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.

Justine Blazer

One of the biggest risks I’ve taken was moving to Nashville to pursue music. 13 years now in Nashville, I eventually opened my own studio, Ten7Teen Studios, which I recently converted it to a Dolby Atmos 7.1.4. As a woman producer, mixing/audio engineer, and artist, I wanted to do it all. I left a comfortable path back in Michigan, a steady stream of gigs clients and collaborations, and instead stepped into a city where I didn’t know if there was space for someone like me to fully be me. I wasn’t just trying to make a living — I was trying to make history. Read more>>

La Tonya Powers

This is certainly a story that I can tell. Growing up, we were instructed to have all the information and all our ducks in a row, per se. But what happens when you need to change your life, you don’t have all the information, and everything is out of order? I had just moved to Georgia, I was newly divorced, a single mother, and trying to figure out how I would create a new narrative for a season that I couldn’t even see what tomorrow would look like. The one thing I knew I could do well was speak, I knew that God had given me the gift of helping others. To do that, I had to create a curriculum to help myself. You can’t be good at telling others to do what you won’t take a chance on yourself, so I took a risk and started my own coaching company. Read more>>

Rain Garcia

Creating the first-ever transgender march in San Antonio, dubbed “ The March of Us,” was a venture that came with significant risks and uncertainties for me. In the beginning, I felt a mix of fear and apprehension. I worried about how everything would unfold and whether my allies and the community would come together to show Texas that San Antonio embodies love and acceptance. Read more>>

Kaui Wilson

I’ve been an artist my whole life; went to school, got my degrees, etc. But I decided on having a family instead of pursuing a career in art. I did do freelance graphics and web design work, but I was a stay-at-home mom, for the most part. Read more>>

Cassidy Dyce

When people think about risk, they often imagine a single big leap. For me, risk has been a series of choices, each one scarier and more meaningful than the last. In 2019, I turned down an offer with a government agency, a “safe” job with benefits, to chase something less certain but far more aligned with who I was becoming: my dream of becoming a full-time writer. Many people in my family thought it was a mistake. Stability was on the table, and I was walking away from it. But I moved to Seattle, Washington, and moved in with my sister, determined to make it work. Read more>>

Devin Richter

I grew up in a home shadowed by an abusive stepfather and all the complicated trauma that follows. My survival tactic? Be the most obedient, quiet, and invisible version of myself to stay safe. But after years of enduring that storm, I finally got out—and somewhere deep inside, a tiny seed of me began to grow. Read more>>

Amickoleh Imani

My business is in the wellness space. Personal growth, energetic strategy / energy healing, and soul medicine for high-level conscious creatives and entrepreneurs. My background is in fashion design. I’m also a photographer and a singer/songwriter and have pursued these avenues as well, photography as a business and singing as a creative expression and soul passion. Read more>>

Joe Cebula

It was around 2009, during a really tough economic period, that I started working for a non-profit. I was a housing counselor, and my focus was on helping people navigate the absolute crisis of potential foreclosure, trying to find ways for them to save their homes. That work, in those difficult times, felt genuinely important. I had a regular paycheck, and for a while, there was a sense of stability. But even then, a feeling of unease started to creep in. Read more>>

Ksenia Mohur

I’ve been in the lash and brow industry for about 9 years — starting in Ukraine and continuing in the U.S. Back home, I went from working at home and in salons to eventually opening my own small studio, which I ran for four years. It was a space I built with care and trust. When the war started, I had to leave. At that time, someone I cared about encouraged me to try building a life together in the U.S., so I decided to take the step. I didn’t have big plans — I just wanted to survive, maybe find work in a salon, and keep supporting my studio team back in Ukraine. Read more>>

