You’re working hard, things are going well, piece by piece you’ve built a life you are proud of, you’ve overcome obstacles and challenges, beat the odds and then you find yourself at the center of an unexpected dilemma – do you risk it all to keep growing? What if growing means leaving the job you worked so hard to get or the industry you worked so hard to break into? How we approach risk often has a huge bearing on our journey and so we’ve asked some of the brightest folks we know to share stories of risks they’ve taken. 

Amber Zaccone

I had moved to South Carolina in 2019 doing my craft already- lashes and brows. When finding a job I was hired at the same franchise I worked for back in PA. A year or so went by and I had worked a total of 3.5 years at the franchise feeling like I’ve out grown and wanted to learn more. Read More>>

Nicole Notar

One of the biggest risks I’ve taken was starting a nonprofit as just a patient, with no medical background, no roadmap, and no guarantee it would work. I was simply driven by a deep desire to be the person I never had during my own diagnostic journey. Read More>>

Anne Keke

The risk didn’t start as a single moment, it built over time. It came from years of sitting in rooms where decisions were being made about students, families, and communities I know deeply. I understood how the system worked. I knew the policies, the process, the pressure points. Read More>>

Lazarya Wilson

I took a risk when I decided to pursue real estate, and at the time, it felt a lot bigger than it might sound on paper. I wasn’t coming from a background where people invested in property or talked about commissions, listings, or closing deals. Read More>>

Logan Massengale

The greatest risk I have taken in my career thus far has been choosing to go all in to pursue it full time and moving back to Nashville while temporarily living out of my car essentially. I grew up in the Nashville area and lived there until May of 2024 when I decided to start over and move to Knoxville, TN. Read More>>

Casey Watts

A few years ago I was hired to train a group of about 100 instructional coaches over the course of the school year. I knew going into these training sessions that it would be a unique situation. Read More>>

Kendra Chanae

One of the risks I HAD to take was walking away from management for my singing career to kick it off the way I want it or need it to be. I was with an ‘anonymous’ music management distribution for a year, that took a not-so-great turn after discovering what was really happening. Read More>>

Kullen Carter

A few years ago, I took a risk that still sticks with me. I walked into WinStar World Casino and Resort with over $2,000 in savings—not to play, but to flip it. I had convinced myself I could turn it into something big. People around me were winning, and I believed my moment was next. Read More>>

Jiajie(Jasper) Liu

One of the more defining risks I have taken comes from my approach to shot design. When I work on commercial projects, I tend to rely on a safer method, building sufficient coverage to ensure flexibility in post-production. However, when I am financing a project myself and creating purely for expression, I make a very different choice. Read More>>

Roscoe Hall

Risk… I’ve taken so many, hahahaha. I like to think risk is woven into African American culture. To live as a minority in the United States is to take countless risks every single day. Wild to actually type that out. Read More>>

Toni Scott

Excerpt from my Memoir *Grow Your Own Way* (July 2025) California Love: I was deeply rooted in nursing and community wellness work across Chicago between 2014 and 2018. Leaders began to take notice, and my name became spoken in rooms I wasn’t always in. My reputation as a wellness nurse consultant and sought-after speaker in yoga, mindfulness and wellness grew. Read More>>

Michael Glassman

I received my degree in Landscape Architecture from the University of California at DAVIS. Before I graduated I got my landscape contractors license and started a design /build business. Business was slow at first since I was young and it was hard getting clients. So I happened to design an Asian inspired landscape and install it for the fire chief of Davis and his wife. Read More>>

Titus Sincere

Take the risk, who cares what they think, How you gonna let somebody who aint never built anything tell you what you can and cant do #Wunluv Read More>>

Jill Marion

At twenty years old, I was engaged to someone who seemed strong and confident, until strength became control, and confidence became cruelty. He opened a business in my name, quietly stacking debt under my identity. He cheated. He manipulated. He used my youth and trust like collateral and left my life in pieces before it had even begun. One night, I ran. Read More>>

