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.

Tanya Spencer

This is a story of NOT taking a risk. Or, more accurately, of being in denial, going through a lot of anguish, and then finally daring to go after my dreams. Why the heck did I put myself through all those doubts?! You know the kind… Don’t – cause I worked so hard to be successful. Don’t – cause people my age don’t change careers. Don’t – cause I had a life that looked so good. How could I even dare think of throwing it all away? So I piled on excuses, weighing myself down with bone-breaking stones – all to keep me stuck. At the time, I was a global security and crisis management specialist. In some bitter twist of irony, my job was helping clients manage risks when their staff worked in dangerous places, yet I couldn’t manage the risk of redefining my life ambitions. Read more>>

Marissa Small

Throughout my life, I have always been drawn to working with and educating our youth, a passion that guided my educational journey at Penn State University, where I prepared for a career in elementary education. However, after much soul-searching and exploration of various creative endeavors, I discovered that my true calling lay not in the classroom, but in crafting beautiful, unique wearable art. My journey into jewelry design began as an invigorating hobby, but it quickly consumed my creative energy and ignited a profound desire for purpose. Perhaps it was my background as a competitive tennis player, which instilled in me a love for working with my hands, or maybe it was the realization that I longed to express my creativity in a more tangible way. Whatever the reason, I knew I needed to harness my God-given talents for something greater. Read more>>

Kate Stanford

I am a firm believer that the best things in life require taking calculated, well thought out risks. When I was seventeen and a senior in high school, I was given the opportunity to release a song for an upcoming Christian movie, called “Palau the Movie.” At the time, I had never released any of my own music, or even stepped foot into a recording studio. So many thoughts came rushing into my mind when trying to make my decision, “What will the people at school think? Will they think I am cringy? Am I even good enough to record music?” The chaos of self-doubt and fear consumed me for a few days, until I got an overwhelming gut-feeling to say “yes.” Without anymore thought, I jumped in head first and recorded my debut EP, “Bloom” and had my song “I’m a Believer” featured in the movie. If seventeen-year-old Kate had not believed in herself and said “yes,” I would not be where I am today. The biggest lesson that I learned from taking that risk 5 years ago is to always “commit to the yes.” Read more>>

Devon Perry

During the pandemic, I, like many people, was abruptly unemployed. I had been working as a professional actor and musician in NYC for about 8 years at that point, and it felt like my career was just really hitting its stride right when everything shut down. For over a year, it was very unclear if/when/how theatres would reopen and what that would mean for the careers of so many actors. In fact, several incredible theatres that had helped shape my career never came back from Covid-19. In the meantime, thousands of people were dying, and thousands of others were putting their lives at risk every single day to help the sick. Needless to say, I sat alone in lockdown in my Brooklyn apartment, listening to ambulances rushing past at all hours, and wondered if I ought to be doing something else with my life. Read more>>

Roxana Pardo Garcia

During the pandemic I was working for a local city government and I was witnessing the synergy that was building around mutual aid efforts in my Community – the reality is that I wanted to be in my Comunity, being of service to the Community that I belonged too. Given the uncertainity that we faced spring of 2020, everyone cautioned me against leaving a stable, government job and my health benefits. I felt so stuck, and so sad; so, in my down time, I was volunteering my time and donating funds. Read more>>

Linda T.

“Life begins at the end of our comfort zone.” — Neale Donald Walsch Everyone always talks about how life is about taking risks and stepping out of your comfort zone— but that’s honestly easier said than done.  Having grown up in a traditional Asian household, I was taught to never shy too far away from our cultural norms and values because it was always either “the right thing to do”, “because our parents said so”, or a little mixture of both— since the last thing you’d ever want to do is not only be a disappointment to yourself but also be a disappointment to your family and the people who raised you. Read more>>

