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.

Jennifer Cahill

The biggest risk I’ve taken is opening a hair salon. I always knew I wanted to do it, and over the years learned from previous employers about how I would like my business model to look. But the execution and all the challenges thrown your way is something that no one tells you about. Read more>>

Olivia Fledderman

I recently read the following quote by an unknown author: “Risk can be dangerous, but routine can be deadly. Comfort has killed more dreams than daring ever did.” Read more>>

Allison Pence

For most of my life, I don’t really consider myself to have been much of a risk taker. I lived more conservatively, more afraid of the possible outcomes of any risky decisions. But five years ago, something changed. I was so unhappy in my profession (teaching), and my passion, creating art, was a burning fire within me that needed to take center stage. Read more>>

Noah Westbrook

In May of 2021, I graduated college with a degree in Business. I had no clue what I wanted to do, but I knew one thing. I couldn’t sit behind a desk all day. My whole life I have had a passion for wildlife, especially mammals. That can be challenging when you live in Maryland, where whitetail deer are the largest animal around. Read more>>

Wing Lam

saying yes to charities when the ROI was not there on the surface , ended up meeting and becoming friends with some amazing people and able to network with great brands Read more>>

Vanessa Medina

Risk is a factor in any decison we make, both personal and professional, In my path, it is about faith, believing that where I am at now is exactly where I was meant to be. Read more>>

Nikola Modrusan

I have a deep belief that if you build something truly exceptional, people will naturally be drawn to it. My mission is to craft mesmerizing kinetic sculptures that not only serve as artistic expressions but also bring people together to experience the wonder of art in our community. Read more>>

Carolada Gilbert

The biggest risk that I have taken has been across the trajectory of my career that has lead me to business ownership. When I started my career I had plans of eventually becoming a therapist but I never suspected I would become a business owner. While in college, around 2007, I started working as an intern under a Case Manager at a juvenile justice facility. Read more>>

Sydney Mills

Since choosing to get my undergraduate degree in art back when I was only 17 years old, it feels like most decisions I’ve had to make throughout my career have been risky. Read more>>

Dexter Walker

I remember being booked for a role in a national commercial out in Austin, Tx. My vehicle at the time was all over the place. My tags were expired, my driver headlights were busted, and two of my tires were bad because of the threads. I was determined to make the 3.5 hour drive from Houston. I didn’t know how the drive was going to be for me, but in my mind I knew that getting there is what mattered to me the most. Read more>>

Kristen McCullough

In my early twenties, I drove with my husband, our pug Mac, and all our worldly possessions from Texas to Los Angeles in a Uhaul that barely went 40 MPH. I had only been to LA once but after a tragic death in the family, I needed a change. I was a Theater major in college and sitting across from my husband at a Chili’s restaurant it was decided that taking a shot at the film and TV industry seemed like the only thing that would bring me out of my funk. Read more>>

Courtland Lee

Starting my artist management company right after graduating from college was the biggest risk I’ve taken. It may not have been the most popular choice among my peers, but I was bold enough to embrace it. What fueled my decision was not mere ambition, but a deep-rooted conviction that I was being led by God. Read more>>

Kati Terray

Being a business owner means getting comfortable with risk. When is the right time to take those risks? Sometimes it takes a push from forces beyond your control. Read more>>

Melinda Quirino

In total honesty opening and establishing Meli Marie Brows was one of my biggest “risk”. Meli Marie became an idea when I was let go from a longtime job in the pharmacy field in 2017. I knew that I didn’t want to work another 9 to 5 job at that time I had just have birth to my second child, and I just knew I was meant for more than a 9-5. Read more>>

Kendra Neidig

Starting this business was probably one of the biggest risks I have ever taken. Unfortunately in October of 2022, I was in a pretty bad car accident. It left me out of work for a couple of weeks and when I returned I wasn’t able to work like I did before. The 40 hour work week was just too much for my healing body. Read more>>

Terri Armenta

Risk: turning an education-based program into a privately held company (LLC, sole proprietor). The program, The Forensic Science Academy, which was founded in 1995, as a program through a local 2-year college. The program was very successful in terms of student enrollment, engagement, and career preparation. Read more>>

