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.

Ekaterina Yachmennikova
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When I look back at my professional career and my background in sports and ballroom dance, I clearly see a driving force that has always been inside me: the courage to take risks, even when the path forward seemed impossible.

The first time I truly embraced this was when I inspired my family to move from Kamchatka to Moscow so I could continue my dance training. We had no place to live and no jobs waiting for my parents, but we started from scratch. Just a year and a half later, I became both a national and a world champion in the junior age group. Read more>>

Jeffrey Hewlett

Starting my wine business, D’ANii Wines involved significant risks, with the primary ones being financial instability, market uncertainty, operational challenges, and potential burnout. We as Entrepreneurs face the risk of insufficient funding, fluctuating cash flow, and the possibility of not achieving a return on investment. Furthermore, competition, lack of market fit, and the need to adapt to changing customer preferences pose strategic risks. Operational hurdles like supply chain issues, legal compliance, and the need for effective time management also contribute to the challenges. Finally, the long hours and intense pressure can lead to burnout if not properly managed. But after a few years of hardwork, good market, and great tasting variety of wine flavors, I’m experiencing great success. Read more>>

Ciera George

A risk I have taken is taking a year off work to follow my dreams by putting all of my effort into Peach Tree for a year. I spent the year making about 40,000 less (with the support of my husband) but it was hard and I questioned whether or not I was doing the right thing but I started working again part time this year somewhere that helps Peach Tree’s mission and Peach Tree is being more impactful than ever working with the youth. Read more>>

Amy Millard Willson

When I was 22, fresh out of college with a degree in graphic design and photography, I decided to take a leap that would completely change my life. It was 2005—before Instagram, before photography and design became the oversaturated fields they are today—and I felt this pull to chase the California dream. Read more>>

Rosemary Lewis

The first big risk I ever took was back in 2014 when my husband and I decided to relocate from Chicago to the Dallas area with our two sons. We didn’t know a single person here, but we both felt a strong call and pull to make the move. Once we settled in and realized how much we loved it, that leap of faith set the stage for me to start embracing even bigger risks and trying new things. Read more>>

Andreece Turner

I have always preferred to have a plan and to stick to it.

I was raised in extreme poverty and inherited generations of abuse and oppression and got married at the age of 23 to the man that I thought I would build life with forever.

I believed that I had made it; I escaped the cycles of abuse that I inherited; yet I found myself in an emotionally abusive marriage that was void of intimacy and hundreds of miles away from my family and homeland and everything that was familiar. Read more>>

Melquea Smith

I’m right in the middle of taking a risk as you’re reading this.

I worked remotely for a national organization that I adored for the past 3 years. Meanwhile, I freelanced and continue to build my illustration business in children’s books.

I started building relationships with other kidlit creators back in 2020: I joined critique groups, took classes and mentorships, and celebrated others’ accomplishments, as I built my children’s book illustration portfolio. Read more>>

Shannon Battle

One of the most significant risks I ever took was deciding to temporarily drop out of school to care for my mom when she was told she had 6 months to live after being diagnosed with small cell lung cancer. At the time, I was not only focused on my education and career but was also pregnant. The diagnosis was devastating, and I knew my mom needed constant care and support during her final days. Read more>>

Molly Robinson

I graduated in 2008 with a bachelors in Public Relations and my first job was at a radio station as the assistant promotions director. I had a small cubicle in the corner. Worked 8am-5pm M-F. On the outside it looked like a great job for someone just starting out after graduating college, but in the inside I was struggling. I realized quickly that I just wasn’t cut out for that type of work. I felt disconnected with my purpose and could not imagine my life continuing this way. So, I took a big risk and decided to go to massage school. I was a figure skater and dancer growing up. Read more>>

Heather Gallegos

Rebuilding HeatPraxia after we flooded in January of 2024 was a huge risk. We did not have the financial resources required to complete the project but we chose to jump in head first anyway. The two years we had been in business before our studio was destroyed made it clear to us that we could not quit, but we also knew we had to relocate to a larger space. We took the BIG, life changing risk to lease a new space & plan a half a million dollar build with only $50K in the bank. Every aspect of the job we could do our selves, we did. It was a scary year of riding the line with revenues & loans coming in right as we desperately needed them & not a minute sooner. Read more>>

April Johnson

I had a very good job—stable, well-paying, and full of responsibility. I was the primary breadwinner for my family and a mother of five. Life was a constant balancing act, trying to juggle the demands of work and home.

