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.

Emma May

My biggest risk was going full time with my own company. I have been making jewelry since high school and always had it as a side hustle. I sold my jewelry out of my college dorm room and loved making fun pieces for my friends to wear. When I graduated college I had a job at a jewelry store and one in tech I followed my gut and kept the one at the shop. Read More>>

Julia

Leaving my home country, Spain, to pursue my dreams (acting and seeing the world), was a big risk for me. It was definitely not an easy choice. I left my family, my friends, my baby (my beautiful orange cat Simba) and I moved first to London and then to New York, where I am living now since 2019. It was truly life changing for me. Read More>>

Johnnyy King

I think the biggest risk is allowing everyone to see you, yeah? Being your biggest self knowing some people will get it and feel it and some people will hate it. It takes a lot of trust and safety to be seen in your realest, most raw form. That’s scary. Read More>>

Yolanda Stoner

One of the biggest risks I’ve taken in my career was deciding to walk away from the stability of the business world and pursue a completely new path in mental health. After earning a degree in business and building a solid professional foundation, I reached a point where I realized my true passion lay elsewhere — in advocacy, education, and creating meaningful change. Read More>>

Tori Whitaker

In 2021, in the middle of a pandemic, I walked away from job security at an upscale gym to build something of my own. On paper, it was reckless. I was one of the top performers in a stable role, but the environment had shifted, and I felt stuck. What I really wanted was to create something that mattered—to support moms in ways I hadn’t seen done before. I just felt I was meant for more. Read More>>

Cory Scheider

Starting my band and then deciding to manage and lead it was a big risk looking back. I definitely didn’t know what I would be getting into at the time. It would lead me down a path of self growth and life changing experiences I may not have ever known otherwise. There was definitely one point in my life where I said I need to pursue this fully, without compromise, diving in head first. Read More>>

Brittany Capozzi

When I was in college, I majored in English, co-edited the campus literary magazine and completed an undergraduate thesis on Therapeutic Writing. I loved writing. Always have. And so, a year after graduating, I started a “Life List” of things I wanted to explore and write freelance articles about. They were mainly physical explorations such as horseback riding, ziplining, and rock climbing. Read More>>

Natalie Saunders

I took a huge risk creating Desert Wild. I moved from Sydney, Australia and quit my job and moved to the desert of California to be all hands on deck and design/build an entire home with the sole purpose of it making a great income. Just moving from the beaches of Australia to the desert of California was a risk let alone putting all this money into such a risky venture. I am so happy I took the risk because it’s the best thing I’ve ever created and I learned so much along the way including self confidence and anything is possible if you put your heart and soul into it. Read More>>

Jillian Barnes

I quit my full-time training job in December 2024 to officially launch my business, Body Is A Sport. We help women build strength, confidence, and long-term health through online training, habit coaching, and lifestyle support — from wherever you are in the world. For years, I had this gut feeling that I wanted to work for myself, but I let doubt creep in: How will I pay rent? Will anyone follow me? What if I fail? At the same time, many of my friends had already taken the leap into entrepreneurship and were thriving, which made me both inspired and restless. Read More>>

Alittlebitlexis (Lex)

Taking a risk? Well, everything about what I do is a risk. Maybe not a risk in the ways that a firefighter attends a call and runs headfirst into imminent danger, but a risk of a more convoluted nature. The nature of ego, personality, emotions- all the things that make us human. putting your own humanity on the line everyday is a risk. Read More>>

Bonnie Ramone

I am both a tattooer/shop owner and a full-time musician. Both the paths I’ve taken are some of the most self-motivated careers a person can choose, and there’s no net to fall back on if it fails. Everything is a risk. No benefits, no time off, no security net. I think true artists are sort of broken in a way, because in talking to friends and colleagues, not a one of us could make it in a “normal” job. This is the option, and it has to work… so you make it work. Read More>>

Demetri Thomas

Seven years ago, my mother, the late Elaine Hrones Thomas passed away at 89 after a heart valve procedure at Cedars Sinai medical center. Following that, My sister and I sold my Mother’s apartment building in West Hollywood and I was blessed with a lot of capital. Having a choice to purchase a condo in Palm Springs vs. a music career investment left me in a quandry. Read More>>

Gahlord Dewald

So much of living life as a creative involves taking a risk but I’ll narrow down to a big one and one that had a strong impact on some of my more recent work. Read More>>

Mellisa Valdivia

The biggest risk I’ve taken in my life relates directly to my current career path.
For the majority of my professional life—up until about two years ago—I dedicated myself entirely to building the success of other people’s businesses. I followed the rules, avoided risk, and worked tirelessly with the belief that hard work alone would eventually lead to success and fulfillment. Read More>>

Paola Gonzalez

Starting my small business, Lady Earth Candle Co., was a leap of faith. I knew from the beginning that pursuing this dream would come with risks just like any major life decision. But I was ready to take that chance because I’ve always been passionate about creating and inspired by the idea of being a businesswoman. What truly gave me the confidence to take that step was the unwavering support of my family and friends. They’ve been my foundation throughout this journey, and I know I couldn’t have done it without them. Read More>>

