You’re working hard, things are going well, piece by piece you’ve built a life you are proud of, you’ve overcome obstacles and challenges, beat the odds and then you find yourself at the center of an unexpected dilemma – do you risk it all to keep growing? What if growing means leaving the job you worked so hard to get or the industry you worked so hard to break into? How we approach risk often has a huge bearing on our journey and so we’ve asked some of the brightest folks we know to share stories of risks they’ve taken.

Simone Reyes

I started working for hip hop mogul Russell Simmons when I was a teenager. Back then there was no internet so pretty much getting anything done took forever. I worked round the clock as Russell Simmons, Rick Rubin and Lyor Cohen grew Rush Communications and Def Jam into the stuff of legend. I was there to watch The Beastie Boys , Public Enemy, LL Cool J and every major rap artist grow into superstars. Read more>>

Rob Grad

I was working on a questionnaire recently that had some prompts for me to answer about my life. I do this kind of stuff all the time. It informs my work as an artist. No matter how much I think I understand about myself or my work, I am always changing. Read more>>

Kelly Silbernagel

We opened River Yoga in 2020–right in the middle of the pandemic and pending shut-downs. We knew there would be a need for a healing space and a safe space to gather when people were ready to do so. At first, most of our classes were online due to restrictions, but once those lifted, people came to us with all sorts of desire (and some with fear) to be in community. We continue to build our community and dispel fears every day — there’s new faces at our studio every week and it’s amazing to share space and energy together! Read more>>

Tracy Bradshaw

Growing with TEA, LLC has been a journey of taking risks that we continue to embrace. The idea behind this adventure came to light when one of our daughters stumbled upon a Facebook memory of casts we made of our busts and auctioned off for charity several years ago. I promised said daughter that I would document the casting process, which eventually led me to create an experiential lesson plan that required careful scaffolding. Read more>>

Rhona McBain

In the face of adversity, sometimes the only way forward is to take a wild leap. After losing my husband to ALS, I made the decision to leave behind the comfort of my life in Pittsburg, Kansas, and embark on a new chapter in Kansas City, MO. Little did I know that this risk would test my resilience and lead me to unexpected successes. Read more>>

Julia Walck

So I actually haven’t talked about this yet, but back in June of 2023, I left the corporate design world to focus on myself and my art. It’s a move I had been contemplating for years, but there was always something holding me back. Whether it was comfort in a certain schedule, health insurance/a steady paycheck, or feeling like it might be a letdown to someone on my team for leaving, I just kept making excuses. Read more>>

Mode Zhao

A few years ago, while I was living in the vibrant city of Los Angeles, I found myself at a crossroads in my career. My work was satisfying, but it was my personal journey that was shaping my life in profound ways. You see, I’m not just a passionate advocate for mental health awareness; I’m also a mental health patient, someone who has personally grappled with mental illnesses. Read more>>

Ilana Turner

I’m in Paris and I rent a car to head west to the Normandy beach on a research quest. A friend of mine, the incredibly talented musician Adrien Reju, and I want to see her great-great grandmother’s country house. About two thirds of the way there, Adrien asks me if I have an address. And I realize I don’t! What I have is a postcard of the house from 1906 — and it has never occurred to me that the house might not be there, fully intact on the beach in Normandy, now very much post World War 2. Read more>>

Shannon Holbrook

Eight years ago our family was really miserable. We barely saw each other and like many people, we were working ourselves ragged and living above our means. My husband and I worked full-time jobs on different shifts and were trying to homeschool our youngest daughter for the first time. We realized something had to change. Read more>>

Jordan Young

Starting an art business has been the greatest risk I have ever taken, I have encountered different challenges and hurdles not faced before but it has given me the opportunity to pursue my love for creating art. Coming out of the pandemic I was looking for a new job, the last thing I wanted was a regular job where I wasn’t able to be creative. It was at this time when I decided to go all in and sell my art for a living. Read more>>

Brooke McKeever

Build and they will come…that’s what they say when you are a budding entrepreneur. What if the very industry you are in does not really even exist? Will it emerge one day in the near future or in a decade? That is the risk that I was willing to take. I knew that the technology I used to help me heal myself from traumatic injury could help others as well. Read more>>

McKenna Anderson

In 2020, I took one of the biggest risk in my life. I quit my secure job of 10 years at an outpatient, orthopedic and neurological clinic, I moved back in with my mother, and I started working for myself 100%. Read more>>

Korey Keels

I’d been working for a local small pest control company and the owner decided he was ready to sell the company. I had a wife and son to take care of. I’d saved up the money to buy the company, but to bet on myself not knowing if I would be successful or if I would fail was nerve wrecking. I hit the ground running. No turning back now. I focused on having excellent response time and customer service. Read more>>

Valentina Martelli

You have to ‘grab the bull by the horns.’ This is the idiom that stuck with me when I came to the US 20 years ago. More than ‘Fake it till you make it’ or ‘When life gives you lemons, make lemonade,’ this phrase resonated with me. They all relate to taking risks and navigating the journey that can lead to success or failure. Read more>>

