The chapters in our stories are often marked by wins and losses. Getting a new job, getting fired. Getting a life-threatening medical diagnosis, beating it and getting a clean bill of health. Too often, due to a societal expectation of modesty and humility we are discouraged from talking about the risks we’ve taken that led to those ups and downs – because often those risks draw attention to how we are responsible for the outcomes – positive or negative. But those risks matter. Those stories matter. We asked some brilliant entrepreneurs, artists, creatives, and leaders to tell us those stories – the stories of the risks they’ve taken, and we’ve shared them with you below.

Andy Law

I’ve always loved watching American movies growing up. I thought they’re so much cooler than HK movies. It is kind of a fallacy though. The media trend has controlled it all. And now, with that effect, I stay open to any art forms from both culture. Read more>>

Lynda Carouthers

In early 2020, just as the world shut down from COVID, I made one of the biggest decisions of my life: I left my steady job to pursue real estate full time. It was a bold move—especially during a global crisis—and even riskier because I’m also the full-time caregiver for my autistic son, who was suddenly home 24/7 due to school closures. Read more>>

Katherine Flores

I would say the Biggest risk I have taken, would be to start my own cleaning business and take a chance to be my own boss. I am very good at quoting reasonable yet affordable Prices.I have very Great,determined, and compassionate hired cleaners who know we work Judgment free, and want the clients to come home and feel that fresh breath of fresh air to have one less thing to do. We also take pride in getting to know our clients on a personal level so they gain trust to have us in their home, or workspace. Before Starting my own business, I used to clean at a hospital, as much as I loved seeing all the sweet patients and making them feel special and heard, by engaging with them as I was cleaning their hospital rooms or lobby areas, the job just occupied a Lot of my time which left me to come home exhausted and not be able to spend as much time with my children as much as i would like, from working long hours and hardly any days off. Read more>>

Clarissa Hoffmann

Ohhh, where do I even begin? Let’s rewind a few years, back to a version of me sitting in Germany, surrounded by textbooks and spreadsheets, dutifully studying Business Administration — and feeling miserable. On paper, it all looked right. In my heart? It felt so wrong. Heavy. Draining. Like wearing a pair of shoes three sizes too small. Read more>>

Jaquil Barnes

I was sitting at home one day and my friend told me I need to chase my dreams and turn my passion for cooking into a business. But I knew I wouldn’t be able to grow my business in Jersey (where I’m from), and I had always wanted to go to LA, even though I had ever been before. So I took a leap of faith and decided to make the move. I got married to my now ex wife and she got me a job at a local bar/restaurant. I quit that job to go full time with my own business and brand and decided to put my head down and focus. I got my first celebrity client two months later, that changed the entire trajectory of my business and it was up from there. Read more>>

Camille Tredoux

There was a time I thought I had my life mapped out. I was a straight-A student with a 4.0 GPA, a collegiate cross country athlete, and headed toward law school—checking every box, following the script, and measuring success by a standard I’d upheld for as long as I could remember. But quietly, something was shifting. Music had always been central to who I was, even if I hadn’t yet allowed myself to pursue it fully. Read more>>

Jennifer Palmer

I own a large wellness center that was started in 2010. Approximately 8 years ago, I expanded my business and moved my location to start a cafe, add more treatment rooms and have a large studio to do more events and build community. It took about 2.5 years to make a profit, which was very good as most people estimated it could take 5 years with the level of expansion… it was like starting a new business. Read more>>

Zishi Liu

My journey into jazz was anything but conventional. Growing up in China, my mother enrolled me in saxophone lessons as a child, inspired by the soaring popularity of Kenny G in the 1990s. However, my city had no proper saxophone instructors, so I studied with a clarinet teacher and played classical music instead. The lack of connection to the instrument and the rigid structure of classical training led me to resent the saxophone, and I eventually quit in 6 months, convinced that music was not meant for me. Read more>>

OnWord Theatre

OnWord Theatre was created by three black women with a passion for theatre. Marti Gobel, Danielle Bunch, and Jamaelya Hines have worked extensively in the theatre for many years honing their craft in all areas of theatre presentation and production. Their combined struggles and triumphs were the topic of much conversation in the dressing room as they prepared to share the stage in a production of “STEW” at Scripps Ranch Theatre. The women quickly teased out that they could add to the tapestry of San Diego theatre with their combined skill sets. But, the creation of a theatre company in the midst of the struggling theatre arts meant that they would be collectively be taking a large risk. The risk, however, wasn’t just financial… Read more>>

