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.

Leigh Brown

I took a risk in simply starting my own small wine label and with very little means financially and without a ton of confidence except that I had a lot of support from coworkers and family. I have worked for so many people and, at the same time, been freelancing as a musician. I really didn’t have a plan when I started my wine brand but my only focus was to make what I like. Read more>>

Kyla Collins

My entire business was a risk taken. I made my first batch of cookies with my sister in law for Christmas in 2016. We went in armed with a family recipe, a google search, and absolutely zero experience. I was NOT a baker/chef, I wasn’t a kid that grew up in the kitchen baking and cooking with family members. Read more>>

Bambi Torres

Quitting my job of 10 years wanting to go into what I went to college for, I started to look for a position as an Assistant Photographer. I found an ad for a catalog company Avanti Press, not knowing it was one of the largest in the Nation. They did catalogs from conception to final product. When I applied for this position, I didn’t hear back from them. Read more>>

Madeline Stewart

Upon graduating, at age 23 was offered a position as the youngest sales representative for Hickory White & Lillian August Fine Furniture in company history representing these brands across five states. At 24, I was the top sales writer at Spring & Fall Furniture Market for the company. At 25, I became the first on-site sales representative for a top 5 customer representing all 8 brands of the Sherrill Furniture Companies. Read more>>

Tammi Sheridan

I was a high school teacher for 18 years. I taught Spanish, AVID, and co-developed a Mindfulness program. I loved the youthful and high energy from guiding teenagers and tried to be as creative as I could be in the classroom. Ironically, developing a Mindfulness program is what sparked me to leave the profession and build a wellness business of my own. Read more>>

Jamar Robinson

The biggest professional risk I’ve taken started this year. On June 2, 2023 at 8:33am, the Universe dropped an order inside of my head. The below message was crafted and sent to a up and coming cannabis brand: Read more>>

Olya Dubatova

I grew up in a small town in the South of Russia during the collapse of the Soviet Union. Nothing really in how I grew up prepared me to be a painter, I was born into real poverty. There were simply no career options for ‘artist’ – I couldn’t even imagine that that was a possibility for my life. In those days, everyone was poor and life was chaotic. Read more>>

Yerrty G

The biggest risk that I’ve ever taken is quitting my sales job at Spectrum to pursue music full time. I was already touring prior to my exit from the company, I just so happened to be placed in a compromising position where the job wanted me to prioritize their needs over my own. So I took a stand & rolled the dice on myself. I’ve yet to look back or regret the decision I made. Read more>>

Michelle Rademacher

I decided to open my first brick and mortar store during a pandemic. While that felt like a huge risk and most everyone thought I was crazy it felt like more of a risk for me NOT to – with the pandemic shutting down all my prior sources of income and ways of showing up in the world. Read more>>

Roger & Laura Siewerth

What makes a business risky is not the fact that you created a business, taking the steps to legalize your business, or even investing your personal money to get it started. Actually, the risk is when we pass up the opportunity to create a business from our own hands, time, and money. There is great reward in a risk but there is great disappointment and regret that comes from the question, “What if?”. Read more>>

Pat Konicki

I attended the American Academy of Art in Chicago which has a renowned reputation with creative agencies, studios, and companies. After graduation I was offered a job at a well-known advertising agency, however, the hiring manager told me to think twice about accepting because it would consist of sitting in a cubicle all day marking up ad layouts. Knowing that I was an entrepreneur at heart with the goal of someday starting a business of my own, I felt like this was not the direction to take. Where would it lead me? How long would it take? Read more>>

Lisa Pozzoni

I’ve been taking risks since I started my first fitness business about 20 years ago and it’s been a constant journey of risk taking and pivoting. I’ve learned that waiting for things to be perfect is a waste of time and it’s best to just put it out there and then you can pivot and tweak along the way. Read more>>

Chauntia Williams

In 2021, I took the risk of leaving my very stable 9-5 job in car insurance, to become an advocate for women who are spiritually stuck and need a mentor or coach to walk them through how to press forward. This was always a desire of mine since 2009, but financially things did not align to allow it. If I’m honest I’m glad it didn’t. I know that sounds crazy, but the truth is, I would have not been ready. Read more>>

Rise Powell

A young adult sits on her bed in Riverside, CA wondering … what next? What else could go wrong? Financial aid has fallen through or as I like to say failed you, your first car as an adult totaled after your “Ex” boyfriend tried to end your journey before it began. In one split second, a risk can change the entire trajectory of your life! What some may say was young and dumb, I say it was Holy Spirit-led, A thought to go to NYC with $100 and a dream. Read more>>

