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.

Ashley Fazio

The biggest risk I’ve ever taken was leaving behind stability, comfort, and certainty to follow my heart and open my dream pole fitness studio, CLAQ HAUS, in 2024. It was a life-changing decision—one I had always imagined for the distant future, especially after becoming a mother of two and buying my first home in October 2022. At the time, I thought my path had already been set. I was immersed in the new venture of homeownership, and I assumed the logical choice was to build a stable, secure life. Pursuing my passion and taking risks seemed like a distant dream. Read more>>

Stephanie Lombardo

One of the biggest risks I’ve taken was the first time I performed as a solo musician at the age of 14. This was a defining moment of the start of a long journey of a pursuit of a music career.

But first … let’s rewind: Before this performance, the only time I ever performed on stage was in my dance class recitals, where I shared the stage with other girls all doing the same choreography. The spotlight was never on me, and I didn’t think I could ever perform on stage alone. Read more>>

KIMBERLY JACKSON

One of the biggest risks I’ve taken was stepping out to establish KCM INT, LLC, my passion business dedicated to leadership development, empowerment, and purpose activation. While I had already been deeply involved in mentorship, ministry, and outreach through Divine Destiny Center and DD Outreach Ministries, I knew that God was calling me to build something more—something that would equip not just women but leaders, entrepreneurs, and visionaries to walk in excellence and purpose. Read more>>

Alexandra Goldman

I would love to feel protected from risk! That would be a superpower. Uncertainty is a tough-to-navigate part of the human experience. The catch is, when passion comes into the picture, what might normally seem like a terrifying risk can turn into a clear and essential decision. Since high school I was very passionate about art, but always questioned if a career in the arts was a practical option. I was a communications major in college and went on to do corporate PR. When I switched from working in corporate PR to having my first job at an art gallery in 2015, I took a significant pay cut that some people might have thought was insane. However, I was, for the first time in my career, finally following my passion. Read more>>

Ritika Tripathee

When I started my career as a full-time influencer, I had no idea if I would succeed. At that time, social media wasn’t widely recognized as a viable career path, and there was a lot of uncertainty around making a living from it. Despite the risks, I decided to take the leap, investing time and effort into building my personal brand, engaging with my audience, and continuously learning about content creation and digital marketing. Read more>>

Danqin Fang

When I reflect on the risks I’ve taken in my life, two pivotal moments stand out – moments that have shaped not just my career, but my entire worldview about what’s possible when we dare to dream bigger.

The first was my decision to become a first-generation immigrant, leaving China for the United States entirely on my own. I arrived as a graduate student pursuing a Master’s degree in Financial Planning. While many might see this as a straightforward academic decision, it represented so much more – it was a leap into the unknown, leaving behind everything familiar to chase a vision of what could be. Read more>>

Kwami Lee

In Winter 2023, I took a risk that almost ruined me. My back was against the wall and much of the business I had coming in was drying up. The clients I had at the time were trying to box me in and I was looking for my pivot. I was down to my last few thousand after paying out my team on a small campaign I did for FootLocker ( shout out Latese and Tannis), and figured the best option I had was to reinvest it into myself. Read more>>

Monze Delgado

Several years ago, I took a significant leap by shifting my career into the healthcare field—a huge departure from my background in sales and a family business. The decision was bold, but I enrolled in nursing school and faced the challenges head-on. The journey wasn’t without its fears, especially when the COVID-19 pandemic hit and the world suddenly shut down. The uncertainty we all felt was overwhelming, and the unknowns about the future of work and life made it feel like an even greater risk. But I pushed forward, graduated, and now I have the privilege of working to advocate for our elderly and veteran communities. Read more>>

Marilena Alcuri

At 19, I took one of the biggest risks of my life—moving to New York City with no degree, barely any savings, and knowing only one person. It felt like the ultimate leap of faith. Growing up in Venezuela, I had followed a conventional path: I graduated from school, attended college, and briefly studied to become an air hostess. But life had other plans. Life brought me to Spain, a place I thought would offer better opportunities, but reality didn’t match my expectations. Read more>>

Gabriela Gonzalez

One of the most transformative risks I’ve ever taken was posting myself on social media and committing to a life of content creation. It might seem like a small act to some, but for me, it was a leap into the unknown—a decision that challenged my self-esteem, tested my resilience, and ultimately reshaped my life. Read more>>

Callie Byerly

No one likes taking risks but sometimes the most difficult journeys are the most worth it. I, along with my partner, have put our financial risk to found Move Club San Antonio, a non-profit organization that aims at enhan Read more>>

Paige Soleimani

The most significant risk I undertook was a complete pivot during my undergraduate years. I entered college with a clear vision: to become an elementary school teacher. My passion for education was deeply ingrained. Throughout high school, I dedicated myself to building a strong foundation. I volunteered extensively, tutoring young children, served as a camp counselor, and mentored students lacking positive role models. This dedication culminated in my acceptance into the highly regarded elementary education undergraduate program at Syracuse University. Read more>>

