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.

Sage Castleberry

A major risk I have taken in the last year is putting out my own music. Playing covers is one thing, but putting your own music out takes a lot of courage. When you put a song out you really hope people will like it but that’s not a given. Some will like it and some won’t, that’s just how it goes, but in that it took me a lot of courage to put my own music out for the world to hear. Read more>>

Alexandra Beller

I got my MFA in 2006 in the hopes of becoming a tenured professor. I did this in large part to create financial stability for my family. Although I love teaching, full-time academia was not my happy place. Teaching seemed to be a fraction of the job, and the rest of it was not satisfying. I took the risk to stop trying to get a full time position, and instead backed myself to be able to support my family through my creation (choreography and direction for theater) and teaching on my own terms through my company, Alexandra Beller/Dances. So far, so good! Read more>>

Morgan + Joel Borcik

The biggest risk we ever took is the only reason we have our business today! In 2019, Joel and I were both working the night shift at a factory. We would wake up at 2 pm, go to work at 3:30 pm, work until 3 am and then go home and fall asleep by 5 am. Rinse and repeat every single day. We were miserable to say the least. Joel was the first to hate the job and would try to convince me to quit and tell me that we could do so much better. Read more>>

Cam Simone

I’ve been a singer since I can remember, ever since I was little I knew I wanted to be an entertainer. As I got older and started to pursue my music career fully, it wasn’t until then that I realized how much hard work and dedication would go into pursing my dreams, and even with all the hard work and dedication i had to learn that there will be losses along the way. I took a break from music and went to school for psychology. Read more>>

Mike W Nelson

I took a risk when I moved to Minnesota for my first full time radio job this past March. It has been a wild journey and I have learned so much the last few months. I am lucky to have been able to fulfill dreams of mine. Read more>>

Michael Oria

When it comes to taking risks, my journey as a farmer has been defined by one pivotal decision that changed the course of my career. It was the year 2014, and the hemp bill had just been passed, allowing for the cultivation of hemp on a federal level. This presented both an opportunity and a challenge. Read more>>

Kourtney Gillespie

I remember the summer of 2015. I had just received my bachelor’s degree from Embry-Riddle Aeronautical University, and I was ready for the world. I thought that having a degree in my hand would unlock all of life’s doors and bestow upon me an array of opportunities. All that degree stood to do at that moment was tell employers that I had zero experience in the field but was over-qualified to do other entry level positions outside of my industry. Read more>>

Lan Akinade

The biggest business risk I have taken in my 19 years of being an entrepreneur is opening my Atelier. The TOL Bespoke Atelier is a luxury custom dressmaking store located in Columbia Town Center. Honestly, I did it afraid. I knew it was going to be a life changing risk; either negatively or positively. It was a scenario in which if it failed, it would be a big financial mess for me but if it succeeded, it will be a very huge turn around for good for my career so when I wanted to do it, I told myself I was going to succeed at it. Read more>>

Rheanna Grooms

As soon as I graduated high school, I took a risk and moved 6 hours from home and started college classes to become a Veterinary Technician. I instantly fell in love with the profession and all it encountered; the good, the bad, the rewarding and the sad. Not many know, but the veterinary medical field is known for its high suicide rates. New research shows nearly 70% of veterinarians have lost a colleague or peer to suicide and about six in 10 have sought professional help for their mental health. Read more>>

Carrie Hyman

Although Holistic Therapy Kneads was started in January of 2021, I took a risk in September of 2022 and quit my full time job to pursue my dream. I took this leap of faith and have not looked back. That September day was one of the best days of my life. Read more>>

Roosevelt “R0$E” Coats III

Taking a leap of faith in myself was my biggest risk. I took a gamble on me – trusting in my own abilities. I left my job to make a change for the better, and it initially appeared like I caused more damage than good. Even so, it was a gamble I had to take a chance to determine if I was cut out and capable of overcoming obstacles. As it happened, it helped me to acquire the skills to navigate challenging times, a skill that is necessary for achieving success. Read more>>

Liberty Worth

These days taking a risk looks like a new business venture for me. I’ve long loved being an artist and sharing my skills with others, teaching them how to be creative. I’ve had my own businesses making and selling my work for over 20 years, I have also been a teacher and a mentor in many capacities… but when I had a studio mate move out from the space next to mine this year, I figured there was “no time like the present” to try something I have long said someone should do. Read more>>