Josh The Bricklayer

One significant risk I’ve taken is pursuing a career in the arts in a country where the government doesn’t recognize artists. This decision wasn’t easy, as it meant venturing into an uncharted territory with limited resources and uncertain prospects. Read more>>

Christian Oropeza

Growing up as the oldest of five in a Mexican-American household in Houston, Texas, I learned early on that risk wasn’t a choice—it was survival. My parents, immigrants determined to carve out a life in a new country, took risks every day. Not the kind glorified on social media or praised in entrepreneurship seminars—these were quiet, grueling risks: changing jobs to feed the family, learning a new language by trial and error, pushing forward with faith alone when the path wasn’t clear. Read more>>

Zakiya Olivier-Thomas

One of the biggest risks I’ve taken was choosing to keep walking in purpose — even when life shifted completely and nothing felt certain. When I became a mother, I knew everything would change, but I also knew I wasn’t going to stop. I decided that I would continue to pursue the dreams God placed in me, even if it meant carrying more than most people thought I could handle. Read more>>

Bledar Gashi

Leaving everything I knew in Belgium behind to pursue an uncertain future in California was the biggest risk I’ve ever taken. I am Albanian, born and raised in a small town near the coast of Belgium, and I came to California when I was 20 years old to play college tennis. Read more>>

Susie Chau

I took a life-changing leap by taking a yearlong sabbatical from my Management Consulting job to travel to all 7 continents with my husband.

Up until that point in life, I had done everything I was “supposed” to do – get good grades, get into a good university, get a good job, get married. But I wasn’t feeling fulfilled. Read more>>

Dr. Tosha Anderson

Taking the risk to create Mothers Divinely Connected Incorporated as a nonprofit was a leap of faith—born from personal pain, fueled by passion, and guided by purpose. It meant stepping into the unknown to turn grief into growth, offering hope and healing to mothers in need. With no guarantees, only a vision, the organization was built to serve, uplift, and connect women through some of life’s hardest moments. All of which was birthed after losing my oldest son in 2020. Part of my healing would be through helping other Mothers through their journey of healing. Read more>>

Christina Greiner

One of the biggest risks I’ve ever taken was moving from Berlin to Los Angeles on my own, building on the foundation of my O1 visa — a process that took months of preparation, collecting evidence, and proving my accomplishments as a creative professional. But even after getting approved, the bigger challenge was ahead: starting over in a new country, far from my family and community. Read more>>

Sharell Katelynn

I’m pretty risk-averse for someone who’s taken a lot of them. But I guess my fear of being stagnant outweighs my fear of change. My biggest recent risk? Walking away from a decade-long hairstyling career—with zero plan. The job was getting harder, the world more expensive, and my body was throwing in the towel. I didn’t know what was next, I just knew that chapter was closed. People still ask if I miss it. I don’t. That season is complete. But that doesn’t mean I was calm about the unknown that followed. Read more>>

April Burch

I took a risk by starting my business and setting up my storefront after leaving a toxic marriage and dealing with the effects of being drugged and sexually assaulted. I started my business early in my career, I had only been licensed for about two years before I opened. I was a stay at home mom for 12 years before deciding to leave my toxic marriage and go back to school. After the assault I borrowed money from my parents to open up my storefront. I started my Business with three Consistent clients and I have built it from there. Four years later, looking to hire employees. Read more>>

Camilla & Raffa DeFaria

Our “risk-taking” journey started with a U-Haul and a dream. My wife Camilla and I have been married for 17 years, but our shared love for music goes back even further. Both of us began performing as young as 4 or 5 years old, participating in choirs, trios, co-ed groups, A cappella ensembles, and solo. Music was always a core part of who we were, even when we found ourselves working in unrelated careers, sales and law, in our early twenties. Read more>>

Emily Romero

After five years in private practice and thirteen years of being a therapist, I took a big leap by following my intuition to shut down my therapy practice. It was a scary thing to venture into the unknown but I’ve learned that listening to the inner whisper is always worth it. I’d spent over a decade empowering other women to chase their dreams and I knew I needed to do the same. After wading through the liminal in-between space, I eventually received clarity about the next steps and have now published two books. My most recent book is all about learning to trust yourself – the exact thing that allowed me to take such a big risk in my business. Read more>>