Jessy Greene

I’ve taken a lot of risks in my life. Hitch hiking from western Massachuestts to Florida after graduating high school was one of the dumbest but felt worth it at the time as staying in my tiny home town was not an option. Turned out Fort Laurderdale didn’t have a good music scene so when I received a postcard of the sun shining on Santa Monica with a hand drawn arrow and the words “come live with me here!” written on it, I decided to jump at the opportunity. Read more>>

Mandysa Brock

I’m all about taking risks! I was always hesitant to take risks at first because I was afraid of other people’s judgments, or afraid to do something wrong. But I’m a rebel at heart, and I truly believe that doing things that work for you in your own style is the best way. I think when it comes to working in this career, you have to be comfortable taking risks. It’s a risk to even want to be a professional actor, model, singer, writer, performer, etc. You’re sacrificing a lot to pursue something thousands of people want at the same time. Read more>>

Priscilla Agyeman

Starting this business required me to take a risk. Deciding one day that I would be investing my time and money into something that wasn’t even tangible at the time took faith, trusting my intuition and going with my gut instinct. I was in a toxic work environment, living paycheck to paycheck, and I was trying to find myself again after I didn’t have any resources, guidance, tools or mentorship prior to starting this business. I allowed my curiosity to be the driving factor, along with my desire for building community and connection. Read more>>

Erman Baradi

You know how The Rock has his “seven bucks” story? I think I’m there now, at the brink of something that’s fingertips away, even if I can’t see how far I’m reaching. The last whole decade has been a risk to me, and I’ve adapted, pivoted, and changed. I remember getting dropped from my office job at my film school during my senior year. I stood at a crossroads: continue to go the office route, or go all in on my creative endeavors. I chose the latter. Read more>>

Kate Pitner

I have worked as a freelancer and contractor in the creative field for the past 25+ years. Taking risks, especially in a creative business, is to be expected, however nothing prepared me for the journey I’ve been on as I set out to create my greeting card company and its accompanying mobile app. Read more>>

Candice Waltrip

My mother is Japanese and my father is American, so I grew up living in two different cultures. I’m an eighties baby and was born on a military base in Fussa, Tokyo. When I was five years old, our family moved from the big city of Tokyo to Omaha, Nebraska where we lived for four years. I was so young that I don’t really remember a whole lot about my time in Nebraska. Just after four years, we moved back to Northern Japan on a military base called Misawa. Read more>>

Ann King

I grew up knowing I would never go to college. I was in a small New England town, in a large family, with parents who had not graduated from high school. I left home early for good reasons and put a roof over my head while I also finished high school. When my friends came home from their first semester of college for Christmas break, they said I belonged at college, that I just had to find a way to go. Read more>>

Ricardo Jattan

Taking risks begins with a certain wisdom, and the inner belief that everything will work out in the end, a positive mindset if you will. And you must also truly believe that everything will work out “for the better.” Risk requires one to be still, quiet, and to listen to the deepest part of your being, your heart. Read more>>

Tatie Kay

Being an influencer or model today is like going on an exciting but tough journey. It’s risky, but the rewards can be amazing. To make it, you have to work hard to connect with different brands and reach a wide audience. Building yourself up takes a lot of effort and dedication. Working with photographers can be tough because you have to show your best side and create interesting content. Read more>>

Nikki Musko

Several years ago, I found myself at a crossroads in my career. I was comfortably employed in a corporate job, performing well and enjoying a sense of security. Yet, there was an itch, a persistent desire to explore a completely different path – starting my own business. Read more>>

Tracy Richardson

Taking a risk.. Read more>>

Roman Lane

My first creative risk was becoming a music video director in 2016. Coming from Louisville, there was a lot of momentum around Louisville artists like Bryson Tiller, Jack Harlow, Vory and Kellz. I saw an opportunity to “level up” the visuals of many performing artists at the time and from that time period, I was able to earn two Emmys, an ADDY and a Promax Gold award. Read more>>

Javion Hall

I first started music at 18 and in the beginning I knew making music and being a creator was something I always wanted to do but I was always hesitant. I had felt like maybe people wouldn’t like my music or I just didn’t want to be like everyone else because the pursuit of music was a trend at the time. Eventually, I had decided to just start dropping my music and showcasing my talent, the first live showcase I had ever went to was my first time ever on stage but i went for it 100%. Read more>>

Dr. Scott Hastings

I have always been passionate about my desire to lower the cost of healthcare for people. As a young doctor just out of residency living the dream as a small-town do-it-all country doctor in Show Low, Arizona, People talk about “helping people afford their healthcare”, but those words seemed so hollow to me. I was young, the my future was bright. I was going to single-handedly take on the medical establishment (much bigger than I thought) using my physician-humanitarian from small-town America ego (much smaller than I thought). Read more>>

Monica Ortega

As someone who’s not a risk-taker, I’ve spent my life taking risks. Chasing the entertainment goals to Nashville to sing and Los Angeles to act, moving to cities without knowing a soul, starting my own travel show, writing a book, you name it, I’ve done some scary stuff! When I started my travel show Monica Goes, I quickly realized I was afraid of almost everything! That quickly became the premise on the show; crying white water rafting, crying rock climbing etc. Read more>>