Issabelle Mello

Growing up, our family was never wealthy. We had always lived paycheck to paycheck or had to wait for tax returns to do school shopping. We completely understand the struggles of life! After years of working for the working man, my father took the biggest risk. With all the money from his savings, he decided that he had enough. Read more>>

Alycia Israel

The most life changing risk I took was leaving my full time job in 2019 to run my online women’s health coaching company. I was the Fitness Programs & Personal Training Coordinator at Ohio State from 2012 – 2019. It was my first job out of college after getting my Master’s Degree in Exercise Physiology. Read more>>

Toni Tomlin

The world had changed. It was 2020 and COVID-19 had shifted not only the way we interacted but also the way we shopped. Online platforms thrived as businesses grappled with the pandemic’s turbulence. For many entrepreneurs, this was a golden period, where sales soared beyond their wildest dreams. Read more>>

Amante Hall

Starting the TrueTone show has been a blessing I didn’t realize I needed. Taking the risk has opened numerous doors to meet new people. The story goes like this: I spent a year contemplating before I finally took the Jump. I kept telling myself to just do it, and I couldn’t have imagined the profound impact that one tiny step would have. Read more>>

Bailey Snider

The biggest and scariest risk I’ve ever taken was actually starting my nail career, but I have no regrets! I am the type of person that will always chase dreams no matter what situation, position, or circumstance I am in, I will always find a way! Let’s go back to before my business, I was a 21 year old, struggling college student, working 2 jobs just trying to make ends meet. Read more>>

Lauren Nadler

The biggest risk I’ve ever taken was making a move from Queens NY, to Los Angeles. Of course the bigger the risk, the bigger the reward. And the choice to make this move was the best I ever made. This was over 20 years ago, but still in some ways feels like yesterday. Read more>>

Jill Gibson

Opening a business mid-pandemic was definitely one of the larger risks I’ve taken in life. I had been directing a ballet program within an existing studio that decided to close its doors suddenly. Within 24 hours of receiving that news, I knew what I had to do and began the work to make it happen. Read more>>

Brent Everett

Through my life I’ve been a moderate risk taker. None bigger than recently quitting my job/career as an environmental consultant and re-opening my custom urn business, Infinite Urns. Working as an environmental consultant can be rewarding and was for more than a decade. Read more>>

Kamila Kowalke

Being a child and a product of Communist Poland was unbelievably difficult to say the least… more so for my parents than for me… as they tried to navigate a government of corruption and greed and false promises to the millions of people who lived in this post war torn country of poverty and neglect. During the years of Communism in the 70’s and then in the early 80’s when I was young… I vividly remember how all my parents had was hope… and the love of and for each other… certainly not money or material things. Read more>>

Danielle Luckett

Being an entrepreneur is a risk in itself. My mindset has always been to be risk adverse. I am also a Christian so I try to put my faith in something greater than just myself or things I see. But starting this business was a risk. I studied business in school, and as a PM, I have managed IT projects, but I am not “technical”. Read more>>

Tom Slack

I had wanted to become a successful portrait artist but didn’t know quite how. I decided to call the office of the mayor of Greenwood, Indiana. I told the person I’d like to do his portrait as a gift to the city. His executive secretary contacted me to see if I was for real. She insisted on visiting me at my studio to see my work. Read more>>

Andressa Pelachi

My life as a Producer started in Brazil when I was really young. After working for 10 years in one of the most famous Late night shows aired by TV Globo, the second biggest Media Conglomerate in the World, I decided that it was time for a change. There was something missing, excitement I guess. Read more>>

Pretendians Band

Pretendians Band, hailing from Northeast Minneapolis, Minnesota, is a rock band that has been making waves since its formation in 2014. What sets us apart is our unique ability to infuse our music with a modern indigenous perspective, creating a vibrant and powerful style of conscious rock music. We take pride in our dynamic and energy-fueled performances, which have earned us a well-deserved reputation in our local music scene. Read more>>

Nicole Weaver

Back in 2005, my husband, Bryan and I (Nicole) were living in Southern California, running a group home for extreme troubled/delinquent boys ages 7-18 years old. We lived with these boys for two years, while also raising our toddler boys, at the time. It became incredibly more dangerous having our family living in this home 24/7. Read more>>