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.

M. Lori Torok

Life is risky. When you cross a busy street, you take a risk.
When you begin a new relationship, you take a risk.
When you create a new poem—risk. You move to a new house, a new town, a new job, a new belief system… risk, risk, risk.But what is the alternative?
To remain unchanged, unmoved, unloving, supposedly safe?
F or me, that’s a slow death. That’s decay.  I learned early on that I needed to be on a path of expansion. As a creative being—part of a co-creative universe—I had to become comfortable with risk. To live fully, to be truly engaged with life, we must take risks. Whether it’s the risk of showing up fully, of putting yourself out there, of being vulnerable—or the risk of doing something with no guarantee of success—that is what it means to be alive.  Read more>>

Katie Mann

When Annie and I had the idea to start a theatre company for people with disabilities, that in of itself was a risk. Were there enough arts-loving people out there to enjoy such a thing? Were the demographics grouped together enough for it to be a practical idea? Did we, a vocal performance major and sign language interpreter, respectively, have enough talents combined to run a business?  Read more>>

Mika Toussaint

One of the biggest risks I’ve ever taken was moving to Dallas, Texas, without knowing a single person. I made the decision after the passing of my mother—a moment that marked a profound death and rebirth in my life. At the time, I was living in Los Angeles, but the city no longer felt like home. I felt disconnected, and I knew I needed a fresh start—spiritually, emotionally, and professionally. Read more>>

Evan Jacobs

What is the biggest risk I’ve ever taken well to answer that question id have to say it was taking a risk in myself and the dreams I’ve created in life. About 10 years ago I would have never seen any of this happening for me I was in an accident that totally changed my life in every way imaginable the idea of me playing music was out of the picture the idea of me being an artist was gone at the age of 24 I suffered from a Major cardiac arrest incident that should leaving me blind deaf and and in a coma for a month after that I was left in a situation where it was either I was gonna let this defeat me or I was going to make something out of it and that’s exactly what I did I took that risk bet on myself and here I am today almost 11,years later alive and better than every all because I bet on myself. Read more>>

Nicky Loudd

So in 2017 Myself and my business partner, Jeff D’Amato, who passed away November 22 rest in peace. We vended the sneakercon in Cleveland. Mind you Jeff used to live in Fort Lauderdale. He used to sell the brand in Florida and I would sell it up here in Cleveland, Ohio. Also, by the way My brand is called Loudd It’s an acronym which stands for live out your dreams daily. Read more>>

Dustin Sutton

One of the biggest risks I’ve ever taken was moving to San Diego after college with no job, no plan, and no real connections. I grew up on the East Coast in Philadelphia and went to the University of Delaware. Like a lot of recent grads, I wasn’t totally sure what I wanted to do—but I knew I needed a change of scenery and a fresh start. Read more>>

Ollie Schoo

Simply sharing my art has been a risk. Being open to whatever the reaction may be. I’ve realized there’s a priceless benefit in sharing, whether people like your art or not. It has helped me to see more clearly how others feel – and how I feel. When I share a piece and receive a different reaction than expected, it teaches me something about the world. And within myself, I can explore whether I agree or disagree with that reaction. Significant realizations would be lost without the act of sharing. Read more>>

Nancy Brittelle

I started painting in my late 40’s and quickly found some success as a realistic painter. After several years of working in watercolor, acrylic and collage, I increasingly felt the urge to take my work in a new direction, one that reflected my own unique vision. I began this quest by asking myself to reconnect with my earliest creative memories and remembered playing with cardboard as a child, creating environments for my dolls. I began adding cardboard to my collages and became more and more inspired as I built up the surface of my work and explored the possibilities this new material presented.  Read more>>

Carrie Dean

Life is about taking risk. That one simple risk can change your life forever. With starting a new business it’s a risk but on the back end it is very rewarding. I can remember when I first started out my business in 2020 I took a risk and went hard at my location and it changed my life forever with faith all things are possible. It turned out to be the best decision I ever made no one believed in me but me and it was something I would do again and again.. Read more>>

Luna Rose Wolf

In 2023, a birthday party evolved into a five-day extravaganza featuring several dozen bands, food trucks, and vendors. It became known as LunaFest ’23, which many complimented for its organization, management, and quality of both artists and vendors. The whole event was run by myself. Read more>>

Ledia Regis

Starting your own business isn’t for the faint of heart—it’s far from a get-rich-quick scheme. It demands resilience, patience, and the courage to step far outside your comfort zone. Success doesn’t come overnight, but if you stay committed, work relentlessly, and learn from every setback, the rewards will follow. Remember: You reap what you sow. Stay focused, keep pushing, and the results will come. Read more>>

Kelly McCaughan

A big risk that I have taken personally, professionally, and artistically was when I took my one-woman show — which I wrote, produced, and starred in — to the largest arts festival in the world: the Edinburgh Fringe. The idea of Edinburgh first started when my professor in undergrad mentioned it during one of our classes. He told us about his experience at the Fringe and romanticized it in a way that was very enticing. He had performed there himself, and I knew that I would eventually want to take my own work there someday. Read more>>

