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.
Char Nelson

One of the biggest risk I’ve taken was this year, when I moved to georgia from Tennessee. I’m an introvert so moving from place to place is already a risk for me in itself but moving with the profession I have & the intent for myself & my business to grow, I needed to just suck it up. I had just graduated esthetician school in September & had a handful of loyal clients already established & coming in regularly, with help from the school. Read more>>
Natisse Thomas

I’ve always been an artist, since I was little. My mind is always going and things like meditation and being still are hard for me. There’s something about creating something, whether it’s painting, drawing, crafting, or tattooing, it’s the only time my mind quiets down and I can stay on place. Creating art has always been my form of meditation. Read more>>
Ethan Salter

Everything about music is like taking a risk, you gotta just go out and take it. Every step of my journey as an artist and a musician has been about taking risks, an unwavering faith in my potential as an artist. It all started back in middle school when I was first introduced to my local choir program. The only reason I joined was because my older brother was in the program, and everyone always said you got to “talk to lot’s of girls” (haha). Read more>>
Michelle Woodruff

The biggest risk I ever took in my life was coming out of the “psychic closet”. This is a phrase commonly used when a lifetime psychic individual decides to quit hiding. The most challenging part of coming out of the “psychic closet” is fear of how others will react. There are so many misunderstood, twisted stereotypes associated with psychics. Read more>>
Jean Denegar

I’ve worked in the film industry for over a decade as a cinematographer. From the beginning, I was told to caution against taking a stand on politics in the film industry and to remain Apolitical. I was told not to make waves for producers when hiring crew. I was told to take every story given to me, no matter the content or context. Read more>>
Tony Dočekal
Working as a photographer and storyteller for the Sheltersuit Foundation meant going out solo in various cities and learning about their unhoused population. I wouldn’t call myself a daredevil, but let’s say I sometimes ventured into situations that, in hindsight, might’ve been a little dicey. But those experiences taught me about navigating the unknown and handling discomfort. Read more>>
Holly Hager

I’ve always been a pretty adventurous spirit. In my personal life, that manifests in off-the-beaten-track travel. I trekked Mongolia—before there was cell service—and I explored Côte d’Ivoire on my own within three weeks of a military coup. One of my favorite trips included flying directly over a brand new volcano erupting in Iceland. Read more>>
Rachel Rowse

Art has always been a part of my life. I was born with an eye condition called Nystagmus which is a fancy way of saying my eyes like to dance back and forth like I do. Due to my visual impairment I became extra interested in art and exploring expressing my self and celebrating how I see the world around me differently from a early age. Read more>>
Tommy Gunns

I will have to go back to Seattle, Washington on a around Thanksgiving about the same time. Thanksgiving and the sound of Christmas starting to sprinkle upon us once again for it might the center stone of the risk that got me into the industry of films. and becoming a CEO of my company. I must go back 15 years ago to start this story Now, let me pave the way for you being lost confuse, a little slow then others and a dreamer. It my indigents to taking a risk in life. Read more>>
Denise Battle

Starting a program off the ground that hasn’t been done before in the Hampton Roads for my business, Opera For Us, LLC. I didn’t know all of what this process entailed but I know it needed to be done. So I pitched the idea to a colleague and fellow creative who provided the space and resources for me to launch this program/business on World Opera Day. Read more>>
Kourt Passero

The biggest risk I have taken is leaving the corporate world or as I like to say retiring from the corporate world. Three years I stepped on my yoga mat for the first time. I honestly was so fearful to go to a class but I found this amazing studio, SOL Yoga. This studio was the start of a life changing journey for me. I had the most amazing teachers who were patient, kind, and encouraging throughout the next 2.5 years. Read more>>
Reina Luna

I wouldn’t say I’m a big risk taker but when I look back I remember all the risks I was willing to take to have the life I wanted. For example after high school I had no idea what I wanted to do my first option was to move to Seattle and pursue my graphic design career (I had a full ride scholarship). Ultimately I decided against this decision as it sounded too fast paced for my liking. Then I decide to enroll in community college for photography and 2 months before that started I withdrew my enrollment and joined the Denver School Of Massage Therapy. Best risk I ever took. Read more>>
Katie Knipper

