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.

Michelle “Mimi’ Rossi

Deciding to start a new career and a new business is always risky. There are many uncertainties, especially when it is a creative path. You can do everything right and still not achieve what you plan. There are simply too many variables. But, you don’t get into this for the money – you do it for the love of the craft. Read more>>

Ms.Joli McTerrell

I want you to sit with me for a moment. Press rewind with me to 2022. My career as a freelance curator was rising — I was traveling across the country, telling the stories of Black artists across disciplines, building exhibitions, shaping narratives, creating space. From the outside, it looked like momentum. Success. Black excellence in motion. But the truth is, I was searching. Read more>>

Aliyah Roettgers

One of the biggest risks I’ve taken was deciding to treat my creative work like a real business instead of keeping it as a safe side project. When I first started, I intentionally kept things small. I loved the work, but I was afraid of failing publicly and overextending myself. Read more>>

Johan Danno

Are your dreams bigger than your fears? Do you choose comfort and the safe, easy road, because you fear risk or losing? Or does a voice within you sing out to live beyond your current life? It daydreams and dares to envision a life different from the one you live now. Read more>>

Ty Osborne

As a creative risk vs reward is something people will deal with in everyday life. Balancing between the two is part of what makes the career so fulfilling. Taking the “risk” of trying out this technique or this voice for a character or just trying out something you may feel out of your depth is where the risk in the creative industry arises. Read more>>

Antwawne Kelly

It was Summer THE YEAR 1988 twelve year old me Antwawne Kelly, raised in West Dayton OH. Hilltop Homes Projects a five year old, one of four children with my mom living there until I was a Junior in High School. Read more>>

Christian Mitchell

Now that I have time to look back, I realize taking a risk was the easiest part of my journey. The urge to begin came naturally. The adrenaline had an unrecognizable grip on my chest, yet I was still determined to leap into uncertainty. It felt like a push from God to honor, love, protect, and serve my surroundings. Read more>>

Courtney Wachal

In 2019 I became the judge presiding over the Kansas City Municipal Drug Court program. At that time we had drug court and a mental health court programs. We spent a lot of time trying to figure out which court was the best fit for the population we serve, losing the court participant in the process. Read more>>

Yannis Ning

When I first arrived in New York as an international artist, I assumed I would step away from making theatre. I didn’t have family here, I didn’t grow up with a network, and I knew how hard it is to build a creative life in a city full of artists. Read more>>

Kylie Kelly

One of the biggest risks I’ve taken as a business owner was choosing to step away from social media – specifically Instagram – at a time when almost everyone around me was doubling down on it. For years, social media was positioned as non-negotiable. If you wanted visibility, clients, or growth, you had to show up constantly. Post daily. Share everything. Perform. Read more>>

Sha-Lai Williams

I’ve taken multiple risks – both personal and professional – over the years. One of the most significant ones would have to be the first time I decided to enter private practice as a licensed clinical social worker providing therapeutic services to teens and adults. Read more>>

Morgan Brink

Leaving healthcare after six years was the biggest risk I’ve ever taken. At the time, I had done everything the “right” way. I had a deposit down for college, a clear academic path, and a projected end goal of becoming a physician assistant. From the outside, my future looked secure and predictable. Read more>>

Michelle Harmon-Malone

I’m not known for taking risks, but I’ve taken two giant leaps of faith within the past five years — one–to leave my marriage of 10 years and two–to leave my career of 30 years while in my 50’s. Also, I did it quietly — no fanfare and no fuss, just a very clear strategy from God on how to leave clean. Read more>>

Amy Goober

One of the biggest risks I’ve taken was forty years ago. At 26 I was deciding if I should leave my career in advertising to open a cake bakery. Having graduated from Cornell University, I moved to Boston with my best friend. I had started at Quinn & Johnson in Boston as a secretary in 1981 Read more>>

Mike Newquist

I can certainly say I’m taking a risk right now by performing in a one man show, however the most life changing risk I’ve taken was to invest in my personal life. I had been chasing theatre for about 14 years after graduating from Columbia and had my first involuntary break during COVID. Read more>>

Ashley Smith

One of the biggest risks I’ve taken was deciding to fully commit to my creative path, even when there was no clear blueprint or safety net. Early on, I realized that waiting for permission—whether from the industry, institutions, or circumstances—would keep me stuck. So instead, I chose to bet on my skills, my adaptability, and my vision. Read more>>