Kwame Terra

The story of bEHR Health really took off after a series of pivotal moments in 2023, following my firing from United Airlines in December 2022. With no job and a dream to build a health platform for the Black community, I went all-in on bEHR Health. The first sign that things were moving in the right direction came in March 2023, when Brent Faiyaz, the talented artist and entrepreneur, gave us our first check for $10,000. It was an incredible moment—getting that early belief and investment from someone outside of the traditional health-tech space was the boost I needed to dive deeper into building bEHR Health. Read more>>

Keeley Collins

When I started my company, I was not making enough to support myself so I had to work an office job. I spent eight months working in an office while I was building my company on the side. As I gained more clients, my office job slowly became a side hustle and my business took center stage. After eight months, I felt that I could no longer do both jobs well. They were both demanding so much of me and I have always been someone that believes in giving 150%, all the time. I was faced with a choice; I could stay at my office job and have benefits, a stable salary, and a set schedule, or I could take a big risk and become a full-time entrepreneur. Read more>>

Kendale King

Starting my consulting firm, KCK CPA, during the pandemic was a leap of faith. The world was facing uncertainty, and many businesses were struggling to adapt. I had a stable job, but I knew there was a bigger impact I could make. I decided to bet on myself, quit my job, and build something that aligned with my vision of serving entertainers and navigating the world of digital assets. Similarly, launching CPAcon amidst a sea of accounting conferences was another bold move. I saw a gap in the industry for an event that celebrated accountants the way NBA All-Star Weekend does for athletes. It was risky, but it was a chance to change the narrative of our profession and offer a new, engaging way to approach financial literacy and professional growth. Read more>>

Dr. Renetta Weaver

Absolutely! So, let me take you back to a time when I took one of the biggest risks in my life. I’d been working as a Licensed Clinical Social Worker for over 20 years, and I was on a steady path to retirement. But, you know, something inside me kept telling me there was more. I had this gut feeling that if I didn’t take the leap and start my own private practice full-time, I’d be holding myself back. It wasn’t an easy decision. I had all the security that comes with a stable job—benefits, retirement plans—the whole package. But I knew that deep down, staying in my comfort zone wasn’t where I was meant to be. So, I made the jump. I left before retirement, started my own practice, and let me tell you, it wasn’t smooth sailing at first. But after a few years, the practice was thriving, and things were going really well. Read more>>

Ivory Thierolf

I have dedicated much of my life to the fields of gymnastics, competitive cheer, and dance. Following my college education, during which I earned a degree in sports management. Like many graduates, I initially found myself in roles that diverged from my intended career in the sports industry, despite my deep passion for sports and business. Throughout this journey, I have consistently maintained part-time positions across various companies to stay current with new skills, coaching styles, and techniques. Read more>>

Tammy Hahn

In 2021, I took a leap of faith with my four daughters by my side and started The Punchy Boutique, a mobile western boutique. We initially focused on women’s clothing with a small selection of children’s items, but quickly discovered that at most events we attended, no one was offering western wear for kids. Recognizing this gap in the market, we shifted our focus to specialize in unique, high-quality children’s western clothing. Together, we’ve faced challenges, taken risks, and built something special—proving that with family, courage, and a little grit, anything is possible. Read more>>

Amber Herrera

The act of being an entrepreneur is a risk by itself, right? Not only are you putting yourself out there, spending money, passion and time on something you believe in, but you’re investing in yourself. When I started out with branding, I was so passionate about working with both products and owners but I was afraid to venture out from families and kids to businesses. It’s a different experience for them! Almost no one can visualize how high-end, indoor branding translates from warm, desert family portraits with little toddlers running around. I let that be a limiting belief, and didn’t believe I could make it work, either…despite having already done it behind the scenes. Read more>>

Niy R

I considered moving out of state to attend Clark Atlanta University, which was a significant risk. It was quite challenging to move to Atlanta without any family, friends, or knowledge of the city; in fact, some family members disapproved of my out-of-state move. However, I can say that since moving, I’ve had a lot of opportunities that I believe I wouldn’t have had if I had stayed at home. Additionally, I believe it has helped me become more independent when I’m on my own in the real world. Read more>>

