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.

William Poncy

I believe life is about taking risks. However, in our modern world of convenience few of us risk anything. Risk is engrained into our primordial brain. Our ancestors could not escape risk, surviving meant risking it all, life itself is a risk, so risk is deeply hardwired into our minds, bodies, and psyche. Read more>>

Kait Schoeb

I feel the biggest wrist that I have taken when it comes to my business is in general, taking the unconventional path of freelance artwork, especially in a world that is dominated by technology and graphic design. I personally am very technologically challenged even though I’m fairly young, but that’s why I still use the old method of hand painting. Read more>>

Eileen Himel

I work with the nonspeaking autism population. For a long time I worked under the mainstream paradigm, which essentially follows the sentiment that these non-speaking autistic individuals are usually not high cognitively and don’t really understand anything that’s being said to them or what’s around them. Read more>>

Carys Haslam

I was 19 and in the middle of college… Nothing felt right. I felt lost and frustrated. I had always loved school and loved learning, but it felt like there was no clear path for me at the university I was attending. Read more>>

Michael D. Cooper

One of the biggest risks I’ve taken was betting on myself and committing to building The Big Scoop with Coop into something meaningful while still balancing a full-time job, college, family, and everyday life responsibilities. When I first started, there was no blueprint, no guarantee, and honestly, no clear path to where The Big Scoop with Coop could go. Read more>>

Ashley Armour

In 2023 I had the darkest moments in life. from being a successful business owner and wife, to being a single mother, and having to leave my shop. I was working jobs trying to make ends meet all while trying to hold myself together. Read more>>

Nahomy Galan

In 2020, I took one of the biggest risks of my life during a time when everything already felt uncertain. I made the decision to leave a relationship that was mentally draining me, and at the same time, I chose to invest in myself in a way that others didn’t fully understand. I decided to become certified in Holistic Nutrition. Read more>>

Jose Navarro

One of the biggest risks I’ve taken wasn’t just one moment. It was a decision I kept making over and over again: choosing to be myself, even when it meant being the outcast. Read more>>

Juni Lynch

Starting Juniper Grove Creative was one of the biggest risks I’ve taken. At the time, I was balancing a full-time role and questioning whether I was “ready” to build something of my own. There was a lot of doubt, imposter syndrome, financial uncertainty, and the very real fear of putting myself out there and failing publicly. Read more>>

Osiris Rain

When Pat McCrory eliminated film incentives in North Carolina, the path I’d been on disappeared almost overnight. I had a clear choice: move to Atlanta and keep chasing a film industry that could shift again at any moment, or stay in Charlotte and figure out how to build something on my own. Read more>>

Kyle Shaw

I made the decision to leave my hometown and move to Atlanta to seriously pursue film. It wasn’t easy. I gave up my apartment and slept on a mattress in a living room just to save money and make it happen. I took every acting job I could—no matter the pay—while also doing DoorDash to stay afloat. But I knew I had outgrown my environment. Read more>>

Leeat Yopp

I have been a Licensed Cosmetologist for over 23yrs. I was the President of Metro Cosmetology Association, a non profit organization on Long Island NY; that taught continuing education to local Stylist and students. I opened my first salon when I was 21, and thought I was on top of the world. I shortly after got married, and started a family. Read more>>

Gina Carrillo

I jumped out of an airplane! I recited my Poem Black Widow from thousands of feet in the air. My Tandem Coach was nicknamed Spidey, he had Spider-Man attire on and I came dressed in my red and black too. He recently passed away due to a tragic skydiving accident and he was definitely a hero! Read more>>

Natalia and Aaron Hopman

One of the biggest risks we’ve taken was starting our business, Polarity Tattoo Studio, right as the world was coming out of the pandemic. Before this, I had spent years working in management across different industries, while my husband Aaron had built his career as a tattoo artist. Read more>>

Brian Jervay

One of the biggest risks I’ve taken was deciding to invest my own money into starting my production company and producing my own films. At the time, I had stability. I had a steady career, a family depending on me, and a predictable path forward. From the outside, it probably didn’t make sense to disrupt that. Read more>>

