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.
Daemon Hilliin
“Every minute of every day as a producer involves risk. Whether it’s navigating physical production, securing financing, or strategizing distribution, each phase presents its own challenges. The key to managing these risks lies in having the knowledge and expertise to hedge against them. Mitigation and crisis management are my strengths, and I’ve honed my ability to handle them effectively. It’s not about avoiding risk but understanding how to face it head-on with the right tools and strategies.” Read more>>
Juliana Valles
Hello, I’m Juliana, originally from Venezuela but now living in the USA since 2017. I have a background in Chemical Engineering and MBA in Marketing, with 14 years of experience working for large companies. During the 2020 pandemic, while working as a Marketing Director for a law firm, I had a realization about the importance of balance in life. I had been solely focused on work and neglected to enjoy life. Dealing with a back injury, I turned to yoga for healing and found solace for both my body and soul. Read more>>
Keynan Wilson
Once I graduated high school on 2003 I started working at warehouses, delivery, and fast food. There was always times that I never enjoyed what I did, my main focus was just making money and surviving. Fast forward till 2019 I took a leap of faith (risk) and do what I loved which was Music, fitness, and start my own courier business. Read more>>
City Girls
In early 2022 I saw a women’s walking group on Instagram in New York City, then Chicago, and thought it would be wonderful to have one in Houston. I waited a few months to see if anyone else had the same thought, hoping someone else would launch a group. At some point I realized that if this was something I wanted in Houston, I’d need to do it myself. I took a chance, put myself out there, and announced a walk for the morning of May 1st meeting in Buffalo Bayou Park at the Wortham Fountain. I arrived that morning not knowing what to expect then a woman walked up and she asked if this was the meeting spot for the City Girls. Yes! Read more>>
Dr. Rebecca Troy
Thank you for having me! When it comes to risk-taking, one of the biggest risks I took was launching a completely new method for helping children with dyslexia. At the time, there was a lot of skepticism because we didn’t follow the well-known methods like the Orton-Gillingham approach, which is often recommended by doctors, but which I personally found to be ineffective for many children. I knew from experience that children with dyslexia needed a different, more empowering approach, so I developed a personalized, at-home learning program. This risk paid off tremendously, and our program now consistently helps children improve their reading and spelling abilities within just four months. It was a leap of faith, but the results have been incredible, and seeing children’s confidence soar is worth every challenge we faced in those early days. Read more>>
Toria Lexus
In September 2023, I found myself at a crossroads—a moment of decision that would either push me forward into my dreams or keep me tethered to comfort and security. At the time, I was working a retail sales job at Hand and Stone. The stability of a paycheck was something I had clung to, even though my passion had always been content creation. I had started to make a name for myself as a UGC creator, but I wasn’t considered a full-time creator yet. There were no guarantees that the next month would bring enough income to survive. But I had this persistent voice in the back of my mind saying, “If not now, when?” Read more>>
Mollie Fox
Teaching, as a rule, is a career path for the risk averse. Your schedule is preset and regular, the parameters of your job are more or less dictated to you, and although a fundamental part of the job description is to encourage risk taking in your students, the fences to swing to are more garden picket than major league outfield. I taught special ed for many years and the majority of that time was teaching art to students with language based learning disabilities. I was daily trying to come up with new ways to encourage the kids to allow themselves to celebrate themselves, and believe in themself. I created systems in my classroom that encouraged risk taking. Read more>>
John Compton
Taking a risk—it sounds bold and a little reckless, doesn’t it? That’s often the mindset before making a decision, when you’re relying on instinct, gut feelings, and perhaps some frustration. “Why not take a chance?” we think. But when viewed in hindsight, a risk is often reinterpreted as an investment—and I’m a big fan of investments. To build something meaningful, you usually have to invest significantly, whether it’s time, money, or both. As Warren Buffett has famously said, imagine you were given a punch card with only 20 investment opportunities for your entire life. You’d invest wisely and only when you were absolutely sure. Abraham Lincoln once remarked, “Discipline is choosing between what you want now and what you want most.” This same discipline applies to risk-taking. Read more>>
Nancy Terrones-haynes
