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.

Joseph Ceja

It’s all in or nothing for me! In my life I’ve risked it all, put everything on the line for my craft. It’s been a rollercoaster for sure! But I wouldnt trade being a musician for anything! Music is my life and pursuing my dreams no matter the cost is key to my success. Read more>>

Andrea Guadalupi

One of my biggest challenge in life has been moving overseas! i come from Brindisi in Puglia, South Italy, and it was in 2014 that i felt that i needed a change in my life as i was feeling stuck and demotivated. I wanted to try something new and an experience overseas was something that i thoght it could give me a new life and something new to work on, especially working on myself. So i ended up booking a one way flight for Melbourne, Australia. i had some pockets money and my english was close to zero, so basically it was a new start, new city, new people and new job opportunities! Read more>>

Josh Moreland

In 2014, I moved to Los Angeles with $34 Dollars in my pocket. All I can say is, where there is a will there is a way. My faith was up for the biggest challenge I had ever faced. By the time I got off the plane, I had $12 Dollars to my name, because of those expensive airplane snacks. Thank God for my good friend Marc Solomon (good friend of 10 years + who was a fellow musician and floridan as well) who picked me up and let me stay with him for 2 weeks. I just knew I needed to be in LA, my life and career depended on it. Taking this risk wasn’t easy, because I knew I was on my own and had to truly depend on God to provide. Read more>>

Z Griss

What do I know about taking a risk? I know that most people don’t expect to meet someone like me. I’m a spiritual love coach, a kink educator for social liberation, a visionary filmmaker, a dancer, a grief ritualist. I live a deeply embodied life, caring for my body as I know it to be where my soul listens from. Being who I really am should not have to feel like “taking a risk.” However, in the U.S. in 2023, most of us are socialized away from our true nature and our true magic. I’m gender transcendent, my pronouns are they/them, and I’ve been polyamorous for 23 years. I know what it’s like to be something I didn’t know was possible as a kid. I know what it’s like to outgrow my relationships and identity and have the courage to expand them to accurately reflect what is true now. Read more>>

Evan Gallagher

Taking risks in the creative process is an integral part of evolving as a photographer. It’s not always about those monumental, life-changing leaps, but often the smaller daily risks that shape our artistic journey. One of the most pivotal moments in my career began with a simple decision to edit and shoot a project differently, ultimately altering my entire approach to photography. Read more>>

Marianne Lettieri

Exiting my successful career as a communications consultant to become a full-time visual artist was a huge risk. Leaving a known world to pursue an uncertain destination, I felt a bit like Frodo at the beginning of his big adventure. Decades earlier I had earned a BFA degree at University of Florida, worked as a graphics designer, and eventually landed in the Silicon Valley of Northern California where I practiced public relations and marketing for some of the world’s most influential technology companies. I knew the infrastructure of that world, the language, and how to navigate its obstacles. Everyone was caught up in a mission to change the world — one computer at a time. By the end of the millennium, I came to the conclusion that for me, art was a more powerful change maker. I made the decision to jump ship. Read more>>

Joy Edwards

I have never considered myself a risk taker, but when I look back on my life, my story is based on the two most significant risks I have ever taken. 2014 I enrolled in a Cold Process Soap-making class and fell in love. At that time, I had been employed by the City of San Diego for over 12 years. My retirement and future were set, or so I thought. Read more>>

Anne Nichelson

At the time, I didn’t see it as a risk…I saw it as an adventure. I was 25 and decided to move from New York City to Peru to take a job and improve my Spanish skills. However, I was leaving friends, roommates, coworkers, my current job, family, my apartment, and the familiarity of everyday life. I didn’t know anyone there, and even though I had lived abroad before I had never been to Peru. But I wanted to pursue things that mattered to me, and living in another country was an ideal way to improve my language skills and better understand another culture. I like to seize opportunities, and that was definitely an opportunity! It’s always good to get out of one’s comfort zone, build resiliency. and learn more about yourself and others. Read more>>

Jessa Zarubica

After twenty years of working and making a full-time living as a writer, producer, director, and showrunner, I believe the most significant lesson I’ve learned is the importance of trusting yourself and embracing daily risks. To propel your career forward, you must be willing to face the possibility of rejection, moments of stumbling, big failures, and even total humiliation. I can’t think of any other way to achieve success than to persevere through the challenges that might try to hold you back. Read more>>

Marya Sherron

Launching my small business, KI Productions, in January of 2021 was the first ‘Big Risk’ — and one that I am so glad a took. I had absolutely nothing when I began … except for my stories and the belief in my storytelling ability. As a professor of creative writing (former), starting is always the hardest thing to do. Years ago, I relied on my resourcefulness and planning to make things happen, but launching my own business was too large to prepare for, so I didn’t. I just jumped in and filed for my LLC. Read more>>