Beatrice Amore

I think the biggest risk I ever took was moving to San Francisco to study acting. Before that, I spent nine months in San Diego in an international school. I always knew that experience had an end, so I thought I would just go back to Italy after. And I did. Read more>>

David Clarke

In 2014, I was teaching in Goose Creek CISD by day and moonlighting as an arts journalist for BroadwayWorld’s Houston page by night. Those two parallel paths hadn’t quite intersected, yet. But that all changed when my reviews of Houston Grand Opera productions caught the attention of the Public Relations team at Lincoln Center for the Performing Arts. Read more>>

Iris Acevedo

I spent years in the fashion industry, working across product development, production, and buying for brands ranging from Perry Ellis and Ralph Lauren. On paper, it was a solid career. In reality, I started to feel like I was building other people’s visions while mine stayed in the background. Read more>>

Alexander Boykins

The biggest risk I’ve taken was betting on myself and trusting God’s plan for my life. I’ve had moments of self-doubt where I would overthink everything and try to analyze my way into certainty. But over time I realized the bigger risk wasn’t stepping out—it was staying stuck and letting my potential sit unused. Read more>>

KIMBERLY A MCNEAL

One of the biggest risks I ever took was stepping out on my own to start Disciplined Design with only $374 in my bank account. No investors, no safety net, no backup plan—just determination, faith, and a belief that I could build something meaningful. Read more>>

Karla Guillen

Opening Simplicity Studio wasn’t something I planned out perfectly it came from a place of necessity. I was going through a divorce and had to figure out how to support myself and my daughter, so I took a leap with what I had… which at the time was essentially nothing. I didn’t have a big financial cushion or a detailed business plan. Read more>>

Melat Ghirmay

In the eldest daughter of 4 siblings all togheter. I’m #3 out of 4, first gen immigrant kids. I was born into dance due to the nature of my culture where dancing is a big part of celebration, as I am of Eritrean heritage. Read more>>

Gina Granert

One of the biggest risks I’ve taken was starting my luxury picnic business First Coast Picnics, in the middle of Covid. This idea started more as a creative outlet than a business plan. I have a stable full-time career in healthcare, so stepping into something new during that time came with a lot of unknowns. In the beginning, there were a lot of unknowns. Read more>>

Dr. Elisa Malangone

There was a moment in my life where everything changed—and it didn’t happen gradually. It was immediate, disorienting, and undeniable. What I thought was stable… wasn’t. What I thought was aligned… wasn’t. And suddenly, I was standing at a crossroads. Read more>>

Heather Rison

As an artist, I’ve had a few day jobs over the past 15 years — jobs I felt I needed to pay the bills, but that also taught me skills related to my craft. What I really want to talk about, though, are the risks I’ve taken each time I decided to quit those jobs and pursue art full time. Read more>>

Shytei Corellian

After my divorce at age 30, I sold the condo I was living in, gave away everything that wouldn’t fit in a friend’s minivan, and set out on the road. I’d always been a writer; couldn’t help it. Long before I considered myself an Author, I was writing. Read more>>

Taylor Cozort

A couple of months before my 18th birthday, I packed up my humble life in Colorado and moved to New York City, a placed I’d only ever been to once before, to pursue a life in the arts. Read more>>

Brynhild Baldrimnir

I spent 15 years operating at the intersection of crisis and community, managing significant risk while supporting those navigating the most difficult social realities. After over a decade of working within the constraints of the social service system, I made a conscious, strategic decision to step outside of traditional career paths. This risk was a necessary leap toward authentic mentorship and community-based liberation work. Read more>>

Angelina Rosario Bright

Growing up in poverty, every single day felt like a risk just to survive. But the biggest risk I ever took was choosing to believe that my story didn’t have to end where it started. I grew up watching the people around me accept limitation as their reality. And for a long time, I did too. Read more>>

Jaris Harrison

I’ve always been a risk taker. I’ve fully embraced betting on myself and it’s worked out for me. It started in my college dorm room, where I launched my first business with more vision than resources. I didn’t have everything figured out, but I had enough belief in myself to start. That’s always been my pattern…move first, figure it out later. Read more>>