March 11, 2020 My husband and I had just come back from a staycation. I had been currently working at a Salon in South Pasadena California and had built a clientele over the past 3 years. We came back to a changed world. The pandemic had hit and the world had closed. It was a complete shock and overwhelming realization as am Independent Contractor to have everything you built just stop with no safety net. The day I went back into the Salon was a new reality. Masks, 6ft distance and high levels of sanitation. I had made a conscious decision to pack up my things and isolate with my family as i had caught wind that we were to go into a full blown lock down. The decision was hard but easy. I had to really think about what my future was to look like at this point. Read more>>
Nikki Rome
When I started writing I soaked up as much information I could to ensure I was successful in my career. However, there was one piece of education that was missing and it had to do with writing realistic kink and BDSM in my books. I didn’t have enough experience with that community but my readers wanted more and more of it in my books. With time I met a few authors who provided guidance but the lack of education for so many romance authors was staggering. Read more>>
Misha Brown
My entire life, as it is today, is the result of taking a risk. Back in 2020 when the Covid-19 pandemic began, I left a job as a singer to go back to my hometown to “wait it out”. My entire life I was laser focused on being a singer and my entire adult life that is what I had done professionally. This was going to be my first time, from the time I can remember anything, that I would not be performing in some way. For a year and a half I worked a part time retail job, sold all of my jewelry for Taco Bell money and started posting on social media as an outlet. What started as a way to pass time, eventually earned me a couple thousand followers and a new sense of joy. Read more>>
Katy Jaquez
I’ve always been into taking risks my whole life. I’m the kind of person that commits to everything I do. When I made the decision to pursue hair I was a stay at home mom of two little boys. I also worked part time and went to hair school at night. I didn’t know for sure that I would make money at doing hair but I had to try. It was something I’ve always been good at. After countless long nights I finally graduated. My first step was to become an assistant at a high end hair salon in Denver. For two years I worked hard to learn the ins and outs of this business before taking my own clients. Once I graduated from assisting I began working on building my clientele. Read more>>
Emily Bartlett
Risk – A catalyst of change; I’ve taken many risks in my life, from drastic medical decisions that would alter the course of my life, to trusting people to have your best interest at heart, and choosing to invest in myself. Risks are the parameters that we find ourselves within whenever we are faced with a choice. With every choice that you make, there is and will always be associated risk. I think that within risk, we have to observe many other factors at play. Risk isn’t just some simple, walk in the park sort of a thing. To our brains it is life or death. And within life and death, as we can see in front of our eyes, things aren’t so simple. Read more>>
Amanda Haro
Starting my own life coaching business was a huge risk. I’m a single mom to four kids and I had a “safe”, stable corporate job as a staff accountant. But I had just experienced huge transformations in my personal life that changed everything for me, and I knew that I was being called to help other moms do the same. I had lost my dad to Covid the year before and had gotten an inheritance that was large enough for me and my family to live off of while I built up my business. But it was still scary to let go of my day job because I kept thinking, ‘what if I fail and I’m left with nothing?’ Ultimately the thought that I clung to as I made the choice to quit my job was: I can always come back to accounting if I want to. So I said ‘f*ck it’ and took the leap. Read more>>
Shannon Konyndyk
Starting Sojourn Bookstore was one of the biggest risks I’ve ever taken. On the financial side, my husband and I couldn’t secure outside funding for the startup, which forced us to take a home equity loan. This put our house on the line, adding an immense layer of pressure to the already daunting process of starting a business. Every decision I make has the potential to affect not only the bookstore but the security of our home. Read more>>
Owen Ragland
Theres something really nostalgic about riding in a school bus for the first time as an adult. The way the seats aren’t really comfortable or uncomfortable, the wonderfully designed windows that seem impossible to break but are always broken… When I found myself riding in a partially converted bluebird in 2023 I couldn’t stop smiling. I began dreaming about living out of a bus, traveling around playing music, watching the land change and writing what I saw… At the time I had just finished my second year of college in NY and became hellbent on touring. I had already formed a band and managed to book us a tour from Austin, TX to NY. A slow and steady beginner course in all things band and booking, my friends and I caravanned in sedans the whole route. That first tour was all I needed to take the risk. I dropped out of college, moved back to my hometown of Saint Louis, MO and bought a 40ft Schoolbus. Read more>>
Christine Smith