Jolene Goring

Taking risks is an essential part of growth, and one of the biggest risks I took was the decision to leave behind the traditional path I was on and fully embrace the concept of limitless living and quantum healing. At the time, it felt like stepping into the unknown—I was leaving a stable career path for something that wasn’t well understood or widely accepted. The backstory begins with a desire for something more fulfilling, not just for myself but for others. I had been feeling a nudge, a calling if you will, to explore how we can tap into our deeper potential through the mind, body, and energy fields. Read more>>

Bezol One

In 2020, I was a manager at a brewery/restaurant called Blind Owl Brewery. I had been there for five years at that point, and I was doing art on the side. I also served as their in-house chalk artist and graphic designer, and I had painted a mural on their patio. After we had to temporarily shut down the restaurant due to COVID-19, I landed my largest mural project up to that point at the IndyHumane Downtown Clinic. While I had painted walls before, the scale of that project was new territory for me. Completing that project and sharing posts about it online resulted in an influx of mural project inquiries. That really opened up my eyes to the possibility of generating a full-time income with art. Read more>>

Diana Beltran

Starting a private practice was definitely intimidating. Making the leap from a steady paycheck to working for myself was a big shift, but I believe everyone needs that push to take risks. I had been working for someone else since I was 13, always relying on my employer for support. As a clinician, I always dreamed of having my own practice, so I gradually gained experience in different areas. In 2022, I took the plunge and joined a group practice. After a year and a half, though, I realized that working for someone else was becoming too draining, so I decided to leave. Read more>>

Jessenia Collazo

Leaving a stable job can be one of the scariest risks to take, especially when you’re a single mother trying to balance career and family. For 13 years, I worked as a paralegal, a role that defined my professional identity and provided for my family. But as the pandemic unfolded in 2021, my priorities shifted dramatically. With my son’s father moving two hours away, I was left to navigate school drop-offs and pick-ups solo. When we were called back to the office full-time, I knew something had to change. My workplace had allowed me to work an altered schedule, enabling me to manage my responsibilities as a mother. However, after months of making it work, my supervisor informed me that the arrangement was no longer feasible. Read more>>

Melissa Preece

Taking the leap to start my own mental health practice was one of the biggest risks I’ve taken in my career. After working over 20 years in organizations, I made the decision to leave behind the security of a steady paycheck, benefits like health insurance, paid time off, and a built-in support system. Working for yourself means you don’t have those safety nets—there’s no one holding you accountable but yourself. However, that same independence is what makes it so rewarding. I now have the freedom to shape my practice based on my vision, to create my own schedule, and to decide how much or how little I work. I no longer have to seek permission for the decisions I want to make. There’s a deep sense of satisfaction in knowing that the fruits of my labor are mine to claim. Read more>>

Qin Yu

Pursuing your passion is both a privilege, and in my opinion, a must – That is, assuming you are lucky enough to have one. I am aware that not everyone does (in which life is still wonderful in its own way) but if you do have anything that makes your heart beat a little faster, I think it is absolutely worth pursuing or else there will be at least a little bit of the “what if” question niggling at you from time to time. It is also a privilege and gift because not everyone has the means or support to do so. If life has given you that gift, then I believe it is a risk absolutely worth taking. Read more>>

Annie Korzen

I had written and performed several solo shows, and frequently appeared in storytelling venues, but I always dreamed of a larger audience. A young friend suggested I post some little clips on TikTok. I thought that was a ridiculous idea since I’m not a 20-something blonde dancer or makeup expert. She kept insisting that I would go viral so I decided to give it a shot. Now, against all odds, I a an 85-year-old woman with over 400,000 followers! Read more>>

Haley Lickstein

A year and a half ago, I made a bold decision to move across the country from Washington, D.C. to Seattle, Washington, to start what I thought was my dream job at a foundation whose mission I wholeheartedly believed in. The excitement of working for an organization that aligned so deeply with my values was undeniable, but the move to a city where I knew fewer than five people came with its own set of challenges. Read more>>