Ashley Koltonski

The biggest risk I took in my life was betting on myself and becoming an entrepreneur full-time. What a terrifying leap off a cliff into the unknown. The fears that held me back are something I had to overcome step-by-step, through mindset work, planning and building an unwavering belief in myself. I left a very successful corporate career and a very cushy paycheck in 2023 because I knew deep inside that I was meant for more. I was meant for pursuing creative passions MY way and being an authentic leader that will help change the world and make a sincere impact on people. Being a task-taker was never going to be enough for me. And now? I get to create full-time, live a life on my own schedule and have deep purpose and happiness in my work. Read more>>

Nicole Korbe

Becoming an entrepreneur in the world of art-related business is the largest risk I have taken and it has been quite a journey. At the end of 2016, I took a big leap and quit my 9-5 job in order to focus on my passion for painting. Initially, I did not have a set idea of what exactly this meant or how to do it. (For the record, I do not necessarily recommend this approach.) Over the next few years, while showing my work in a local cooperative gallery, I worked a multitude of odd jobs which included everything from painting peoples’ walls, helping with domestic and light handy(wo)man tasks, and also some contracting work here and there in my previous line of work. Read more>>

Lauren Tetenbaum

I’ve taken a few risks throughout my career, and I’ve never looked back. I started law school right after college in my early 20s because I wanted to advocate for women, and I loved writing; so, I thought being a lawyer would be a good career for me. I immediately sensed that it wasn’t, and took a risk by taking a leave of absence from my law school to pursue my Master’s in Social Work. Getting a more comprehensive education on how to best support people at their most vulnerable was the right choice for me. I ultimately returned to law school and completed both degrees within four years and then spent a decade in the legal industry, practicing through a compassionate lens that was honed from my studies in mental health. Read more>>

Dr. Valerie Scott

At age 65, after a successful career in K-12 public school education, I decided to create my own nonprofit. I had no experience working for a nonprofit, no experience as a business owner, and no source of funding. What I did have was strong leadership skills, great health for my age, and the knowledge to be able to provide support services to a population of individuals who are often ignored when they struggle because of their high level of intelligence. Read more>>

Deborah Hughes

Risk looks different for everyone. For me, one of the biggest risks I ever took was starting my own clinic. After more than 20 years as a hardware/software integration engineer, transitioning from a veteran of the industry to owning an outpatient pediatric therapy clinic was a bold move. But my decision was made even more daunting when the clinic opened the very same week the state was shut down due to the onset of the COVID-19 pandemic. Read more>>

Cai Grodek

On November 1st, 2024, I quit my part-time job – a job that gave me a stable income, full-time benefits, and a clear path to higher-paying positions if I wanted them. On paper, it made no sense to walk away. WhyWithCai wasn’t stable at the time. Sure, my book launch had given me a lump sum of money, and I had just completed my first brand partnership, but I had no guarantees of consistent income. Read more>>

Karissa Whitman

Becoming a mother is life-changing in ways you can never fully prepare for. I knew motherhood would bring joy, challenges, and a whole new identity shift, but I didn’t expect to feel like a part of me was missing—like I had lost the creative, driven version of myself. I loved being a mom, but I also had this deep, constant feeling that I needed something more—a way to pour into myself beyond the day-to-day of raising little ones. Coming from a background in Emergency Veterinary Medicine, I really missed the challenges working in an ER setting brought, but I knew I didn’t want to go back to that while raising a family. Read more>>

Catheliya

My family and I came from Thailand as a child. My parents are two very intelligent people. But they were not familiar with the country that they moved their whole family to. They were in their 20’s.

My mom and I didn’t get along as I got older. She raised me to be an American. But when we go back to visit our family in Thailand. She wanted me to be like a Thai child. And I didn’t know how to do it. So we clashed a lot. I didn’t understand her culture. I was too younger. She didn’t really understand mine. She sent us to some of the best Catholic private schools. Worked hard so that my brother and I could have the best education. But then it all fell apart. My parents divorced. Things went downhill from there. Read more>>

Chasity Jernigan

In the last 365 days, I took a leap of faith that changed everything. I left behind Tupelo, Mississippi, the place where I built my life, my family, my career, and my brand to follow my son to College Station, Texas, as he embarked on his first year playing SEC football at Texas A&M University. Everything I had ever known was in Tupelo, from the 20 years of marriage to raising my boys, to my very first Zumba class and ministry work, to becoming an influencer and landing my first brand collab. Read more>>

Amanda Hargett

Although it seems like a natural fit for me now, a career as a tattoo artist was not something I had ever imagined for myself, and diving into an apprenticeship in my 30s felt like an intimidating risk at the time. I had taken a slow journey through higher education and wasn’t sure what my next step would be. I was freelancing as an illustrator for a few years to keep my portfolio up to date and had my heart set on an animation program – though the thought of taking out student loans was making me hesitant. Essentially I was in the state that so many creatives find themselves in: unsure of how to make a stable living doing something I loved, and not knowing if the work I was already doing was sustainable long-term. Read more>>

