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.

Anna Love

In my 30s, I was a full time me kindergarten teacher, passionate, creative, and outwardly successful, but inside, I was struggling. I was living in a fog, deeply disconnected from my true self, and silently battling cycles of self-sabotage. Alcohol and other vices helped me escape the nagging feeling that I wasn’t fully aligned with who I was meant to be. I was showing up for my students every day, but I hadn’t yet learned how to show up for myself. Read More>>

Betsy Anderson

As someone who has been in the Personal Training/Wellness Coaching field for the last 15 years, I knew that I was meant to do more for myself than punch a time card, submit PTO when needed and stress over business performance metrics set by someone other than myself. I enjoyed helping people change their perception of health and wellness and I enjoyed seeing their personal growth, which always translates nicely into their fitness goals. But big, box gyms were not it for me. Read More>>

Zuri Lioness

“Chottomatte onegaishimasu”
One rainy evening, I was walking through the streets of Japan with my 4-year-old son. The rain began to fall without warning, the streets glistened, footsteps moved quickly, echoing around us. I had no umbrella, completely unprepared, but we kept on walking. Read More>>

Anna(bug) Jarvis

My dad always told me: “Find a way to get paid for doing something you love.” That advice stuck with me, even during the times I wasn’t sure what that “something” was.

I met Megan at the tattoo shop she was working at and asked if she’d take me on as an apprentice. She couldn’t say yes at the time, but that didn’t stop me. I kept asking—every time I saw her—for almost two years. Eventually, when she opened her own shop, she brought me on board. Read More>>

Valeriia Telemaniuk

One of the biggest and most life-changing risks I’ve ever taken was moving to the United States from Ukraine, leaving behind everything I had built — my home, my career, and my comfort zone. I had been a successful nail artist in Ukraine for many years, with a strong reputation and a loyal client base. But when the war started, I made the difficult decision to relocate to a new country with a new language, new culture, and no guarantees. Read More>>

Sam Greer

I think the biggest risk I’ve taken is not following the typical path after high school. It was the Summer of 2007. I was 18 years old, and my friends were going off to college. I was so close to signing on the dotted line, taking out student loans, and heading off to college like the rest of them. Instead, I made a last minute decision not to go. Read More>>

Gene Clerkin

Looking back, my biggest transformations came from moments of uncertainty. Chiropractic school. It was a huge financial and time investment with no guarantees—but it changed my life.
Later, struggling with my health, I discovered a year-long functional nutrition program. It cost $26,000, and I didn’t have the money. But I knew I had to do it. I literally used credit card checks to pay for it. It was terrifying—but it helped me heal and gave me the tools to help thousands of others. Read More>>

Dr. DeAnna Daniels

For years, I worked as a full-time speech-language pathologist in a structured setting with predictable hours, steady income, a clear career path. On paper, it was everything I was supposed to want. I was grateful, of course. I was helping people. But there was always a quiet pull beneath the surface, a whisper that maybe there was more, that I could do more, if I had the freedom to build something of my own. Read More>>

Coach Torrez

Risk-Taking and the Road to TNT Gym Getting TNT Gym to where it is today has been a journey paved entirely with risk—calculated, passion-driven risk. After earning my second degree in Exercise Science, I landed a secure job as an Exercise Specialist in Cardiac Rehab. Good pay, great benefits, stability. But deep down, I knew it wasn’t where I wanted to be in five years. That’s when the first leap came. Read More>>

Erza Zylfijaj

One of the most defining decisions I made was building a career in an unfamiliar industry, and doing so in a country far from home, without a technical degree, local network, or safety net.
I wasn’t a software engineer, and I didn’t grow up around tech. But I was deeply curious about developer tools and how they shape the digital world. I saw a gap in how these tools were communicated and marketed, and believed I could help bridge it. I joined a fast-growing startup in the reliability space, immersed myself in the product, the audience, and the culture, and quickly took the lead on major initiatives. Read More>>

Irene Nelson

As an abstract painter I create impressions constructed from the thin line between memory and imagination. Each painting involves risk. I face the blank canvas without a sketch or preconceived idea. My gestural marks are organic and free from formula and conscious constraint. Whether painting, drawing or working with monotypes, my process is guided by a mix of intuition and tenacious experimentation. Read More>>

Demetrius Thigpen

One of the biggest risks I’ve ever taken was creating content around mental health while still actively serving in the United States Marine Corps.

