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.

Jennifer Keane

Deciding to be an actor is an exciting adventure that is both scary and exhilarating. I decided to be an actor after graduating high school. I had been training as a dancer for ten years at that point and had no connections in the entertainment industry. After training at the American Musical and Dramatic Academy in New York I auditioned for hundreds of roles that I didn’t book. I lived in Los Angeles for years and moved back to New York. After tons of extra work I auditioned for Stella Adler and attended their three year conservatory. Read more>>

Steven Celi

First leap was attempting to train myself to dunk at 5’10”. Not only did that accomplish a childhood dream, it completely removed all my limiting beliefs. it taught me believing is seeing (not the other way around). This journey led to my spiritual awakening and self discovery path. Read more>>

Samuel Garcia

I am a Respiratory Therapist and work 6 12 hour shifts a week. I needed something new. Inwanted to start a business but was unsure of what I was interested in. My initial idea as to open up a torta shop that was Americanized and using Subway as a blueprint. After researching startup costs, I realized it would be too expensive for me. I aleays wanted to start a clothing brand and with my recent love for motorcycles, I felt it would be the perfect fit. I started my Motorcycle Gear and Apparel company march 2025 and felt it was a risk that needed to be taken. Clutch and Throttle Gear Company was the name I settled on. Read more>>

Amy Elizabeth Davis

Recently, I left teaching after a 25-year career to go full-time into cut flower farming. The flower farm was established in 2023, but I was still holding on to teaching as my main source of income. As my flower business began to grow, so did a longing to be gardening and farming every day. Read more>>

Jan Watermann

Back in middle school, I realized something most people don’t even question until much later: the traditional path just wasn’t for me. I couldn’t imagine spending my life in a classroom, followed by decades in a 9-to-5 office job. So instead of going on to high school, I made a decision that shocked pretty much everyone around me-I left the traditional education system entirely. Read more>>

Brittney Coleman

I took the biggest risk of my life while I was pregnant. I found out I was being cheated on. I was carrying life inside of me, while the life I had planned was falling apart. I had every reason to stay quiet, settle, and “keep the peace.”
But I didn’t. I chose me. I walked away. No plan B. No safety net. Just me, a broken heart, swollen ankles and all, knowing I deserved better—even if I didn’t know what “better” looked like yet. Read more>>

Natalie Yale

This month, I performed my first One Woman Show to a sold-out crowd in a 50-seat theater. It wasn’t just a milestone—it was a defiant act of self-rescue. A few weeks earlier, I hit rock bottom—just blocks from my apartment. I was crouched against a concrete ledge on the side of a New York City street, alone. I was a senior at NYU Tisch, twenty-one years old, about to graduate. I had spent the last year and a half chasing this dream with everything I had—auditions, training, relentless effort, unwavering belief. And still, I felt like a failure. The future looked like a black hole. I couldn’t picture anything ahead. Read more>>

Tarul Kode

The biggest risk I’ve taken is betting on myself. I grew up as the eldest daughter of immigrant parents. Until I approached my 40s, I spent my life taking care of my loved ones at all costs, personally and professionally. Every decision I made was based on what others needed me to be to them. I graduated with a doctorate in pharmacy at the age of 22, knowing I did not want to be a pharmacist; I had wanted to be a family practice doctor like my mom. My parents were divorced while I was in my graduate program, so instead of pursuing medical school, I went to work with the hope of helping my mom with my younger siblings. I carved a niche career for myself as a managed care executive and leaned into growth, building a dynamic skillset. Read more>>

Jeni Holla

One of the biggest risks I’ve ever taken wasn’t moving across the country, selling everything I owned to live nomadically for three years, or even walking away from a six-figure job — twice. It was saying yes to something I couldn’t fully explain. Something that didn’t come with a roadmap. Something I knew people might not understand. Read more>>

Meghan Stimmel

My entire life is all about jumping. Leaping. Free falling even when my hands are shaking.

A little over 6 years ago, I burned my entire life to the ground. So when I say I went from literally $0 to a 6 figure brand and growing, I mean it.