Stacey Deville

I grew up knowing I wanted to be a crime scene investigator. My entire path was carved out. I was going to get my bachelors, my masters and eventually my PhD in forensic science. I had the path drawn and the dedication and drive to do it, but what I didn’t realize is that things change along the way. You may fall in love, have kids, lose a family member, or just change courses and that too is ok. Read more>>

Jamaal Lewis

I started my career and Arizona, and it was something I never planned on. I started booking local jobs out there and found a real love for the entertainment industry. before I knew it I was traveling back-and-forth between LA and Arizona for gigs. after only a couple of months, I decided to take a risk and pack up and move to Los Angeles. Read more>>

Kali Somerville

I started in the insurance industry in 2013. I was recently and suddenly a single mom of a 10 year old. I knew that getting a part time job wasn’t the answer. When I started, my goal was to make an extra $1000-$1500 a month working on my own time. I never expected to make a career out of this industry. Initially there was no risks. The worse case scenario would be that I would learn more about life insurance and how it works while still being able to work my full time. Read more>>

Daniela Acevedo

Growing up in Indiana for over 20 years called for a change in my life. Although my loved ones currently reside there, it was always a goal of mine to live elsewhere. Early 2021, I proposed to myself to work hard all year to be able to move by the following year. I am grateful for all of the opportunities in my hometown, but I felt stumped. I always knew there were many more experiences to come. I began to act as if the move was approaching by slowly packing my things and soaking in all time with my family. There were tears of joy and sadness, but overall an immense amount of support. In February of 2022, I gathered the last of my belongings in my compact car and I felt more ready than ever. Read more>>

April Eckwielen

I worked for a hospital for 13 years, teaching classes to expectant parents. I had always wanted to open my own metaphysical store and share my practice with others. While still working at the hospital full-time, I decided to start with an online shop. I had a very limited stock and offerings, but I made it work, making the front room of my house my workroom. Read more>>

Stephanie Ordaz

One of the biggest risks I’ve taken was moving out to Colorado in 2021. I grew up in Los Angeles and thought, enough was enough. I left behind my family and friends with no notice to pursue my own dreams. (Heights they can imagine but would never be able to understand)
For me personally it was becoming stagnant and flooded with other “dreamers”/“creatives” Read more>>

Devin Roscillo

I was at a pivotal point in my life….I had just asked my husband for a divorce, and I still lived in a place that really was never meant for me. It was a pivotal time in my life because I had just chosen myself over anyone else. I had just put myself first, and it was time to continue making that decision over and over. I knew I didn’t like where I was living, I had really just moved there two years ago for my marriage. But now that my marriage was ending, I had the opportunity to explore…”where did I truly want to be in the world?” Read more>>

George Peterson

Taking a leap of faith, whether leaving your job to go all in on your dream or something else, is scary. But there’s a reason it’s called a leap of faith, not a leap of certainty. In other words, you aren’t going to know how it’s all going to turn out beforehand. Instead, taking a leap of faith requires trusting that the only way the net appears is by leaping and that no matter what happens, it will all work out for the best. In real-time, when my wife, Plant-Based Chef Sydney Ione, and I quit our jobs to go all in on hosting Meditation and Breathwork retreats for a living, that decision seemed like the riskiest decision we could make. However, now that multiple years have passed since that decision, we can see that not taking the leap when we did would have been the more risky decision. If we had been faithful to the “fear” voice within us, today we would be nowhere close to where we are. Read more>>

SEKTOR 8

In a whirlwind of audacity and uncertainty, I embarked on a life-altering journey in the world of artistry. Imagine this: a spontaneous move to the heart of Los Angeles, armed with less than $500 and accompanied by newfound friends I’d known for mere months. Income? A distant mirage. A concrete survival plan? Nonexistent. Read more>>

Tempestt Harris

I took a risk by building platforms and opening up opportunities on the arts community in Charlotte NC. As a artist myself , helping other artist make it out here in their career is important to me . Many doubt the validity and value of the fashion & design industry here. Through my experience and what I’ve seen here; the talent here is worth the risk. I was born and raised here so giving back and not expecting a return feels like the right thing to do. Our teams have created opportunities for artist & Models to book NYFW shows and have television recognition for their great work. Lately Good Look Productions, Level21 Magazine and my film production team “By Tempestt” have taken a risk by filming a few fashion films to support the arts. We’ve now partnered with the North West school Of The Arts to make it all possible. Read more>>