Alyshia Jackson

Starting my own business as a single mom of 2. I started my company during the pandemic trying to create a flexible/reliable income for my family. Not having the savings or even resources to enter the business world but having the mindset I will get it done is what has got me this far. From spending my last savings on equipment and supplies to gain my first customer which was extremely hard. I knew I had major responsibilities but I knew I could bet on myself. The process wasn’t easy but I wouldn’t trade it for nothing I am going on 3 years in business and 1.5 working full time for myself. Read more>>

Davina Rocha

“You can either live a life of comfort. Or a life of purpose. It’s up to you to choose.” My grandmother once told me this, ironically enough in a dream years after she passed and it’s a statement that has profoundly impacted my life. Life is all about choices. Small every day choices like what kind of coffee you order from your local coffee shop, or what outfit you’ll wear today, wether or not you snooze that alarm that rings at 5:45 am to start the day or sleeping in an additional 15 minutes. Read more>>

Paxton Conners

I would say starting my business was the biggest risk I had to take in life. It was the timing at situation I was in that made it extremely controversial amongst my family and peers. The sacrifices my wife and I had to make in order for the business to become reality were life changing and a lot of people just wouldn’t be able to do it or even be willing to do it. Read more>>

DeShuna Waters

I started my business Skin Therapy by Shuna Cha-Nee in November 2021. I knew I always wanted to be a business owner but I was afraid. I had people telling me that I needed to start my business once I graduated from cosmetology school. I wasn’t prepared to be a business owner and I didn’t know anything about owning a business. I wanted to follow the advice that I received from my instructor which was to work for other people first to gain experience and knowledge and the start my own business. Read more>>

Randy & Lisa Lee

Biggest risk we recently took was opening our own gallery/shop in a local, small town in what is essentially a farming community. It was not a part of our vision for 2021, but a chance meeting and a deal to good to pass up made us say- what the heck, why not? We opened the doors just 5 weeks after signing the lease. We knew it was a risk because of the location, so we made sure to be careful not to invest too much in case we ever needed to close. We took on 90% of the artists on consignment, Read more>>

Imani McCray

One of the biggest risks I have taken in my artistic career is traveling to DC to document the 2021 Insurrection. January 6th was a sight that should have been relegated only to horror movies and pre-reconstruction ignorance—not 2021. Black Lives Matter Plaza sets the scene for my day. All of DC was swarmed by the delusional and privileged as they marched on the Capitol, inflamed by the (former) President of the United States and a barrage of lies about election fraud. Individuals proudly carrying racist and hateful symbols appropriated a form of protest often utilized by marginalized, at-risk, and oppressed minorities. Read more>>

Michael Freetage

When my job was cut in mid 2019, I took a few weeks to figure out what I wanted to do next. As I pondered my options finding another 9-5 wasn’t an option so, I started my own confectionary business. Read more>>

Jade Syan McKissick

A few years ago, I took my first trip to Miami. This pushed me to take modeling more seriously. I was invited to Miami to be a brand ambassador for an Instagram store called Sauced Outfitters. I have never travelled alone or been on a plane at the time, but something told me to take that risk. My social media presence increased a lot just from that trip alone. Eventually, I got to where I was doing a photoshoot basically every weekend. Read more>>

Weam Namou

Early in my writing and film career, I realized that in order to turn my dreams into a reality I had to take certain actions (what others call risks). For instance, in 2003, I was at the Surrey Writer’s Conference in Vancouver, and met with three producers: one who’d produced Father of the Bride II, one who produced Pay it Forward, and the third, I forgot what he produced. I pitched to them my Iraqi American stories and their reactions were quite unique. They didn’t see how they could possibly adapt them into film. “It would be difficult to cast an Arabic movie,” one said. “Who would we cast for the leading role? Tom Hanks?” Read more>>

Jamia Hicks

I would say I definitely wasn’t a person who took huge risk, but I’ve always taken some sort of a risk in life even as a child. I was considered the wild child the one who took chances and did things others wouldn’t. But, this risk started my senior year of college, I can say I have Covid to thank for this risk, Covid really opened my eyes to see how important it is to work for yourself. Which all in all, it was God telling me to stop thinking small and that there is so much more for me to do. Read more>>

Daisy Zimmer

When I first started my business about 5 years ago, I was a multi-faceted photographer who shot a variety of genres. Whether someone was contacting me about a wedding, professional headshots, newborn photos, or pet photography, my answer was always, “sure!” Even though I made a meager salary, weddings represented the majority my income, so it was hard to imagine not shooting at least a handful of them every year to keep things afloat. Read more>>