I started graduate school at 33 years old, with a 2 year old on my hip, newly sober, and living back with my parents. Completely starting over. I remember believing in myself so much and knowing deep down in my soul that I could not live the rest of my life feeling imprisoned to a life that was not authentic to my heart. So I took the biggest risk of my life and prayed. I literally heard God tell me through my tears and my fear that everything would be okay. Read more>>

Anitra Lavanhar

My love of photography started back in high school (many moons ago) in the darkroom. After high school I seriously considered starting a career in photography, but I was too intimidated by the competitiveness, and the technical challenges of the art form so I ended up letting my dream go and pursuing other things. Then, in 2015, when I was just about to turn 50, I found myself at the end of one career and not knowing what to do “when I grow up.” A friend suggested that I join her on a 2 week walking pilgrimage on the Camino de Santiago. I went, with only 6 weeks to prepare, and during the pilgrimage having the time to walk, talk and reflect with my friend, I decided to finally pursue my dream of becoming a photographer. Read more>>

Kenna Harrington

From a young age I realized that taking risks in life may be my only chance to get to where I desired to go. While in my last year of undergraduate school at Bowling Green State University I was nominated to perform at The Kennedy Center American College Theater Festival/Competition. This was my second time performing at the festival. This time the competition held more weight. As I was approaching my final months at the university level, I had no idea where my career would take me, but I knew that something needed to be done. I was walking down a dark tunnel in life, fearful of where the path was leading. Yet, I kept walking. Read more>>

Hayden Newland

Being a musician is a long journey of continually taking risks. Risk of judgement, people making fun, failure, going broke, and never actually getting where you want to go. I used to not show my face on camera because I was terrified of getting made fun of by even my best friends. A little over a year ago I moved to LA to take the next leap in my music career and it was terrifying. I’d never lived outside of my home state of Idaho. I left everything behind to go to a music school that I had gotten accepted into. I didn’t know a single person and was honestly terrified. Read more>>

Ry Armstrong

One of the biggest risks I’ve ever taken was deciding to run for Mayor of Seattle. Not just because it’s a massive undertaking—but because I’m running as an openly trans, nonbinary person in a time when our very existence is being politicized and legislated against across the country. Read more>>

Tea Fannie

Pretty wild that just 6 years ago I had massive stage fright. When i left my ex husband I made the decision to start doing music, but the planned path in my head was to just be a recording artist and ghostwrite for the greats. But just under a year in, and the studio I recorded out of was doing a release party and he said I had to come up with a 15 minute set. I said no quite a few times, but as you’re probably guessing, I ended up on that stage. I enlisted my cousin to come up on stage with me for moral and vocal support because she can sing, I’ve never even had the courage to do a karaoke before this moment hehe. Read more>>

Shauyan Noorfeshan

One of the biggest risks I had ever taken was starting to make content. For the longest time, when I knew I fell in love with soccer, I would talk about it nonstop to my friends or family. Sadly, there weren’t many people in my circle who shared my passion for the game, as it wasn’t as popular in the United States at the time. So I would watch countless hours of YouTube videos of other content creators who played FIFA or just spoke about the sport. I knew I always wanted to do what they did. Read more>>

Rose Anderson

Have you ever had that gnawing feeling in your gut that you should do something? make a change? decide on something? well, that was me in March 2025. I will share the decision first, and then provide the backstory on how I arrived at that decision. So the decision is, I decided to move back to South Florida from Orlando to help care for my aging parents, who are 100 and 93 years old. Before this decision, I had a plan. I planned to live in Orlando (which I did for a short time), build my new life, make new friends, enjoy my new home (that I bought in November 2023), one day meet the love of my life, get married, and just live a whole new life in Central Florida! Read more>>

Lucy Sun

A risk that I took was the summer course I participated at GOBELINS Paris. Originally, my friend and I were working on a project together when I had found that GOBELINS, a school that we had always looked up to was accepting people from all walks of life to take a class in Visual Storytelling. I was in my 4th year of university, continuing into my 5th to finish both of my degrees (mechanical engineering and art and design). It was over the summer, expensive, and would severely limit my internship possibilities due to the dates that the course would be in, but after much consideration, I knew in my heart that this was a risk that I was willing to take. My friend and I of course both applied together, got in together, and before we knew it, we were on our flights to Paris not knowing the people we would meet and the stories that we would create. Read more>>

Samantha Bowens

Taking the path of a creative is the risk here. Moving to a city like Los Angeles, where you have never been before is a risk. Trusting those in the industry and community to help you along the way is a risk. Trusting that the things you want to aspire to be and grow in will benefit you in ways that the system doesn’t do for you, is a risk! Seeing a vision for yourself that might not be seen by others and thought of as a waste of time, is a risk! A risk that is worth it in the end regardless of the outcome, because it felt good to you. To have something that came from your person. Risking the human experience to the fullest, I think! Read more>>

Erdem Ülker

Moving to the NJ/NYC area has been the biggest step of my life, by far. I realized near the end of high school that a lot of my friends would be continuing on with the plan they had set for themselves by pursuing their degrees in college. As the months passed, it kept hitting me that my path wasn’t entirely clear regarding a higher education. I did not know what college I wanted to go to, what kind of degree I should pursue– it seemed hopeless, in a way. I just could not bring myself to commit to something that did not speak to me. Read more>>