Destiny Faith Nelson

Moving to Los Angeles during the pandmeic was a big, life-changing risk for me but was the best decision I’ve made in a long time. I’m someone who is good at strategizing, planning, and coming up with big ideas, but I haven’t always been stellar at executing. I used to take big risks when I was younger because there was less to lose, however, the older I’ve become, the more cautious and careful I’ve learned to become. Read more>>

Jaime Geist

I took a big risk this year by leaving my job to be a content creator and voice actor. I was at my job for almost 3 years and decided it wasn’t for me. I wanted to have a chance to explore what I’m good at and to enjoy being creative. I told my boss that I was quitting and I appreciated the chance to be working for the company but I wanted to follow my dreams. It’s scary to take such a risk but I know it will pay off in the end. Read more>>

LATOYA Rucker

Venturing into the unknown with my move to Los Angeles was a decision teetering on the edge of audacity. Prior to this bold leap, my life had adhered to a rather conventional script. I was comfortably settled in a house, occupied a coveted position at a Power, Oil, and Gas Company where I meticulously reviewed contracts. But, alas, the predictable nature of it all had cast a veil of tedium over my existence. Read more>>

Alyssa Loxart

The biggest risk I have ever taken was publishing my first book. As a poet, the page is a bit of a diary to me. I explore my experiences and relationships within my writing, and to allow someone else to see into that can be terrifying. It took me a very long time to be ready to publish (years), but the day that I did was the most freeing day of my life. Read more>>

Michael Oldroyd

Risk-taking is what defines capitalism. It is the only thing we have that helps level the playing field. I’m not saying all is fair because it’s not, but we all have the opportunity to enter the poker game of American capitalism, even if we don’t have many chips. The more chips and skill we have, the greater chance we have of winning of course, but the willingness to take risks is everything… & the greater the risk, the greater the reward. Read more>>

Michaela Yarbrough

The biggest risk I took was betting on myself when I took a year-long sabbatical from my corporate dream job to reconnect with my art and ended up starting a small product business selling my artwork. Read more>>

Timothea Biermann

About 2 years ago, I decided to start an art collective. At the time, I was teaching professional development classes to other art teachers employed by Denver Public Schools. Several of us art teachers began the Chameleon Collective to collaboratively create, critique, exhibit and sell art. As educators, we are overworked and don’t always have time to create our own art. Read more>>

Valentina Loaiza Jaramillo

Since I was little, I decided I wanted to be a professional musician. When I graduated from high school, I started studying music in Colombia, but that wasn’t what I really wanted. After a lot of thinking and the support of my parents, I decided to apply to different colleges outside my country, and I got accepted into Musicians Institute, which was one of my dream schools. I decided to take the risk and leave my country, family, and friends to pursue my dream of studying music in LA and becoming a professional musician. Read more>>

James Oliver

It is important to know that when you’ve made a decision to pursue the creative path that you are full in to put in the work. i knew that in my case as a 22 year old, fresh out of college. I knew at this point if I would take the easier path of having a day job that it would zap my energy and psyche. Read more>>

Jessica Lausell

So, after years of working “muggle” jobs I decided to take the risk and pursue theater! My son was about 6 years old and I was a young mom and I got alot of push back from people, but my support system was stronger and I made the move! I started with going back to school to get my Associates in Theater Arts. This alone was a chance, will I be able to do school work? Attend class? All while still working to put food on the table. Read more>>

Dania Calvillo

A little about myself, my close family and friends would say I’m a natural risk taker. As the oldest and only sister it is a super traditional Mexican household. I was often pushing boundaries to find myself and what my purpose was. At just 18 I set out on my own moving from Fresno CA, to LA. Moving to LA was always part of the plan but one day it just happened. Read more>>

Stacie Aamon Yeldell, MA, MT-BC, AVPT

By far, one of the biggest risks I have ever taken as an artist is packing up my entire life and flying off to a land full of strangers, a foreign country where I didn’t know a soul. Frustrated and spent from years of grueling indie-artist life in NYC, I got a “calling” to go to Bahia, Brazil. I had only been there once for a quick birthday trip. I knew nothing about this country. Read more>>

Alex Hallerman

I think “risk” best describes the role of a manager in the music business, especially those who are independent with no company backing other than their own. Time is currency, and we have to spend it wisely. When taking on a new client, or even evaluating relationships with current clients, I have to weigh decisions between passion, faith, and the data. Risk versus reward is real and there’s only so much time in a day for one person to work on multiple acts/producers. Read more>>

Marissa Lange

Building our winery! Our family’s viticulture business was thriving with long-tenured clients and long-term contracts with a diversified group of winegrape buyers when we determined that to cultivate a lasting impact through our family business, we needed to diversify our route to market to be able to sell our fruit by the ton, by the gallon and by the case. The wine business is extremely asset-heavy, so we pushed our chips to the center of the table and leveraged our vineyard land to secure the financing to build our generational, state-of-the-art winery in the heart of our estate vineyards while keeping it privately-held. Read more>>