Now, mental health is a big topic, sure – but it rarely captures the voice of the service member still in uniform. There’s various niches within the mental health space, but nobody was really speaking to us, the ones still in the trenches. So I took a leap of faith and decided to be that voice. Read More>>

Taurus Graham

Starting my own photography business and spending all the money on equipment in such a saturated field was a risk in itself. Coming from Florida where everybody is a photographer, this was a challenging task I took on. To make it even riskier, I began promoting myself by offering my services for free (as in, 100% free, not even tips) and ran the risk of being known as the free photographer and never being able to break out of this bubble I’ve created for myself. Read More>>

Marie Nguyen

One life changing risk I’ve taken is starting my own personal training business! I had been training for 7 years at a commercial gym, and I was doing really well, but I felt there was no more room for growth. In addition, I wanted more creativity and freedom within my personal training business. I was also going through a difficult time in my personal life. Towards the end of 2022, my sister was in a moped accident, and my grandfather passed away a few months after. Read More>>

C.S. McIntire

After earning a BA in advertising from San José State University, I started my first career as a graphic designer. I slowly worked my way up to Art Director for a small design firm in San Francisco. Long days and the ever-demanding corporate clients lead to quick burnout and I quickly realized that I needed to make a change. I decided I needed to leave the corporate world with hopes of landing a position in a non-profit job. After months of searching, I finally found an assistant position at an adult day program for individuals with dementia. Read More>>

Alejandra Tucker

I was raised by 2 loving Panamaian parents who worked hard. I was raised to get a job that provided stability: One with benefits, a 401K, and security. I pursued the medical field, enrolled in school, and worked a retail job to help support myself. But when I received a paycheck for just \$40 after two weeks of work, something in me shifted. I knew I needed more — not just financially, but emotionally. I wanted to feel fulfilled. Read More>>

Christopher Alan Maloney

Five years ago, I sat motionless in a second-hand rocking chair beside my bed. I looked down at my feet, firmly planted in a new reality. I had just, for the first time, accepted something about my life that I never thought I would have to accept:

I don’t get to do what I wanted to do. I don’t get to be who I wanted to be. Read More>>

Cate Tinker

After eight years in nonprofit leadership, I faced a choice: stay comfortable or take on the challenge of rebuilding a distressed children’s museum. The Above and Beyond Children’s Museum in Sheboygan had been hit hard – closed for a year during the pandemic, damaged by flooding, and in need of fresh direction. I saw the potential to create something meaningful for my community, but it meant leaving behind a job I loved and knew well. Read More>>

Dipa Halder

About a year and a half ago, I quit my stable, well-paying job as a software engineer to pursue art full-time.

Taking my art seriously as a career was never something I thought was possible for me until recently. Like so many others, I had absorbed the pervasive message that art isn’t a “real” career path, so I let inertia carry me toward computer science, which opened doors to a career that offered an intellectual challenge, financial security, and social validation. Yet despite how perfect my professional life appeared on paper, I couldn’t shake the feeling that I wasn’t in the right place—as if I had been swept along by a current I never consciously chose to enter. Read More>>

Laura Kestenbaum

To answer this I would have to take you back to 2023 when I was 6 months pregnant with my now 2 year old daughter. I was working for a big tech company at the time, that I had been at for nearly 10 years and getting ready to take maternity leave, closing out projects etc., when the company announced they would be doing lay offs. Not even 1 hour later I was one of 3,000+ employees that had lost their jobs. Read More>>

Sara Stafford

I was raised in a Penetecostal church and started singing in the church choir and in the choir at school. I had so much fun singing. I always had envied the people in church that played instruments but was mostly a male dominated area. Around the time I was a senior in high school, I made a group of new friends that sat around a fire and shared songs on an old guitar. Some would bring other instruments to the table too depending on the night like harmonica, tambourine or a cajon. Read More>>

Melanie Robinson

For many years, I had a fear of aging due to the messages I received from my mother and grandmother. My mom cried on her 30th birthday, and our family never knew my grandmother’s age until she passed away. Adding to these attitudes, I was keenly aware as a performer that getting older typically meant fewer roles for women. I spent a significant portion of my adult life fearing that I would not be considered relevant after the age of 50. Read More>>

Ruben St.Vilus

As a first-generation Haitian-American, I was raised with a deep respect for hard work, education, and the kind of career that promised stability. For years, I was on the fast track to becoming an OB/GYN — fully committed to a future in medicine. But even while immersed in my pre-med studies, something in me kept being drawn to the stage. Performing wasn’t just a hobby; it was where I felt most alive. Read More>>

Makhosi Nejeser

One of the most significant risks I’ve taken in my business is making the leap from selling $297 a month group coaching offers to establishing myself in the luxury category, where my private work started at $100k. For a few years, I struggled to gain significant traction because whenever I scaled more mainstream, scalable offers, I found that I had to do a lot of convincing to secure clients. Read More>>

