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.

Eva Metz-Tolliver

The biggest risk I ever took was my move to the United States – and it wasn’t even planned. I came to this country in my twenties. At that point in my life I was enrolled in college in Munich, Germany, pursuing a degree in business administration. Read more >>>

Nina Piccini

A few years ago, I made a decision that, on paper, didn’t make a lot of sense. I walked away from a steady corporate marketing career — complete with the stability, benefits, and predictability that most people aim for — to bet fully on myself. At the time, I was feeling deeply out of alignment. Read more >>>

Mazi Visualz

In June 2025, I chose to take accountability for my past by turning myself in to authorities for several outstanding warrants. During that time, I made a personal commitment to transform my life and focus on something positive. Read more >>>

Santanna Martin

I’m going to start by being blunt: I’m a woman. This may not seem like such a big deal, except that I own an engine shop. Entering into this industry was terrifying. Read more >>>

Rashida Hughes

The Risk That Led to My Purpose One of the greatest risks I’ve ever taken was walking away from a stable, full-time job in downtown Chicago to follow a passion rooted in both pain and purpose. I am a 20-year survivor of domestic violence. Read more >>>

Carol White

For me, just calling myself an artist felt like a risk. I don’t have a fine arts degree. I didn’t go to art school. I’m mostly self-taught—learning through trial and error, late nights, and a deep love for creating. Joining Art in the Village was a big leap. It’s a cooperative gallery, which means every artist has skin in the game. Read more >>>

Chanel Rodrigues

Back in the turbulence of 2020, during the pandemic, I found myself in a tough spot. I was trying to go to school in person, but my courses kept getting canceled and I kept losing my job (I lost my job 4x as the world shut down again and again). Read more >>>

Lingshan Zhao

From the moment I chose to pursue art, I believe I have been taking a risk. Studying art is never an easy path in any country. Many people see it as a passion rather than a profession—too idealistic, too uncertain, too fragile to build a stable life upon. Before I applied to art school, I was often told to be practical, to pick something safer. Read more >>>

Nikita

“Take the risk or lose the chance.” I opened an auto repair shop with $43 in the bank account, not to mention the $22,000 worth of debt I paid off this year. I graduated from NASCAR Technical Institute in 2020, and 100 miles into the 900-mile trip back to my hometown, my school bus home broke down. Read more >>>

Thalia Ranjbar

When I was in the third year of undergrad, I decided to make a major change in my academic and subsequently professional career. At the time I was enrolled in a Bachelor of Science in the School of Kinesiology and on the path to a career in Sports Medicine. Read more >>>

Adam Crist

By the summer of 2022, I found myself creating art again after having stepped away from it for many years. For the better part of a year before that, I’d been feeling this deep, restless longing—an ache to express myself creatively—but I just couldn’t bring myself to do it. I felt stuck. More than that, I felt not good enough. Read more >>>

Sam Fraley

At 19, I had just been hired full-time at the local library where I’d already spent over three years volunteering and working part-time. I became the youngest full-time librarian in the county. I had the chance to learn from an amazing team and give back to my community. Read more >>>

Hannah Kelley

I’ve always been passionate about helping people define and achieve their goals, so I began my career as an educator, teaching both internationally and in my hometown of Las Vegas, Nevada. A common complaint among teachers is that students lack motivation to learn and are more apathetic than they’ve ever been. Read more >>>

Tiffany Stepney

This year, I made one of the biggest risks of my life—I left a stable corporate job to become an independent contractor and entrepreneur. For years, I worked in structured environments where I received a steady paycheck, clear benefits, and predictable routines. On paper, it made sense to stay. But deep down, I knew I wanted more freedom, creativity, and purpose in my work. Read more >>>

Aaron Rice

A few years ago, I took one of the biggest risks of my life — leaving a steady job to start my own company, Quality Demolition and Land Clearing. At the time, I didn’t have a big savings account or investors behind me. Read more >>>

Venazir

I have done a lot of significant leaps in my life. The first was when I decided to do street art and discovered the red thread that changed my life. I’ve always been fascinated by street art, even before I knew what it was. I’m not talking about murals in public spaces; we didn’t have those in my hometown. Read more >>>

