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.

Annmarie Gajdos

I did not grow up in an environment that encouraged risk. As a young Slovak-American girl, taking the safe and predictable route felt like an unspoken rule. My family imagined I would go into something structured like law or medicine. So choosing entertainment and accepting a job at HBO was already a quiet rebellion. Read more>>

Monique Berisha

One of the biggest risks I ever took was starting my business at 21 — right in the middle of college, when I was still trying to figure out my path like everyone else. At the time, I was going to class, working as a marketing executive, and trying to convince myself I knew what I wanted long-term. Read more>>

Alpha Omega Fry

Right before starting the business opportunity I sold timeshare for Wyndham Resorts. I wanted to get out of timeshare because the product was good but when it came to my owners making reservation was nearly impossible for the time they needed to take vacations. I wanted to do something to truly help others. Knowing when I lay my head down I had peace. Read more>>

Tanesha McQueen

I was never the girl who followed the rulebook. I was always so sure of myself and if I put my mind to it, I knew I could do it! Down to getting married young and starting a family early. Some thought that would be the end of my story but baby it was only the beginning. Read more>>

Amy Pearson

I took a risk by going to the Wedding MBA last week. I haven’t been to an in-person conference since starting my business. However, Enji (the marketing/social media posting software that I use in my business was going and asked for booth volunteers. Read more>>

Zach Kidwell

A few years ago, I walked away from a 13-year career in business development and experiential marketing to become a full-time abstract artist. On paper, it was a terrible idea. I had a wife, kids, bills, and no guarantee where this road would go. Read more>>

Carolina Henao Feliu

Reinventing Myself: Building My Kingdom from the Ground Up I started Kingdom Investment Services after leaving my previous career, knowing I needed to reinvent myself. Real estate investment had always been a dream of mine, but I used to think it was impossible — you needed money, contacts, and experience I didn’t have. Flipping homes was especially intimidating. Read more>>

Tamara Davis-Jack

THE RISK OF STARTING OVER When people hear me speak today or see beautiful images focused on positivity, purpose, and choosing to live with intention every single day — they see Tamara Davis-Jack, a woman standing strong, confident, and victorious. But the greatest risk I ever took wasn’t financial, wasn’t about love, and wasn’t tied to moving across the country. Read more>>

Rachel Forehand

I started my songwriting and live music journey in 2019 when I was a sophomore in college. Everyday as a musician, singer, and songwriter feels like taking a risk to me, but a risk worth taking. Fast forward to graduating during the Winter of 2020, the COVID year, I felt like my future was up in the wind. Read more>>

Teresa ‘MiZZ Entertainment’ Edwards

Taking A Risk I believe life isn’t worth living if you don’t take risks. Now…risk means something different to everyone. For one of my risks…its writing and telling my story. Ever since being a little girl…I enjoyed storytelling. And the best ones when people are their authentic selves telling their own story. I love documentaries and just well told stories. Read more>>

Joy McLaughlin-Harris

So Business was booming and all of a sudden things took a turn for the worst. It was looking like I was going have to close the doors bit instead I pivot. My numbers took a 60% hit with the emerging of AI, CHAT GPT and so many other new marketplace trends around branding. Read more>>

David Foster

I’ve been creating art for a while now — both visual and spoken word. But as a spoken word artist, I always struggled to find a consistent place to perform. I didn’t really have a “home” for my poetry. Then, out of nowhere, opportunity showed up. Read more>>

Jyssica White

The biggest risk I’ve taken was betting on my self , I bet on myself every single time . There’s been times where business was slow and I’d have to come up with a marketing idea to climb myself out of a dark place . I count on my creativity and drive to succeed. Read more>>

Erica Humphrey

The biggest risk I’ve taken was deciding my business wasn’t just going to sell pretzel necklaces- it was going to create real change, even if it blew up every “easy” path in front of me. In the beginning, my help came from family and friends. Then, as demand grew, I turned to PRIDE Industries (teams of persons with disabilities). Read more>>

Sally Shaar

Everything I have in this life is thanks to risks. To paint the picture: I was jumping off diving boards at four years old. For whatever reason, I’ve always been drawn to the paths other people hesitate to take. Read more>>