Aaron Hines

One of the biggest risks I’ve taken in my life was leaving a stable corporate career to pursue my passion for health and fitness. It was a life-changing decision that shaped my path in ways I never imagined. About 9 years ago, I was working in a steady, well-paying job. It provided security, benefits, and a clear career path, but there was always something missing. Fitness had always been a passion of mine, and I had been training people on the side for years, just for the joy of it. As time went on, I realized my true calling was helping others transform their lives through fitness working for myself and not a big corporation. Read more>>

Shawn Esho

One of the biggest risks I’ve taken was deciding to leave a stable career path in marketing to pursue acting full-time. I had been working at a tech job, a company that offered incredible opportunities and a secure future, and while I enjoyed the work, there was always this lingering feeling that I wasn’t doing what I truly wanted. Acting was always my passion, but it was something I explored on the side—small theater productions, local acting classes. It felt like a dream I couldn’t fully chase because of the practical demands of life. Read more>>

Esperanza Pope

The risk I’ve taken has been the biggest one ever; believing in myself. I had to take the risk and believe I can do it in order to reach my goals whether they’re career or personal. It doesn’t matter if anyone else believes in me, they’re not in control of my outcome, I am. If I listened to what others say about my decisions, I wouldn’t be reaching my goals. You have to do it whether you have the support or not, you have to do it scared and anxious but if you really want it, none of that will matter because you have so much faith in yourself that you make it no matter what. I recently moved back to the big city from a small city for more career opportunities and that decision has caused some discourse in my personal life but without that I wouldn’t have the opportunities I have now. I wouldn’t have the confidence I have now because I’ve seen I can trust myself to make these big life decisions. Read more>>

Penny & Dime

The biggest risk we’ve taken was probably forming the band. We actually met through Craigslist—back when we were both a little younger and a lot more trusting of strangers. Kylie posted an ad, and after wading through a few sketchy responses, got a message from Krystle. It wasn’t long before we clicked, became close friends, and started this journey together. What was once just a fun jam session turned into so much more. Read more>>

Jonathon Smith

Around 2018, I took a risk and left a stable full-time job and profession to pursue a career in film and acting. It was a difficult decision and for years I wondered if I made the right decision to move to LA in late 2018. During the struggling years in Los Angeles, I wanted to quit multiple times and I wondered if I made the right decision to pursue this craft. Thankfully the risk paid off in 2024. Recently, I did a film screening and charity event for my first feature film, Broken City (2023), in my hometown of Barstow, California. It’s a small town with about 20,000 residents. I am one of the few filmmakers from Barstow to create a feature film. The knowledge of how to create a business plan, make a film, and distribute a film isn’t readily available. Read more>>

Angela Gentile

This is a great question! I truly believe that you have to train and practice to be ok with risk. So much of what we are taught makes us risk averse. We, especially as millennials, were conditioned in deference. And now, I think being able to counter those really harmful teachings and going in the most polarizing direction is key. Risk taking starts with self awareness and self connection. When you know who you are and what you want, there really isn’t hesitation. You just go toward what serves you because being where you are, remaining in places or with people who aren’t working for you is way more of a risk to your happiness than taking a chance into the unknown. Read more>>

Ken Crost

I think being a creative person constantly entails the process of risk taking. But one particular risk-taking journey occurred many years ago when I was beginning to break free from the constraints of my prior life. I had always wanted to try my hand at performing but was terrified by the idea. Since I was living in Chicago, there were many possibilities for heading down that path. I, however, decided to take acting classes at Second City, one of the most important improvisational theatres in the world. I showed up at an old church that was going to be our classroom and stood outside watching as people showed up for the first class. Read more>>