I’m generally a pretty risk-averse person, so when I knew I needed to quit a generally decent job because I wasn’t getting any fulfillment I was terrified. My position at the time was comfortable enough, paid decently and had some benefits, but it was the type of job where no matter how hard I worked there wouldn’t be an opportunity to grow. My only issue was that I wasn’t sure what I wanted to do instead. So as I started quietly applying for new positions I did some soul-searching and listed out the things that I wanted from my “dream life” instead of just my “dream job.” Read more>>
Tina Landrum

I had spent my entire adult life working in the field of healthy lifestyles and wellness, from age 17 to 50, always in health food stores and finally at the biggest retail chain store in that category. I was enveloped by a fascination of how our bodies work, the benefits of simple whole foods, the dedication of herb farmers, holistic practitioners and cultural artisans making products according to ancient traditions or family recipes. My values aligned with my employer, a rare accomplishment I was continually told, and I felt seen and appreciated. Read more>>
Cindy Christi

Believe it or not, everyone wants to contribute at some level, to be someone’s hero and make a lasting difference. When you can help your audience see themselves as thriving in the world you are creating, they will naturally raise their hands to become a part of your narrative. Read more>>
Dr. Tierini Hodges-Murad

The story of my life is filled with risks (both big and small) that have challenged my tenacity, bolstered my courage, and required me to choose if I was going to listen to my fears or walk in my faith. From applying to the University of Miami (much to the chagrin of my high school guidance counselor, who stated that I wouldn’t gain admission) to buying my home at the height of the COVID pandemic and severe economic decline, taking a risk is as natural to me now as breathing…..but that does not mean it is easy. Read more>>
Valerie Dumas

As an artist, you take a risk everyday by putting your artwork out there on display for everyone to judge. Whether it’s in a gallery or on social media, you’ll hear both positive and negative comments about your creations. It is all part of the practice but at the end of the day, it’s a risk worth taking. Read more>>
JULIUS EULBERG

I believe in destiny and when my gut feeling agrees i follow through. I am not into business plans – i go for what I believe in. It took my almost 7 years to make the first money when I launched Julisis skin care. At the time it was not common to talk about a product that is energetically charged that follows strict alchemistic production guidelines. Only then a product can support your own biorythm. Read more>>
Thomas Eggensberger

I believe that taking risks is a vital part of being happy and successful in the music industry and in life, in general. Taking risks allows you to learn, make mistakes in the process from which you can learn even more, and allows you to understand yourself and your goals. Read more>>
Kyle Heinen

I started my career in hair not as an 18 or 19 year old, but in my 30’s. Prior to this creative gear switch I was producing fashion photography for some great and very well respected photographers, Steven Klein, Mert and Marcus, Craig McDean, and the like. While I loved working in fashion, watching the creative on paper come to life with a team on a set and eventually end up on a billboard or on the cover of a magazine, I started to burn out. Read more>>
Diego Pavoni

On the third generation of hairstylists in the family, I am from Brazil, and I have been doing hair for almost 18 years now. 4 years ago, I decided that I would try a new path, move to the United States of America. Read more>>
Brando Zellars

It feels like my whole life has been one leap of faith to the next. At some point I got used to being in that space. it wasn’t until my job with Clemson to when I finally understand the comforts of job security. I resigned from my position in 2021. it was the biggest risk in my life at the time. Covid was still a thing affecting daily life and to make matters better, we had recently become parents to our wonderful little boy. So the timing of it all wasn’t ideal, but then again is it ever. Read more>>
Sara Segar

As a young person, I was the epitome of a homebody, finding solace in familiarity. Change and risk-taking were foreign concepts that induced fear, making me shy away from anything new or uncomfortable. However, the turning point in my life came during my senior year of college when my botany professor lit a fire, encouraging me to step out of my comfort zone. Read more>>
Michael Gray

I happen to be on the complete crazy edge of this risk vibe. Meaning….I take the risks every time! haha. Some people think I am crazy and some, see the genius in the crazy. I always try to see the value in the intersection of art and commerce and will take a risk with time, resources, money if I can see through all the fluff and get right into that intersection vibe. I left a lucrative marketing agency I ran to dive into the film business with basically no experience. Read more>>
Stephanie Cox

I think that in order to take a risk you have to be willing to make sure that you believe in what it is that you have a passion for. It can’t be something that you take lightly, and you have to be willing to give it your all. Drown out the negatives that try to swindle their way into your mind and surround yourself around other like-minded individuals that truly want to see you win in your craft. I believe that when you put these key components into your toolkit of life, you can truly conquer the world. Read more>>
Jennifer Armer

