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.

Simone Jaggers

Before I became a licensed massage therapist I worked for the University of Alaska doing project management. It was a steady job that had good benefits and allowed my to live a comfortable life, and yet I always felt like something was missing. When my project ended at the University I was presented with a cross roads, stay in Alaska and try to find another office job or take a risk and drastically change me life. I chose the latter! I loved down to Seattle enrolled in massage school and became a massage therapist. That was 6 years ago and I am so happy that i took that step. I love my job, I love working with people one on one and seeing the change from the start of the session to the end. No longer wondering if I made I difference, I know that I have. There are definitely trails when taking on service oriented work that revolves around client bookings. Like learning to accept the ups and downs of money flow, no longer always making the same paycheck no matter what. But i have found it worth it in the long run, for overall life satisfaction. Read more>>

Paula Sluder

Risk is often associated with change that affects the trajectory in how you see living your life. Surgeries and unknown health struggles from the past five years has refocused my attention and pushed me to change my perspective in how I needed to move forward. Did my career (then) fulfill me and support me? It absolutely did, but having to choose health over work was the biggest battle I had to face. Prior to the culture shift on career and life balance, the term “work hard play hard” was my norm, until my health reminded me that I needed to prioritize myself. While I was too busy competing in the culture of what “success” should look like, I was failing in the other. Read more>>

Aren Johnstone

The biggest risk I’ve ever taken was jumping into entrepreneurship during my senior year of high school. My mentor—who’s now one of my closest friends—introduced me to the opportunity. A business associate of his was selling a small e-commerce figure skating store and needed to offload it fast to move on to his next venture. Less than 24 hours after hearing about it, I was sitting in a Starbucks meeting the owner. Less than 30 days later, we’d closed the deal in March of my senior year of highschool. At the time, I was already committed to Denver University’s business school and decided to take a gap year to pursue entrepreneurship. I took out a loan, owner-financed the inventory, and just like that, I was running a small business while balancing soccer playoffs, IB exams, finals, and everything else that comes with being 18. Read more>>

Tianna Gonzales

Growing up, I always dreamed of becoming a nurse, drawn to the fast-paced hospital environment and the reward of caring for others. However, baking was another passion that brought me joy, especially when sharing treats with loved ones and seeing smiles on their faces. At 10, I was already assisting my mother in the kitchen, where she taught me how to make Filipino cassava cakes. By 12, I started taking custom orders from family members, discovering my entrepreneurial spirit. Pursuing a nursing degree at Mount Sac Community College, I was just one course shy of completing my Associate’s in Science and Nursing. That was until, the pandemic hit. I clearly remember the day I headed to class. I stumbled upon the culinary arts program. Transfixed, I peeked through the window, and in that moment, my heart shifted. I knew God wanted me to abandon my nursing aspirations and pursue becoming a baker, in hopes that one day I would own a successful bakery. Read more>>

Gao Lee

My husband, Saeng and I started Uprooted Coffee in 2022 in the middle of the Pandemic. It felt like a good time to venture into something we both had interest in. The company didn’t grow right away, first of all, there’s not a market for Southeast Asian-produced coffee in the U.S., the usual response we hear from people is “we didn’t know coffee was even being grown in Southeast Asia”. We knew we wanted to bring specialty coffee grown in Laos, Thailand, and Vietnam into the spotlight but neither of us has a background in business, we were both working full time, and we had two kids who had busy schedules of their own. Read more>>

Anil Polat

When contemplating a career risk often the answer to the question, “what’s the worst that could happen” is happening right now. You know what will happen if you never take the risk because nothing is likely to change. For some people though, the allure of not knowing what’s possible after taking a leap drives them, and to me, that’s the sign of an entrepreneur in the making. Don’t procrastinate through over-planning, either do it or don’t and accept the decision once you’ve made it. Read more>>

Dave Faluna

Doing anything creative is a risk. At first, I wasn’t planning to start Faluna. I thought that fashion was too risky, and that I had to do only the “traditional” path. And then I had a health scare. Everything’s fine now, but there’s this moment that you have, when you are hit with your mortality. You think about your life not just in present tense but in past, as well. You think to yourself “how would people speak about me if I passed today?”. And in that moment, I knew that the things that I felt were risky, paled in comparison to the much greater threat of having people tell the wrong stories about me. At some point I decided that even if I tried and failed, at least I would be known for my passions, and when a success that deep in meaningful underlies even failure, there wasn’t nearly as much risk as I initially feared. Read more>>