Gauldan Gio

maybe the story sounds cliché, but moving to New York on my own with no one I knew beyond surface level, with no family here, with no job, with no plan with Nowhere I knew I’d be welcome for sure in my heart… Was one of the greatest risks I’ve ever taken . when I was 16, I moved to New York for the first time on my own. My mother has always been an amazing mother, and she’s always trusted me in a very different way. She was afraid, and she also had her apprehensions, but she was also very sure of the light that I had in the skills that I had only learned from being raised by her . I wasn’t doing well in school back in my hometown, Ohio, I guess we should’ve started there first Toledo to be exact.. Read more>>

Hannah Gerrity

The story that comes to mind when I think of taking risks has to do with my first job out of college. I was newly married and living downtown Chicago. My music degree wasn’t earning me any money yet, so I decided to find a retail job to help make ends meet. I walked into my favorite brand and asked if they were hiring. I returned a week later to join a group interview, and thankfully, I was told to return for one more one-to-one interview with the store manager. She asked me to style some outfits, and then followed up with a slew of fashion questions that I had no idea how to answer. Read more>>

Alexander Jeffery

Towards the end of 2019, myself and a few friends went to Sicily to make a feature film. On the surface, that might sound pretty glamorous — and in lots of ways, it was — but it was a huge leap of faith to make an extremely low-budget indie film in a foreign country where we only had two local connections that could help us navigate the waters. Read more>>

Ilyssa And Dave Kyu

When we first started dreaming up ‘Campfire Stories’, Dave and I had steady full-time careers in our fields. We felt like we did all the things we were supposed to—go to college, get a job, get married, buy a house—but felt unfulfilled… perhaps because we hadn’t taken any big risks. Read more>>

Nathaniel Mervar

The year was 2016 and I found myself as a freshly-graduated student from high school. Homeschool high school, I might add—with an ambition to turn my hobby for film into a business—Because of Jesus Films. Read more>>

Sean Draper

In 2016 after graduating from the university of Iowa. I moved to Kobe Japan where I played American Football for a tech company called Elecom Kobe Finies for 5 years. While I was there I also coached at various universities (Kobe Uni, Kyoto Uni, Kindai Uni, etc). Coached at Minoo Jiyu high school in kansai, while teaching various elementary school kids how to play flag football and basketball. Read more>>

Niro Feliciano

I have taken big career risks in my life that have been spiritually led. The first was was at 27 leaving medical school- a goal I had worked towards for a decade. I was not sure what life would look like after that, but it was a decision based on what I was feeling spiritually and intuitively and one that seemed like the right one for my husband, I, and our future family. Coming from 2 physician parents, it was not an easy one and everyone around me discouraged me from making it. But something within me knew it was the right one. The second time it was when I had a thriving, flourishing, lucrative practice. I had a sense that I needed to do much less to make room for new things. Read more>>

JALEN ST.ROMAIN

I arrived in Los Angeles in late April of 2023, my beat-up suitcase and two turntables tucked under my arms, a faded dream cradled in my heart. I had no money, no connections, and definitely no plan. Just the rhythm of the city pulsating in my veins like a bassline begging to be dropped.

The first days blurred into nights as I crashed on a friend’s couch in East Hollywood. The overhead lights buzzed like they were on a perpetual caffeine high while I watched the city come alive. Every weekend, different neighborhoods turned into sprawling dancefloors—people swaying to the music that filled the streets, the air thick with the scent of ambition and possibility. Read more>>

Emme Diane Burg

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that, can you take a minute to introduce yourself and give our readers some of your background and context? Read more>>

Alyoska Diaz

One of the biggest risks I’ve ever taken was leaving behind my career, family, my home, and everything familiar to start a new life in the United States.
I was born and raised in Cumaná, Venezuela, and earned my dental degree from the Universidad de Carabobo in Valencia. I built a meaningful career, running my own dental clinic, providing care to underserved communities, and serving as a dentist at the Universidad de Oriente. Dentistry wasn’t just my profession; it was a deep part of my identity and a way I connected with and helped people. Read more>>