Devonric Johnson

Ever wonder what it’s like to leave what everyone else sees as the perfect career? Well…that was me when I left my career as the Regional Fitness Director for Mayweather Boxing and Fitness in Los Angeles and went back into the entertainment industry full time as an actor and model, Read more>>

Jo Fischer

As an artist, I find that everything I create is inherently risky. Whether I’m behind my keyboard writing my debut novel series or behind my phone posting to my audience, everything I create and share is a piece of myself. Being vulnerable enough to share something transformative with your audience is a huge risk—the risk of the work being rejected, stolen, or scrutinized. I’ve had my fair share of hateful comments online, and it can sting, for sure. But for me, that risk is worth it. There will always be an audience with which my work doesn’t resonate. I’ve found the reward of connecting with those who do find value in my art to be worth the risk. Read more>>

Laurisha Cotton

Rewind to 2018, New York City. Juggling freelance videography to pay the bills and really searching for that solid, main gig doing something cutting edge.

That’s when I found myself at this crossroads. I had two job offers on the table. One was a stable, well-paying position at a legal law firm. I’d worked in those environments before, and I knew what that path looked like – predictable, secure, but maybe a little… ‘golden handcuffs,’ as some might say. Read more>>

Nicole McLean

For as long as I can remember, I’ve had this deep, restless craving to travel. Not just weekend getaways or family vacations—real, immersive, soul-stirring adventure. But for most of my 20s and 30s, that dream felt like a far-off fantasy, constantly overshadowed by the practicalities of life: kids, work, routine. Then, in January 2022, everything changed over a simple cup of coffee. Read more>>

Kim Gros

My first career was as an environmental attorney in DC. I was always passionate about protecting those who couldn’t speak for themselves and I really wanted to make a difference in the world. I specialized in international environmental law so being involved in policy-making and raising awareness at a large-scale level is how I thought I would achieve that. Unfortunately, after years of working in that field, I became discouraged when I realized I wasn’t making any difference. Read more>>

Adrian Johnson

One risk I’ve taken was going all in on social media. Being vulnerable enough to do what I love on camera in front of the whole world. Read more>>

Maria Clemente Morresi

Several years ago, right in the middle of our lives during Covid, I was presented with an opportunity to apply for a large contract to build a trauma-informed school-based therapy program for a large school district. At the time, I was working in a wonderful school as a Student Assistance Coordinator, supporting students with higher level mental health and substance use challenges. I also ran my own private practice, which at the time, was just a small caseload of clients. I loved working in the school and having a small private caseload. It was a great balance and it allowed me a lot of freedom to enjoy aspects of my personal life. Read more>>

Noah Levine

The biggest risk I’ve taken during my career as a magician is choosing to have a career as a magician. Being self-employed and/or running your own business is always going to be dicey. Add arts into the mix and you’ve got a heck of a wall to scale. I try to focus on the immediate tasks at hand, work through emails, get practice time in, and some long-term planning. Without some good structure, the overall sense of risk can be overwhelming. Read more>>

Natalie Migliarini

In 2013, I was laid off from my public health job at the University of Washington in Seattle. Up until then, I had always lived a predictable life with a steady job and a low risk tolerance. Losing that job was a huge shift, and although I started applying for similar positions, I also felt a strong urge to explore a creative outlet. That’s when I began sharing cocktail recipes on my blog and Instagram. Read more>>

Macelyn Batten

Before February 2024, I had never played or sang in front of anyone other than my immediate family. I had always had a deep love and appreciation for all types of music, which I think stems from my experience in dance, however I never thought that I could be capable of performing music of my own. A friend of mine owns a brewery where, at the time, they were having a weekly open mic. After much persuasion on his part, I finally decided to stop by. A sang “Tin Man” by Miranda Lambert, a song that still resonates with me to this day. A short while after I left the mic, the musician running the open mic walked over and introduced himself. Read more>>

Nora Sherwood

Deciding to become a science illustrator at the age of 50 was an enormous risk. I really struggled with what I wanted for the next chapter in my life and I spent quite a few years trying to figure out what I should pursue next.

I had enjoyed a successful career in geographic information systems, getting a masters degree in the field in 1987 when it was very early days, and very “bleeding edge.” I can still speak fairly frequent DOS and am one of the few people I know with extensive experience with VAX machines. Read more>>

Dr. Niesha Davis-Massey

Taking a risk often feels like standing on the edge of something unknown, right before you take that leap. For me It’s that moment when you weigh the possibilities; what could go wrong, or what could go right— weighing the pros and cons and just deciding to make the decision to go for it anyway even when you don’t have the ultimate plan or knowing how you are going to do it. Have you ever been in this space? I sure have when I decided to step in the role of starting my first and second mental health practice! This was a big risk for me both times, however I’m so glad that I did. Being able to walk alongside my clients and patients and being a part of their healing journey is such a blessing and humbling experience! Read more>>