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.
Jacob Tegtman
Starting any business is inherently risky, at least when compared to the “stability” of a 9-5 job. I use the word “stability” in quotations there because there’s also inherent risk involved with trusting your future to someone else – your boss, your company, stockholders, board of directors, franchise, etc. Of course, we live in a world where trust is essential, so there’s nothing wrong with teaming up with people you love and respect to build a future suitable for all. However, when you reframe starting a business into the idea of “trusting yourself” with your future, it suddenly seems less risky. The fact is that each person, no matter how good they are instinctively puts themselves and their families first. So, it was risky to start a business. But it felt, at least to me, riskier not to get started. I knew that if I ever wanted to make the kind of money I wanted to make, and more importantly, to have the kind of freedom with time that I wanted, there wasn’t any other option available. I knew that I could trust myself to build the future that I wanted for myself. What I lost in stability, especially the first few years of owning a business, I made up for in opportunity. Read more>>
Luis Martinez
I was always passionate about studying and addressing aging as a key process in most (if not all) chronic degenerative diseases. However, nobody was taking about this when I was in medical school. When I graduated med school, it was expected that everyone would go into one of the traditional specialties. More so, having a physician father (a gastroenterologist), I was expected to follow in his footsteps. I decided to take a risk by focusing on aging and regeneration as my areas of practice, shying away from the traditional insurance based model (which is very difficult for a recent grad) and focusing on patient wellness. Back then, people said I was crazy for going this route. But now a days, I have many physicians reaching out to me for advice on how to transition. Read more>>
Paty And Samantha
Taking the leap to start Mingle Masters TX at the beginning of the year was a major decision for us. We both have demanding full-time jobs and are raising our children as single moms, so the idea of adding a business to the mix seemed crazy at first! But we had this shared vision of creating something that would not only serve others but also give us the flexibility to grow personally and professionally. We wanted to show our kids that it’s possible to go after your dreams, no matter how busy or uncertain life may feel. We started with a passion for hosting and making events special, and from there, Mingle Masters TX was born. The journey hasn’t been easy—there have been plenty of late nights, early mornings, and moments of self-doubt—but the rewards have been incredible. Seeing the smiles on our clients’ faces, knowing that we helped make their events unforgettable, makes every challenge worth it. We’ve really leaned into our partnership; we balance each other out perfectly and have built something we’re both incredibly proud of. Read more>>
Michelle Campbell
In 2017, I made a very risky move from LA to New Mexico. A little backstory… I’m from Orlando, FL. And in my early 20s, despite my family’s worry and concern, I made the big leap to LA to pursue a career as an actress– so that would be the first big life risk! While my friends were starting corporate jobs and getting married, I was auditioning for TV, Film and Commercials, and spending most nights waiting tables at West Hollywood hotspots. Now, being on the other side of that risk nearly 20 years later, I can tell you, it was all worth it… and continues to be. Back in 2016, I found myself working a Golden Globes party at a new LA hot spot restaurant that I’d just starting working at as a server. That night, I happened to see Taylor Sheridan, who was in fact one of my first acting coaches and mentors. I say mentor, because he always believed in me and had labored in trying to get me representation (an agent or a manager) when no one would take me on. In many ways, he saw me and supported me when no one else would. Anyways, we see each other, and I hadn’t seen him in years — he’d gone on to become a successful screenwriter and was promoting “Hell or High Water.” And he told me that night that I needed to move to New Mexico. Read more>>
Angela Romero
In 2014, I had a wake-up call that changed everything. I was working my “hobby job” at a horse ranch—a place that drained my spirit and undervalued my potential. My boss constantly doubted me, and while I didn’t realize it at the time, she was teaching me exactly what kind of leader I never wanted to be. One Saturday, as I toiled away, realizing I was missing my son’s football game. It hit me hard: What am I doing here? Read more>>
Monica Nagy
The biggest risk I’ve ever taken was deciding to share my story as a survivor of familial trafficking. Growing up, I was trafficked right here in Southwest Florida by the very people who were supposed to protect me—my own family. For years, I carried the weight of that trauma in silence, too afraid to speak out. My traffickers still live in this community, and the fear of retaliation, judgment, and disbelief kept me quiet for so long. But there came a moment when the silence became unbearable. I had escaped the life I was forced into and was slowly rebuilding my life, even finding success in working with celebrities. Yet, I couldn’t shake the feeling that I was called to do more. I knew there were others—women just like me—who were still trapped, feeling invisible and voiceless. I wanted to be the person I needed when I was stuck in that dark place. Read more>>
Her Excellency United Nations Peace Ambassador Ngo Ecosoc Dr. Angela J. Nealy, B.s., M.s., Ph.d.