Ian Langtree

I left home at 15 to join the Royal Australian Air Force. (They were trying out an apprentice program at the time so my youth – along with an ability to pass several challenging tests – was an asset. The program lasted a number of years.) The driving force for that risk was a need to leave, though I was also interested in military service. Read more >>>

Sharon Burstein

Life is about choice and the choices we make good and bad, and hopefully more good. Life is also learning to believe in yourself and trust your instincts. Without risk there is no reward. You will never know how amazing you can be unless you try! Life is about doing, not simply watching, at least for me. Life is a wonderful journey and great adventure. Read more >>>

Subei Kyle

I didn’t begin my career in film with the goal of being a business owner. Actually, the founding of my production company was an unintentional byproduct of working in an industry filled with so many different paths to ‘success’. SK Productions was, in hindsight, a slow and steady culmination of my years in film study and production. Read more >>>

Gia Ray

My senior year of high school I went to a performing arts school and the director of the school used to always say ‘if you have a fallback plan you will fall back on it.’ Meaning, don’t have a fall back plan. I’m not sure I would ever give that advice to someone else, but it sure worked on me. Read more >>>

Dennis,Loni Crawford

We’re originally from Detroit, but over the years, God has led us to take some bold steps of faith as a couple and as a family. With small kids in tow, we’ve packed up our lives and moved to three different states. Each move came with its share of challenges—new jobs, new schools, new communities, and the uncertainty of starting over. Read more >>>

Jinette Cartagena

The biggest risk I ever took was deciding to start my own businesses, a leap that was both emotional and deeply personal. At the time, I felt stuck in life. I was afraid of not being able to provide for myself and my daughter, and even more afraid of starting over if things didn’t work out. Read more >>>

Ildar Kamalov

In 2023, after almost a year of living abroad, I made the bold decision to return to Russia and begin preparing my application for one of the world’s top media composition programs — at Columbia College Chicago. Read more >>>

Anthony Badalian

As I reflect on my professional career, the moment I took my biggest risk came in 2020, after nearly a decade with 24 Hour Fitness, where  I held a range of leadership and management roles. My world revolved around the big-box gym industry. Read more >>> 

Dr. Tameitha Hicks

About Chicago 300 Black Women: I founded Chicago 300 Black Women as an organization committed to advancing leadership development and gender equity for Black women and girls. Our mission is rooted in creating sustainable pathways to success through a focused lens on health, education, and economic empowerment. We amplify voices that have long been underrepresented and work to dismantle systemic barriers that hinder progress. Read more >>>

Noa Morchi

my Name is Noa, i’m 25 and i’m originaly from Israel. i’ve been dancing all my life and i always had the dream of moving to states to pursue a dance career in the ‘big world’. back home i danced with all the famous artists , on Israel’s biggest satges, music videos ets. Read more >>>

Victor Olaoye

I think my entire practice is all about taking risk and shifting boundaries. Challenging myself and entering into uncomfortable places. I grew up from a very rural area in Nigeria su Read more >>>

Aja Nova

A significant life-changing risk I took was founding the mutual aid group, Nu HeART Collective. As the owner of a creative wellness studio and a passionate advocate for art as therapy, I’ve always wanted to make a positive impact beyond business. I felt compelled to create a space where I could give back to the community without the expectation of profit. Read more >>>

Inga Davidian

Moving from Seattle, WA to Las Vegas to open an Italian restaurant was not just a change of scenery—it was a leap of faith. Las Vegas is known for its world-class dining scene and its fierce competition, especially when it comes to Italian cuisine. Read more >>>

Ashley Boynes-Shuck

’ve always been career-focused, working steadily since I was 15. Along the way, I earned multiple professional certifications in addition to my Bachelor’s degree from the University of Pittsburgh. Read more >>>

Mei Tham

When I was a freshman in high school, I decided to take a risk that felt far bigger than it looked from the outside: I started posting content online. Read more >>>

Savannah Wyatt

When I first started Savvy Shotss Photography, I actually was so terrified to start my own business. I always told myself that my work wasn’t good enough, the market was to saturated, the area I am in will never give me the clientele I hoped for. Read more >>>