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.

Rosana Antoli

One of the biggest risks I’ve taken happened during my solo exhibition at Fundació Joan Miró. Until then, my work was strongly associated with drawing — line on paper, choreography translated into two dimensions. It was recognizable. It worked. For that show, I decided to change everything. The risk wasn’t conceptual. I knew what I wanted to investigate. The risk was material. Read more>>

Teaira Abston

For years, I built my business around execution. I was the one bringing brands to life through strategy-backed visuals, websites, and SEO. The work was tangible, measurable, and transformative, and I became known for turning ideas into something real. As the business evolved, I started to recognize where my real value was showing up. Before any design started, I was deep in the bigger picture. Read more>>

Michelle Bethea

One of the biggest risks I’ve ever taken wasn’t starting a business. It was outgrowing one. I built Elaborate Outings from the ground up. What started as luxury picnics quickly became a recognizable brand. We were curated, elevated, detailed. The setups were beautiful. The community loved it. I had awards. Media features. Loyal clients. It was safe but it was also small. Read more>>

Dr Michelle Gill

Being a black woman and creating a digital radio station in a man driven environment was something I decided to go for not knowing what the outcome would be, how I will be accepted, how to hire DJ’s and personalities, how to manage the overall aspect of being a business owner was definitely a challenge, I was told “you would have to get rid of your radio station to be on others” having people in my community create their own platforms to compete with mine then start to constantly bash me on the internet, blocking and reporting my Instagram so I couldn’t go live, the challenges were many, but I am still here standing tall in what I’ve created and now I am involved in a prominent Reggae artist project and not looking back. Read more>>

Tianna Cunningham

Nine months ago I made one of the biggest decisions of my life today. I wasn’t sure what this decision would hold for my future, but in that moment I didn’t care because I knew I was following my purpose. In May of 2025, I walked away from my 9 to 5 to follow my passion as a full time entrepreneur. Read more>>

Jennifer Halla

I still remember the moment I decided to bring ninja warrior training to Austin. There was no spotlight, no dramatic music, no guarantee it would work. Just a quiet realization that Austin didn’t have a ninja warrior gym yet—and that someone had to be the first. The risk wasn’t just financial (though that part was very real). Read more>>

Nick Page

I’ve Taken risks all my life. Well, I was rather comfortable with who I was up until about 17 years old. I started to take much more risks in my life. I started to question authority, at what I think was a late age. I stopped going to school for a business risk. Read more>>

Hailey Gearo-Chang

It was the end of 2019 I was working a job I hated. I was drained, frustrated, and unfulfilled. And just a month later Covid happened. After seeing that nothing was truly stable I took a leap and decided to pursue painting as a career. Read more>>

DANIELLE ARMSTRONG

Taking the leap to start my business was the greatest risk I’ve ever taken — and the most meaningful. For years, I was a driven corporate professional, but deep down I felt creatively unfulfilled and disconnected from the things that once lit me up. Read more>>

Leah Eber

Before I started Life with Leah, I was working in my corporate job and excelling quickly. There was just one problem, I wasn’t fulfilled. Outside of work, I started leaning into my passion for health, wellness, and fitness by helping people transform their lives and their health. Read more>>

Jarmal Burton

I embarked on a Journey to write my first book 3 years ago. I really didnt know how it would go but the challenge was something I wanted to take. It turned out to be a very fun risk because I’m 4 books in now Yall check out all my books 1.Dear God It’s Written- Available on Amazon 2. Read more>>

Lerae Funderburg

The biggest risk I’ve taken was choosing to redesign my entire life at a time when, on paper, it made very little sense. I was already successful. I was practicing law, building businesses, raising two children, and doing what many people would consider “making it.” But internally, I felt the strain of constantly running. Read more>>

Daphne Dash

There is a specific kind of silence that happens right before you click ‘confirm’ on a bank transfer that empties your savings account. It’s not a peaceful silence; it’s the sound of every safety net you’ve ever built being pulled away. For me, as Daphne Dash, that was my ‘all-in’ moment. For years, I played it smart. Read more>>

Amy Schmidt

One of the biggest risks I’ve taken didn’t look dramatic from the outside — but internally, it required enormous courage. After years of building momentum through speaking, media, and my platform Fearlessly Facing Fifty, my husband and I felt a pull to change the rhythm of our lives. At the time, everything looked stable. The business was growing. Our children were older. Read more>>

Anthony Clark

One of the biggest risks I’ve taken was starting my retail business with very limited resources and no guarantees of success. Before opening my boutique, I was selling clothing out of my vehicle, traveling to different locations and building relationships with customers one sale at a time. Read more>>