CiCi Appel

The biggest risk I ever took wasn’t starting a t-shirt business, it was betting on myself and deciding I was allowed to take up space. When I started The Snarky Lemon, I wasn’t stepping into entrepreneurship with a polished business plan and investors behind me. Read More>>

Lorvins Eugene

Taking a risk has never been abstract for me it was deeply personal, uncomfortable, and costly in ways that went far beyond money. Six years ago, I made the decision to create an umbrella organization made up of HEM Alliance (a non-profit), 2nd Mountain, and Pillars Group. Read More>>

Sir Michael Fomkin

I remember the day I sold my restaurant. On paper, it made no sense. The business was doing well. It was stable. Predictable. The kind of thing most people spend years trying to build. But I knew I couldn’t stay. There’s a feeling you get when you’ve outgrown your life and it doesn’t go away just because things are “working.” It gets louder. More persistent. Read More>>

Chairman Nick Fiani

Since I can remember, I have held a desire to make a positive, lasting impact within my community and throughout Michigan. Early on, I discovered that public service is a remarkable opportunity to help others and assist in shaping the future. Born in Michigan, I graduated from Detroit Country Day School with Summa Cum Laude honors. Read More>>

Mai Stitik

When I first envisioned starting my own micro-bakery, most people around me saw it as something small, like school fundraisers or a few dozen cookies here and there. As a full-time teacher, a single mother, and someone deeply committed to her well-being, even I questioned whether it was truly possible to build and scale a real business. Read More>>

Deon Jenkins

We are often advised to complete our education, pursue higher education, obtain a degree, secure a well-paying job, and pursue the American dream. I completed all of those steps, and then the recession occurred in 2009; as a result, I was laid off. I transitioned from an engineering job to juggling two jobs, one in retail and the other in security, to sustain myself. Read More>>

Sharon Mckayanguin

I took a leap that most people only talk about—I walked away from the stability of a full-time career in Human Resources to pursue something that had always called to me: storytelling. HR gave me structure, security, and a clear path forward, but deep down, I knew my passion lived somewhere else. Read More>>

Al Huggins

The risk didn’t look dramatic from the outside. There was no big announcement, no applause, no clear moment where everything changed. It was a quiet decision—one that sat heavy in my mind for weeks before I acted on it. At the time, I was working in a stable role. The kind of job people tell you to hold onto. Read More>>

Ayana Abdul Raheem

The biggest risk I’ve ever taken was betting on myself with nothing but faith and a gift I knew was real. Before launching Timbuk2 Academy, I worked in municipal government, deeply rooted in the community and the lives of young people. Read More>>

Jessica Redish

At USC I took many multicam classes. Read More>>

Amber Gaige

Here’s the revised version: — **The Risk That Rewired Everything** The week before Christmas, I got the news that stopped me cold. After implementing a new CRM, streamlining operations, and building marketing systems that generated over $1 million in new sales for the company — I was told my position was being given to someone else. A man. For half my salary. Read More>>

Liska Sims

One of the biggest risks I’ve taken was transitioning from a stable career in mortgage underwriting into real estate sales. For over 20 years, I worked in the mortgage industry as an underwriter. I had a consistent income, a structured environment, and a deep understanding of how loans are approved. On paper, it was secure. Read More>>

Kiersten Brown

One of the biggest risks I’ve ever taken was walking away from a stable, successful career to build a life centered around something most people wouldn’t consider a “real” path at the time, caring for dogs. My inspiration started with my own dog, Porter. She was with me for 16 years and gave me the most genuine, steady companionship I’ve ever experienced. Read More>>

Rachel ‘Ray-D’ Dowl

I Took A Risk On Myself, 10 Toes Down Everytime! While Navigating Being A Single Parent To An Amazing King ( He Now Graduates Next Month!!! Ty Lord! ), I Stepped Out Into Multiple Hats Of Life, Love, Learning & Self Expression. Read More>>