Dillon Williams

It was 2022, and I was sitting in Brooklyn Bridge Park, waiting to meet up with a friend. At the time, I was preparing for my sophomore year of college and enjoying my last days of summer vacation before starting school again. On that day, I took one of the biggest risks in my life by creating a photography page. At that point, I had learned how to operate a camera, but I wouldn’t have called myself a photographer by any stretch of the imagination. Read More>>

Diana London

I spent 16 years as a specialty plumber, eventually running the company—no college degree, just grit and determination. I loved helping people, but I never imagined I’d one day become an investment advisor. Truthfully, I didn’t think I was capable. My mentor told me, “There will be tests—we’ll help you pass them.” After that first exam, something shifted. I realized this was my path. Read More>>

Dannie Sinisi

A risk I took was rebuilding my life from scratch during one of the most challenging times in our country’s history. In the midst of COVID, I went through a divorce, became homeless with my child, and chose to take the bold step of earning my BA in Film and a Master’s in Art Administration while launching Dannie Boi LLC—a production house creating films, movie posters, America’s Epic Film Festival (Actress Danielle Harper is the Executive Director of the film festival) , and offering DJ and party planning services. Read More>>

Sara Pinson

I was always a quiet, shy and interoverted person living in the Midwest just doing the usual “go to school, get a job, eventually get married, etc…”. When I was 27 (2012) I started craving something different from the norm and had an opportunity to move to California and go back to school to start a new career as a medical laboratory technician. I had also met and married my husband there. We were having fun, bought a house, and he began his career as a motorcycle officer with the California Highway Patrol. In 2019 he was tragically killed in the line of duty. I moved to Texas a few months later to be close to family. Read More>>

Michael Glascott

Taking risks and making decisions are the normal procedures of being a visual artist. The SMALL risks are involved in selecting colors, fonts, and design choices that might need to be intriguing as well as informative. On one hand you might want to include and inspire your potential audience. On the other hand you might also want to rattle their cages, with surprising originality that results in a surprising response. It’s always a challenge to combine these two ideas within one project. Read More>>

Bryce Gaston

When I graduated from the University of California, Davis, I dove straight into the corporate world, planning large-scale events for major tech companies, because at the time, I believed being in the corporate world was the only way to be “successful.” But everything shifted when a wedding planner stumbled across my website on Instagram and invited me to coffee. She offered me an opportunity to be a lead wedding planner for her, and I was suddenly faced with a choice: keep chasing the security of a salaried corporate career or take the leap into an industry that had unexpectedly captured my heart. Read More>>

Alex Triantis

How I ended up getting started as a photographer was by taking a risk. One day my good friend called me asking if I wanted to quit my job and pursue photography as a career. At the time I was working for an exotic car dealership as a lot porter and had never used a camera before. I trusted my good friend to take care of me in my endeavors with him and it has rewarded me with 5+ years of owning my own business as a photographer/videographer. I have never looked back since. Read More>>

Anshul Katkar

The risk that I have taken was choosing a field that was discouraged in my community. Traditionally, in India, fields creative fields have a stigma associated with them. I was discouraged by my peers and teachers and was advised to pursue a field that was more conventionally accepted like engineering. However, I knew that 3D animation was what I wanted to do and chose to push through. At the time of making that decision, I was filled with self doubt. Looking back, that was a risky decision. Read More>>

Christine Traylor

One of the biggest risks I’ve ever taken was leaving behind my 15-year career in international development to pursue a longtime dream of running a bed and breakfast. Read More>>

Jennifer Kravassi

Betting on a sports team, or a career change when you’re working for someone else, always comes with the easy out. If things don’t end up the way you thought they should, if team X loses the game you put money on, or if you don’t like your boss or your job description… there’s someone or something else that can help you justify why you failed. Read More>>

Morgan Sullivan

As a transgender actor beginning my career in 2013, there weren’t many opportunities for me. Some trans roles were being written, but a lot of them felt reductive and didn’t reflect my own lived experience. I knew that if I was able to show casting directors the work I was capable of doing outside of these roles, then I might have a chance to work on roles that felt like a better fit. Read More>>

Cara Benson

After graduating college, I wasn’t sure what I wanted to do. I majored in Political Science, but law school seemed daunting, and a life behind a desk didn’t excite me. One day, my mom called after reading an article in the paper about a culinary institute and encouraged me to look into it. I had always loved cooking and baking, so I decided to apply. Read More>>

Dan Mulenda

One of the biggest leaps of faith I’ve taken in my life was placing myself into the U.S. real estate market at 23 with absolutely zero personal capital, no credit history, and no one I knew within a few thousand miles. Most of the people I spoke to said I should wait until I had more money or more experience, but I felt waiting was slowing down the vision inside me. Read More>>

Heather Saran

A meaningful risk I took was leaving the security of a traditional medical group to start my own independent endocrinology practice, Bright Endocrinology. At the time, it felt daunting to step away from an established system, but I believed patients deserved more than rushed, formulaic visits—I envisioned a practice that uses evidence-based medicine while going beyond traditional care to address root causes, empower lifestyle change, and truly partner with patients. Read More>>