Kyra Jefferson

I’m taking a risk and have taken a risk helping my city rebuild a block and ultimately a neighborhood. I live in the City of Detroit and have been a real estate investor for over 20 years. In 2018 I applied for a program called the Equitable Minority Developers program, where they select 20 minorities to transition to developers. 20 people are selected and over 100 applicants apply for this program. I was chosen in 2018 and graduated in 2019. After graduating, I began to look for a project I could take on. I decided to get connected to the area I live in & own property to see what else the area had to offer. I began going to events to see what’s going on in the area. Read more>>

Corina Nika

The story of Cocorrina is, at its heart, a story of risk—and of faith. Looking back, it feels like a series of leaps into the unknown, each one scarier and more transformative than the last. Read more>>

Jasmine Bunn

My entire career has honestly been a risk. A risk worth taking without a doubt. Before moving to Los Angeles, I lived in Charlotte, NC. Most people in NC are not considering being a dancer as an actual career choice. Maybe, if you go on to be in a ballet or modern company, but so many people I crossed paths with tried to steer me away from this choice. There were even people that I thought supported me that tried to steer me away from moving and putting my marbles in this particular jar. Read more>>

Neema Nene

I have taken many risks in my life. Back when there was no GPS and I needed the TripTik made by AAA or an atlas map of where you were going, I chose a job which involves traveling because I wanted to see more than 4 walls of the workplace. My second job of out of college was of an installer/teacher of 4th Generation software and I travelled to Mexico, Chicago, Detroit, Connecticut, Florida, New York, basically all over the US and got lost many times but found my way and became more confident in my abilities to navigate through anything that came my way. Read more>>

Shreya Talwar

Starting So Sweet Dessert Emporium when I was just 11 years old was probably the boldest risk I’ve ever taken, mostly because I didn’t even realize it was a risk at the time. I didn’t have a concept of marketing, margins, or brand building. I had just barely begun to know how to talk to others and get out of my shell, let alone being able to converse on the phone with customers. I just knew I loved to bake, and I loved the idea of making people happy through what I created. Read more>>

Jonathan Adams

I didn’t recognize it as a risk at first. It felt more like a natural unfolding — a calling, really. But looking back, what I did was nothing short of life-altering.
The seed was planted long before I knew what it would become. I grew up witnessing family members silently battle chronic illnesses and deteriorating health. Their struggles sparked something in me — not fear, but curiosity. Why were so many people sick? Could nature hold the answers? I started small, making shifts in my own life: I exercised more consistently, paid close attention to what I was putting in my body, and began studying herbs and natural remedies. What started as personal wellness soon became something much bigger. Read more>>

Hannah Cullen

Being raw and honest in my lyrics has been a staple throughout the music I’ve made. In my first EP, Letters to a Non-Lover, the rawness felt very necessary for the story I wanted to tell. And it felt almost easy to share. On my most recent project, Allelopathy, I felt vulnerable. There was a rawness that felt gratuitous and exposing. There were songs that I didn’t want to include because they were too honest and open, but I decided to share them anyway. The risk was damaging relationships, damaging the way people saw me, or seeming over dramatic. I’m glad I took that risk because I think people can relate to those feelings, even though they might not paint the prettiest picture. Read more>>

Katie Rapisardo Griffith

Leaping into being a full-time artist before I was ready this winter. But here’s the thing – are we ever really ready? No, but leap anyway. I wanted to have all my ducks lined up in the proverbial row ie the perfect website that I could manage myself on the back end, a number of series ready to launch, new branding photography, an email newsletter up and running etc. all before I told myself I could dive into this gig fulltime. But a series of events caused me to jump in sooner than anticipated and I’m glad I did. Has it been a resounding success with all the fame and glory? No. It has been a steady slow crawl of small victories and setbacks. Read more>>

Angelina Harper

Moving to Los Angeles at 18! At the time I just graduated from high school in Texas and had my sights SET on Los Angeles to pursue dance. Since I was about 10 and understood I could really make a living off doing what I loved most. I came up with a plan to apply to only California colleges so I could live on campus, go to school like my parents want, and can do entertainment all at the same time without doing any prior research about out of state fees and what the price of living would be in a big city like LA. I got accepted into Cal State LA and I packed up my car and drove to Los Angeles. Read more>>

Ezra Sholeh

The last time I saw my mom in Iran, she was crying at the airport, clutching my hand like she could stop time. I was 18. Just a kid with a duffel bag, a half-baked plan, and a heart pounding out of my chest. I told her I’d be fine. She knew I was lying. So did I.

