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.

Mark Neuenschwander

The biggest risk we’ve taken at our indie arts organization “the Joplin Toad” was the move toward printing a physical magazine. And for us, this meant not *only* producing a real, physical media item in time when decades-old-established magazines were shutting down physical operations and moving everything online. It meant doing so in a small city- in the heart of the midwest- gearing it stubbornly around local creatives, and even more stubbornly refusing to build ad revenue in a typical way. Read more>>

Shannon Collins

I’ve been writing for as long as I can remember—ever since I first learned how to hold a pen. But honestly, I never imagined that writing could become a career. As a child, I wrote story after story, pouring my thoughts onto paper. The quality has certainly evolved over time, but the urge to write, to let the words flow, has always been there. Whether the words were good, bad, or completely incoherent, writing was—and still is—a compulsion, something I feel like I was born to do. Yet, the idea of being a published author, with real people enjoying my work, seemed almost impossible. Read more>>

Gabriella Westwood

Inherently, to be an artist is to take a risk. It is always a risk taking what you feel inside and putting it on display for others to see, whether it is on a written page, a performance, or fine art. We are raised in a way that many of us learn to avoid sticking out, afraid of being noticed and singled out for either a good or bad reason. And yet the only way to really achieve anything exceptional means taking a big risk. And with that the chance that you might completely and horribly fail. For me, the reward of a success on a big risk is completely worth all the chance of failure and I certainly have failed many times. Read more>>

Ilana Greenberg

In 2018, Ilana Greenberg took a bold risk by opening her own gallery in the Columbia Waterfront District of Brooklyn. Ilana Greenberg Gallery is nestled in the back of her family-run vintage store, Union Max. The space is dedicated to showcasing the artist’s compelling black-and-white artwork and supporting and promoting local artists. Opening a gallery requires a considerable time investment, as it involves the ongoing curation of exhibitions, daily operational management, and cultivating relationships with artists, curators, and collectors. However, one of the greatest risks Greenberg faced was the vulnerability inherent in presenting her work to the public in such a high-profile space. Galleries are places where an artist’s vision is subject to scrutiny, and as both the gallery owner and artist, Read more>>

Shannon Fowler

I sort of fell into the financial services industry after college. I knew I loved helping people, and my first job as a Client Service Manager for a financial advisor seemed like a solid place to start. It didn’t take long before I was acquiring my securities licenses, making myself more valuable to the firm and more marketable for future opportunities. Read more>>

Shane Harris

It was 2023, I had been Sign Painting for roughly 8 to 9 years at that point. I worked out of a 12’x16′ shed I had converted into a little sign studio. I spent every night In there chipping away at sign work. At the time I worked full time as an in house graphic designer for a Beer Brewery in Frederick MD. I had known for several years that I needed to quit and go full time with my sign business, but having just had my daughter (3 at the time) and recently purchased a house, leaving the salary was terrifying. It was a great job, I had no “business model” or projected revenue, just a gut feeling I was supposed to do it. Read more>>

Angela Zachary

A risk I took was to invite local business owners over my home to learn a skill (needle felting) and made clear my intention of wanting to teach this skill at their establishments. It was a risk because I had spent my career in the corporate setting and had never taught a fiber arts class professionally. I didn’t know what their reaction would be, if they’d like it, let alone want me to teach it at their establishment. Read more>>

Rosa Paiva

Two years ago, I was working at a university, spending nine hours a day leading two interesting projects. On paper, it seemed like a great job—creative, full of challenges—but I wasn’t happy. My mind was constantly occupied, leaving me drained. On weekends, when I should have been songwriting or creating, all I could do was sleep and scroll through my phone. My creative energy was completely invested in other responsibilities, leaving nothing for my own artistic work. Read more>>

Lia Yoon

I’ve come to realize that life never stops moving forward, and the things we hesitate to pursue often turn into regrets. For as long as I can remember, I’ve dreamed of running my own business and being my own boss—but fear held me back. So many people warn you that it’s too risky, too much work, or simply a bad idea. But eventually, I took the leap and started Radiant Lab—as an unemployed single mother, no less. Read more>>

Ian Joseph Panelo

I did not have the edge to take the risk when I started taking photographs. I do not have the money to buy what I need to capture the photo that I want. I just dream of it. One day, I tried to borrow a Canon digital camera, thinking that it would help me grow as an individual. I feel bad about my shots. I watch, study, learn, and apply principles from other photographers. I take the risk of being laughed at about my photographs. Then the right time comes that I learned to appreciate my own photographs and take the edge of competing with other aspiring photographers. Gladly, I’ve won a few photography competitions. Read more>>

Diamond Jones

For years, I worked in HR, navigating the ins and outs of employee relations, recruitment, and corporate policy. On the surface, it was a career that offered stability, steady growth, and a clear path forward. I was good at what I did, and I knew the ropes. I found joy in my ability to make a difference in the lives of others, but underneath the surface, the job had started to take a toll. Read more>>

Musette Caing Hart

As a Filipino immigrant and daughter of medical professionals, I was always expected to do something to follow in my parents footsteps – get a degree that would add initials at the end of my name. That was great, but after finishing Nursing school being a nurse was NOT what I wanted to do. I got married, had 4 kids and settled into motherhood until I needed to do something other than waiting for my kids to get home each day. Read more>>