SAAPS

Like many children, I started out fairly young decoding the intricacies of my personal likes to discover the answer to one of the first ever pressuring questions: Read more>>

Gretchen Zelek

I have always wondered what it would be like to work at a popular “technical athletic apparel” company. I loved their purpose, their vision and their core values. I loved shopping in the store, but I realized I had never seen anyone my age represented there and I decided I could change that. The first 3 interviews were virtual and I watched on the Zoom screen the fresh faces of college students and those who had just graduated, all hoping for a part time job. I was 3x the age of most of the applicants. Read more>>

Monét Walker

I always dreamt of starting a business after culinary school but never thought I would be able to afford to do so by the age of 30. I had been in my mother’s kitchen making cakes, pies, cookies, and catering for so long that after a while, it felt natural to stay there and had become my brick and mortar. For over 12 years, I perfected my recipes, completed many jobs that were out of my league, and had only imagined what my bakery/bistro would one day look like if I could ever make my dreams come true. Read more>>

Matteo Papa

Life constantly challenges me with trials, tribulations and amazing opportunities and I’m grateful for them all. All of my experiences shaped me to who I am today, and I’m constantly evolving, so I took and will take risks in order to continue my life journey. I left my family at 19 when I moved to the UK leaving friends and a secure job to move to London. I didn’t speak English, I hustled to find a job to pay rent and continue boxing training because l always wanted to go professional and live abroad. Read more>>

Savannah Miller

My whole life I knew I had interests in becoming a professional artist. I sold painted rocks when I was younger, and eventually moved into drawing characters for people online (usually for free to get practice). However, when the time came, I knew I had to decide if I wanted / needed to go to college for art. I had maintained a 4.0 GPA throughout high school, and even considered going into the medical field with art as a hobby. That’s when the choice came. Read more>>

Darren Fishman

Well my biggest risk was deciding to move to the US from Australia. I had visited Palm Springs often as have always been infatuated with retro culture, be that movies, music, television, fashion, graphic design, interiors and architecture. So with Palm Springs being the mecca for mid century I definitely resonated with the vibe of the area. Read more>> 

Amy Bumpus

I have always been a bit of a risk taker. One of the lasting lessons from my parents was that taking risks was a part of life. But, one of the first steps in pursuing any new direction is to realistically calculate how you are going to pull it off. Taking a well thought out risk, along with hard work, gives it a better chance of success. Read more>>

Karen Sparacio

In October of 2005 I traveled to Uganda to volunteer my skills as a photographer to help several relief organizations. A professional photographer since 1997, my intention was to better create a portfolio to enable me to find work photographing for relief organizations. However, that all changed once I was introduced to the Acholi Quarter. Read more>>

Paige Taylor

Some things in life will come as a win and others will come as lesson, the common factor in both for anything worth gaining is always going to be sacrifice. How much are you willing to lose for a chance to gain what you want? I learned alot about risk and sacrifice from how i grew up. We didnt always have alot but my parents, somehow, would always make sure me and my brothers were okay. Read more>>

Pascale Bourne

I am a licensed Speech-Language Pathologist. I had been working in management for 12 years when I took the biggest risk of my life to date. I was working for the largest health care organization in my home state. I was leading a team that felt more like a family. A great salary, pension, benefits, 401K, paid time off…all the stability I could ever want and yet I knew I was not as happy as I could be. Read more>>

Keicon Cherry

In the world of television, there’s a common misconception that one can’t effectively juggle multiple pursuits simultaneously. But I firmly stand against that notion; I consider it a myth. Day in and day out, I’m living proof that you can indeed do more than one thing at a time. Read more>>

Amy Yoshitsu

I co-founded Converge Collaborative during the first year of the pandemic with two close friends. In speaking only for myself, I was motivated to co-create what became Converge out of grief and disillusionment over a previous venture; disappointment in myself that said endeavor caused such mourning; scared (obviously) and pessimistic about the course of society and our collective future; and driven to carve a path closer to my artistic dreams. Read more>>

Katharine Nicole Magsaysay

talk about the risk I took on my journey to entrepreneurship. I was sitting in a hospital bed at 23 years old, completely burned out from working at the bank. I was hospitalized because I stopped breathing at work, and they couldn’t figure out what was wrong. I spent almost a month going back and forth between the hospital and the office. Every time I returned to the office, my body would go into shock, and I’d stop breathing. Read more>>