Then one day, I was introduced to light therapy. I went in for a session at a local spa, not knowing what to expect. When I walked out, something had shifted. The world looked a little brighter—literally and figuratively. Read more>>

Dr. Katherin “Kathy” Duong

One of the biggest risks I had taken was opening up my own physical therapy practice on the tail end of the pandemic and with less than a year of working experience in my profession. While it was a huge risk to take, I knew that the timing was right. Having left my first clinical job at a corporate, outpatient clinic to what I thought would be my dream job at an Assisted Living Facility working with my favorite population – geriatrics, the vision of it being a dream job was quickly vanished. Riddled with management and ethical issues, causing disruptions in my ability to provide quality care for my patients, I knew I had to leave. Read more>>

WILDY RIFTIAN

I’ve always considered myself a risk-taker. Growth comes from stepping into discomfort, and I believe some of the best things in life happen when you take a leap.

I’m from Indonesia, where art wasn’t widely seen as a stable career. Choosing to move to Seoul, South Korea, right after high school was a huge gamble. I knew I would have to delay my graduation by two years to complete the Korean language program, putting me behind my peers back home. Read more>>

Sydney Weable

Early March 2020 I was in the middle of an amazing 8 year career with the salon called Bubbles. I was a full time stylist behind the chair and also a full time educator for the company. I traveled the DMV teaching new techniques and also had a full book of loyal clients in Columbia Maryland. Then boom the world shut down completely…I was literally the last person in my salon. I didn’t know it at the time but that was my last day working there. What happened in the next couple weeks rocked my world. Read more>>

Rick Bumgardner

I often find myself at the corner of Walk/Don’t Walk. Eight years ago something appeared on the opposite side of the street and moving me in a completely different direction than where I was going. I rarely stop walking. Even if I am not completely aware of the direction I am heading – I tend to walk. Read more>>

Sally Forcier

I started my casting company, Forcier Casting, in 1999. But in 2008, while navigating a sudden divorce, I found myself needing more stability and took a full-time position with the California State Lottery, directing and producing for them.
Despite the demands of that job, I made it my mission not to give up on my business—my true passion. For the next eight years, I essentially worked two full-time jobs. Deep down, I knew I had outgrown the Lottery role after about three or four years, but the comfort of a steady paycheck and health benefits kept me there. I was afraid to walk away. Read more>>

Tanya Michelle

I was always in the restaurant/hospitality indrusty because I was a young single mom and that was were I could work the hours I needed while being able to do my mom duties during the day. I kept feeling like something was missing when I went to work everyday. I wanted more freedom and the chance to create something of my own. One day I realized the bigger risk was staying comfortable but unfulfilled. That’s when I decided to bet on myself, go back to school and start my business. Read more>>

Brittany ‘Bre’ Anderson

I was battling depression after my grandfathers passing. And I would sit over at his house, and just rummage through his old things. He was known as a “medicine man” – always having a herbal/botanical cure for almost all ailments, pains, and more. One day as I was going through things, I’d stumbled across a container full of African Shea Butter. And we were familiar with is as kids; instead of Vaseline or lotion, he would always be seen using the “yellow stuff” as we called it, as kids. Read more>>

Gianna Sutley

One of the biggest risks I’ve ever taken was quitting my corporate job in innovation and business strategy without anything else lined up. On paper, it looked like I was thriving—I had the kind of role people often strive for, with stability and opportunity for growth. But beneath the surface, I was unraveling. I was constantly exhausted, irritable, and disengaged from the things I used to love. I had gained weight, my energy was depleted, and I felt like I was sleepwalking through my days. Read more>>