Justine Anthony

In March of 2021, after almost a full year of pandemic energy, I reached my wits end with the company I was working for. I had ulcers for the 2nd year in a row during the spring market, was losing valuable time with my son, and was so riddled with anxiety that I couldn’t sleep at night. I was afraid to leave my company because there was a constant influx of leads, and I was never short of clients. If I left, I would give up the solid stream of business that was always guaranteed to come my way. Read more>>

Nicole Francis

Oh, there have been so many risks that I have had to take for my business and social platforms. However, the biggest risk was simply starting my account. It’s so scary putting yourself, your family, and your home for all the world to see. I was a new mom, who just quit my teaching career to stay at home with my little gal. I was dealing with postpartum anxiety and always loved to decorate, we were building our new home and had so many ideas for the direction I wanted to take our builder-grade home in and I just needed something for me. Read more>>

Victoria L. Szulc

One of the biggest risks I’ve ever taken was approaching Big River Steampunk Festival about starting and organizing their first fashion show. Big River is now the largest outdoor Steampunk Festival in the nation and in 2017 they had close to 22,000 people attending. Read more>>

Jenae’ Criswell

The biggest risk I’ve taken was starting my business and going full-time. I’ve had various jobs since graduating college and I had been at my last job for almost 7 years. Due to unforeseen circumstances, I decided to leave my job. I stepped out on faith to pursue, what was at the time a side business, as my full-time income. Baking is something that I just enjoy doing! Read more>>

Alexis Williams

Alexis ended her career in the dental industry in 2020 after making a difficult decision between pursuing her dreams as an entrepreneur or financial stability during one of the most uncertain times in history, the pandemic. Prior to the pandemic, she knew something was missing in the restaurant industry that seemed so familiar but so far fetch when dining out. After many trips back home to Baton Rouge, Alexis knew she had to get her family’s recipes and start practicing. Read more>>

Katelynn Ostruszka

The biggest business risk I took was when I quit my high-paying 9-5 corporate job to pursue my passion for interior design. Sometimes we have to choose to play it safe or take a risk. I choose to get out of my comfort zone. I decided to take the risk because of the strong urgency I have to create a life I love and to only focus my time and energy on the things that truly make me happy. Read more>>

Patrick Artus

Moving to California in 2011, not knowing anyone there, straight out of college was an eye opening experience for me. I moved to Los Angeles to pursue a career in the Film and Television world. After a few years I was Associate Producing projects and was successful in that all the way until I left in 2017 to find a new adventure. Read more>>

Adrian Rashad Driscoll

Well I’ve taken many risks in life but I have to say one of the most recent, was when we started Collimation. I was coming off a really profitable year and a system that was working. But I had this lingering idea in my head that wouldn’t stop, about creating immersive experiences. I was already in the industry & well known, but this was tapping into a space that I had never touched, game development. Read more>>

Mona Spellman-Benjamin

I AM A SINGLE PARENT DIVORCED MOTHER OF FIVE. I AM FIGHTING TO HAVE MY TWO YOUNGEST CHILDREN RETURNED AFTER GOING THROUGH A GRUESOME DIVORCE. I HAVE RESEARCHED THE TOPIC OF CONSTITUTIONAL RIGHTS VIOLATIONS AND THE RIGHTS PARENTS HAVE TO RAISE THEIR CHILDREN WITHOUT UNNECESSARY GOVERNMENT INTERFERENCE. THUS FAR I HAVE WORKED TO RAISE AWARENESS AND PROMOTE FAMILY REUNIFICATION. Read more>>

Maria Di Meo

Having just graduated from college, I moved back to Cincinnati and was looking for a creative outlet and a way to make new friends. I took a risk and decided to be a part of a team of people who were organizing a community dance crew which would embrace inclusion and diversity through dance. This was the genesis of the CinCity Shakers, a parading dance crew that is founded on the principles of being an open and inviting group of dancers that want to mutually share in the fun of dancing throughout Cincinnati. Read more>>

Paula aka PracticallyPerfectFamily

When I started my social media page, my biggest fear was putting myself out there! I didn’t know if I was interesting, or funny, or able to put out a product that people found informative. Eventually I decided to just be me. In doing so, everything I do feels extremely natural and I can honestly say I am portraying myself in my natural element. Read more>>