Rosalie Maduro

As I approached my high school graduation in 1993, I made a bold decision that would change the trajectory of my life. Instead of taking the expected path of attending a UC school close to home, I chose to accept an offer from George Washington University—3,000 miles away in Washington, D.C. At the time, I didn’t know anyone there and had never been so far from my family. It was a leap into the unknown, filled with uncertainty and fear, but deep down, I knew it was the right choice. Read more>>

Amanda Cortez

Taking the Leap: Building My Mental Health Group Practice Starting my own mental health group practice was one of the biggest risks I have ever taken. Leaving the security of my full-time position was daunting, but I was driven by a deep awareness of the gap in mental health care within my community. Over time, I realized that individuals were struggling to access timely, compassionate, and effective care. This unmet need became the foundation of my vision. The decision to branch out on my own was not made lightly. I knew it would require stepping into uncharted territory, balancing clinical work with the demands of running a business. I faced questions about financial stability, growing a client base, and building a team. Yet, I felt strongly that the potential to make a meaningful impact far outweighed the uncertainties. I wanted to create a space where clients felt truly supported, and clinicians could thrive in a collaborative and innovative environment. Read more>>

Brenda Denny

One of the most defining risks I’ve taken was making the decision to leave a steady job to pursue a career in real estate while also maintaining my figure skating coaching business. At the time, I’d been coaching for 15 years and felt deeply passionate about helping young athletes reach their potential, but real estate was a new direction that also fascinated me. I knew it would take a leap of faith to balance both careers, mainly because I was committed to providing excellent service to my skating students and real estate clients. Read more>>

Samya Johnson

A big risk I took was leaving a dance team I was with from the beginning of it’s creation and starting from scratch again. While I won’t mention the team’s name, it was something I had been part of from the very beginning. I contributed to creating the name, laying the foundation, and helping the team grow. When we started, we discussed our shared goals and vision, but as time went on, there weren’t any clear, set goals or direction. What we had talked about no longer aligned with what was happening, and that disconnect started to weigh on me – both emotionally and physically. Read more>>

Ayse Ergin

One of the biggest risks my twin sister, Zeynep, and I took was leaving our full-time jobs to focus on Aster Society just as the COVID-19 pandemic began impacting the U.S. Starting a business is challenging under any circumstances, but the early months of the pandemic—with lockdowns and travel restrictions—tested the strength of our partnership. When we launched Aster Society, we anticipated scaling up would be a significant challenge (even under normal circumstances) because each piece takes hours or even days to create, but this became an even more complex problem to solve with all of the uncertainties introduced by the pandemic. Read more>>

Deniz Eyuboglu

One of the biggest risks I’ve ever taken was quitting my job in Turkey and moving to the United States, a country where I barely knew the language and had no established network. At the time, I was working in a stable role in Turkey, but I felt that my growth was limited. I had always dreamed of pushing my creative boundaries on a global stage, and the U.S. seemed like the perfect place to challenge myself. It wasn’t an easy decision. Leaving behind family, friends, and the familiarity of home for the unknown was daunting. I remember arriving in New York City and being overwhelmed—not just by the pace of life, but also by the language barrier. Simple tasks like grocery shopping or navigating public transportation became significant challenges. Read more>>

Marisa Crandall

In the Fall of 2015, I was working as the Director of Educational and Counseling Services at an elite independent school in Philadelphia, PA. I had been at that school for 12 years, and my 2 daughters were enrolled there in 12th and 9th grades. My husband loved his job at a healthcare data company in Center City Philadelphia, and we lived in a wonderful neighborhood called Mount Airy. Life was good! In early October, I received a call from my former Head of School who had recently taken over as the Head of a prestigious girl’s school in Los Angeles. She was wondering: would I be interested in moving to Los Angeles to found and lead a new department of educational and counseling services at this well-known school? Read more>>

Ana Carla Laidley

I decided to immigrate after separating from my first husband and because my father begged for my assistance after his turbulent divorce. Leaving behind my life as a teacher in Rio de Janeiro, Brazil, I thought I was embarking on a temporary journey to help my father. Little did I know this decision would alter the course of my life in profound ways. Arriving in the United States was filled with uncertainty and emotional turmoil. I left my two-year-old daughter under my mother’s and ex-husband’s care, believing I would soon return to Brazil. However, life had other plans for me. I met my current husband while adapting to a new culture and helping my father. This unexpected encounter led to a new chapter in my life, and I decided to stay in the US. Read more>>