The Armer Foundation For Kids is a non-profit organization dedicated to easing the financial burdens of families with children battling extreme medical conditions. When health insurance is not enough, we assist with copays, premiums, deductibles, and any medical-related out-of-pocket expenses. We took the risk and started our nonprofit right before COVID and there are so many wonderful nonprofits we didnt want to compete we wanted to expanded. Read more>>
Sam Hagy

I had been a Orthodontic Assistant for a little under 8 years and after becoming a clinic manager I realized that this was not what I saw myself doing for the next 30 years. So after coming back from vacation, I put in my notice and decided to pursue fitness full time until I figured out what I wanted to do. I was offered a full time position at hygge Fit and later that year was offered the opportunity to take over ownership of the gym. Read more>>
Albert Gonzales

With no training or education in art I quit my job in 2014, and was determined to achieve the goal of becoming a full time professional artist. Every dollar I made from that point on was dependent on sales I made of my artwork. I made some very drastic sacrifices at that point to keep taking babysteps forward to being this full time artist that I wanted to become. Read more>>
Jasmin Mieles

risks are taken everyday, yes? something as simple as like when we walk out of our home, not knowing if we’ll even make it back home! One of the many risks I’ve taken in this lifetime was when I left everything I knew & loved in NYC for the Wild Wild West. Read more>>
Jaci Marie Williams

By normal societal rules, I took a risk resigning from my full time job in the hospital which was my first job out of nursing school. I was a person who used to play by the societal rules. Which usually sounds like this… go to college, decide on a career, settle down, have kids, retire, The End. So I did, I received four college degrees, had the 6 figure career, bought a house 2 years after college, settled down and had a baby. Read more>>
Ana Odle

The biggest risk I’ve taken has been the most fun and rewarding adventure of all. Flashback to eleven years ago, fresh out of college with a biology degree, wide-eyed and excited to step into the ‘real world,’ I started a new job making allergy medicine for people. It didn’t take long until I realized that even though I’m a science lover, Biology wasn’t for me. Read more>>
Ash Ritter

From a young age, I always knew I wanted to study plants. Yet as I approached my college years, the practicality or hire-ability of ethnobotany was limited only to careers in academia or pharmaceutical development- or so it seemed! Herbalism was still far from trendy, and had only recently been made legal for First Nations peoples of the United States. Read more>>
Shawna Enright

When the pandemic hit, I was forced to shut down my business. I was devastated. It was a scary time for everyone. Especially those who only make money while working behind the chair with a client. Read more>>
Nomad Mr. Murk City

I feel that taking professional risks early is crucial. A lot of people are afraid to make mistakes not realizing that every loss is not a “loss”, it’s in fact a lesson. We can learn so much through initial trial & error. Take what’s working and build onto that. Whatever didn’t work shows us what not to do the next go round. Read more>>
Dorin Mogda

While in high school my parents encouraged me to pursue a college degree in Architecture since it was a more stable source of income than being an artist. After I graduated high school, I went to college and started taking architecture courses, but I still had an inner longing for creating. I’ve always been passionate about art, but passion doesn’t exactly put food on the table, or so my parents said. Read more>>
Jasmin Waters

For years, I knew I was designed to be more significant. I fully support people I love, and I am the happiest when they succeed and get everything they want. At some point, I thought, now it is my time. Being a mom/parent is always a challenge. School drop-offs/pick-ups, doctors’ appointments, play dates, after-school activities, you name it! The program is complete. Read more>>
Celesa Lucien

At 27 I was working in the Banking industry in Dallas. I’d gotten into banking while going to college and because my first husband and I had been doing it for years. But I was a creative person, not a left brain thinker. After my divorce, I’d drop off my daughter at a daycare and ride the bus downtown. I would go to the restroom and fall to pieces, feeling like I was having a breakdown. Read more>>
Katy Lemieux

My most considerable risk was, of course, launching a Kickstarter to start the store. I had no other job options besides the freelance writing I had always done, writing grants for nonprofit arts organizations and as a theater reporter for over eight years. I knew how public the campaign needed to be, which meant I could fail massively on a stage for all of my friends, family, and colleagues to see. Read more>>
JaVanta Haskins