I first met former NASA Astronaut Dr. Mae C. Jemison, M.D.in March 1994 at the Madam C.J. Walker Building in Indianapolis, Indiana when our lecture series, StewardSpeakers.com invited Dr. Jemison, M.D. to speak. I was chairwoman of the Logistics Committee, which gave me access to every speaker from 1986 until 2010. On this particular occasion I was asked to stay with Dr. Jemison, M.D. in the lobby of the Madame C.J. Walker where a table had been set up so all of the middle school and high school students could meet and receive an autograph from Dr. Jemison. I knelt down next to Dr. Jemison waiting on the students to each present their books to be autographed. Dr. Jemison asked me what I did. I responded that I was over Logistics’ for the series and an Educator by trade. Dr. Jemison asked what I taught? I responded, chemistry! She then asked and answered, “Would you work for me?” before I could say yes, she said “of course you will and when I return to my office in two weeks, I will send the application. You can write three essays no problem? Yes of course you can write three essays.!” The rest is the herstory these last 30 years. Read more>>
Lester Rowe
When I was a commercial producer I was feeling unfulfilled in the work i was doing. I knew it was good work but I felt like i was constantly fighting to show my skillset. A project would be assigned to me I would want to give it my best work and effort but the way things was structure there is financial value and qualitative value and sometimes those two things do not align. To remedy that I would be tasked with a shorter turn period. which means I would be giving less time to create a final product so that it would reduce the amount of time spent on creativity in comparison to the budget. What it did was was help me work faster. Instead of work quality being reduced I only became more efficient. The task was becoming more like an excercise in quality and effeceny. In this time I had an idea for a project. Before coming to the job I had made documentaries and narrative short film projects and had been hungry to make another. I wanted to do something to prove I can be trusted and that I knew what I was doing and that I can manage projects at scale. Read more>>
Americus Counts
The biggest risk I have taken so far with my modeling career is starting to model overall! I have always loved fashion and modeling since I was a little girl. I watched “America’s Next Top Model” & all the Victoria’s Secret fashion shows, just wishing that I could be a model like the women I see on TV and in magazines. So, after keeping modeling at the back of my mind while I was in school, I focused on being a photographer. Which I honestly believe helped me be a good model I know how stuff translates on camera. After I graduated in 2021, I focused full-time on modeling. I did that by working out, building my portfolio, and, most importantly I, networked myself. Read more>>
Alexia Perkins
One of the biggest risks I’ve ever taken was leaving the security of a corporate job to pursue my dream of becoming an educator. It was a decision that required faith, resilience, and a deep belief in my purpose, but it shaped the course of my life and career. At the time, I was working in a corporate role that provided financial stability—a necessity as an adult with bills and monetary responsibilities. However, deep down, I knew this wasn’t where I was meant to be. My true passion was teaching, and I couldn’t ignore the call any longer. After much reflection and prayer, I made the bold decision to quit my job and dedicate myself fully to earning both my bachelor’s and master’s degrees in education. Read more>>
Jaunessia Porter
I have taken many risks in my life, but a major one since starting my Spiritual journey is walking away from my last job. I know so many people are always preaching about making sure you “have enough saved up” before you leave. Well, I didn’t. I knew this was a huge faith walk and I was following my intuition to the Tee! I was pushed out of my comfort zone. I enjoyed my job as a Pediatric Triage RN, but I became bored. I was a fast learner and I typed pretty fast, but each day was like the day before. I felt stuck at my desk with mt headset glued to my ears. There was no growth. Read more>>
Ximena Jimenez
Growing up between sports and music, I learned that taking risks is essential for growth and improvement in any area of life. Looking back, I can see that the defining moments of my professional career have been shaped by embracing those risks. I stumbled into lettering almost by accident. At the time, my life revolved around Ultimate Frisbee, but after a knee injury and two surgeries, I was forced to step away. This meant leaving behind my social circle, completely changing my routine, and searching for something new to hold onto. Read more>>
Yesenia Bocanegra