Kyle Costal

Five years ago I quit my day job to pursue music full time. I was about to release my first album. I didn’t have a label; I didn’t have a following; and I didn’t have a lot of money. The plan was simple.. hit the road and figure it out along the way. Read more>>

Rena Mohamed

I was born in May 1969 to a teenage mother and was placed for adoption. My adoptive family is a big family with West Indian roots who loved me immensely and I love them right back. As a family we are connected in ways that is not typical, my cousins are like my siblings, we spent summers and holidays together ever year. Read more>>

Kelsey MacMinn

Starting my photography business was one of the biggest risks I’ve ever taken—because on paper, I had no business doing it. I wasn’t formally trained. I didn’t go to school for photography. I didn’t have a mentor or a roadmap. Read more>>

Linda Tatum

One of the biggest risks I ever took came later in life—when most people believe risk-taking is behind them. In my 70s, I found myself moving to Las Vegas, a place I never imagined I would live. I didn’t know anyone there, and it wasn’t a natural fit for me. But life led me there, and instead of resisting it, I leaned in. Read more>>

Bamn Ford

One of the biggest risks I took was walking away from stability before I had proof that my vision would work. I wasn’t in a position where everything lined up perfectly—there was no guaranteed income, no massive following, no safety net waiting on the other side. What I did have and still have is conviction. Read more>>

Kyrsten Wright

So I had just moved back to nc early March, I’m sitting on the couch scrolling on ig and come across a post from the round table game where they are choosing 20 people to come to the premiere for their new season. I saw it within 2 minutes of being posted, saw it was being held in Atlanta, so I scrolled past it. Read more>>

Sylvia Arbelaez

A real risk I took was stepping out of what I’ve known for over 20 years as a commercial photographer and finally leaning into my work as an artist. I’ve always created for clients, so putting my own art out there felt a little scary and very uncertain. Read more>>

Jennifer Noel

Starting a business is by far one of the biggest risks I’ve ever taken. While I have been an artist all my life, there’s nothing more heart-pounding than deciding you’ll rely on doing what you love to provide for yourself and family. Talk about pressure. I’ll never forget when I decided to dive in head first. Read more>>

Amy Klingele Garman

I was in a role at a Senior Care community for 10 years managing clinical nutrition as well as the dietary teams responsible for preparing and serving all meals to our beloved residents. We had the best team! New owners took over and at first there were no changes. Read more>>

Lauren Noble

In 2019, I took a risk by applying for a home remodel television show called ‘Cash Pad’ that I had seen advertised on social media. The premise of the show was to take a homeowner’s unused space and turn it into a short term rental. Read more>>

Tori Musciano

I was not at all prepared for running a business when I first started. In fact, while I was first starting, I was still applying to full-time jobs hoping something would work out. I knew I had a skill but I was not at all a business person, and to start the business with my skill I knew I needed both. Right?! One would think. Read more>>

Heather Kathryn

I knew from an early age that I wanted to do music and be an artist but what I didn’t know was everything that would entail and the first step I had to take outside of actually performing was moving to Los Angeles. Read more>>

Angelina M. Farris

In life, risk is inherent. Stepping outside your home carries risk and so does staying in. This difference isn’t whether risk exists, it’s the level of risk you’ve grown comfortable living in. Most of us are experienced in the risk of quitting a job, starting a new one, or trying for a new position. Read more>>

Linda Curry

After my divorce, everything felt unfamiliar—like the life I had built had been taken apart and I was standing in the middle of the pieces, trying to figure out what was next. I didn’t just lose a relationship… I lost direction. I lost routine. I lost the version of myself that once felt secure. And for a while, I stayed in that space. Read more>>

Marcela Gasparian

The biggest risk I’ve taken wasn’t a single decision — it was choosing, over and over again, not to play it safe. I think it all started when I left Brazil and moved to Los Angeles for a postgraduate program at UCLA. I came without a network, without familiarity, without any guarantee that things would work out, just a sense that I had to try. Read more>>

Joshua Planz

I was asked to come and teach at the Film University Babelsberg in Germany for 6 months. Taking the opportunity to teach in Berlin for six months was a deliberate leap into the unknown. I had never lived outside the U.S. for that long, and stepping away from my life and momentum in New York meant accepting real professional and personal risks. Read more>>