Chance Dubinick

Growing up in a small town in Kansas, social media didn’t really seem like an option. No one around me had a camera or knew how to use it. After highschool I created content on TikTok while working at a plumbing factory and going to college full time. After many sleepless nights I knew that neither college or a traditional job was for me. Read more>>

Bianca Rochell

After working 6–7 days a week for over seven years, I took a huge risk last year and finally gave myself permission to slow down. As a wellness professional, I constantly emphasize the importance of a healthy work–life balance to my clients — yet for so long, I believed I had to operate at that pace just to make a decent living. Read more>>

Quentin arispe

The biggest risk I took in my music career was creating my album ‘Tomgirl.’ Over the course of three years, I poured my heart into the project, tackling complex themes of grief, pain, and identity. The real challenge was navigating the fine line between raw honesty and positivity, ensuring the album wasn’t just a reflection of negativity but also a journey of healing. Read more>>

Misty Stevenson

The biggest risk I ever took was walking away from certainty to build something that mattered. I left corporate America with a stable career as a Registered Nurse because I could see the gaps in senior care—and I knew I was called to do more than maintain the status quo. But believing in the vision wasn’t enough. Read more>>

Jess Moran

I had studied acting years ago in college, but pursued a different direction in life for the sake of a romance. While that relationship didn’t last, I never lost the need to live creatively. Read more>>

Jim Freed

My decission to base my new book, You Won’t See Me, on situations I have experienced working with the paparazzi in my professional capacity as a Photo Editor and write it much more commercially friendly than my earlier more literary work was a major risk. Read more>>

Margherita Lega

Leaving my hometown of Milan, Italy to pursue a career in the performing arts in New York City was the biggest risk I have taken so far, and also the most defining one. Before making that decision, my life looked very different. I had earned a degree in Economics and Management and followed a well-structured, “safe” path that made sense on paper. Read more>>

Christy Vatter

Becoming an underwater photographer was not something that just fell into my lap. I had been doing wedding and portrait photography for about 9 years. I found an underwater photographer on instagram and it instantly caught my eye – and my heart. I started to dream and save up my extra funds I had to purchase an underwater housing for my digital camera. Read more>>

Marie Stutz

We import a lot of records­–and, increasingly, other items and products–from all over the world. The cost of importing, shipping, exchange rate and other fees for items from Japan and other far-off lands that we frequently bring things in from are pretty high. In fact the price of some of these records are often double or even triple the average price of a domestic record. Read more>>

DeAndre Jacob

Five years ago, I took a bold step into the corporate world, leaving behind the restaurant industry. My mission was clear: to craft a stellar corporate resume by mastering every aspect of corporate building, from catering to banquet services and cooking. Read more>>

Joanna Whaley

I recently took a major risk by declaring my candidacy for the state House of Representatives. With the current climate in this nation, and the targets placed on someone like myself as a transgender woman, choosing to lead within a government that has shown signs of hostility towards who I am is a significant gamble. Read more>>

Symone Lakes

While I don’t consider myself a risk taker, my willingness to say yes to things I’m not yet prepared for tells a different story. A few years ago, somebody asked me to live paint a mural (and vend) at a large event. I’m talkin’ thousands of people and only 13 days notice. Had I ever done a mural? No. Did I have the necessary inventory? Read more>>

Jasmine Jonte

A few years into my business, it was clear that I could genuinely help people—but I couldn’t crack the marketing game. So I made what felt like a very grown-up, very responsible decision: I invested $7,500 into a course that promised to teach me how to scale through marketing. Read more>>

Marsh Arts

I have so many stories I can choose from throughout my lifetime as a risk taker. However, the last risk I took is what has me smiling from ear to ear each and every day. Read more>>

Angel Dobine

For twenty years, I mastered transformation — just not my own. I painted confidence onto strangers in department store lighting, taught women how to contour their cheekbones and reclaim their power, and made beauty feel accessible. But in 2020, the world shut down, and somewhere along the way, my own reflection started asking bigger questions. Read more>>

Demetris Elia

The first risk I took was launching PEAKiropractic in 2020, offering mobile chiropractic care. By 2025, my schedule had become incredibly full. I was working seven days a week, from 8 a.m. to 8 p.m., seeing anywhere from seven to seventeen patients a day while also managing every other responsibility that comes with owning a business. Read more>>