Melnora Tan Cruz

My life has been a continuous journey of taking bold risks that shaped who I am today. Each decision, whether born out of necessity or ambition, became a defining moment in my pursuit of growth, independence, and fulfillment. The first major risk I took was becoming a young mother and wife at 19, shortly after moving from the Philippines to the United States. Read more>>

Katie Oleksiak Burns

I’ve always been into letters. Since I can remember, I was doodling quotes from my favorite songs on the back of my notebooks and practicing all different ways to write my signature. I have naturally good handwriting, and I always received loads of compliments on it. But becoming an artist? Let alone, an artist who does something with letters? And actually… makes money??? Read more>>

Sooyeon Yoon

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One of the biggest risks I’ve ever taken in my life was when I was 19, I decided to completely change all my plans and move to the U.S from South Korea, my home country. Ever since I was a child, I’ve been extremely passionate about musical theatre. Read more>>

Manda Jones

In 2018 I lived through a harrowing experience with the mental healthcare system in Colorado. Until that point I was published only as a magazine columnist, but this tale of suffering and perseverance needed told. I wrote the book Defeating My Demons, My Mental Breakdown, through Darkness to the Light from that journey. Read more>>

Stephen Sweezey

My name is Stephen Sweezey and I’m the new owner of The Running Hub in Santa Fe, NM. Taking over the business in May 2025 was a significant risk and life-changing moment. I was the store manager for 9 years, and the previous owner approached me with the opportunity to purchase the business when he was ready to retire. Read more>>

Nar Tadevosyan

The biggest risk I ever took was trusting myself to navigate life the way I did, despite the turbulence, the noise, and every obstacle thrown at me. It was a risk because, honestly, what did I even know? Who was I to trust myself that deeply? Something in me chose to follow my own voice instead of the fears and projections of other people. Read more>>

Alyssa Pettingill

If you ask my friends or family, they’ll tell you I’m a planner through and through. I haven’t always been crystal-clear about my long-term professional goals (at least not until recently), but I’ve always been Type A—organized, meticulous, ambitious, and quick to take initiative. Read more>>

Charrita Nelson

All my life, I aimed toward one thing—greatness. Not the “big dream” kind you pin to a vision board or recite in five-year plans. For me, greatness was smaller, quieter. It lived in the everyday things: showing up, doing good work, being dependable. I didn’t grow up imagining myself taking up space in boardrooms or creative circles. Read more>>

Marie-France Merisier

I took a risk this year by stepping into a new creative territory and incorporating fabric into my handcrafted jewelry designs. It was something I had never done before, but it felt like a natural extension of who I am and where I come from. Read more>>

Donna Morris

One of the biggest risks I’ve taken was leaving my entire support system in North Carolina: my family, friends, and the community that helped shape me, to move to Texas and rebuild my life and my business from the ground up. At the time, everything in my life was familiar and comfortable. Read more>>

Terri Ford

A Leap of Faith: My Journey from Banking to Entrepreneurship How One Life-Changing Risk Redefined My Purpose The Comfortable Routine For thirty-five years, my life unfolded behind the polished glass doors of a bustling commercial bank in downtown Macon, Georgia. Read more>>

Sinthya Melean

I’m a Venezuelan entrepreneur who left my country and started from zero in a new place, with a new language and culture. During COVID, while becoming a first-time mom and unable to work outside the home, I took my first big risk: creating a small jewelry business from my living room. Read more>>

Keala Ramos

I’ve taken many risks in my life from coming out of the closet, to leaving the island where I was born to attend college in California, to leaving California for New York City. But one of the biggest, if not the biggest, was abandoning the safety of my job to start my own business while still pursuing my art. Read more>>

Ashley Vazquez

The biggest risk I took was deciding to become a chef. No one I knew was a chef, and the thought of creating foods was definitely not something that was encouraged while I was growing up. All I knew was that I loved everything about food. Read more>>

Alina Gordon

On May 8th, 2020, in the middle of a shut-down world, I took a risk that changed my life—and San Diego—forever. Read more>>

Jessica Higgins

Being an esthetician was not my first job. I was in sales before going to esthetics school in 2020. I decided to take the next step and invest in myself because all I did was talk about skin. I had cystic acne in high school and it came back when I was in college. Read more>>

Katey Blaire

I grew up in Portland, Oregon, and earned my degree in Apparel Design from Oregon State University. Just two days after graduating, I began my professional journey as a Global Merchandising intern at Nike’s World Headquarters. That internship evolved into a full-time position as a Print & Pattern Developer in early 2015, where I spent nearly seven years building my career in corporate America. Read more>>