I’d say the biggest risk I’ve taken is Self-ownership in my health and my wealth. I once had a mentor tell me to not seek masters, but instead seek what they sought, and it has colored my path ever since. Self-ownership in health has looked like choosing to educate myself to make informed decisions when the system made me feel like a victim to my body. I realized that mindset was fruitless, and ultimately abusive and neglectful to my body. Instead, I have focused on learning to speak the language of the body, and teaching my clients the same, in order to create a sustainable, healthy, balanced lifestyle based on my body’s needs. Truly, we are the only ones who can tell what our body needs – most people have just forgotten how to listen and track. I take people through one on one care and group courses to learn how to do this in a customized way. Read more>>
Annette Anderson
Deciding to open 1st Step Healthcare Training was the biggest risk I’ve taken. I decided to take a leap of faith and execute my plan of opening a training school. I was working as a registered nurse and noticed that patient care was lacking due to nursing assistants not receiving classroom training. So, I decided to open 1st Step Healthcare Training and train them to the standard I believe would be a gold standard. I also knew I had to do something bigger and train and educate my community to help get them employed quick to help them with providing for themselves and /or family. Read more>>
Joanna Sanchez
As I sat in my cubicle at a corporate job I had held for over 10 years, the steady rhythm of typing on keyboards and the soft chatter around me felt both comforting and stifling. Each day blended into the last, and while I was grateful for the security and routine, I couldn’t shake the feeling of unfulfilled potential lingering in the back of my mind. Read more>>
Nick Alvarez
A risk that I took in life was when I moved from Massachusetts to Texas. In November 2022 is when I made the drive with a friend to start a new life in Austin, Tx. We didn’t know anyone when we first came down or have ever been to Texas. We packed up what we could fit in the car and we started our journey. The drive was around. 30 hours. We stopped in Nashville for our halfway point and stayed there for a couple days in a airbnb, and checked out some places around. Then we kept going, stopped at a hotel in Dallas for a night and made the last 3 hours to Austin. Read more>>
Clementine
Unlike the countless young women of my age craving influencer status via social media, I rebel with a purpose to shake society and aid its awakening from autopilot scrolls. I utilize contemporary fine art as my channel. I access off-the-grid villages in the far reaches of the world where I photograph those facing humanitarian challenges; these are individuals without handheld priority access to social media. I juxtapose their imagery with overlaying paintings that symbolize the mental health issues and egocentrism social platforms breed. Facing precarious circumstances as a young caucasian woman in the risky areas where I delve for material, I dedicate my life to artwork that serves as a call for our social media obsessed society to look beyond the self and restore true human connection. This art series, titled “Selfless in a Selfie World,” has thus far earned solo exhibitions with galleries in the Hamptons, New York and Milan, Italy. Read more>>
Natasha Colon Ortiz
I started my business with a program full of other entrepreneurs in 2016. I was running my business, Paper City Art Kids a Fun & Paint art services business. Business was growing and expanding with community events, art education in after school programs, paint parties, vendor events, and the fun and paints all through 2017 and parts of 2018. I had partnered with another small business that went through the program to be a contracted art educator for an elementary school in Holyoke while helping them with their business of movement education. I worked along side them from 2016 to 2018 when I applied for a job in the Holyoke School Department that fit me very well in 2019. Read more>>
Ayisha Green
A few years back, I found myself at an exciting crossroads. I had just started my journey in network marketing within the wellness industry, and after experiencing incredible results for myself, I felt this strong desire to share those benefits with others. It was more than just selling products; I wanted to create a community where people could embrace a healthier lifestyle. With that vision in mind, I decided to take a leap of faith and open a brick-and-mortar wellness center with my then-boyfriend, now-husband. It felt like a big step, especially since many around us were skeptical about our chances of success. My family was supportive, which meant a lot, but his family had some reservations. They just wanted us to be careful, and honestly, who could blame them? It was a big risk! Read more>>
Katie Frondarina
One of the biggest risks I’ve ever taken was leaving my role as a manager at a large medical facility without having another job lined up. It wasn’t an easy decision, but I knew the position was no longer aligning with my personal or professional goals. I was constantly stressed and burnt out, and I knew I deserved more for the hard work I was putting in. I knew I could bring real value to a company that aligned with my goals and appreciated my contributions. Even though I didn’t have a new job secured, I trusted my faith to guide me in the right direction. Read more>>
David Leong
Risk taking- something as a problem gambler that I was EXCELLENT at doing. I used to tell myself,” No risk, no reward,” just to justify my gambling behavior as I put in a ridiculous 5-team parlay on Saturday afternoon while watching College Football. I believe the chances of getting struck by lightning were higher, than me winning that bet. Today with almost 8 years of abstinence from my last bet, I still weigh out benefits and risks of my choices. Everything is a risk. Being vulnerable in this news article is a risk, but at what expense? If one person can learn/benefit from my story, it is a chance I am willing to take. Read more>>