Crystal Stucker

For over six years, I was an Educator at the Aveda Institute Houston. It was stable, familiar, and meaningful work—I was shaping future professionals, building relationships, and operating in a space where I felt confident. But over time, I started to feel a pull. I missed the energy of the salon—the pace, the creativity, the direct connection with guests. Read more>>

Sydney Guerrette

My family has always lived by this motto: there is no Plan B. At first, it can sound rigid, almost unforgiving. But over the last decade, I’ve found it to be one of the most clarifying principles I’ve ever held. Taking risks with a closed hand, gripping tightly to outcomes, can feel suffocating, like everything hinges on ‘success’ or ‘failure’. Read more>>

Gabriela Sales Cabral

In December 2016, just as I was about to become a mother for the second time and was in the middle of negotiations to acquire the school where I worked, I discovered, completely unexpectedly, that the company had been sold… just not to me. The opportunity I believed was mine vanished overnight. Shortly after, my son was born, and everything seemed to happen at once. Read more>>

Emily Depasse

The biggest risk I’ve taken is stepping into my dad’s shoes and running his fence company after he died in its 40th year. Fences By Doug (FBD), which is now under my leadership, was my dad’s company. He formally started it in 1986 after his father passed away when he was 32. Read more>>

Le Stadler

Before consulting, I spent years inside companies doing the unglamorous tech work: fixing data, automating manual processes, and wiring systems together so people could actually do their jobs. Read more>>

Chantrelle

As a creative, I feel like taking risk is apart of the job description. The willingness to explore new ideas that may have otherwise not been attempted, reimagining the world around us through different mediums is a risk within itself. Creating space for myself to explore the world unapologetically through my art has been the biggest risk I’ve ever taken. Read more>>

Marie Valencia

Started my own small business,without any formal education on or background loans to start up..Risked a lot of stability short-term,in the early days but have self-taught myself everything I need to know about navigating small business ownership.In 2026,I am celebrating 12 years of Mystic Herbs Shop being in business,since it’s founding in 2014.Through the pandemic, multiple moves across the U.S. Read more>>

Benjamin Kosubevsky

When I decided to open Longevity Centers of Florida in West Palm Beach in October 2024, I wasn’t chasing a dream. I was walking away from three of them. At the time, I had medical director offers on the table from new ventures in regenerative medicine — the kind of roles most physicians in this space spend years trying to land. Read more>>

Saudine Alexis Luceñara

One of the biggest risks I’ve taken was leaving my previous job without any savings or backup plan to pursue a completely new career path. At the time, I was working as a Customer Associate, earning a modest income while dealing with daily commutes that were both time-consuming and physically draining. Read more>>

Dagmar Spremberg

I grew up in Germany and never felt that I belonged. I got married, worked a great job in the music industry, and when I turned 30 I had the inner call of Now or Never, so I left my job, my husband and moved to Los Angeles, without knowing anybody there. Read more>>

Nickita Breaux

After two decades of building a career within the structured walls of the world’s most prominent financial institutions, the greatest risk I ever took was the decision to step out of the comfort of the boardroom to champion economic equity in the public square. The Backstory I had spent twenty years mastering the technicalities of banking, strategic underwriting, and complex lending. Read more>>

Danielle Rubenstein

I remember the exact feeling before I remember the exact day. It wasn’t confidence. It wasn’t even clarity. It was this quiet, persistent pull—like something inside me had already decided, and I was the last one to catch up. I was sitting at work, doing what I had always been told was “the right thing.” Stable job. Consistent paycheck. Predictable routine. Read more>>

Caitlin Grace

Becoming an artist takes courage. It is a leap of faith to pursue a career without guaranteed income, solely based on our own ability to show up and create a body of work that a customer base will resonate with. It is risking comfort; learning new skills, learning to deal with potential rejection and judgement, staying self motivated, continuing on when results are slow. Read more>>

Daniel Borthwick

One risk I took that had a big impact on me was deciding to fully commit to content creation and videography rather than keeping it as just a side hobby. At the time, I was balancing it alongside more stable work, which felt like the safer option. But I realized that splitting my focus was holding me back from improving and building something meaningful. Read more>>