Al Davey

If you had asked 14-year-old me how I thought my life would turn out, I probably would’ve said something noble and wildly impractical like, “I’m going to be a vet!”—because I assumed the job was 90% cuddling puppies and 10% getting every senior cat adopted. Fast forward to adulthood, and—surprise—veterinary work actually requires science. Like, a lotof it. Also, math. And blood. And student loans. Read More>>

Wendy Medley

The biggest risk I took was when I left my steady job to pursue a full-time career as an artist. I was a recent divorcee with 2 small children and a new mortgage. I recently switched professions from childcare director to property manager. I was creating art and doing residential and commercial painting part-time beginning in March of 2017. After a year of creating, I noticed that I had to turn down a lot of commissions because of my current job as a property manager. Read More>>

Sara Nevius

After graduating with my BFA in 2022, I was hit with the uncertainty that often follows: What’s next? I debated whether to start applying for MFA programs, go solo traveling, look for a steady job back in Texas, or take the risk of trying to launch an artistic career. One evening at the dinner table in the early summer, I shared these thoughts with my parents. My dad, after listening quietly, said something that stuck with me: “It only takes one.” One yes. One opportunity. One door opening. That’s all it takes to get started. Read More>>

Cathie Beck

In 2008, I was a bitter book author. I’d written a memoir and even as I’d had many the short story published, had been a working (award-winning) journalist and was, at that time, a Rocky Mountain News books reviewer – I couldn’t get an agent, let alone a sale.

So, as a paid books reviewer, I had to read mediocre books and give them ratings and my editor at the time thought I was too hard on book authors and that every “C Level” book deserved to be an A – or at least a B. My background is in literature, including Russian literature, so I’d a read a thing or two. I had a clue what beautiful writing is and how the best of the best sustains. Read More>>

 Z! Haukeness

Two risks in my life mirror each other. 1 – Deciding to switch my major to Black Literature and Art during my undergrad at the University of Wisconsin-Madison, and 2 – Deciding to leave my long-term job at Showing Up for Racial Justice (SURJ) in order to launch my spiritual healing business. Read More>>

Cari Alam

One of the biggest and most transformative risks I’ve ever taken was leaving my corporate job after nearly 20 years to fully embrace life as a creative entrepreneur. I had spent the majority of my adult life climbing the corporate ladder but I knew I was being called to something more aligned with my soul: a life of creativity, artistry, sensuality, and freedom. Read More>>

Eloise Harpas

Risk is a powerful thing. It can change a persons life in an instant. Taking a risk for me means growth and growth means knowledge and knowledge is power. I believe you learn from taking a risk to only become the best version of yourself for life.

In my career as a professional performer i’ve taken many risks one of which was moving across country to pursue a dream, but recently i took the biggest risk of my career so far. I decided to change course within the entertainment industry or should i say expand myself within the industry. Read More>>

Christen Ball

Honestly, creative risk is something I deal with on a daily basis. I’m an alternative rock music artist in Nashville, TN, a place that is celebrated for being country music capitol of the world. For the career path I’ve chosen, at this point in history and in this region of the world, it would be a lot less of a risk for me to lean into writing, performing, and recording country music. Read More>>

Coya Paz

In 2011, Free Street was at the point of closing after over 40 years of providing free theater and free theater training across Chicago. A series of administrative shifts, staff turnover, and funding challenges left the company at the verge of collapse, and the board hired Caroline O’Boyle to essentially do the administrative work of shuttering Free Street. Instead, she saw possibility. Read More>>

Elizabeth Corey

Risk Story – Reuniting with My Birth Mother After 25 Years
Taking a risk doesn’t always look like launching a startup or jumping out of a plane. Sometimes, it looks like packing up your car and driving straight into the unknown — emotionally, mentally, spiritually.

For years, I quietly carried a longing to reconnect with my biological mother — not out of nostalgia or sentiment, but from a deep need for personal clarity. I had questions no one else could answer. Why do I tie hairbands around my brushes? Read More>>

Fiona Coakley

Leaving home and moving over 1,800 miles was the best decision I could have made for myself. For the first 22 years of my life, I lived in the Northeast, living in nine different places, from a small farm town in New Hampshire, to the city of Boston, Massachusetts. In each location, I gained new lessons, skills, and experiences. However, at a certain point, I felt like I had overstayed my welcome. Boston no longer felt the same; the art scene had diminished, and the city was rapidly becoming an expensive tech hub. Read More>>

Makayla Renoos

Working in the wedding industry comes with a lot of expectations, both for vendors and couples that are navigating it. There’s this unwritten idea/script about what it’s all supposed to look and feel like, and oftentimes we can’t shake that weight off of ourselves. Read More>>