In 2011, I left Puerto Rico for San Francisco to complete my MFA in Photography. The plan was simple: finish the degree and figure out the rest later. At the time, my mindset was, “Let’s see what happens.” A year and a half later, what started as a short holiday visit to North Carolina unexpectedly became a permanent move. While visiting, I decided to see if I could secure a job while there. While I did manage to find a job, it wasn’t what I had hoped for. Still, I stayed, kept searching, and eventually landed a teaching position at a university and an internship with a renowned portrait photographer. That internship evolved into a paid role as an Associate Photographer and YouTube Video Producer. It was this experience that sparked the idea of starting my own business. Read more>>
Lauren Brown
I have taken risks throughout my life, from participating in a volunteer busing program in Chicago during the civil rights movement to starting my own business and law practice. The busing program involved attending a high school outside of my neighborhood. As a black female, I was a minority in a mostly white school miles from my comfort zone. We faced hostility from the neighborhood, and our parents demanded police protection from gangs. Despite being escorted from classrooms at gunpoint and assaulted, I persevered and graduated with honors! Read more>>
Wendy Lee Paquette
In 2001, I was forced to give up my career as an administrator of a university graduate studies program, due to a work related injury, and opted for creating my own business using the right side of my brain (the artsy side 😉) as an author and artist. At the time, my husband had a very well-paying job and it afforded me the opportunity to finally venture out to do what I’m most passionate about. It also allowed me the flexibility to care for our children, home, and my in-laws. In 2004, I opened a studio in our small town offering my services as a muralist, art/furniture restorer and kid’s party animator of arts and craft themed parties. I also had a contract as a Volunteer Coordinator in a large hospital where I founded 2 volunteer programs (training volunteers to do art and music with patients). I’m proud to say these volunteer programs continue to this day. It was during this time I wrote my first children’s book, entitled: A Parade to Remember, and began the long process of getting it published. I was in right-side of the brain heaven. Read more>>
Amarnath Muchandi
I was born and raised in India, in a middle-class, spiritual family where stability and steady income were seen as the ultimate goals. Education was highly valued, but opportunities were limited. In fact, I was the first in my family generation to pursue a degree in Mechanical Engineering—a huge milestone, given that no one before me had even completed high school, except for my sister. Like many young graduates, I assumed that earning a degree would lead to a fulfilling life. I landed a job in the mechanical field, and within just 11 months, I was promoted to manage a team of 13 people. By traditional measures, I was doing well, but deep down, I knew something was missing. Despite my accomplishments, I felt disconnected from the work I was doing. It was as though I was living someone else’s dream, not mine. Read more>>
Lindsay Dyan
Leaving the safety of a corporate job to build something from the ground up was terrifying but I knew I couldn’t ignore the fire inside me any longer. I started Cosmic Outlaw as a creative experiment, but it quickly became my dream: a bold, unapologetic brand for rebels, trailblazers, and creative souls like me. I poured my heart into every design, every detail, and every late night spent working to bring my vision to life. Taking the leap wasn’t easy—starting your own business never is—but trusting myself, even in the face of uncertainty, has been the most rewarding risk I’ve ever taken. Cosmic Outlaw isn’t just a brand; it’s proof that betting on yourself can lead to something extraordinary. :) Read more>>
Justin Lopez
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Zara Ducrôs
The biggest risk I’ve ever taken would certainly be packing up my life and moving to the other side of the world to pursue acting. When I made the call, I was a 19-year-old girl fresh out of high school in New Zealand. It was a daunting prospect in theory; the thought of leaving everything and everyone I knew to try and make things work completely on my own, and having to do so in an entirely different hemisphere. It was life-changing in every sense of the word. For me, it was something I knew I had to do – the only thing that I could really see myself doing for the long haul was performing. I have been acting and singing since I was four, and no other area of my life quite gave me the feeling, or outlet, that performing does. Truth be told, the thought of being chained to a desk in the corporate world for the majority of my life was more frightening than the chance of my dream not working out. Read more>>