Sterling Cabbiness

Right now, creatively, I’m taking the biggest risk I ever have: choosing to be the most vulnerable and brutally honest I’ve ever been. I’ve always prided myself on being open and honest in my music. But I started noticing that I often wrap sensitive topics in metaphor. So I asked myself a simple question: What would it look like to say exactly what I mean, without hiding behind metaphor or analogy? Read more>>

Tori Stanley

It all started when I met my now business partner back in 2007. She had hired me as a manager of a specialty facial threading salon she had opened with another business partner. After a year in business the partnership fell apart and they decided to close permanently. I had helped open their business and ran it for that year, I absolutely loved the idea behind bringing such a wonderful and unique beauty technique to Arizona and I believed in facial threading very much. When they decided to close I told my now Business partner Mercie Loftus I would love to try again with her idea but as a business partner this time. She had told me all her savings had gone to her previous venture and didn’t have any more money to invest. Read more>>

Martha Carter

I’ve always been a risk-taker. From moving from North Carolina to Colorado by myself to learning how to snowboard at age 30, I’ve leaned into challenges that pushed me out of my comfort zone. But what people don’t often talk about is how chasing your authentic dreams—the ones that matter most to you—can feel riskier than any of those external leaps. Read more>>

James Davis McAllister

“At 18, I faced a pivotal choice: follow the traditional path of prestigious drama school offers, or chase the raw, unpredictable energy of touring with a band. I chose the latter, a leap into the unknown that defied conventional expectations. For nearly two decades, the road was my home, the stage my classroom. However, the birth of my daughter, Haven, brought a new chapter and a need for stability. That’s when Heart Of Haven Entertainment LLC was born. Read more>>

Christa Holland

I got my cosmetology license in high school. I always knew that was my passion. I went to college and got my degree in social work found out that I wasn’t a fan of cooperate America or the politics of social work after working in the field for a few years. I knew where my heart was and where I could be happy. That was in the natural hair space and helping woman with textured hair feel safe and seen. I left Virginia and moved to Miami to pursue this dream. I t was hard and I fought so hard to gain more skills and perfect my craft. Fast forward a few short years later I have a booming clientele and my own salon space. Took the risk and it paid off resulting in me making 6 figures a year on my own. Read more>>

Nyle Grigsby

I feel like our entire story is risk based. We knew how to groom and had some experience in mobile grooming but had no idea how to start out own business. I just remember Josie calling me fed up with who we worked for, that day I registered our business online. We didn’t have a plan but that was the first step. We bought a used, cheap cargo trailer and hid it in our backyard. We worked on it every day while still working for another company. Eventually we took the leap and started our own business! I’ll always remember our first client, it was humiliating we went from these fancy vans to this small trailer. Read more>>

SASCHELLE MANDOZA

A life changing risk I took came at one of the most vulnerable times in my life, while I was going through breast cancer treatment. In the midst of facing the unknown, grappling with pain, fear, sickness, and fatigue, I made a decision that would alter the course of my life. I started my candle business called Journey’s Quote Candles and began sharing my personal stories with the world by self publishing my first book balled Unforeseen Struggles of Life. Read more>>

Neda Hovaizi

A year after finishing dental school, while most of my peers were still working under other doctors, gaining experience and “waiting for the right time,” I took what many around me considered a reckless risk: I opened my own dental practice. Read more>>

Kyle Brown-Bowens

I’ll never forget the moment I told someone close to me that I wanted to be a creative. That I wanted to build a production company and tell stories through visuals that moved people. The response wasn’t what I expected. It wasn’t applause. It wasn’t support. It was a mix of silence, concern, and discouragement. The kind that lingers and echoes louder than any applause ever could. For a while, I questioned everything, thinking that maybe they were right and that I was dreaming too big. Read more>>

Twannia Clark

I hadn’t set out to become a business owner; I set out to give children a home, to offer stability where there had been uncertainty. Being a foster parent wasn’t just a calling—it was a reflection of my own story, a way to turn my experiences into something meaningful. Read more>>

Paul Shinneman

I’m currently farming seasonal fruits and vegetables and fruits with my wife, Christina. We’re in our first season of selling the products that we grow. I’ve left more traditional lines of work to pursue farming full time while my wife still works full time as a physician assistant for Memorial Hermann. I hope to grow the business over the next couple years to the point where she can leave her full time job as well. To get to this point it’s been about 9 years and several big decisions or risks. In 2017 I was working as an engineer in oil & gas in Houston. I had been in the industry for about 11 years. I really felt dissatisfied with the work from the beginning. Read more>>

Dalan Griffin

When I first became vegan at age 15, I didn’t realize the risk that being completely plant-based would involve when it came to business. I immediately had to start self-educating myself on vegan cooking techniques and recipes, as 20 years ago the idea of a vegan diet hadn’t been normalized in the nutrition and food culture. Trial and error were huge in perfecting the textures, looks, and flavors of recreating proteins that vegan diets lacked, yet I still missed eating. Normal breakfast foods like eggs and bacon, became a thing of the past, but I didn’t want it to be that way. That’s why I started my business Rascal’s Vegan, to bring back the foods that most vegans miss eating, just in a totally plant-based form. Read more>>