Jeremiah Douglass
I would have to say that the biggest risk I have taken in my musical career so far it’s becoming a solo artist this year. A couple of months ago, the idea of being a solo artist seemed impossible. It was weird, because for some things I do like to be the center of the attention (like making people laugh). But for other things such as performing in front of people…. seemed to vulnerable. But one thing I learned is that people appreciate when you are vulnerable with them because in return they now also feel that they can be vulnerable with you especially through music. Every now and then I accomplish something that lets me know that I can do anything that I put my mind to. Stepping out and becoming a solo artist was one of those things this year. Read more>>
Smitty Smith
In 2009 I decided to do something I had no business doing. I only had the overwhelming desire to do something extraordinary. It was more of an accidental start, really. I had no real direction, only certain gifts as a leader and creative that I didn’t know what do with. Out of the corner of my eye while driving I noticed an old empty laundry mat building that was in a prime location. The sign posted said it was available, and to call today! The dream of what could be began instantly. I got that fluttery feeling and within an afternoon and few note pages later I had fully visualized and branded my first business. I could conceptually see every detail, the new layout, the cost, the fabric, the lighting, the menu and so on. Read more>>
Sarah Degray
I have come to realize that I am not a risk averse person. I love change. I thrive when I have to adapt. I like to go against the grain but I am the most successful when I follow my gut and intuition. The first big risk I took was deciding not to finish my PhD program in Political Science. From the first day on campus at The New School for Social Research in New York City, I knew I had made a wrong turn. Upon completing the Masters portion of program, I walked into my PhD advisor’s office and informed him that I would not be returning. I moved back to Burlington, Vermont, accepted a job at The Federal Public Defender Office, and began to plot my next course. Read more>>
Sarah Marnell
One of the biggest and most calculated risks I’ve taken was leaving my six-figure corporate fashion design job in New York City to start a vegetable farm with my husband, new baby and another couple. It was a risk that changed the entire trajectory of my career and life. The backstory is that I’d been working in corporate for years, steadily climbing the ladder and enjoying the financial security that came with it. But, I reached a point where I felt unfulfilled. I was craving something more aligned with my values—something that gave me control over my time and a real sense of purpose. The corporate world was comfortable, but I wanted to challenge myself in a completely different way. Read more>>
Chealsea Wierbonski
The first risk that I ever took was signing up for a study abroad program when I was at University. I had signed up to study in Caen, France (in Normandy) after one of my friends had done it. It was sort of strange because when my friend got back I said in sort of a joking way, “Maybe I’ll do the study abroad program” and I hadn’t even ever considered something like that. I had spent my entire life in a small town in West Virginia and had never left the country. I don’t come from a family who travels a lot, at least not any further than anywhere that’s not driving distance, so I was never exposed to this idea of traveling abroad. Read more>>
Thomas Mahar
In terms of playing music professionally, doing what you really want to do with it, and making a living, I find it necessary to take risks. And by taking risks I mean stepping out to do something and feeling like I could fall flat on my face. Before I went to any jam sessions in LA I felt terrified about being able to play with the musicians who regularly play in those jams and are experienced at it. I didn’t know if I would be able to float. One night I decided to go with my bass player to a jam that was held at a bar in the Valley. It was my first time hopping in on a pro jam and I was nervous. I knew I wanted to be able to hang with those musicians. Read more>>
Jack Edward
It was 2020 and I was living in New York City. I had barely started my second semester of college when Covid closed everything down and the two week break from school turned into a summer at my childhood home in Michigan. While I love my parents dearly, I couldn’t bring myself to go from doing whatever I pleased in Manhattan, to living in the rural and republican midwest. Read more>>
Antoinette Morris
The best risk I have ever taken was becoming a full time Entrepreneur. I will give you a little backstory about my family history and childhood to explain who Antoinette Morris is .And why moved to California with $900. And why didn’t I do it? I didn’t grow up in a traditional family where everyone worked 9-5 or had careers .Honestly I can count on one hand how many family members of mine actually worked a job, went to college, or have had a career. I grew up hearing my whole family say everyone in my family saying”No risk no reward”. I am a Huge risk taker which can be a blessing and a lesson for me. I love being an entrepreneur / risk taker. I would trade it for anything in the world .And here why. Read more>>