Eric Theodore

A couple years ago I decided to move across the country, from Texas to California, to pursue my MFA in Painting at Laguna College of Art + Design. While in Texas I had befriended some competitive divers, and as an artist trained in painting the human body, I had the idea to paint divers as part of my graduate body of work. I discovered that I would be moving near Mission Viejo Nadadores, where many Olympic swimmers and divers have trained. The first place I stayed in California was actually directly across the street from the diving tower. I took this as a sign. What better way to get closer to my subject than to actually put myself in their position? I decided that if I was to pursue painting divers, I would need to – through risk and all – become one. In my first practice, I remember standing at the edge of the board, shivering, feeling exposed and self-conscious, nervous about trying something completely new. I felt afraid of heights, of humiliating myself, of throwing my body into positions I had only ever imagined. I began diving lessons at the beginning of my MFA program, and now, having graduated recently, I continue to both dive and paint divers. The gamble of getting out of my comfort zone, out of the stands and onto the board, has definitely paid off. My museum graduate show sold out and I have since shown at three California art museums. My life since has entailed going back and forth between the diving pool and my art studio, keeping me refreshed and motivated to pursue my career as a professional artist. Read more>>

Rachel Engelmann

From 2019 to 2024 I worked in an office setting, and after the pandemic, mostly from home. I felt unfulfilled once again, despite tufting as frequently as possible. I missed interactions with coworkers and friends and being in an active environment, like my past jobs in the service industry. As time passed, I realized that my job was grating against everything I wanted for myself in life. In May of 2024, I officially quit my day job to work part-time in a local restaurant and focus on tufting.  Read more>>

Austin Liu

Risk is a funny thing—it’s like a wall, guarding whatever lies behind it. Most of the time, risk scares us, as that’s human instinct. But sometimes, we take a leap into the unknown. I encountered such a moment during a project where I had to create a font. Within just two weeks, I needed to define its general direction, draw inspiration, and identify its deeper meaning. At first, I was conflicted. Should I build upon a font I had previously designed or start from scratch? In the end, I decided to create a new one. Why? Because it was a risk I was willing to take—a commitment I made for the rest of the project. Read more>>

Julie Styles

Taking Risks Is My Middle Name Taking risks has always been second nature to me, even when the odds were stacked against me. The biggest leap I ever took came after a devastating loss—the death of my sister, who passed away by suicide just before I earned my esthetician license. That moment broke me in ways I didn’t think were possible, but it also ignited a fire within me. I knew I needed to make a change—not just for myself but for my children, who were still young at the time. I packed up my boys, leaving behind Modesto, a place that had always felt suffocating, and headed for what I consider the most beautiful place in California. It also happens to be one of the most expensive. Starting over in such an unfamiliar and challenging environment was terrifying. Read more>>

Amanda Aguilar

Leaving my career in TV news to become an entrepreneur was one of the most significant risks I’ve ever taken. For nearly a decade, I had dedicated myself to journalism, working tirelessly to climb the ladder in an industry that was both fast-paced and unpredictable. On the surface, I had achieved what many would consider success: a stable career, a decent salary, and recognition for my work. However, deep down, I felt stuck. The constant pressure, long hours, and emotional toll of covering complex stories had started to chip away at my mental and physical health. More importantly, I realized I wasn’t living in alignment with my values and passions. Read more>>

Stacey Field

Four years ago, I stood in the doorway of my newly opened yoga studio, heart pounding and palms sweating. I had no prior business experience, just a vision and a deep love for the practice of yoga. Teaching my first class on opening day was both thrilling and terrifying. The room filled with expectant faces, all seeking something…connection, balance, community, a good workout… I stumbled over my words at first, but as we flowed through poses, I found my rhythm, and a spark of confidence ignited within me, along with a passion I’d never before experienced. Read more>>

Charles Hammer

For many entrepreneurs, the path to success is often shaped by unexpected moments of inspiration. For me the journey to founding Music City Taco began not in a traditional business setting, but after the global COVID-19 pandemic. As healthcare workers, we were putting in long hours with little time to eat and very few options available in the hospital. It was a challenging time, and I started thinking about how I could create a solution that would serve not only healthcare workers but also the wider community in a way that was flexible and mobile. Read more>>