Chantelle Ramcharan

One of the biggest risks we’ve taken as business owners is stepping into coffee roasting, especially after everything it took just to keep our doors open. We opened The Sippery Coffee Co. during COVID, which meant learning how to run a business in constant uncertainty. Read More>>

Rachel Barnes

The risk that I took was leaving my 9-5 job: Leaving my 9–5 wasn’t just a career move—it was a risk that forced me to choose myself. On paper, my job made sense. I was good at it, stable, consistent. But deep down, I knew I was meant for more. Read More>>

Sadie Peterson

I have been a professional family photographer for over 7 years now and I’ve typically stuck to the “usual” family portraits. You know, everyone shows up in nicer clothes, we pick a beautiful spot, I pull out the tricks to make the kids smile. We play a few games to get “candid” shots and then we call it good. Read More>>

Gavin Ambrose

Quitting a stable job to build leather goods full-time was the first risky leap we took, but the risk that truly changed the trajectory of Hellhound Leather Co. happened about two years in, completely by accident. A local event planner reached out with an unusual request. Read More>>

Jody Rappaport

In spring 2025, after more than 25 years in outpatient physical therapy, I took a leap of faith and stepped away from a stable career to pursue something new. Read More>>

Sean Burns

A principal express to me that I was wasting my time with the art of stepping & I would never make a career impacting our youth with step. Since her comment; I teach the art of stepping full time at Prodeo Academy & founded a 501c organization of Step with soul. Impacting youth all over the twin cities & beyond. Read More>>

Ale Medina

One of the biggest risks I’ve taken wasn’t just a single moment it was choosing to bet on myself again after already experiencing both success and setbacks in music. I started in the industry early, back when I was part of a group and later a duo that was gaining real traction. Read More>>

Cassandra Jenkins

As a child of a small business owner, I feel I had the entrepreneur spirit. As a nurse since I was 20 years old I have always worked within the healthcare system. After having an ill child and trying to balance working and being a mom of a child with needs my way of thinking started to change. Read More>>

Nichole Suemnick

One of the biggest risks I’ve taken was leaving behind a steady, structured income and a very predictable path to pursue my photography business full time. At the time, I was working multiple jobs—at a tanning salon and in a physical therapy clinic—while also going to school full time. Read More>>

Antonella Scibilia

My biggest risk was opening my restaurant downtown as a single woman. So many friends and family told me I was making a big mistake by putting everything I had into this small corner spot located downtown Hay St but I envisioned something completely the opposite. Even though there wasn’t much at the time downtown, I felt in the future there would be. Read More>>

Kimberly Bernal

I was born and raised in Chicago. Life often felt fast, and every day seemed like the same routine. But over time, I realized that both my job and my relationship weren’t healthy for me. I had already lost parts of myself by staying as long as I did, and I knew I couldn’t keep going that way. Read More>>

Lelund Hollins

Life is about taking risks. We take them for work, for our careers, and for love — because without risk, there is no real reward. Read More>>

Natalie Lall

Two years ago, I was supposed to stage a one actor, one audience member play at my local acting studio. It was a 20 minute piece I had done in college that I never felt like I fully understood. Read More>>

Patricia Mitchell

The biggest risk I’ve taken wasn’t a single moment — it was choosing to end a decade‑long chapter of my life and step into an identity that didn’t exist yet. After ten years of running my small business, I reached a point where the version of myself I had built no longer fit the woman I was becoming. Read More>>

Ayoka B.

