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.

Joanna Armijo

Before I was a tattoo artist, I was jumping around from job to job just trying to find something that made me happy. I was a vet tech, a hostess, a call center agent, and lastly worked in marketing. The idea of tattooing was such a random thought in my mind and I was honestly scared to pursue it. I dropped a pretty penny on a beginner’s tiny tattoo class and it all escalated from there. About five or six months into tattooing, I was able to quit my marketing job and have a financially stable career in tattooing. Read more>>

Jo-anne Suriel

I don’t think anyone comes to work in a healing vocation without taking a hefty amount of risk. Previously, I’d been working in finance for over a dozen years, had earned an Ivy league MBA, and was a business analyst at a top private equity firm in New York City. From the outside looking in, it was a highly successful, dream career. But on the inside, for most of my waking hours, I felt really uninspired and spiritually empty. Read more>>

Just Me Podcast, Llc

The biggest risk that the three professionals of Just Me Podcast, LLC have taken is moving our passion, experience and talent from the ‘Idea Phase’ to a ‘Startup Business’. A business can take approximately 2-7 years before it becomes profitable. However, the reality of this timeframe does not truly become impactful until you’ve moved your business from an ‘Idea’ to a Startup, and you add another role to your list of responsibilities. Read more>>

Karen Pride

I come from a very small town in Southwest Michigan where the course of life is clearly laid out for little girls. We are told to be good, look cute, be nice, find a decent man to marry, have some babies, be a good wife, a good cook, a good mother. Normal, consistent, achingly good, and god loving are really all that is required to be awarded with a seal of approval by the townspeople and the church. Read more>>

Kelsey Pierson

It was always on my bucket list to live in another country. Nearing graduation from college, I didn’t have any job prospects until a friend of a friend mentioned they had family in France who needed a nanny for the coming fall & I said hell yes! I got in touch with the family, we got all the details & visas sorted out and I was officially moving to France in the fall. While I was there I was in charge of cooking, cleaning, teaching the 5 children (all under 10) English, laundry and basic household duties. Read more>>

Kristie Hill

Life often pushes us into situations where we must choose between remaining in our comfort zones or taking risks that could change everything. My journey has been defined by moments where I faced this choice head-on, and each time, I chose to leap into the unknown, not knowing what awaited me. These risks have shaped who I am today. Read more>>

Laura Frantz

I realized at the age of 7 that reading held a special magic and that writing was even more transforming. To put words on paper and create another world entirely through one’s imagination was truly mind-boggling even as a child. I wasn’t good at sports or music or much of anything but something resonated with writing. I am risk averse and always have been. Wariness and careful consideration are my watchwords. But after writing for myself for almost 40 years, my brother dared me to do something with my writing & share them with others. I set out to prove him wrong. Read more>>

Lauren Ora

The biggest risk I have taken is pursuing a career in esthetics. Before deciding to enroll in an esthetics program, I was working an office job that I had been at for over 5 years. I completed my Bachelors in Psychology two years prior and was taking courses in Chinese medicine in my free time. My plan was to either continue my studies in Psychology, become an Acupuncturist, or go to medical school. I thought I needed to pursue a more “traditional & steady” career, but I was wrong. Read more>>

Leonard Bryan

One of the biggest risks was betting on myself, it seems like an easy thing to do but it isn’t. I decided to write a short film that was based on modern relationships. The caveat was, it’s a silent film. Due to the nature of social media, I relied on Dm’s, text messages and music to articulate the conversations in the movie. A silent film in this day in age was risky but paid off handsomely, especially with the younger audience. It was the first-time people really saw how the loss of love is transcribed today. Read more>>

Lin Tam

The making of the short film “Friendship” during the height of the COVID-19 pandemic was a journey fraught with risks and uncertainties. This period was defined by worldwide lockdowns, remote work challenges, and a general sense of unpredictability in both personal and professional spheres. Before the pandemic, the concept for “Friendship” had already been developed, and the excitement around its potential was palpable among the team.  Read more>>