Brinley Steen
I took the risk of not going to college and following a traditional career path. Instead, I chose to follow my dreams of being a model and actor – along with that came social media and content creation. At times I do wonder what my life would be like had I gone to college and started working a “normal” job, but overall I wouldn’t change anything about my current lifestyle. Through this line of work I have met the most amazing individuals, and I feel that I have learned more about life and people than if I had chosen the traditional route. Read more>>
Jennifer Lopez
My big risk would be leaving my fantastic paying job, with benefits, 401k, and a sense of security, to start my own business and freelance. I am typically a person who chooses the most ethical path that provides the most beneficial outcome, which I did. When I graduated college in 2022, I got a job at a commercial architectural and interior design firm, I left that job because I was doing more drafting than designing, and then I got another commercial design job, where I did exactly what I wanted to do, design. Both jobs served me well and while I learned a lot, I found myself being unhappy. I was receiving great pay and benefits, but I woke up every day depressed about going to do work. I didn’t feel like it was making a difference. I would complete the work and then be shuffled to the next project without being able to communicate or create a relationship with the client, and that crushed me. I would drive my 1.5 hours home and think, “There has to be something better…” I would think, “This 8am-5pm groundhog day can’t be what I do the rest of my life.” Read more>>
Lindsey Boedicker
Owning a business has completely changed my mindset. The most successful people always take risks. What is a risk? I like to say a risk is this: something worth giving it your all. What makes a risk so risky? All the possibilities of failure. Taking a risk in any business is about commitment. When I decided this year to commit more time than ever on growing through social media I knew there was going to be the risk of losing an account or inconsistencies of views and exposure to customers online in a saturated market. But I decided it was a risk worth taking. I spent endless hours going on TikTok live and selling Serenity The Brand clothing and jewelry (day and night.) I created a schedule that was overflowing and jammed packed. One day I went live for 11 hours!!! By creating a plan I was able to coordinate my next goal: opening a storefront. The risky decision to commit to a home for our first storefront location in Louisburg, KS felt so rewarding. Although spending my summer so focused on growing the business may have prevented me from the experiences other kids my age are entertaining. I’m happy to say if I hadn’t chosen the risk of being an entrepreneur I wouldn’t be taking this next big step. Read more>>
Stephanie Dillon
Taking risks as a painter is essential for creative growth and artistic evolution. By stepping outside of familiar techniques or subjects, artists can push the boundaries of their craft, discover new forms of expression, and cultivate a unique voice. Risk-taking allows painters to embrace vulnerability, experiment with bold ideas, and confront failure as a necessary part of the creative process. It often leads to unexpected breakthroughs, unlocking potential that might otherwise remain hidden in the comfort of routine. Ultimately, taking risks enriches the artistic journey and can lead to deeper, more authentic works that resonate powerfully with audiences. I hardly ever paint the same way twice. For me it’s more authentic to have no style of painting and just embrace how I want to create in the moment! I believe this has worked out well for me in that I’m hired to do a variety of artistic styles since I’m not known for just one! Read more>>
Mcclain Sampson
I consider myself to be a risk taker in my personal and professional life. I’ve tried to live my life and build a career by staying connected to my own self-awareness and self-growth. I took a risk when Ieft my job, a place to live and the safety and security of “doing what is expected” of a 25 year old to backpack around the world for a year. I took a risk when I decided to end a marriage that wasn’t providing the supportive partnership or the model of love I wanted to emulate for my small children. And, I’m currently taking a risk by starting a new career as a coach at the tender age of 53. All of these decisions required me to honor what my inner voice is telling me and to have the audacity to believe that I can make my dreams come true. I think that sometimes it can feel like the biggest risk is just betting on yourself! Read more>>
Alina Starunskaya
I am adopted from Russia, into an American household, more specifically Washington state (PNW). Where I grew up very christian. I was heavily involved in the church world and youth group world, bible studies, everything! In this I also was apart of “mission trips”. After dropping out of college at PSU after only four days…I went and took a major risk to be one of the very few (especially at the time in 2015) to bail on school and choose to live instead. I was so scared at the time ofcourse and everyone around me was under the impression anyone who doesn’t go to college/ higher education will for sure end up homeless or on drugs etc! Read more>>