Tara LaDue

I went back to graduate school to get my Master’s Degree in Marriage and Family Therapy at 44 years old. I grew up with lack mentality, so the idea of taking out $60,000 in loans terrified me. But, I was working in a job where I was on my feet all day with a chronic foot disability in immense pain. I knew I couldn’t do the job anymore, and I wanted a stable career where I could help people. School would be hard, especially while taking care of my elderly mother while working. This was a huge risk financially in many ways: the school loans, working less at the job I went home in pain from every day all while knowing that LMFT’s do not make a lot of money for quite a few years. Getting my Master’s Degree is one of my biggest accomplishments that I am so proud of. Read more>>

Renee Lee

By nature, I’m a risk-taker. I’ve never been one to “stay in my lane.” Instead, I’ve made it a habit to build new lanes—ones I own with authority.

Before launching my own business, I served as a Senior Director for a program that was part of a national network. Under my leadership, we were recognized as a Center of Excellence—the gold standard that other agencies and centers across the country looked to for best practices. Eventually, our work became the blueprint for the State of Tennessee’s own network of centers. Watching those centers thrive today, knowing I helped lay the foundation, is incredibly rewarding. Read more>>

Jordan LaCore

I started journaling back in my teen years to cope with all of my various emotions, which then trailed into poetry and songwriting.
I’ve never been great at expressing my emotions in person/being confrontational with the things I believed in out of fear that I would be judged or disliked. That being said, journaling was probably the most therapeutic hobby I’ve ever experienced for the fact that I can share exactly what I want and deliver it in all honesty without someone standing in front of me. Read more>>

Xavier Sáez

\I was born and raised in Puerto Rico, and ever since I was little, all I could see around me was art. Whether it was editing videos or seeing performances, I was always surrounded by creativity. In the end, I landed on music. I started playing the piano and I eventually got a Novation Launchpad which introduced me to the musical software called Ableton Live. Initially, I used it for other purposes, but after learning that I could create music with it, new doors opened up for me. I became more invested — I decided to get a keyboard for Music Production and I got a bass guitar which ended up being my main instrument of choice. Read more>>

Quinn Cosby

I had lived in San Diego, CA for 23 years and it was always home to me, but during and after Covid things started to change. With so many people flocking to San Diego to live, housing rates skyrocketed, and I soon became priced out of my living situation. I also had lost my passion for the job I had at the time and noticed the energy of San Diego was also changing. I realized I also wasn’t trying to look for new jobs in San Diego and felt a change was coming but I didn’t know what. Read more>>

Michelle Alexander

Some background to elucidate the risk: I have wanted to be a creative writer since I quit my serious study of ballet to pursue a career in writing when I was 14. I knew I wanted to be in New York to learn the craft on a serious level, so I set my sights on NYU. I believed in Fitzgerald’s description of the simultaneous enchantment and repulsion that the city affords. When I left for school, I left my friends with a little poetry collection, which took up their brilliance. At NYU, I crafted a concentration: “What it Means to be A Poet: Interweaving a Study of the Humanities with the Human Experience.” Read more>>

Elaine Querry

I was working as chief photographer for a wonderful weekly newspaper in Northern New Mexico. It was interesting, a great place to work and learn with good pay and benefits. I was responsible for developing and printing black & white film and photos for the editorial and advertising departments, finding feature photos, covering a variety of beats, etc. This was pre-digital, pre-cell phone and pre-modern computer. It was a great job and a wonderful time in my life! But . . . I quit so my writer husband and I along with our two dogs could set out in a small trailer to explore, travel, work on our art, and to rethink our lives. That all happened! Read more>>

David Fogel

Seven years ago, on a Sunday afternoon, I went to a performance of the San Diego Symphony. I arrived a bit early and looking around, I saw I was pretty much the youngest person in the audience. I was 54! I started thinking where is everyone going to be in 20 years, and even more importantly, where are the young people? When I was younger I went to the symphony, and when I was really young, my parents took me, and we had school field trips. But not so much any more. I felt this was unacceptable. Read more>>