I moved my family to Costa Rica. It didn’t feel like a risk, it felt like I was running toward my life. After being quarantined and further traumatized by the barrage of police killings of Black people, I was drowning. I’d already quit a job of seven years that I was brilliant at because I was tired of the daily disregard and resulting invisibility. Read More>>

Jocelyn Gresham

One risk I’ve taken recently was deciding to transition out of the traditional classroom and pursue a career in instructional design. For a long time, I identified myself as an educator, but I began to realize that while I loved creating lessons and supporting students, the classroom environment itself was no longer aligned with where I wanted to grow. Read More>>

Jeffrey Rucker

Making ‘Crossfaded: Thesis Film’ has been quite the risk from the beginning. I’m from Dayton, OH, but I attended Cleveland State University to study film acting. Until my senior year, I acted on every student project that I was available to work with (+30). However, I had never directed a piece before. So my senior year I was looking to change that. Read More>>

Sigalit Heby

My life story begins when I was four and a half years old, on the day my father, God blessed is memory , he was killed on his way to the army. He was only twenty-four years old and had just begun his officers’ course. At the time. I didn’t truly understand what just happened … Read More>>

Brandon Dawson

I was 24 years old working as a recruiter in accounting and finance. I was making good money but I was very unhappy with my job, and needed a change. One day I put in my two weeks notice and decided to bet on myself that I would figure it out. After some reflection I decided that I wanted to try college again. Read More>>

Vanessa Gonzalez

One of the biggest risks I’ve taken is the one I’m living right now, choosing not to limit myself to just one path. At this point in my life, I wear a lot of hats. I work in real estate, title, permitting, I run my own businesses, and I am also an artist and a writer. Read More>>

Caroline Mazzarella

May 3rd, 2023….the day I made my first social media post advertising the establishment of my small business baby, Rye Street Events! This is when taking risks became just another normal daily task in the life of Caroline Mazzarella. Read More>>

Rouge Rose

While developing my first psychological thriller short, ‘The Visuals’, I was working with a very limited budget and a small crew, and there was pressure to make something more unique rather than conventional and safe. Instead of following a traditional narrative, I chose to center the film around abstract visual storytelling—and outspoken dialogue, unsettling imagery, and symbolism that could be interpreted in multiple ways. Read More>>

Michelle Daily

In early 2025, after seven years of teaching, I took a leap and opened my own studio. Some questioned the decision to open a small studio while larger gyms expand into reformer Pilates and franchise models continue to pop up everywhere. Read More>>

DeLores Pressley

One of the most meaningful risks I’ve taken was stepping into the world of children’s literature with my book Deonna Dares to Dance. On the surface, it might seem like a natural extension of my work in confidence and empowerment, but for me, it was deeply personal and required a different kind of vulnerability. Read More>>

Heather & Joseph McGarty

All it takes is one bold decision to rewrite your entire life. The two of us were living in a 1 bedroom apartment outside of New York City, we were drowning in $3500 monthly rent payments, and we were recently married. We really began to feel the pressures of the career race and the pressure to buy a house and start planning for a family. Read More>>

Karee Laing

For most of my career, I was the expert behind the expert. I had a JD/MBA, a decade of experience, and a client roster I was genuinely proud of, and almost no one knew my name. I told myself that was fine. That the work spoke for itself. That I didn’t need to be visible because I wasn’t that kind of person. Read More>>

Porsche Wilson

I remember the moment like it was yesterday. No investors. No handouts. No safety net. Just me, a vision, and a decision that could either build me… or break me. Starting my business wasn’t cute. It wasn’t Instagram. It wasn’t “I woke up like this.” It was pressure. Real pressure. Bills still due. Life still life-ing. Read More>>

Shelby Hall

One of the most beautiful lessons that I have learned along my journey of entrepreneurship is the value of taking risks. The importance of the leap into the unknown as an absolute necessity to create something real in your life. I would be nowhere without all the beautiful ‘risks’ I have taken. My first big risk was quitting the corporate world. Read More>>

Mauricia Banks

The biggest risk I’ve taken recently was diving headfirst into land ownership. As a first-generation landowner, I didn’t have a family roadmap or a guide on the pros and cons; I just had a vision fueled by years of watching HGTV and dreaming of off-grid living. I had the capital, and I chose to bet on myself. It hasn’t been without its trials. Read More>>