Dr. Denise Wiesner

I grew up with a mother who was a Songwriter, however, I veered off and became a Dr. of Chinese Medicine, Certified sex coach, exercise physiologist and all things health related. When my husband died of Cancer, 14 years ago, I took a writing workshop. Read more>>

Berlaine Sanchez

I think one of the biggest risks I’ve ever taken was moving to the United States at 21. I left behind my family, my home, my university studies… everything I knew — and came to a country where I didn’t even speak the language. Starting over from zero wasn’t easy. Read more>>

Tara Polley

Twenty-five years selling luxury real estate in Sonoma County teaches you a lot about calculated risk. You get very good at knowing when to move and when to wait. What it doesn’t prepare you for is someone pointing a television camera at your face and saying ‘action.’ I had a reputation, a client base, a business I had built from the ground up. Read more>>

Jamie Nelson

It became clear to me very early in my pursuit of a career in the arts that, at first glance, I was “nothing special.” Coaches, teachers, and classes reinforced that perception. Coming out of school for Musical Theatre performance, I believed there were enough roles for anyone willing to put in the time, effort, and dedication. I quickly learned otherwise. Read more>>

Taylor Garzolás

I’ve been an Industry Accountant in Corporate America since I graduated college at 20. However, during the pandemic the grand idea was born to begin my own catering and private chef service (a field of work that saved my life right after high school. Without that, I wouldn’t have increased the level of discipline and true grit that’s necessary in life). Read more>>

Caitlin Silverstein

The biggest risk I’ve taken wasn’t just starting my practice. It was starting it in one of the most vulnerable seasons of my life… being postpartum. At the time, I was navigating one of the most vulnerable transitions of my life. Read more>>

Katy Beltran

I left my four-year-old daughter behind with $200 in my pocket and no English, hoping I wasn’t making the biggest mistake of my life. At the time, I was a single mom living in an abusive environment, working long hours for almost nothing. I knew that where I was, I could survive, but not grow. The risk wasn’t just for me. It was for her. Read more>>

Camila Hojas

For a long time, I thought the safest path as an artist was to be understood as quickly as possible. But if I’m being honest, the real “safe path” in my life wasn’t even art. Before this, I had already built something stable. I studied business in Chile, completed my degree, and even went on to get my master’s. Read more>>

Liz August

The biggest risk I’ve taken in my business actually wasn’t leaving my decade-long teaching career behind. That felt terrifying at the time, but looking back, I had nothing to lose. I had no clients, no reputation, no team. If it failed, I’d go back to the classroom. The real risk came later, when I had something to protect. Read more>>

Shahasia Harris

The greatest risk taken was opening a vegan mobile business that was self- funded. However, I took a chance on my skills and on myself and now here we are bigger and better than ever. It was a risk; because most businesses fail within the first 3-5 years and, we Definity have had our share of ups and downs. Read more>>

Arnoldo Diaz

The subject I address here is the act of living—something inextricably linked to the presence of risk. This occurs every time we make a decision, whether small or large; what happens is that we step onto a different plane of uncertainty—one over which, most of the time, we have little to no control. Read more>>

Laura Van Buskirk

Taking a risk is very loaded. It is often said that the greatest risk is doing nothing. In my experience taking risks represents confronting your feelings. I am going through that right now. I was the pedestrian in a hit and run car accident at the end of March. Currently I have a broken ankle, that left me re-evaluating my work-life. Read more>>

Jerome K. Miller

A story on a risk that I taken. Well, if I’m being transparent. The entirety of my life has been about taking risks. However, I’ll share the story of a recent risk that I have taken. Read more>>

Kym Renner

Starting RennerVation Foundation while Jeremy was still very much in the middle of his recovery was, without question, a big risk. When he had his accident, our family was in the middle of something unimaginable. Read more>>

Brynn Gerner

I was born and raised in the Midwest, Wisconsin to be exact. Go packers! But I recently took a risk and uprooted my life to start over completely. I’ve been calling it my “quarter-life crisis,” considering it all unfolded just a few months before turning 25. Truthfully, I’ve always felt more aligned with sun and sand, so staying in the Midwest never quite fit. Read more>>

