. I dabbled in tweeting for a few months in high school, but besides that, my Facebook had a profile picture updated every few years and my (original) Instagram stopped posting new pictures after a few months. I’m a certified meme queen, so I kept the accounts to keep up with the latest in pop culture, but I never had the urge to post. Read more>>

Sequena “Queen” Alexander

In my journey, relocating to a new city sparked my realization of the untapped potential for up-and-coming black and brown artists. Witnessing this need, I founded an art gallery to provide a platform for these talented individuals, offering them an avenue to showcase their work, engage in artist talks, and market their exhibitions. My vision extended beyond the gallery walls – I aimed to cultivate a community where artists could build their brand and following. Read more>>

Aaniya Asrani

If you consider risk to be taking on the unknown, uncertain and/or unexpected – I’d say I’ve made some pretty risky choices in my life. Read more>>

Robert Gomez

Taking a risk is a lot easier than said. Taking a risk means you have to be prepared to take a chance to fail, to succeed, to make bad investments, to make a shim of a positive investment, to get out of your comfort zone and elevate your ways of thinking, to be misunderstood while being understood at the same time. You have to be willing to go that extra mile that the next person wouldn’t dare risk and that’s how you know you made a difference. Read more>>

Cynthia Agyeman-Anane

I was one of the lucky ones that received a job out of my undergraduate social work program. My employer helped me pay for my graduate education and I received my MSW shortly after. To my immigrant family, I was the “good daughter” making certain all their hard work and dedication had paid off and that their dreams had come to fruition. To my family, I was in a good and stable situation personally and professionally. Read more>>

Jordan Hauger

My first year in my nursing career is when the pandemic started which was a challenge I, much like the rest of the world, was not prepared for. I was working on an in-patient psychiatric unit when it started and I was on a specialized unit for eating disorders and malnutrition when the pandemic began to be somewhat managed. Read more>>

Nunu Hung

I come from a family of educators, which in Taiwan is a secure form of government employment. But in 2014, after five years working for art dealers in New York and Singapore, I decided to open my own gallery in Taipei. I took a 2000 square-foot space and started showing both international artists and emerging Taiwanese artists. Read more>>

Anna Blake

The risk was not my decision. I was born on a farm and my first words were “I’ll do it myself.” My mother’s health was such that she didn’t want me underfoot and farmers are lousy babysitters by definition, so I spent my days running wild with the animals. My first babysitter was a tall gray mare. They put me on her back when I was in the way at sheep-shearing time. She was too tall to jump from, and she only walked no matter how I kicked. She had a dicey reputation, so naturally, I thought I was special. Read more>>

Casey Engel

This year, I took a significant artistic risk with my quilt, “Shutter,” which was featured in a group exhibition at Blue Spiral 1 gallery in July. Initially constructed from scrap white, cream, and gray fabric, the piece felt predictable, with the focal point being a densely stitched shutter. Dissatisfied, I decided to bring it home and dye it a rich teal forest green. Read more>>

Shaunic Stanford

I felt called to be a writer in 2011. It couldn’t have come at a more inconvenient time as I was finishing up my doctorate in physical therapy. My first thought was, really? I would have gone to school for my MFA instead had I known. Nevertheless, I listened to the small voice, began researching how to write a script, and slowly started working on my first feature film. Read more>>

Ashley Ambrosio

Life’s journey, with its inherent risks, is much like molding a piece of clay into a work of art. Read more>>

Alexis Floyd

My decision to pursue photography professionally was a huge risk for me. At the time, I had just moved back home and was starting my career from scratch. I always had high expectations for my life, but I needed a clear plan or outline for achieving them. I’m an artist by nature, and working in any field that doesn’t honor my artistry is soul-crushing. Read more>>

Brielle Gibson

Hello, I am Brielle Gibson and I am a newly influencer/content creator. I took a risk and began consistently influencing in the summer of 2023. I started working at JusTini’s and my boss made a 30 day bet with my to post on the media consistently, no matter the content just post. Read more>>

Karen Bowersox

Back in 2018, my late husband Rob came to me with the idea of Major League Eventing. He wanted to highlight the sport of Eventing and find ways to highlight everyone’s story. At first I thought he was crazy but then the idea grew on me and then we started the Major League Eventing podcast where we would interview riders from up and coming to Olympians and everyone in between. It was a slow start at first, but now we have listeners from all over the world. Read more>>

Jarrod Royles-Atkins

The biggest risk I took was going to LA with no friends or family or contacts in the whole country! I was set to be a part of a learning experience with composer JunkieXL, learning the industry and how to be a top tier composer and assistant for Hollywood movies. Read more>>