Rachel Altvater
Risk-taking has been an intrinsic part of my career and life — a journey defined by continuous growth, creative challenges, and a drive to push the boundaries of what is possible in the mental health field. Every major decision I’ve made has carried a level of uncertainty, but each has shaped my path toward advancing the field of play therapy and fostering mental well-being. One of the most defining risks of my career was my decision, nearly a decade ago, to explore and advocate for the integration of digital tools into play therapy. Several years before the COVID-19 pandemic underscored the necessity of virtual services and digital interventions, I was already engaging in conversations and exploring methodologies to incorporate technology in developmentally appropriate ways for children. This wasn’t an easy path, as it was met with skepticism from many traditionalists in the field. Nevertheless, I persisted, believing that bridging traditional therapeutic approaches with the evolving technological landscape would become critical for accessibility and innovation. Read more>>
Shelly O’donin
You know, I thought about this question for a long, long time and I think that my biggest risk was starting my business. Puppy Belly Deli was always in the back of my mind. I was passionate about home cooking for all dog babies since I adopted my first chihuahua pup in 1997. I had just completed graduate school with a Masters degree in Music and moved to New York City. After a period of burn out, I decided to enroll at The French Culinary Institute in Soho because I needed to work with my hands and have something concrete to show for my efforts at the end of the day. I always loved cooking. Some of my favorite memories from my young adulthood was my afterschool job at Longacres Horse Race Track in Washington State. I managed concession stands and my favorite assignments involved the hamburger shack, the sandwich shop and the huge open steak grill pit during the summer. I loved making people happy with food. Some stints in the NYC restaurant scene made me understand that I should be my own executive chef and find a way to cook for the most important people in my life. After moving to Arizona in 2011, I decided that it was time to share my passion for home-cooked dog meals and treats with the dog parents in my community. My husband is an accomplished finance executive but he stepped back and let me find my own path and make my own mistakes. Tons of uncertainty and too much anxiety for my liking… but everything worked out. I’ve been profitable for all twelve years and I have loved being highly productive and creative. And with all of the product development and taste testing required, my dogs love me more than you can imagine. Read more>>
Baby Reckless
Risk-taking and showing up authentically have been so important to my journey, artistic vision, and business. I’ve lived many a life in my few years on this earth but breaking out of the restrictive cages, projections, and ideologies others have placed on me whether it be religious, academic, or social – each time I have chosen myself and stayed true to myself it has always been the best decision. The one that seems to have the biggest impact on me has been leaving a cultic, evangelical religious background, finding myself and now my relationship to religion in general has such a huge impact on my creative work and the work that I do with others. One of my main pillars is choosing freedom and helping or inspiring others to do the same is so important to me. freeing yourself from the chains and cages others have put you in is one of the bravest and most important things one can do. We only get to do this life, in our current incarnations once, why let someone else drive the experience for you, especially if it causes you more harm than good? Read more>>
Rhonda Coleman
I transitioned from being a teacher to law school. I quit my teaching job, and moved from Memphis (where all of my family was) to Chicago, IL (where I had very little family) with 2 young kids in tow. I knew that where I was in my professional life was not enough, I wanted more. I gambled on law school. This blog post that I wrote captures why I made the move and how it turned out for me: By Rhonda Coleman Wandel Read about how Rhonda transitioned into a legal career with young children after teaching for ten years. Tip #1: Trust yourself, plan for what you can, be prepared to swerve, and have faith that things will come together in the end. Read more>>
Rhonda Faison
The biggest risk I ever took was stepping away from my lifelong dream of becoming a doctor to explore different paths and discover what truly inspired me. Ever since I was a little girl, I’ve felt a deep calling to heal. One of my earliest memories is of my older brothers taking me to the park—I couldn’t leave home without my makeshift first-aid kit, packed with bandages and alcohol wipes my aunt, a registered nurse, would bring me from the hospital. I always wanted to be prepared in case someone needed help. Read more>>