Angelica Partidas

The biggest risk I’ve taken has been moving to another country. I had to do it for my family. The things is, In my home country economical security, freedom and safety did not exist. So I had to make the choice with my children and husband to move out for our future. When we got here, every choice we made was a risk, not knowing where life would take us. However, it lead me to this moment. I’ve accomplished things only one could dream off. And I feel strong, beautiful and confident. My advise to everyone is take risks and step out of your comfort zone. Only that way you will achieve imaginable things! Read more>>

Alexa Goldie

I took a risk by moving to Nashville back in 2021. Back home in Ontario, Canada, I own a music school where I teach local students how to play the guitar, ukulele, piano and vocal lessons. In 2021, I had just graduated from University and started building up my teaching clientele. I had the opportunity to go to Nashville for a quick trip to do some writing and small writers rounds. Although I had a steady job at home and had just graduated with a degree, there was something pulling me to visit Nashville. After my quick trip to Nashville, I fell in love. 2 months after that trip, I packed my bags and moved to Nashville. This was a risk because I didn’t have a community of support in Nashville, I didn’t have a steady job, connections or a way to promise income at the time. Taking that risk was one of the best things I have ever done for my career. It forced me to truly learn how to write music, perform for all types of crowds and how to build relationships in a completely new place…a new country. Read more>>

Gianna Cabrera

I’ve taken several risks in my life, and one of the latest was moving to South Florida without a clear plan, giving myself the space to fully develop as a creator. At the time, I was living rent-free in a rent-controlled, three-bedroom apartment in New York City, thanks to tenants who covered all the rent. It was an incredibly comfortable situation, one that most people would never leave. But I felt a deep, undeniable pull to step away from that security and embrace a new chapter of self-discovery as an artist. With no job lined up and no place to stay, I gave away most of my belongings, left New York, and trusted the uncertainty ahead. For two months, I searched for a place, driving back and forth from my father’s in Orlando to Miami, only to find nothing. Eventually, I came across a home near the ocean that I had only seen in three photos. I moved in without ever having stepped foot inside, and when I finally did, it was far from what was promised—unclean and unprepared. Read more>>

Nina Anderson

Taking a Risk: My Journey to Entrepreneurship Taking a risk is one of the greatest life lessons we can gift ourselves. For me, it’s always been both exciting and scary. Risk means stepping into vulnerability—opening the door to rejection, failure, and leaving the safety of a comfort zone. Yet, risk also holds the potential to unlock incredible opportunities, open new doors, create meaningful relationships, and benefit from personal growth. Sixteen years ago, I took a big leap. I left the stability of the corporate world—a steady income, benefits, the comfort of familiarity—and decided to become my own boss. With a $500 budget and big dreams, I was ready to take on the world as an entrepreneur. Read more>>

Definite Origin

“Biggest risk I took was believing in myself to be a full time dad. My journey with being a parent has been rocky from the beginning to currently. From paternity test, to court rooms, to custody battles.. the whole nine yards. My kids originally were living with my big sister, and when she fell short I had to step up. Nobody on all sides of my kids life felt I was capable of stepping up. It fueled me to do so. What’s crazy is I had just came off of a 13 city tour, and had no idea I would be walking into the biggest life change I’ve ever experienced. Somehow through prayer, finesse , and hard work I made it work. Shortly after getting them in the first year Covid 19 hit and the job I was just promoted on had no hours to offer me. I was stressing out cause I had just took on a bigger responsibility. Read more>>

Jennifer Holmes

When it comes to taking risks, one moment that stands out to me is the decision to grow Blackbird Salon after being on my own in a suite for 5 years. Prior to that I was a commission stylist for 7 years. It might seem like a calculated business move on the surface, but for me, it felt like leaping into the unknown, driven by a vision that was deeply personal. Here’s the backstory: I had been renting a suite, averaging solid sales, but I knew I had hit a ceiling. I had ideas, big ideas, about creating a space that wasn’t just a salon but a community — a place where clients could experience more than just hair services. I envisioned hospitality being at the heart of every interaction, from the moment someone walked through the door until they left feeling empowered and beautiful. Read more>>