Alyssa Chambers

Story of a Risk I Took: Launching Winnie’s Way Mobile Candle Café The backstory For a long time, NOVA Essence Inside Out was my “yes” to myself. It started as a hobby in 2020—candles, affirmations, and little pockets of peace I could create with my own hands. It was healing, it was creative, and it was mine. Read more>>

Chanel Williams

I didn’t set out to become a plant-based chef. I set out to survive. When I was diagnosed with lupus, my life quietly split into a before and an after. Before, I moved fast, pushed through exhaustion, and trusted my body to keep up. Read more>>

Anukkah Laquette

The biggest risk I took this year was quitting my 9–5 to pursue my dreams full time and fully step into my God-given talents. I’ve always known I had an entrepreneurial spirit. But for a long time, I was afraid to walk boldly in my purpose. I didn’t know what was on the other side. Read more>>

Courtney Hedrick

The risk I took didn’t begin as a carefully mapped business plan. It started as a quiet, persistent idea rooted in two things I know deeply: my love for stories and my belief in creating spaces where people feel seen and connected. Read more>>

Khadizah Amos

Two months after my grandfather passed away, I flew to Los Angeles to showcase my brand at Los Angeles Fashion Week. On paper, it didn’t make sense. I was grieving. I was mentally exhausted. I was unemployed. I had no savings for a flight or hotel. Six months before the show, I had unexpectedly lost my job, and everything felt unstable. Read more>>

DeBo Secured LLC

One of the biggest risks I’ve taken was stepping into the world of celebrity protection; a profession where the margin for error is razor thin and the consequences can be permanent. When most people picture bodyguard work, they imagine red carpets, flashing cameras, and standing tall in a black suit with an earpiece. The reality is very different. Read more>>

Denise Randall

I’v taken many of risk in my business. From the time I moved from North Myrtle Beach,Sc to Atlanta. That was scary move from A small town to A big city. I took risk within my business sometimes failing. Whether the outcome was good or bad I never gave up. Read more>>

Nura Rachelle

One of the biggest risks I’ve taken has been building a practice that refuses to oversimplify astrology or over-commercialize it, while still showing up consistently and making the value of the work visible. Early on, I saw how easily this field can slide into certainty, pressure tactics, or reductive messaging in order to grow faster. Read more>>

Crystal Reidy

One of the biggest risks I ever took started with a simple, honest comment. Years ago, I mentioned to Patrice — a woman bravely fighting stage 4 cancer — that I was going on a cruise. She looked at me and said, “I would love to go and relax on a cruise.” It wasn’t dramatic. It wasn’t a request. Read more>>

Gandhi Joseph

One of the biggest risks I’ve taken isn’t something people would necessarily call dramatic but for me, it feels huge every single time. I travel out of state for art events without knowing if I’ll even break even. To some people, that might just sound like business. Read more>>

Julie Ley

One of the biggest risks I’ve ever taken as Founder and Creative Director of Modern Posh/Vanilla Print was deciding to go all in and exhibit at the National Stationery Show at the iconic Javits Center in New York City. At the time, Modern Posh/Vanilla Print was growing, but we were still a small, independent brand. Read more>>

Diamond Gist

Taking a risk can feel paralyzing. Your heart races, your mind questions everything, and comfort suddenly feels safer than growth. But I once heard something that shifted my mindset: If you’re not taking risks, you’re not planting seeds, And seeds can’t grow if they’re never planted. The biggest risk I’ve ever taken was starting my business. Read more>>

Lindsey Lochner

One of the biggest risks I have ever taken was starting our farm after my husband retired from the military. My husband, Clem, served 21 years in the United States Army as a Green Beret. For two decades, our life was structured, mission-driven, and secure in the sense that there was a steady paycheck and a clear next step. Read more>>

Sara Green

Starting my own business back in 1998, only a year after graduating college, felt like a huge risk! But having worked early on for a person I didn’t respect, helped me recognize the value of ‘setting a tone’ for a business. I wanted to lead with kindness and work with people whom I respected and who respected me and my craft the same. Read more>>

Lorenzo Halloran

When we first began working with retirement communities, it was a complete gamble. We didn’t know whether this transition would be the right move for the business. I was brought on to pilot the initiative with full transparency that there were no guarantees of success. We ran several free trial programs to test demand. Read more>>

Rebecca Fellenbaum

I’ve been fortunate to take many risks in my life. I say fortunate because taking risks doesn’t come in isolation. My family, friends, and inner confidence and abilities all supported me in making some challenging and surprising choices. Read more>>

Bennord Lee

The biggest risk I’ve taken has been deciding to create art again. In 2015, I started to experience severe mental and emotional breakdowns. Life was life-ing something serious! Remnants of my traumatic childhood began to appear and manifested itself in night terrors and constant sleep paralysis. I felt like I was dying inside. Read more>>