Julie Ramos

I went to beauty school in 2010 and graduated in 2012. I was so scared to get my cosmetology license, I didn’t feel prepared so I waited. I waited a long time. I got licensed in 2020 after the restrictions in Nevada were lifted. I cried before and after I took my tests and I passed first time! I worked in corporate salons for almost 2 years and I knew it was not for me. I was terrified to step out on my own but something inside me wasn’t happy working for someone else. I never got the holidays off I never could take time off I was missing out on things with my son and that was enough to push me to go to booth rent. I was doing booth rent for 2 years. Read more>>

Laurel Cannon

I’ve always been a low-risk person with a plan: become a doctor. It was the “safe” dream. But along the way, my love for psychology, true crime, and Dr. Phil, sparked a deeper curiosity about people. How we break, how we heal, and what peace really looks like. This pushed me to start a PhD program in health psychology; I’m wrapping up my dissertation so in this aspect of my life, playing it “safe” has paid off. Read more>>

Joey Min

I think, one of the most obvious life changing risk I took was to go all in into being a Youtuber.

But the truth is, long before YouTube even existed, I was already telling stories. In my younger years, I was that kid with a camera, filming martial arts shorts and sharing them on Myspace or niche filmmaking forums. This was during the time when you had to pay for web hosting just to get your videos online. Read more>>

Margarita Ryan

The first big risk I took was coming to live in the United States, and more specifically to a town of scientists where art didn’t seem to have a place. That was three years ago. I married my partner in crime, who accepted a job at LANL. Coming here meant leaving everything I had built in Argentina: my country, my artistic career there, my family and friends, my culture. I arrived here with no connections, no command of the language—a disaster. Read more>>

Bingle Pizarro

In 2020, when the world went under quarantine, I decided to take the biggest risk of my life – leaving the only home I’d ever known. I traded in paradise for a pair of dice. Figuratively speaking, I left an island in the Pacific Ocean called Guam, and took a bet on myself when I moved to Las Vegas.  Read more>>

Anna Gusselnikova

I initially studied fashion design with a focus in menswear. After almost a decade of working in design roles I decided to take a sabbatical and explore what I wanted to do career wise/creatively for a whole year. During this time I fell back into fashion illustration, and instead of doing the quick work sketches I did in my corporate jobs, I had the luxury of taking the time to make them more elaborate. It quickly clicked that this creative part is what I really enjoy in the design process. As I spent more time drawing and flexing my creative muscle, my illustrations and style started emerging at a faster speed. Read more>>

Amanda Billhartz

Starting a business always feels like a risk. But taking the last bit of money out of your bank account to start a business can feel like downright insanity. I remember the giddy, thrill-charged, what-am-I-doing feeling like it was yesterday. I had this crazy idea to take every bit of money we had left in our account and order hundreds of plants from Florida. Read more>>

Gregory Greene

The founder of Fork Spoon and Plate is lead by Gods calling to serve those in need. Our motto is – God said it, we’re doing it. No risk is too great in serving the kingdom of God through his children and serving our neighbors with dignity and care. Read more>>

Nicolette Williams

A few months after my husband, our four children, and I sold our home in New Jersey, we made the bold decision to uproot our lives and move to North Carolina, specifically to Wake County, a part of the state we had never even visited before. We were drawn to the area by its family-oriented atmosphere, growing opportunities, and diversity. It was a leap of faith in every sense. Read more>>

Katie Filer

I was raised to follow a path—a clear, well-paved blueprint for how to become a functioning adult in the world. My parents (who split when I was five) made it clear: get good grades in high school, get into an esteemed undergraduate program, go on to get your master’s degree, and land a great job at a well-known company. As the oldest of five, it was my job to execute each step with excellence, to model success by staying the course. Read more>>

Evgeny Pisarev

In October 2019, we raised our first investment for Qummy — $200K structured as five tranches of $40K each. After receiving the first three tranches, we launched food production, refined our proprietary freezing technology and smart ovens so that our meals, once defrosted, would taste as fresh as if they were just cooked. We opened our first locations and began selling our ready-made meals. Read more>>

Sherri Plotke

I’ve been taking risks in business since 2009, when I opened my own real estate brokerage. Over the past 14 years, I’ve grown that company through both market shifts and personal growth. More recently, I took a leap by investing in two TOX territories in Greater Phoenix. Read more>>

Khabu Young

I went to the High School for the Performing & Visual Arts (HSPVA) in Houston TX. I earned my first pay check at age 15 playing guitar for a production of Joseph & The Amazing Technicolor Dreamcoat and then playing jazz music professionally. I was being groomed to go to New York City to pursue being a ‘Jazz Guitarist’ to hopefully play with some of the Jazz Giants along the yellow brick road to success. The reality of living in NYC was something else completely different and being in a highly conservative and myopic Jazz Studies environment turned out to feel very stifling and creatively unsatisfying. Read more>>