Lorena Villegas

I have to admit that I am a bit of a leap taker. It hasn’t always worked out for the best but I like to reflect on the lessons learned and experiences had. In 2014, I took a leap to move across the country to California from my hometown of New York City. At the time, my partner and I were divorced and we were raising a 5 year old. He was finishing graduate school in Boston and I was dealing with a four hour daily commute from Upstate New York to Hoboken, New Jersey. Read more>>

Marianne Connolly

I grew up in the sixties and came of age in the seventies. My late teens and early twenties where a time of risk taking. I skydived, moved alone to a new city, hitchhiked, got mystical, stowed away on a ferry, tried every new food offered to me, and had my heart broken again and again. In the eighties I lived in Boston, wrote poetry and—here’s another risk—read my poetry in front of audiences, later calling it performance art. Read more>>

Matt Robb

I’m a content creator from the UK, and for the longest time, I felt like the most successful people were in North America. There seemed to be more opportunities in Canada and the US, not just to make money, but to live a better lifestyle. One day, I decided to take a leap of faith—I applied for residency in Canada, packed my bags, and made the move. I had never been to Canada before, knew no one, and had no idea where I would live or how things would turn out. But I was ready for personal development and new opportunities, despite the fear that came with such a big change. Read more>>

Melissa Jackson

Entrepreneurship can feel incredibly daunting because it inherently involves risk. But that risk can be managed through intention and focus. When I opened my brick-and-mortar business, I took a major leap. While I’m not exactly where I envisioned I’d be when I first started, I’ve come to understand that this journey is about growth and adaptation. Read more>>

Meredith Villaseñor

Graduating from art school felt like getting kicked out of your parent’s house. There were lessons I learned and tips on how to make it in the world, but the security and comfort of doing what I love vanished. Suddenly, it was very scary to be an artist. The market for artists was changing, and much of what I had learned couldn’t be applied to any real job. I was at a loss. Read more>>

Michael Caradonna

I have over 30 years of experience in the entertainment industry and, starting out in front of the camera many moons ago, that was, and still is, the biggest risk of my life… I won’t bore you with the details leading up to getting my first acting job, but after growing up in Oklahoma, I passed on a career in the US Air Force and as a nurse, getting my first acting role in a film titled Foreign Student in Virginia, of all places.  Read more>>

Napolean Mcnair

Taking a risk can be scary because you have no idea whats out there, I get it! But, how do you know if you can be great at something if you never try?!When it come to starting a business, many people have great ideas. Lingering in their minds for weeks, months, and years. You ask them why they havent moved forward with those thoughts and you’ll hear. Many are afraid to take that leap of faith because its to much of a risk. Before starting my business, I was one of those many people. Read more>>

Nicole Lofton

So, I’ve always been a bit of a risk taker and this day in 2016 was no different. I had been thinking about moving on from my full-time job for a long time but being single I knew that I needed to prepare, as best as I could, for my future as a possible entrepreneur. In 2016, I began to rent out my home so I could learn the process of how to make extra income and I began to think about adding a room addition for a roommate in the future, but I decided to build a tiny house instead. Read more>>

Nina Hersher

****THE HOW I GOT INTO THIS FIELD QUESTION SHOULD BE LOOKED AT TO FURTHER SET THE STAGE FOR THIS RESPONSE**** I was halfway through my counseling degree, doing a clinical practicum at the student health center which focused on the impact of self-care and digital habits on undergraduate achievement. It became clear to me that our tech-driven world was creating unperfected distractions and mental health challenges which were only increasing. Despite the lack of guidance and established career paths in this niche, I took the bold step to individualize my counseling degree in digital culture and program development. Read more>>

Qualiéma (kwa•lee•ma) Green

Taking a significant risk by choosing to heal rather than hide marked a pivotal moment in my life—a profound pause where my purpose and passion began to blossom through the roots of self-love and healing. In 2020, amidst the chaos of the COVID-19 pandemic, I faced a life-altering diagnosis: Lichen Planopilaris (LLP), a rare autoimmune condition mirroring lupus, causing chronic pain and hair loss. This diagnosis wasn’t just a medical event; it was a profound awakening. Read more>>