Suzie Buchholz

The risk that changed my life forever was to leave the business world to take a year off and travel. Setting out on my own to travel for a year was challenging in the best ways. Traveling alone makes you much more vulnerable, but also more open to meet and enjoy the company of delightful strangers. I landed in Aix-en-Provence, France, without a clear plan. Read More>>

Shamonique Mattox

Before I had my current business, I took a risk that cost me nearly $20,000. It also taught me one of the most important lessons I know about resilience and continuing to build, even when you lose money along the way. This idea came from my partner and me. At the time, Uber was just starting to take off, and we noticed something. Read More>>

Kiara Cymone

First and foremost it’s nice to speak with you all again! I’m always greatful when you reach out for an interview. It’s like we’re family now! Lol. But to answer your question, The biggest yet smallest risk I’ve ever taken was starting my online bridal shop Isn’t She Lovely Bridal Boutique. Read More>>

Kelly Thomas

Leaving a stable teaching job to pursue an MFA in creative writing—poetry, no less—felt like a pretty big risk. At the time, it didn’t seem like the practical choice, and honestly, I wondered if I was a little crazy. The year before, my life had been turned upside down. My mom died suddenly and without warning, and I was completely blindsided. Read More>>

Brittany Lanier

One of the biggest risks I’ve taken in my life was leaving my corporate job to pursue nails full-time. At the time, I had stability, consistent income, structure, and a clear path, but I also felt unfulfilled. Doing nails started as something I enjoyed on the side, but over time, it became more than just a hobby. Read More>>

Bev Bailey

I started my comedy career in Chicago. Improv, sketch, musicals. That was my first risk: getting into comedy at 30. I had a good amount of success but always felt like I wanted more challenges, more opportunities. When I was younger, I wanted to go to Los Angeles and try to get an agent, do commercials, tv, film, whatever. Read More>>

Kelly Smith

The biggest risk I’ve taken wasn’t a single moment it was a season of uncertainty that asked me to bet on myself over and over again. As a self employed business owner the path to purchasing land wasn’t straightforward. Traditional systems aren’t always built for people like me people whose income doesn’t fit neatly into boxes. I faced rejection after rejection. Read More>>

Star Breedlove

Taking a risk on myself wasn’t a leap—it was a calculated next step, built on years of proven instinct, discipline, and results. My confidence was forged early, during an internship at Florida Hospital in Orlando through the University of Central Florida, where I discovered something that would define my career: there was no task beyond my capability. Read More>>

Ketan Strong

My name is Anirvan. It was a name that was given to me by my birth parents in Calcutta, India. It means eternal flame that can never be extinguished. I was adopted when I was six months old to upper-middle class, Caucasian American parents. They renamed me Ketan Strong, and they tried as hard as they could to extinguish my flame. Read More>>

Vickie Closson

One of the biggest risks I’ve ever taken was walking away from something that was working… to build something that felt right. Back in 2021, I co-owned a successful apparel and promotional products company. On the outside, everything looked solid: revenue was coming in, clients were happy, and the business was growing. By most standards, it was a “don’t mess this up” situation. Read More>>

Matondo Kiantandu

The biggest risk was pursuing acting full time. I had a regular job, a relationship and family living near me. The relationship ended and I moved cross country. I didn’t see my family for 7 years. I crashed in hotels and eventually the car. I remember an instance where I couldn’t use the bank to cash my check because my balance was negative. Read More>>

Chandlar Glassett

After I graduated design school, I was working in the industry for other people. A pretty well known (in Utah) architect called me out of the blue and said ‘It’s time to quit your job and I’ll send you my clients to get your business started. Read More>>

Jen Hobbs

I began my journey in Capoeira (an Afro-Brazilian martial art) 25 years ago. At that time I was working as a graphic designer at a tech company, which had been my career for some time. I continued to work in graphic design as my dedication to Capoeira training grew. I started teaching and began to realize that I wanted a future working in Capoeira. Read More>>