Dee Christie

I was once a Graphic Designer for a year or two in my early early 20’s. I didn’t have the confidence to really successful, and even though I loved the design work, I hated having to “sell” myself. I decided to go back to school for Art Education. I received my Certification for 7-12 and got my first and only art teaching job right after! I believe I had a successful teaching career of 35 years and then I decided to take the risk. I quit my teaching job ( some say I retired, but being too young to retire I like to say I chose a new career path.) Read more>>

Michelle Roberts

One of the biggest risks I’ve taken was starting Stryke Vintage. In the spring of 2022, I stepped away from my career due to health challenges. It was a difficult transition—I had always worked, and suddenly I found myself in a space where I had to redefine my daily life and sense of purpose. During that time, I focused on things that brought me joy: gardening, traveling, cooking, spending time with my pets, and most importantly, creating art. Read more>>

Miriam Jones

I was born in the States but lived most of my life in Australia. I had moved to LA with my then husband for his acting career. I had a successful business in Australia I had co founded using actors in change work in organizations – in fact it had been booming. We had built it from nothing to a 20 million dollar business with 50 employees and an A list client portfolio. It was becoming more and more obvious however that I could not manage it from the States. Read more>>

Carol Milne

I knit with glass. But I don’t knit with HOT glass. It’s an indirect process where I knit with wax, make a mold around the wax, melt the wax out, put the mold in a kiln and melt glass into the space where the wax was.

Let me just say that glass does not want to do this. In fact, when I first began creating knitted glass, I was told it wasn’t possible. I could have given up at that point, and chosen an easier route. Instead, I took on the challenge. Read more>>

Deborah Levine

If you don’t take risks, how do you know you’ve tapped your potential? Playing it safe of course lends itself security, stability and most times predictability, but where is the adventure in that? I would say I have been a person who has always taken risks. I am not afraid to fail, rather I use all my experiences as opportunities to learn lessons and further my own personal growth. I think the biggest risk I have taken that comes to mind in general is being vulnerable. To be a performer, writer and singer there is a vulnerability exposing yourself and your words to the world. There is usually judgement, criticism or praise associated with any musical release or live performance. Read more>>

Chance Archer

IB/AP classes, year-round swimming, being class president—all while living without parents, working 2+ jobs to support myself, and handling every responsibility independently. I knew the workload would be overwhelming, but I refused to let my circumstances define my limits. Read more>>

Tristan Jass

One of the biggest risks I’ve ever taken was deciding between going to college or pursuing content creation full-time. It was a tough call because, like most people, I grew up hearing that college was the path to success. My whole family wanted me to go to school—and I understood why. My parents couldn’t afford to pay for college, so there was this feeling that if I got the opportunity to go, I almost had to take it. It felt like the “right” thing to do. Read more>>

Katherine Buckley

I’ve always loved making movies. When I was eight, I made my first video on a VHS camera with my brothers, and I was hooked. I loved directing, acting, and bringing my ideas to life. As I got older, I taught myself how to edit, shoot, and do everything necessary to produce short films. That passion led me to study film in New York, where I eventually got a job as an editor. But acting was always my ultimate goal—I just knew that my other skills would help me stay afloat in the meantime. Read more>>

Margarita Orange

The overall starting a business was a huge risk. But, with high risk, comes high reward. Every risk I have ever taken has led to something big. When I first started photography, I was at home with my newborn, getting ready to call my boss to quit my job (couldn’t find childcare, couldn’t AFFORD it anyway). A HUGE RISK, but I knew I’d be working to just pay bills and miss out on time with my son. I remember calculating how many sessions ($100 each) I’d have to do to cover my bills. Scared. Horrified. But I made the call anyway. Read more>>

Eric Murphy

For 20 years, I dedicated my life to serving in the U.S. Air Force, diligently saving and investing to secure a stable future for my family. With four kids—three of them on the brink of starting college—every financial decision I made was calculated to ensure they had the best opportunities ahead. I had built up a strong financial foundation, setting aside funds for retirement and investments that would carry us through the next phase of life. Read more>>

Krystal Lambert

When I was a child, I used to dream of being an actress – particularly an occupational one that could be anything she wanted to be. I also wanted to write, make art and run businesses, and I enjoyed delivering speeches at school. So, naturally, as I grew older, I gravitated toward jobs that incorporated business, art, writing – and the stage. Read more>>

Susan M. Story

My life has been one risk after another. The way I like to think of it is, charting my own path and trusting my intuition. One of the most impactful was deciding to leave the exciting and glamorous world of fashion design. At one point I was jet setting around the world. I was married at the time but was usually traveling. That experience and what I observed about life around the world made me think twice about what the real value of my career. was. I asked myself: what was I contributing? After a short ten or twelve year career I decided to make a change. Read more>>

Madelene Ba, Melinda Long

Our business itself was a risk we took. In the beginning, it was just me (Mads) handling the backend—making sure we had the right certificates, legal documents, and everything we needed to be a legitimate LLC. Even before MadLove officially became what it is today, both Mel and I questioned whether we were ready for such a big responsibility. We knew it would be a lot of work, so we sat on the idea, debated it, and even ignored it for a while. Read more>>