Krista Hawkins

The first part of my professional career was spent as a counselor. First, in outpatient addictions, helping young adults recover from addiction, and later, in the field of adoption, guiding prospective families and birth mothers through the adoption process. Read more>>

O. Victoria Lakes-Battle

IFF agreeing to administer Chicago’s Cultural Treasures (ChiTreasures), while really exciting, was also a big risk as it’s a departure from what we have historically been a part of. IFF plays many roles in community development, but grantmaker was not one of them. Read more>>

Meg Ten Eyck

My entire career trajectory has been a risk. The story of EveryQueer starts when I decided to leave a lucrative job, the city I love, and move to another country on a whim. I went from New York City, to Seoul, South Korea without knowing anything about Korean culture. I plunged head first into expat life, travel, and eventually building a brand I love. Had I not taken that risk, my life would be radically different today. Read more>>

Paige Parrucci

From early childhood on, like most musicians, I always knew I wanted to pursue music in some way or form. My parents put (forced), me into piano lessons at age 8, where I unwillingly learned that piano was pretty fun to play once you got the hang of it. When middle school came around, I had to find a way to cope with the inevitable friend, boys, and raging hormone issues. Read more>>

Brooklyn Buzzy

I actually have a really good example of when taking a risk paid off. I was recently commissioned to paint a mural on the outside of a very cool bar called The Springs in Greenpoint, Brooklyn (NYC). I was equal parts terrified and excited. I had never painted a mural before and I had no idea how to begin. There were so many unknowns, how much paint I would need, what supplies to get, will there be people watching me, how long will it take, what if I have to go to the bathroom, etc. Read more>>

Hope Schwing

I grew up in a very small town in central Minnesota. Everyone knows everyone. We even had “drive your tractor to school” day believe it or not. I lived within a 30 mile radius of my hometown until I was 23 years old. I had never lived in a city with more than 5,000 people. I realized, with the help of my agency, that if I wanted to be as successful as I can be, I needed to move. Read more>>

Lanie Hobbs

Taking the plunge into podcasting and co-founding a festival centered around the True Crime and Paranormal Community has been one wild ride. When I started this journey, I had no clue what to expect. It’s been a rollercoaster of excitement, challenges, and unexpected turns, but boy, has it been worth it. Read more>>

Andreea Bodnari

As a serial entrepreneur deeply entrenched in the realm of business risks, I found an unexpected intersection between my startup ventures and my artistic pursuits. I believe in the power of user testing, even within the domain of my creative expressions. For me, art is not just a personal indulgence; it’s a service to the people, a means to comfort the disturbed and disturb the comfortable. My artistic journey is a quest to convey a universal truth that resonates with a diverse audience. Read more>>

Felicia Jackson

In the quiet corners of my mind, a spark ignited—an idea that had the potential to redefine life-saving practices. CPRWrap, my brainchild, wasn’t just an innovation; it was a vision to transform emergency response and empower individuals to be heroes in critical moments. Read more>>

Jennifer Sims

I was deep into my career as an ad agency producer – I was actually the Director of Broadcast at an agency here in Los Angeles when I decided to give my two-week’s notice and quit my job to pursue a voice over career, full-time. I did not have a “plan B,” other than to freelance as a producer/project manager while pursuing voice over. Read more>>

Jaylon Young

Just as an artist, calling yourself an artist is risk. i feel like there’s so much pressure put on the name “artist” What makes you an artist? how much you practice? how much pain, or joy you have that your art reflects? Where does your art come from? is it internal or an external place? is it both? is that place valid enough to call it art? is it good enough for you? is it good enough for people? is it good enough for others to call and see you as an artist? Read more>>

Zā Harris

Do not be afraid to take those risks. No, not the ones that make you look over your shoulders. It’s always a better way. The kind of risks that you use your last on, the “not knowing what will come next” or “will this plan even work?” kind of risks. You will never know what is in store for you until you make that jump! Read more>>

Alfonso Petersen O’Farrill

I always dreamed of working in a prestigious animation studio. While still in Mexico, I applied for the Fulbright Scholarship, designed for individuals outside the US to pursue a master’s degree in an American university of their choice. A few months into the application process, I secured a six-month internship at Buck Design, a top-tier animation studio known for innovation. Read more>>

BJ Seidel

Sometimes, the best idea comes from someone else. I like to travel and see new places. It is exciting to try new activities like caving, climbing and scuba diving. Each of those involve risk, but putting my art out there on my website or at a public venue is much harder for me. Read more>>