Karla E Freeze

I thought I was relatively healthy, despite being morbidly obese at 371 lbs. In January 2008 I was diagnosed with several health conditions; type 2 diabetes, and high cholesterol, I’d been suffering with psoriasis, gum disease, plantar fasciitis, anxiety and sleep apnea. Read More>>

Courtney Winston

By betting on myself and my artistic abilities wholeheartedly enough to start my own business Zenia’s Studio is a risk I’ve taken. It’s a risk because where I was a year ago til now is a complete 180. A year ago I was in rehab trying to get my life together and now I’m a business owner who loves what I do. Read More>>

Elizabeth Feder-Hosey

After a decade of dedicating my practice to child advocacy, investigating abuse, acting as an arm of the Court, I took the leap towards medical cannabis advocacy. I had too much work and a steady stream of income. Financially I was growing, but my personal trauma was being compounded by the trauma of my work. My mental and physical health was deteriorating. Read More>>

Kalle Hellzén

Taking a risk usually implies a fear of losing something secure. For me, the actual risk was remaining exactly where I was. My background is in advertising, digital innovation, and film. In the beginning, I viewed creativity as a tool to build something meaningful, even within a commercial framework. Read More>>

Michelle Aaraichi

The greatest risk I ever took was choosing to transform my survival into something larger than myself. After fleeing domestic violence and experiencing homelessness not once, but twice, I was left asking the kind of questions that echo long after the crisis ends: Why me? Why did this happen? Why were my cries for help ignored? Read More>>

Holly Kell Nelson

Honestly, the biggest risk I’ve taken was starting Holly Kell Creative. After graduating from the University of Nebraska-Lincoln I worked two corporate jobs and two startup jobs. I either quit or was laid off from all of them. My husband (boyfriend at the time) and I had just moved from Nebraska to Michigan and something just didn’t feel right. Read More>>

Tisha Kirkland

Taking a risk for me was investing in myself and my brand, at a time in my life when I had just lost my job after 8 years. The money that I began using was all I had to my name. There were bills, car notes, rent, etc, Collecting unemployment wasn’t enough to suffice. Read More>>

Blake Stargel

At 20, I moved from Omaha to Los Angeles without knowing anyone and chose to go into commission-only real estate. At first, I was questioning the decision. It takes time to get things rolling, and early on, deals weren’t coming together. Read More>>

Monique Cartwright

The first real risk I took was in 2015, when I decided to step into modeling—completely on my own. At the time, I was in a season of life where, on paper, everything made sense. I was a wife, a mother, and established in my career. But internally, I felt disconnected from myself. Read More>>

Brenton Weaver

– Tattoos for a Cause (and collaborating with other artists) – Read More>>

Nakendra Harris-Mason

When it comes to risk taking to me it’s pretty much what it means taking risk, and what I mean by that is, you have to know what it is that you want out of your business and you have to believe in yourself and your business. Some of that comes with making sacrifices and taking risk, say for example. Read More>>

Bizzaro Galore

For 20+ years I had made my living in the entertainment business, mostly live performing as a professional magician. Over the years I picked up various skills and know a little bit about a lot of things. This meant I could diversify, so that when one thing was slow, something else might be picking up. Anything from prop making, to performing, to lecturing, to freelance graphics and video, etc. Read More>>

Oksi Govanovskaya

Taking a risk, for me, meant leaving behind everything I had built and stepping into complete uncertainty in Los Angeles. Read More>>

Krystle Connor

I was born and raised in Las Vegas and I always wanted to be an entertainer in Hollywood. Sing Dance Act, all of it. So after high school I took the risk of moving to Los Angeles to study my craft. Stayed there for 7 years. Then I booked a job with Disney which took me out of the country, another risk, for about a year on a cruise ship! When coming back I decided to visit NYC and I fell in love with the city and took yet another risk of moving there permanently, and stayed for 5 years. In 2018 Read More>>