Lacie Walters

I have always worked from home while raising our 3 children. i am creative and enjoyed designing, decorating, being crafty and making things pretty. i made cookies with buttercream for our children over the years and as they got older it was more for the holidays. Read more>>

Marko Cervantes

The biggest risk I’ve ever taken was my first trip to Miami. Back in 2020, I was a senior in high school working at a movie theater during the COVID shutdown. Around that time, I was sending beats to an artist from Florida named Hotboii. I started sending spamming him constantly, and he recorded on them and began releasing the songs. Read more>>

Sylvia Blanco

The biggest risk I ever took was betting on myself at a time when I didn’t fully believe in who I was. Growing up, I drew a lot, but no one encouraged it and I didn’t think anything special of it. I didn’t take my first art class until my senior year of high school, and then I stopped creating for almost a decade. Read more>>

Dena Meeder

For most of my life, I played small. I hid behind my family, behind my work, and honestly, behind my own fear. I was always the one supporting everyone else—never the one stepping into the spotlight. The risk I took wasn’t a single moment; it was a decision to stop disappearing. Read more>>

Golden Child

I take risks often. And the I’ve realized that the common thread between them all is that they occur around change. Leaving college was one of the biggest risks I’ve ever taken, and it wasn’t necessarily a hard decision. For a long time, I followed the path that I assumed everyone around me expected. Graduate high school, pick a major, and work toward a degree. Read more>>

Jay Holloway

I’m a portrait photographer turned sports photographer who decided to start women’s basketball show without any real connections in women’s basketball. I jumped head first into the women’s basketball community without any friend there. I met Lo and Nick Andre on twitter and I decided to reach out to them to by co host. Read more>>

Grisel Ortiz

The journey of a thousand miles begins with a single step’ by Lao Tzu is what inspires me in my life. Manifesting our dreams takes stepping into the unknown and taking risks. When I became a mom I decided to take the risk of starting my own line of clothing made from deadstock materials. Was I scared of what the outcome would be? Yes. Read more>>

Tatiana Dolfine

My painting career started with a strange dream and a quiet wish for more artist friends. I’ve always created things. I taught art, worked as a graphic designer, and could draw anything I focused on, but my paintings hadn’t bloomed yet. I didn’t have a voice. Years ago, sunlight filled the white cubicles in my office. Read more>>

Briona Clyburn

Before my life’s venture took hold in the field of entrepreneurship, in early 2019, my life took an unexpected turn when I faced a sudden and debilitating illness that led to hospitalization. I was only two years in to my post-college career, working in a dual administrative role, when my health began to deteriorate rapidly. Read more>>

Lai Sha Bugado

The biggest risk I’ve ever taken was saying “yes” to creating Kumumea during one of the hardest times of my life. It was born from pain, uncertainty, and survival — but also from a deep calling to build something beautiful out of what tried to break me. After surviving breast cancer, I knew life would never look the same. Read more>>

Othencia Yacinthe

The biggest risk I ever took was leaving a toxic home environment with nothing but my faith, a small amount of savings, and a vision of peace. Read more>>

Emmanuel Morales

One of the biggest risks I ever took was deciding to take my band, Los Paisanos, seriously instead of treating it like a casual side project. We started in backyard shows with borrowed gear and no real plan, but something in me knew that if I didn’t commit fully, the band would never grow. Read more>>

Tiffany Acosta

One of the biggest risks I’ve taken recently wasn’t financial or technical. It was personal. One morning, sitting in my car before starting my day, I decided to finally show up on Instagram and share the knowledge I’ve built from years of designing signage, stationery, and event details. Read more>>

Coco Johari

In my opinion, life is about taking risk and I truly believe you miss 100 % of the opportunities that may be for you by not taking that risk. I’m very adventurous, outgoing and sometimes I tend to live life on the edge. I was born in a small town in Michigan called Niles. Read more>>

Kendra Cherrington

Betting on myself and choosing to build a business while supporting my husband through medical school and raising three kids has been the riskiest and craziest thing I’ve ever done! Most people don’t realize just how heavy that season is (financially, emotionally, mentally, and even physically). Medical training is all-consuming. Read more>>