Nikita Francois

The biggest risk I’ve taken is relocating from NY to Los Angeles in 2017. I found myself at the proverbial crossroads in my life. I could either continue working my “regular” job and live a comfortable, predictable life, or I could take a leap of faith and pursue my acting career with a fresh start in LA. While the decision wasn’t easy, it has been the most profound and amazing choice I’ve made for my life thus far, and I wouldn’t change it for anything. Read more>>

DeQwan Young

I moved to California at the beginning of the pandemic with the intention of finishing my MFA in Digital Cinema and starting my career in Hollywood. I moved here with $3,000 and my two cameras. It took me a lot of time, work, and self-confidence to even show people my film, let alone finish it. After three years, I’ve completed the degree, and continued my journey in this industry, with the hope of improving with each project. Read more>>

Jakeena Geobani

Having a career and stability in life is something that has been preached to me since I was a young child. Getting a job, doing well in said job, making your mark and living a good life were the golden rules to be significant in this world. So, I did just that and held a job since the age of 12 years old. When I was 24, I landed an amazing position with a telecommunication company and worked there for almost two decades holding several roles, was able to travel throughout the United States and abroad. Read more>>

Sean Kurtz

In the spring of 2021, life seemed to be closing in on me from all sides. I was working a job that was not very stable. To add to the tension, my wife had just been handed laid off from her high-paying job. We were now a family with two small children, dependent on my sole income, and the prospect of uncertainty loomed large. Read more>>

Otez Gary

It’s hard to pin point on one story. I can tell you the start of the risks that were taken was when I moved to Chicago almost 14 years ago at 17; first time being on my own; first time feeling free, first time having to figure it all out. The reason to take any risk is to live. If you are afraid of taking a risk then you won’t know how to live a full life. Starting project, reinventing oneself, going to a different career and so on, all of it has risk attached to it. It’s something you learn to accept and understand. Read more>>

Nir Guzinski

About 10 years ago, I was working full-time in Marketing and pursuing acting by taking workshops in the evenings and weekends, reading acting/technique books, watching movies, doing theatre and immersing myself in anything related to acting, in the hopes of imrproving my skills, gaining visibility locally, in the hopes of being seen by industry professionals and getting opportunities to showcase my skills (i.e auditions). Montreal is a small community and with a small amount of casting agencies and getting your foot in the door can be frustrating. In addition to that obstacle, Back then, the technology wasn’t as accessible and so making short films or creating videos was a challenge. Read more>>

ACQUAETTA WILLIAMS

I grew up in Los Angeles, California, the only girl with 5 brothers in a Black American family. My parents offered my brothers the military for direction after high school; me — the local community college. Life at home was ruled by an authoritarian father and communication was poor. I had high energy and was full of enthusiasm and extremely optimistic about life. Read more>>

Jodi Peltier

There are many things that motivate people inasmuch discourage them. There are risk-takers and those that are risk-averse. Sometimes, a person’s motivation may change a more natural risk-averse individual into more of a risk-taker. I think that’s where it began for me. Read more>>

Carol Chan

In 2021, I took a big risk by quitting my job to chase a long-held dream with my partner. This dream? To travel nomadically abroad while pursuing full-time entrepreneurship. At that time, I had started a brand studio on the side dedicated to helping creative women entrepreneurs with brand strategy and design. Read more>>

Bess Lovern

The risk of starting a business is always challenging and nerve-wracking. I think if you would have asked me when I graduated University of Virginia if I would be starting Bess Lovern Designs, a full-service interior design business, by now, the answer probably would have been no. I always knew that I had the entrepreneurial spirit, but what really changed my timeline was my work experience. Read more>>

Brandon Zellers

My journey started back home in Kansas City, Mo. I woke up on August 22, 2019, extremely hungover, hopeless, and ultimately defeated. I knew I needed a change in my life and alcohol was the root of my problems. I began my sobriety journey on this day and on August 28, 2019, I packed a bag and hopped on a one-way flight down to Florida seeking clarity and mental stability. Read more>>

Lucia Flors

Starting Siesta Co. was a significant leap for Carlos and me. We were both established in our medical careers, comfortable in our routines, but we felt a deep longing to connect more with our Spanish roots and share that part of our heritage with our new home in the US. Read more>>

Ashley Burt

Starting a small business is a big risk. It is scary and intimidating however, it is also completely worth it. I left my full time job as an assistant underwriter to pursue my dream of jewelry making. I spent several years working at festivals and craft fairs as a vendor before I had the opportunity to open my brick and mortar location in Clinton,TN. It was exciting as well as intimidating to open a retail shop and I wondered if I had done the right thing by leaving my job in insurance. Read more>>