Lilith Von Tal
Can I tell you about my favorite poem? It’s “Strawberry” by Paisley Rekdal and it’s about failure and kinetic potential. It’s about bravely staring failure in the face until you find yourself perceiving and being perceived. It’s about how a strawberry plant always has the latent potential to bear fruit, but will not and cannot without a second strawberry plant. I take a lot of risks. I got strawberries tattooed on myself at a time when I really could not afford to do so. I’m chock full of kitschy little phrases that embrace the unknown and encourage taking risks. I love to tell people, my students and audiences especially, to do big, scary things. I say to them the only standing between themselves now and who they want to be is a singular word: yes. I also say to them that in order for that yes to have gravitas, they have to say no (to the things that contradict their yes). Read more>>
Doug Hammer
I see the value in taking risks and even failing. Failing is a good thing. It’s all a learning process. One of the most uncomfortable things I’ve done was working on my Heart video. I am introverted and I went up to strangers and asked them to be part of my video. It came out beautifully but was very difficult for me. It was a wonderful way of connecting with all kinds of people, even the homeless. I also created a video for my song, Sway. I am a very self-conscious dancer and I danced and strutted backwards in public all over Boston to make that video. It came out brilliantly and I only bumped into one person. So I see the value in doing uncomfortable and difficult things. Read more>>
I’geal (che’rie) Turner
Starting Mommy Scrubs was a significant risk for me—both personally and financially. The decision to launch this business stemmed from a deep desire to serve others, particularly the healthcare professionals I’ve seen struggle with the same challenges I faced as a working mother. The need for accessible, pump-friendly scrubs was clear, and I knew it was a gap in the market that had to be addressed. Bootstrapping my business has been a major financial risk, especially during times of economic uncertainty and rising costs. However, I believe in the vision and the mission behind Mommy Scrubs, and I know that taking calculated risks is often part of the journey toward fulfilling a greater purpose. My husband has been an incredible source of support throughout this process. His belief in my dreams, and unwavering encouragement as we navigate the challenges of bootstrapping, has been invaluable. I am forever grateful for his partnership. Additionally, my family are my biggest cheerleaders and I am very thankful for them. Read more>>
Ak Dozanti
In 2015 I went from being Officer of the Year as a Deputy Sheriff to a very crispy burnout and took the leap to leave fulltime law enforcement. Having entered into law enforcement at just 19 years old working undercover internet investigations, I didn’t know that I entered into the field with a lot of unresolved trauma. I was experiencing burnout, severe depression, post traumatic stress disorder, adrenal fatigue and suicidal ideation. Despite not know how to do any other job, I left the “sure thing” job and prioritized my own mental health. I then became a criminal court victim advocate and while working fulltime I went back to school and got my master’s Magna Cum Laude in Criminology with a concentration in Victimology. This is where I discovered a deeper understanding of trauma. I also attended a 10 month yoga teacher training to become a registered yoga instructor and dove into multiple modalities of healing like meditation and even reiki. I studied the neurobiology and physiology of stress and trauma and how that affects our first responders. I gained many certifications on additional modalities of healing. Read more>>
Capassio Cherry
For me, my whole life has been about taking risks. Each time I took one, I either came out stronger or succeeded in ways I never imagined. People often think that taking risks gets easier as time goes on, especially after you’ve had some accomplishments under your belt. But in reality, it’s all about building the confidence to take those risks and truly believing in yourself. Before I started making clothes and getting into design and fashion, I played football. I was 9 years old when I first began, and football became a huge part of my life. But after high school, I faced what felt like the biggest and most humbling risk of my life: I moved to California to live with my Aunt. My goal? To attend junior college and create an opportunity for myself to play football at a big university. Read more>>