I was born in Shiraz, Iran, into a secular middle-class family. We didn’t pray. We didn’t preach. My mom’s great-grandmother was Jewish. My parents were open-minded and hardworking. I grew up with a love for movies — not just as entertainment, but as a portal. Films showed me a world beyond the grey ceilings of control, censorship, and fear. They gave me freedom before I ever tasted it. Read more>>

Catalina Garza

One of the biggest risks we’ve taken as business owners and educators is currently in progress: we are building a brand-new facility for our dance school. This is not just an expansion—it’s a leap of faith in our mission, our community, and the next generation of dancers. Read more>>

Tosha Holmes

One of the biggest risks I have taken was working for myself. After graduating from college, I held a job that did not suit me. I decided to attend cosmetology school, and once I completed my certification and became licensed, I was too afraid to start working. I didn’t feel well-prepared to work in a salon at the time and didn’t work in one for two years.  Read more>>

Blair Cantrell

In November of 2019 I was popping up at a big Holiday Bazaar in Fort Worth. I had been doing pop ups for my business those last two years and I was just about done. I was exhausted and was thinking to myself, “this is it; this is my last show…”. During the event a vendor friend (Lizzy Bentley, owner & creator of City Boots) approached me about doing a 3-month pop-up at LOCAL Design Studios. Local is well known collaborative retail space with women designers who own their own businesses. I remember feeling honored they asked me and thought this could be a good way to end things. Having a successful 3-month pop and then shutting down the fur doors. Read more>>

Brookelen

So, I decided to drive myself cross-country from Arlington, VA to Los Angeles, CA to pursue music. Music—it’s such a broad and encompassing word, but I knew I wanted to be part of its world. I wanted to be consumed by it, married to it, and I knew I had to make a grand gesture. I packed all my belongings into my car, with no job leads, no housing plans, and no community waiting to welcome me. I had about two friends from my hometown who had moved to LA and encouraged me to come out. One of them generously let me (over)stay on their couch for a month. Read more>>

Alina Shkolnikov

In my career, the most significant risk I’ve taken is one that many perceive as counterintuitive: aligning financial objectives with social change. While conventional wisdom often separates profit from purpose, I’ve consistently chosen to intertwine them, believing that doing well and doing good are not mutually exclusive but mutually reinforcing. Read more>>

Mary Weaver

A couple of years ago, I was feeling unfulfilled and burned out in my marketing job. I’ve always been a crafty person, so I decided to reconnect with that side of myself. I’d been obsessed with stained glass since moving to NYC from Houston 12 years ago, so I took a one-day class and was instantly hooked! Read more>>

Kaelyn Gray

In August 2024, I stood on the edge of a decision that would change everything. It wasn’t just a career move. It was a reckoning with fear, self-doubt, and years of waiting for the “perfect” time to bet on myself.
As a tap dancer, educator, and mentor with 25 years under my belt, I had poured my heart into teaching others to find their rhythm—literally and figuratively. I had judged competitions, mentored rising stars, and developed an entire curriculum from scratch. I even launched Bring Tap to the People, a small side project that organically grew into a global resource sold in over 100 countries. But despite all of that, I realized I had never fully owned my talent. Read more>>

Johanna Riddle

For twenty five years, I worked in arts education in my community and state as a museum curator, an arts administrator, a board member of several arts non-profit organizations, and an art instructor from pre-K through university. I loved my work, but I’d let my work as an artist take a back seat. Now I was going home. I was making the leap from talking about the art on the wall to creating the art on the wall. And it scared me! What if I wasn’t “good enough?” My style and use of materials is unique. What if my paintings were rejected? I had a positive reputation in the arts community. What if everybody heard about it and thought, “And she’s been teaching about this all these years?” All of my insecurities rose to the surface. Read more>>

John Tibbetts

Like many in the performing arts, I watched my career vanish almost overnight during the pandemic. Contracts were canceled. Auditions disappeared. Read more>>