Jacob Miguel

Taking a risk isn’t just a phrase—it’s something I’ve lived. I poured over $60,000 of my own money into self-funding a documentary that I believed needed to be made. No investors, no guarantees, just a vision and the drive to see it through. Every dollar was a decision: to keep going, to bet on myself, to trust that the story I was telling would matter to someone out there. There were countless moments of doubt, but I knew that if I didn’t take the leap, no one else would do it for me. Read more>>

Chhaya Nene

Taking a risk is the biggest act of courage and love you can have for yourself. I’ve kind of just always leapt and trusted that a net will appear. I like to think of taking a risk as going on the monkey bars and trusting you will find your way to the next rung. Read more>>

Suzi

Being a business owner means constantly making decisions — and most of them involve some degree of risk. After more than 30 years as a business owner, I’ve certainly taken my fair share. But the biggest, boldest risk I ever took? Following my passion. Capitol Realty has been in my family longer than I’ve been alive — and I’m 66. I took the helm as broker/owner over 30 years ago. Based in Newport, Capitol is one of Rhode Island’s oldest real estate firms and built its success on a reputation for exceptional client service. Read more>>

Irene Jiang

I never used to consider myself a literary writer. I’ve always wanted to write for television and imagined myself in the writers’ room of some campy, irreverent sci-fi show with great cast chemistry. In 2023, I moved to Los Angeles in search of a TV writing job. I had some great generals, and one, “If this show goes, I’ll call you.” Then, the entertainment industry imploded. Read more>>

Bunnie Reiss

I think about risk alot, or mostly the privilege I have to take risks. I have a fairly dedicated practice that includes listening to Esther Hicks regularly, and her idea of risk is so interesting. She believes the odds are always in your favor, so risk is really just an illusion. She also believes in ease with life. Not necessarily easy life, which is very different, but a kind of flow that comes from ease, and truly understanding your purpose (and stepping into it). In my opinion, flow can only really come if you are challenging yourself and taking risks. Read more>>

Jessica Moore

For 18 years, I worked in the service industry. Fast-paced, demanding, and relentless. The money was easy, and I was good at it. I learned to move quickly, think on my feet, and solve problems as they came—usually at the worst possible moments. I helped build creative, successful businesses. I led teams. I hit goals. On paper, it looked like success. But something was missing. Read more>>

Sam Benjamin

The biggest risk I’ve taken was leaving my home town and moving to London to make it as an actor. I was born in Birkenhead in the North West of England. As the son of a hairdresser and a taxi driver my desire to pursue a career as an actor was not exactly a path well trodden. Nor was my closest city, Liverpool, particularly flush with opportunities for professional actors at the time. London was the place to be. Where the major theatres were, where most of the filming happened, and where most of the auditions, agents, directors and production companies were based.  Read more>>

Sammy Burke

I had developed a successful routine as a bassist. Playing in one of Orange County’s most popular cover bands, we had residencies at nearly a dozen venues throughout the county. People would follow us from club to club, week after week. It was consistent work, as clubs would book out the twelve months in advance. But something was lacking. Read more>>

Gabrielle Lyles Lyles

In 2016, I was a freshman at Jackson State University when I first stumbled across a post from a photo booth supplier showcasing their new and improved photo booth design. Something about it immediately caught my attention — the idea of creating joyful, memorable moments for people stuck with me. I told myself that someday, I would go back and invest in one. It became one of those little dreams that quietly sat in the back of my mind while life moved forward. Read more>>

Alfonso Apodaca III

When I was working as a medical illustrator, I had the incredible privilege of working alongside Rusty Jones — an artist whose talent was only matched by his generosity and leadership. Rusty wasn’t officially my boss, but he became a mentor in every sense of the word. He took the time to guide me, offering not just technical advice about technique and precision, but also inspiring me to see the deeper storytelling power behind our work. Read more>>

Melissa Avila

My first boss out of Esthetics school taught me a lot! In the interview with her at the age of 21, I told her “I know I know nothing and I’m just here to learn”. These were my own thoughts and words, I didn’t pick this saying from anyone, it’s truly how I felt and I was excited and scared. She was no nonsense and very direct and serious about making sure I was trained properly. Read more>>