The biggest risk in life that I’ve ever taken was 8yrs ago when I stepped out on faith as a single mother, moving from Kentucky to Atlanta on April 25th, 2015 with two kids, no job & only 2 thousand dollars to my name. I didn’t have a plan on how I would make it with two kids on my own coming from a small town to a HUGE CITY, but I knew I wanted to be successful & I had the tools to be successful because going to school & getting good grades was nothing to me, in fact, it was pretty easy. Moving to Atlanta was not by coincidence, a dear friend whom I look up to as a sister named Latise Vaughn Davis (Marsh Vaughn) who’s originally from Hopkinsville, Kentucky, like me, reached out & guided me every step of the way when me & my kids made it to the Georgia Peach State. Read more>>
Esmeralda Gonzalez

Starting a business felt like diving headfirst into uncertainty – the ultimate risk. Juggling time and money is a challenge for this momma of three and a part time photographer. With minimal resources at my disposal, I rolled the dice. Committing to an office lease, I was forced to take this business to the next level. Read more>>
Shawn Derby

What are the risks of starting a business? Are you willing to take that risk for your dreams to come true? Those are the questions you need to ask yourself when starting your business. Those are the questions I asked my self before starting Triple Js BBQ & Catering. The biggest risk of starting a business is there is a possibility that it don’t work out and you can loose your whole life savings that you invested into your business. Was I willing to take that risk? Read more>>
Puneet Singh Singhal

From the confines of a cramped Delhi slum to the structured corridors of an international bank, my journey has been anything but ordinary. Growing up amidst extreme poverty, my teenage years were a relentless battle against not just financial constraints but also the relentless shadows of dyslexia, dyspraxia, and a stammer. These challenges, coupled with ableism and bullying, sculpted a resilience in me that I didn’t recognize at first. Read more>>
Sani Baladi

In my opinion, you have to take a risk to fully commit to something and achieve your goals. When I was still in school as a kid, I told my friends and teachers that I wanted to become a musician. Their response would always be, ”Okay, but what’s your Plan B? You need to study something ”real,” something ”safe,” in case you don’t earn money with your music, like most artists.” I always thought to myself, ”Plan B?” Read more>>
Holli Kenley

I am a Licensed Marriage and Family Therapist in the state of California. Although I had been treating clients in the areas of abuse and trauma since becoming an intern in 1998, it wasn’t until the fall of 2003 that the issue of betrayal really began to tug at me. I was practicing in a counseling center that had been established at a large church in my community. Read more>>
Darin Rios

These are all so good but this really resonates. Read more>>
Elaina St James

I have taken many risks in my life, but always well thought out. Having weighed the pros and cons, I consider it “Calculated Risk Taking.” I have started businesses on my own since I was in my 20’s. None were what one would consider successful, but I learned from each one. Some were gratifying creatively, some were challenging from a design standpoint, and one made me “heart rich” but lost a lot of money. Read more>>
Jeff Blue

“You miss 100% of the shots you don’t take.” It’s true. The greater the risk the greater the reward. I live by these mantras. My entire career was betting on myself. I decided to intern for music companies while in law school and after I passed the California Bar exam, I worked my way into becoming a music journalist as a point of entry into the music business. Read more>>
Bridget Choi

Embarking on my artistic journey was a leap into the unknown. I was a regular academic student surrounded by peers just like me. I wasn’t the artsy type during my school days—perhaps more versed in art history than wielding a paintbrush. Read more>>
Ivan Lloyd Chung

All my life, I’ve been taking risks, small and big, fully aware that I could just smack up against a wall. Everything I worked so hard for could be over in a heartbeat. In the beginning, pursuing a job in fashion didn’t seem to be a big risk. What do I have to lose! But then there was the risk of opening my own store. I saw a space and decided to rent it before having a detailed plan on what the vibe should be or what product I would sell. There was a good energy in the two-storey building with up to 30 artists. Read more>>
Eva Hooft

My move out to California was taking a risk. I had been modeling for the past 10 years all over Europe and in New York, where I was always just getting by. I knew I wanted to exit the modeling industry, but without a greencard this didn’t seem possible to me. I made the move out to California after an ex-boyfriend moved here, knowing that this wasn’t going to be the high-fashion modeling industry that I was used to. I booked one job in the entire year, but I knew something bigger had guided me here. Read more>>