Tara Tranum

One of the biggest risks I’ve ever taken was starting my company, Shine Bright Sparty Bus. At the time, it felt like I was jumping into an unknown world- I didn’t know anything about the industry and I didn’t have any real experience. As an executive in corporate for 10+ years, jumping into a kids business was pretty insane and honestly never a part of my goals or dreams at the time. It was also risky to quickly spend thousands of dollars on a party bus that I really had no clue about, other than I liked the idea – I thought it was truly a brilliant idea. Others were already doing this business but my mind always operates on how can I do it better? My husband also (oddly enough) believed in the idea and purchased the bus for me which was a big risk on him and our family. Read more>>

Antoine Pearce

It was January, the air still crisp with the remnants of winter. But within me, there was a fire—a spark of something greater, something burning deep inside. I could feel it, that divine whisper urging me forward. The risk seemed impossibly high, but so did the potential for something greater. It was time to take the leap, to follow the path that had been unfolding before me for years, but had never seemed so real as it did in that moment. This was the beginning of my journey as a Chosen One Read more>>

Almaz Adeigbola

one of the biggest risks I’ve ever taken was entering the cannabis industry before it was fully legalized. I started Brwnbox in 2015 as a food company, initially selling small finger foods at events and parties. While it was a challenging market, I quickly realized that the edible cannabis space had a lot of unmet potential. At the time, edibles could be unpredictable, and reliable, safe options were hard to find. I began experimenting with creating my own edibles, which became quite popular. Then, in 2017, my mentor and former boss, Emeka, suggested we host an infused dinner party at his Newark café, Freetown. It was an enormous leap for me—I had never hosted a dinner party, let alone an infused one. But the event was a resounding success and opened my eyes to the opportunity to combine cannabis with education and curated experiences.  Read more>>

Isabella Traboscia

My Journey to Pursuing a Career in Esthetics During the height of the COVID-19 pandemic, I made one of the most challenging decisions of my life. For years, I had dedicated myself to getting accepted into my dream college, Penn State University—an achievement that required endless hours of hard work, determination, and sacrifice. I additionally attended community college courses during high school which resulted in more than half of an associates degree completed before I graduated high school.  When I finally achieved that goal, it felt like a dream come true. Yet, as the pandemic disrupted life as we knew it, I found myself questioning everything I had worked toward. Read more>>

River Lyons

I have a million stories but the one that I feel really shifted everything happened last November. I decided to leave my job because I was no longer satisfied with my work, and it was affecting my mental health. What’s funny is as soon as I left, I wrote almost 5 songs that week. I was so stressed at that job, it was keeping me from doing what I love, which is music. I started working two jobs just to barely scrape by, but I kept my faith. I took it one day at a time, knowing an opportunity had to fall into my lap. Well one day, On The Radar announced they were coming into town and I reached out to them. At first, I didn’t hear anything back and I got comfortable with the idea that it wasn’t my time. Then I got that DM to connect with them. Read more>>

Cay Mims

I, like most new and earnest artists, approached my work very linearly. I remember the day we had to pitch the ideas for our thesis projects my senior year of university. I had an idea, mapped out the steps to execute that idea, and thought that I would follow those steps through to completion. I walked up to my professor, confident that after a small conceptual and logistical probe (an art school formality), I would get the go-ahead to jump in and start executing. Read more>>

Kelvin Davis

Taking a risk is often betting on yourself and skills. No one knows you better than YOU, so it’s important to trust yourself and to invest in yourself. I know for me personally, I wasn’t going to be taken seriously in the fashion industry unless I created a name for myself. I started a body positive menswear blog called Notoriously Dapper, this blog was meant to give everyday men solid and reasonable style tips while also giving them giving them real life advice. I took the risk by creating the blog, producing my won content, writing my own blog posts and posting them. Read more>>

Elina Lukas

When I went back into art in my mid 20s, I dedicated several years to making art that is perceived as more popular. Art that is easy to understand and appreciate, the type of art that most people enjoy. After trying out different styles and techniques, I realised that I am never satisfied with the art I make – all because I was not creating it from the heart. Two years ago I took the leap into the world of abstract art. Starting from scratch seemed like something I desperately needed, while also being something that could potentially fully block my creativity and my own belief in my creative gifts.  While I still have a long and exciting road ahead of me forging a name for myself and experimenting more with my art, I am the happiest at creating than ever before. Read more>>