Brianna McKay

I remember losing my job during the COVID-19 shutdown and the fear that came with it: making money, paying bills, navigating the unknown of a world that had paused indefinitely. I decided to sit in my sadness, but instead of staying silent, I started expressing myself through painting again. Read more>>

Jessica Alexander

I believe that becoming a small business owner (especially around 2012!) was a huge risk! I had very little capital and took the small downpayment I was saving for purchasing a home and put it towards investing in my LLC and new camera gear. Read more>>

Deb Davis

One of the biggest risks I’ve taken was retiring from a 24 year career at AT&T Wireless at the age of 55 and stepping into an entirely new chapter. I had spent my entire professional life in people facing industries, from restaurants and hotels to more than two decades in sales. My career was stable, predictable, and successful. Read more>>

Jefferson Rojas

Taking a risk has been a constant theme in my life. Moving from Colombia to the U.S. and starting over was the first major leap. The second was deciding to pursue stand-up comedy in a language that wasn’t my first. Professionally, I work as a Project Manager with SCDOT, where structure and precision matter. Comedy is the opposite environment — unpredictable, vulnerable, and immediate. Read more>>

LAKWESHIA EWING

One of the biggest risks I ever took didn’t look like a business decision on paper. It looked like a life interruption. At the time, I had done what many people consider “making it.” I was young, successful in my career, financially stable, and on a very clear trajectory. My life was structured, efficient, and predictable. Read more>>

Sharon Inostroza

The biggest risk I’ve taken hasn’t just been starting a business — it’s choosing to build again while I’m already carrying so much. In 2020, I started working for an auto glass company, knowing absolutely nothing about the industry. I was learning from scratch every single day — asking questions, making mistakes, figuring it out as I went. Read more>>

Jacqueline Crider

One of the biggest risks I’ve taken didn’t look risky from the outside — but internally, it felt like jumping without a parachute. I built my business in mortgages. For years, that was the lane. I knew it, I was good at it, and I had helped thousands of people become homeowners. Then the market shifted. Read more>>

904Matcha

I took the risk of moving up to Detroit for my music career back in October 2021? Taking that risk opened a lot of opportunities for me and those around me. I am thankful for all the memories it brought me since I’ve been here. Read more>>

Kira Simmons

One of the most significant risks I took was leaving a stable career in HR to start my own small business. I had built a strong foundation in human resources, with steady income, clear expectations, and professional credibility. From the outside, it looked like a secure and successful path. Read more>>

Sabrina Newby

One of the biggest risks I’ve taken was stepping from business ownership and community advocacy into a run for the Georgia State House. For years, I worked behind the scenes, supporting entrepreneurs, serving families, and pushing for change. But I reached a point where advocacy wasn’t enough. Read more>>

Donna Bragg

The risk began when I decided to ignore the ‘safe’ trajectory for both my brick-and-mortar operations and my personal brand. After years of grinding to build a stable, self-funded business, I realized that playing it safe had led to a plateau. Simultaneously, I felt a calling to begin competing on the pageant stage as an ‘older’ contestant—a space often dominated by younger voices. Read more>>

Austin Hair

I’m Austin Hair, an American Ninja Warrior national finalist, world champion wakeboarder, and an investor focused on helping others achieve financial freedom through passive real estate investing. One of the biggest risks I’ve ever taken didn’t look dramatic from the outside. Just a contract, a signature, and a deep sense that I was stepping into the unknown. It was April of 2011. Read more>>

Alexis Alsup

One of the greatest risks I’ve taken was deciding to publicly pursue becoming a Certified Professional Midwife in a region where there are very few midwives who look like me — and even fewer outside of hospital systems. Read more>>

Jordyn Smith

When I decided to pursue astrology, I knew I would be taking a risk. I grew up in Oklahoma in a religious fundamentalist family. On my maternal side they are Catholic and on my paternal side they are Southern Baptist. I grew up going to private Catholic school. On Easter Sunday’s I would go to my great Uncle’s church and hear either him or my own father preach. I had always leaned into my indigenous roots (paternal grandmother) and had an affinity for Star knowledge and natural medicines. Read more>>

Kelli Stebler

When I look back, I know that if I hadn’t been willing to take risks, I wouldn’t be where I am in my career today. Starting a business without any formal business background felt overwhelming at times. There were moments of doubt, a lot of figuring things out as I went, and more than a few deep breaths along the way. What made that time more bearable was that I wasn’t doing it alone. Read more>>

Carol Zatt

I’ve always been drawn to the creative world, not just as an observer, but as someone who wants to help bring art to life. My journey began in music and media, learning the ropes by working with artists, attending events, and figuring out how to help creative visions reach the world. Over time, I realized that my work could exist on two fronts: as an artist myself, and as someone who supports other artists in telling their stories. Read more>>