Sophia

I was raised in a Christian cult and stayed in it for 25 years. When I escaped at age 38, I had a lot of catching up to do in life, but mostly socially and sexually. Fast forward to less than a year out of the cult to when I meet a Dominatrix. She identifies me as a “Baby Domme.” Now did I even know what BDSM was? Not really. She saw in me an Alpha woman who was destined to grow into herself as a Dominatrix. And it turns out she was right. I loved Domination and I was good at it. It called in all my creative strengths as a director, image maker, and visionary. Read more>>

Carolyn Arredondo

A lot of people think risks are about starting over—but for me, it was about expanding what I had already built. I had traveled the world with my camera, lived as a working photographer, and turned my art into a business. Read more>>

Chaz D’Avino

Starting up “Chazzy Productions” at first was definitely a big risk. I just got fired from my 9 to 5 job at the time and I had no source of income coming in. It was I either find another 9 to 5 job to work for, or just believe in myself and start promoting my film company to new people. Of course I took the film route and took the risk to work for myself. I always wanted to be my own boss. I always wanted to work on my own time and not have someone above me telling me what to do. I refused to be bossed around by someone any longer and I took a leap to getting my film business off the ground. Read more>>

Seyla Khoem

Starting Jungle Kitchen was undoubtedly one of the most significant and daunting decisions we’ve ever made. My business partner and I entered the restaurant industry with no prior experience—my background lies in software engineering, and he worked in banking. I was familiar with writing code, troubleshooting technical issues, and working behind a screen. The jump to opening a restaurant, where I would find myself cooking in a bustling kitchen, managing operations, and engaging directly with customers, felt like a complete transformation. Yet, we had a firm conviction in our vision. For years, we catered homemade Cambodian and Southeast Asian dishes to local businesses around Chanhassen, and the response was overwhelmingly positive: “This food is amazing; you should open a restaurant!” Read more>>

Lauren Levi

When it comes to my career, I am what you’d call a late bloomer. In 2023 I was asked to be the head of the Costume Department for a documentary on the founding of America. This entailed renting a 16 ft. box truck and driving filled with rented period-piece costumes from Fort Worth, Texas to Richmond, Virginia, and subsequently all over the Northeast. I accepted the job, procrastinated getting started, and quickly realized just how in over my head I was. This was my first time as Costume Designer and head of the department, and I naively believed I could approach it like an assistant. Soberly, I took one day at a time, even telling myself I could back out and would eat the shame of it like any other failure. Read more>>

Ashley Brothers

I was born “awake” which means I could see, hear, feel, and interact with spirits since I was born. In fact, my first memory was prenatal. I still remember it like it was yesterday. I also remember being weighed as baby, getting my first shots, and standing on the edge of my crib watching spirits walk around the room. My poor parents could hear me screaming through the floor for years because I was being touched and taunted by these spirits. As I grew older, I had premonitions that would prevent accidents and death for myself, members of my family, friends, and later with clients, but there was a time when I was diagnosed with depression, anxiety, and a form of schizophrenia which a treated for two years because I told the doctor I heard voices and saw spirits since I was child. I haven’t been on any medication since 2004 . . . after my first healing from a shaman. Read more>>

Myshelle Peguero

The idea for what I do today came from survival, healing and something in me that just wouldn’t let go. In 2014, after trying to take my own life, I started therapy. Through support of my therapist, other patients and my willingness to keep going, I began my spiritual journey through tarot and started exploring holistic and practical healing. These were things I had never been taught growing up. For the first time, I had language for what I was feeling. I started to process my trauma, understand my patterns, and really see how much I had been carrying. Being a teen mom from the Bronx, growing up around trauma and loss, I had always been in survival mode but I knew I didn’t want to stay there. I had dreams and I wanted more. Read more>>

Jake Wildhorn

I think going into the music industry itself is a risk. I dropped out of college when I started getting more opportunities to write songs and play live but it doesn’t just happen. There’s no real blueprint for this, and if there is, it’s ever-changing. Read more>>

Lora Tautavicius

My story starts my senior year of college. I went to a big state school in Kentucky (University of Kentucky, GO CATS), where I studied Political Science on the Pre-Law track. It being my last semester, I picked up a job being a bartender at a music venue. And like many of us in the music industry, I absolutely fell in love with electronic music and the community it came with, and what was a weekend job soon sparked to be one of my biggest passions + now full time career. Read more>>

Andrea Chase

Back in 2019, I was working a full-time corporate job in Memphis, TN, while also holding a part-time position as a Makeup Advisor at Estée Lauder and doing freelance makeup on the side. It was a busy season, but I genuinely loved what I was doing. During that time, a waxer I really admired encouraged me to look into becoming a licensed Esthetician. She opened my eyes to the idea that I could expand my skill set beyond makeup and really understand the science of skin care. Read more>>