Aaliyah Strong

On February 2,2022 my fiancé Tyshon Ross was shot and killed while we were working at a lounge downtown Atlanta. In the days to follow , the expenses for his funeral on top of bills began to pile up. I had no idea how I would raise the money to lay him to rest, without falling behind on household expenses . Nonetheless, the establishment we were working at was not willing to help with his funeral costs or costs to support my son and I . Read more>>

Ashley Lanna

Taking a risk and doing what you love is crucial for personal growth and fulfillment. It allows you to break free from your comfort zone, explore new possibilities, and discover your true potential. By pursuing your passions (for me podcasting), you can find joy and purpose in your work, leading to increased motivation and productivity. Read more>>

DJ Bitty

A time in my life where a risk was taken would be in 2019. This could have possibly been one of the biggest, off-the-wall decisions I’ve ever made. My choice to accept admission into NCAT. You’d ask, how was that a risk? Well, I’d never visited the school, looked at its accolades or even knew anyone within a 50 mile radius of Greensboro. Read more>>

Marilyn Anderson

The truth is, just being in show business is a risk! Risk #1: A few decades ago, I left my full-time job as a scientist to move to New York and go into acting. Read more>>

Alejandra Alanis Ortiz

I am glad to be here, thank you very much for your kind invitation, my story of risk-taking, yes well there’s a story. I’ll try to be as brief as possible, as an artist we understand that sometimes we have to explore different areas in the art industry from the one that bought in the first place. Well, that’s what happened to me at least, when I was growing up, I wanted to be an actress and a writer but later in life, I understood that teachers can also have their bad days and moments. Read more>>

Erika JaNaé

The biggest and most meaningful risk is the one I’m taking right now, the one to be myself fully. That may either be profound or cliché, but we all know how tough it can be to be authentically you in this world. Read more>>

Rex Dsouza

So I am from a very lower middle class family and I was always been told I need to get a job whcih would give me stable pay..But I wanted to be a singer performer and I started off working at a call center doing night shifts and performing in small gigs for 100 indian rupees that is around 1 dollars right now..My dad didn’t appreciate me singing in shows but then I got into this reality show auditioned and my life changed in 6 months.. Read more>>

Sarah McAllister

I think risk in the modern sense is pretty sanitized. Risk with a physical sense of danger has been mitigated in our society which is obsessed with comfort and control. The risk I am referring to is less of a tight rope walk or Alex Honnold level feat, and more of risk that is inherent in breaking with societal norms. There is an awareness of what is safe and comfortable and then there is being pushed and led to move through that, facing the arising discomfort with bravery to mine the gem of life. Read more>>

Craig Hendricks

My whole career is based on a level of “Risk Taking”. I was a little late to the party. I had a decent job for over 20 years, while I pursued music intermittently on the side. One day, with the encouragement of my wife, I decided to pursue music fulltime. I walked away from that steady paycheck into the unknown, solely based on faith, hard work, and the belief that We WOULD make it! Read more>>

Viral The DJ

In my opinion “Taking A Risk” is maybe one of the hardest things we can do as humans. We all get comfortable with how things might be going on in our lives and change can be scary at times. Many people think that taking a risk and not achieving what they set out to do is failure, but I’m here to tell you that nothing in life is a failure! It’s an opportunity to learn yourself and change the trajectory of your life. Read more>>

Spencer Madison

In 2022 i was fired from my job. Im not going to sugar coat my experience for you all. I wasn’t laid off, i didn’t quit- i was fired. Quite frankly, it was a blessing disguised as what felt like a huge failure. My job and i just didn’t fit, and that is okay. Read more>>

Brian Hyman

One of the biggest risks I’ve taken in my life was getting sober. I was 34 years old, and had no idea what sobriety, recovery, or spirituality looked like. I didn’t know anyone who was sober. I didn’t have much money, I didn’t have health insurance, and I wasn’t sure how to approach the recovery world or how to access any sort of treatment. Read more>>

Marisa Milroy

While I was working for a production company out of college, I was given an insight into understanding the functioning of what it means to make a film in a completely different light. It opened up a new path into the complex realm of filmmaking and the business behind the start to finish. I carefully paid attention to the dialogue of certain conversations, the movement of material, and what it meant to build a strong network. Read more>>