Rachel Hutcheson

I have found that sometimes, not knowing what you’re doing helps you be brave enough to go for it.  In 2017, I was loving my life writing songs in Nashville, TN, and had for six years. Sometimes there was a bit of success and other times no success though it was always fun.  At the same time, I was writing short and funny pieces about life, love, and being human which I’d been doing for many years. Read more>>

Rachel Parrish

I’ve taken several risks in my career, it’s one of the things my friends and family know me for. I’ve taken a paycut and moved to NYC to pursue my dream of working for the NBA and WNBA. But my biggest risk to date is the one I’m currently taking – stepping away from my full-time corporate position to pursue my business, Rae Christine Agency, full-time. I’ve had my marketing and communication agency in a smaller capacity for three years, taking on clients sporadically as opportunities would present. Read more>>

Riccy Deleon

OOF!! Ok, I wasn’t the best student when I was in school. I was taught from a young age the normality of working to survive and when I graduated high school as badly as I wanted to pursue a college degree, I just couldn’t see myself affording it nor being able to work and have the mental capacity to study. On top of that stress, my heart was in my artistic direction and with no time or energy to point at it I just couldn’t figure out where I was supposed to head. I dropped out of college to work restoration (blue collar) full time and try to figure out my music career on the side. Read more>>

Ron Jackson

Making a living as a musician, especially as a 7-string jazz guitarist, can be challenging. At one point in my career, I found myself taking jobs primarily for the money, rather than for their artistic value. However, since the pandemic, I made the decision to focus solely on building and promoting the Ron Jackson brand. While I realize it took me a while to reach this point, I believe now is the right time to fully commit. Taking a risk can be daunting, but I’ve learned that when you pursue your true passion, the rewards come in many forms. Read more>>

Ross Geraci

Originally moving out from the East Coast Boston, Massachusetts where I had spent my entire life, to San Diego in 2017. However this greatly helped my Film company, and channel projects. Shortly after starting my true crime series on the Zodiac Killer, typically known for a crime spree, and letter writing campaign in the SF Bay area of the late 1960s. We quickly learned there were several much similar MO attacks in southern California in the early 1960s. Read more>>

Russell Sun Eagle

Taking a risk is huge. Especially if its for yourself. The most recent risk I took was back in 2020. This is when Covid took over and I was working a job that I started to hate. When Covid hit it made our job shut down for three months. And during that three months, everyone was on lockdown. No places to go nothing to really do. So during this time I start thinking about what I would like to do with my life rather than just working a 9 to 5. Read more>>

Sandra Rocha

Moving to NYC from Mexico City to study acting meant a big risk in my life. It was August 2021, the COVID pandemic was just getting under control and all I had was this inner calling telling me to persue acting once again, telling me that it was time. And that calling was strong enough that I put over 2000 miles between myself and everything that meant home to me. I had no idea if I was going to like NYC, I had never wanted to move there; I didn’t know if I was any good at acting, I had only ever wanted to do it. Read more>>

Taylor Widmann

My career started in reality television, as I worked my way up the food chain to lead development editor, in charge of creating sizzles and pilots for a large production company. After 6 years there, I realized that I had hit a ceiling in terms of earning potential and acquiring new skills. Even though it was a secure, high paying job, I left to start my own business in the middle of winter, with a 4 month old baby, and bought a house I wasn’t quite sure I could afford. Read more>>

Torean Thomas

My whole life has been risks! Not going to college, moving away from my family, and traveling around the country were all big risks. I had no real plans or focus was just drifting. I eventually decided after some scam experiences with “agents” in NYC to move west. The closest I could get was to Las Vegas with the end goal someday being LA. I got stuck in a beautiful life full of amazing friends, amazing experiences and cherished memories. Read more>>

Victoria Valdez

As a young child, I was naturally inquisitive. I wanted to know how things worked, what made it tick, how it made that sound, and it was worth taking things apart to find out. I wanted to know what it felt like to stand on the roof of my home at the age of 7, even though my parents said it was dangerous. I wanted to know what it felt like to drive my neighbor’s four-wheeler down the backyard hill at top speed; the river at the end of the hill would catch me. Read more>>