Cam Bogle

Though I was born in the beautiful city of Portland, Maine, we moved a little when I was young, and spent my youth in the city of Burlington, Ontario Canada. For as long as I can remember, Burlington was considered one of the top communities for exceptional quality of life, and had a thriving economy ripe with opportunity for businesses — ranked 5th in Canada. Read more>>

Jaclyn Paradise

I remember the moment everything finally clicked—every ounce of confusion, every second-guessing thought suddenly made sense. I was sitting in a room, listening to how rehabs actually stayed open—not just from big pharma reps dropping off samples, but from something far more insidious. It was the behind-the-scenes reality that sparked a deep fury in me. Body brokering. A system designed to keep the boys’ club in business—profiting off pain, disguising greed as care. And in that moment, I knew I couldn’t stay silent. Read more>>

Jasmine Davis

Deciding to quit my job bartending and college to become a entrepreneur was quite the risk. I knew helping others and fitness was my passion and focusing on entrepreneurship was necessary. The main reasons i decided to own a personal training business was to make a impact in African American households and demonstrate that being healthy is necessary to prevent health problems. A lot of my immediate family members suffer with diabetes, high cholesterol, etc. I knew that my purpose was bigger than me. When I first quit college I had no direction on what i wanted to do so i started bartending. Read more>>

Megan Howell

My life changed when I took a major risk to pursue helping people full-time. I was working on my Master’s degree, employed at a local restaurant with a reliable wage, and had just opened my first business that helped house homeless individuals with mental illnesses through subleasing and providing concierge services. Read more>>

Tricia Battani

At 17, I was laser-focused on graduating high school a year early and had stepped away from dance to make it happen. One afternoon, I was driving home from school and an ad came on 96.7 KIIS FM announcing open auditions—happening right then—for their hip hop dance crew at Atomic Dance Factory. I hadn’t performed in months, but something inside me told me to go. I rushed home, changed, and made it just in time to catch the end of the audition. Read more>>

Shradha Challa

One of the biggest risks I’ve taken recently was launching Nari’s chai concentrate. For the first year of the business, we focused on loose-leaf blends—and they did well. But I kept thinking back to my college days, when I didn’t have time to brew chai from scratch. I wished there was something quick, already brewed, but still tasted like the real thing. Read more>>

Damien Baskette

For me, the most significant risk I’ve taken was definitely a life-changing one. That was the risk and the decision I made to start living my life based on my intuition and what truly brings me joy and happiness. I decided to let myself and my ego take a back seat in my life and the decision-making process, and see what happens if I just let go of the wheel and go with the flow, wherever that takes me. Read more>>

Luis Solo

The biggest risk I’ve taken in the entertainment world was walking away from my podcast. After nearly three years of building and maintaining it on digital platforms, deciding to shut it down wasn’t easy. I clearly remember that after releasing the final episode, the first question I asked myself was: “What’s next?” Read more>>

Matt Boren

I have been a storyteller my entire life. Creating characters and new worlds for them to occupy was always the thing that lit me up most. So, whether it was developing new work in the theater or at Tuesdays @ 9 (a phenomenal creative space for emerging ideas/voices which was launched years ago at the Naked Angels Theater Company) I was always in the practice of refining – while failing and succeeding in equal parts – my voice as a storyteller. With the story as my compass, I never cared much about what it would ultimately be, albeit a TV show, a screenplay, a play or just some long-winded, experimental thing. But as I got deeper into my twenties, I realized that selling a project here and there, as joyful and rewarding as it was, didn’t provide enough financial stability. Read more>>

Kayla Nettleton

One of the biggest risks I’ve taken was shifting from a full caseload of insurance-based therapy clients to building a completely private pay practice—and later expanding into couples intensives, group therapy, and business coaching for other therapists. It was terrifying to move away from the “guaranteed” flow of clients that insurance panels bring. But I was burning out fast and realized I wasn’t showing up as my best self—for my clients or my family. Read more>>

Shavon Johnson

Before I started my business anointed braids, I worked as a full-time medical assistant in the hospital during this time, I was doing hair part time on the side just to make some extra money. A year later I ended up expecting with my youngest son and so I decided to quit my full-time job and establish my business full-time working from home without knowing the outcome I was able to find a workspace for a decent price, and as soon as I quit my full-time job, Covid hit and I was not allowed to work in my shop the first four months I was working that was the most. I’ve been tested in my entire life as an adult when it comes to my career it took a lot of faith and patience to stay consistent and not give up and now I am one of the fastest braiders in Minnesota and I have a clientele base of over 600 clients. Read more>>