Bamo Karem

People always expect a big risk to feel intense… like your heart’s racing, like everything’s loud. For me, it was quiet. It was the moment I decided to bet on myself instead of staying in a path that already made sense. Everything around me was stable. I had structure, a clear direction, and a version of life that ‘on paper’ looked solid. Read more>>

Nina Naval

I don’t think of myself as a particularly risky person, but my friends would disagree. First of all, I moved from the Philippines to the United States of America in 2019 on a scholarship from New York University to be an actor. I was eighteen years old when I had to navigate living on my own, the American healthcare system—the pandemic. Read more>>

Tonya Greig

For me, the most significant risk I’ve taken wasn’t a single event, but a series of firm ‘no’s’ that started when I was sixteen. ​In a world where the standard blueprint for success is finishing high school and immediately heading to university to secure a degree, I decided to stop. Read more>>

Jordan Briones-Schmitz

Taking a risk is quite honestly the most exhilarating and most nerve wracking thing most people will encounter. Whether that’s taking a career risk or a risk in any business/personal relationship, the unknown is also really scary. I am a person that is consistently ten steps ahead in everything I do. Read more>>

Montana O’Neill

Taking a risk, for me, wasn’t just one moment—it was a season of my life where everything felt uncertain all at once. I opened my salon at 21 years old, which on paper sounds exciting and impressive, but behind the scenes, it was honestly terrifying. Read more>>

Linda Russell

“One of the biggest risks I’ve taken was transitioning into real estate after being laid off from my role as Head of Creative Marketing and Sales. That moment could have easily been a setback, but instead, I chose to see it as an opportunity to pivot into something I had always been curious about but hadn’t pursued yet. Read more>>

Bonnie Bradley

I began making cakepops when my kids were small. I wasn’t technically ‘full time’. We were blessed to be able to have the option to stay home, but as they got bigger, so did the cost of sports, clothes, etc. Read more>>

Kevin Jenson

I’m an educator and researcher before I’m a business person, so for me the most natural way to make a decision is to gather my data and find the most highly recommended strategy. When I launched this business, I wanted the best advice from the leaders of the industry. But I’m working a very particular niche with an audience few people even know about. Read more>>

Bethany MacLachlan

A huge risk I took was embracing my multidisciplinary identity rather than choosing just one creative avenue to pursue. I became the landscape designer who also runs a crochet boutique and writes poetry. On the surface none of these creative outlets tie into one another, and for a long time I struggled to create a brand from that. Read more>>

Sylvana Nogueira

The biggest risk I’ve taken wasn’t just starting my own firm — it was choosing to build it differently. I began working with entrepreneurs and small business owners in the U.S., but over time I saw both an opportunity and a challenge in working with international clients. Expanding into that space meant navigating more complex regulations, cultural differences, and a higher level of responsibility. Read more>>

Alex Z. Wang

The honest answer is that I still don’t know exactly when the decision was made. There wasn’t a single moment where I said, ‘I’m going to open an art gallery.’ It was more like I kept walking toward a door, and one day I realized I was already through it. Read more>>

Karem Zafra-Vera

I have always been open to taking risks. One of the most defining lessons in my journey came when I chose to put my personal business on hold and step away from something I had spent seven years building. At the time, I believed I had found a path that would finally allow me to do what I truly loved: solely coach. Let me explain. Read more>>

Rashounae Paulk

My entire entrepreneurial journey has been built on risk, but the most defining one was my decision to relocate to Charlotte, North Carolina, at 23. At the time, I was living in Savannah, Georgia, a city that played a significant role in my early growth. Read more>>

Briar McMahon

I was building my freelance video production presence when the pandemic started in 2020. All the jobs I booked were canceled and I had to pivot fast. I decided to get a part time job to pay the bills and wait out the pandemic (little did I know). I ended up working there full time for the next five years. Read more>>

Christina Scalzo

I lost my job two weeks before Christmas December 2019. This is what prompted me to open my business in the first place. I had just bought a house and my boyfriend and I had four kids together. It felt like a huge risk however with such a big life change that had just happened I felt it was my only option. Read more>>