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.

Sarah Haftorson

“The hardest thing to do is leaving your comfort zone. But you have to let go of the life you’re familiar with and take the risk to live the life you dream about.” This quote comes from a post I saw on LinkedIn one day when I was living in my comfort zone. At the time, my days were predictable, stable, and routine. I had finished my time at Savannah College of Art and Design, was getting my foot in the door as a freelance Illustrator and Motion Designer, and had a stable living arrangement—but, I wasn’t happy. Read more>>

Brittany Dickinson

Persistence! I had just moved to Chicago where I had zero network… I heard about a position that would have me working side by side with 15 very experienced older dentists and knew it would be the perfect place for me to hone my skills. I applied for that position three times before I got it! The company wanted someone who had experience with a CEREC technology… I said give me one weekend to learn it and I’ll be your go-to person for same-day crowns. I think it was this confidence in my abilities (as well as my follow through) that ultimately won me the position. Read more>>

William Lee Martin

Just your Typical 25-Year Overnight Success Story Before I started in comedy in 1996, there was one sure fire way to have success and that was to get on the Tonight Show with Johnny Carson. A nod from Johnny meant that you would go from unknown comedian to the literal overnight sensation. Read more>>

Nicole Williams

The biggest risk I’ve ever taken was to start this practice, The Gynecology Institute of Chicago. I had just received severance from my last job and had nothing else. While the safety of a hospital was a possibility, I knew that I had to take that chance, and so I did. Nearly 10 years later, we’re still here, caring for patients and growing. Read more>>

Marta Spirk

The biggest risk I’ve taken was leaving Brazil, my parents house and everything I’d ever known for 23 years to move to the US and marry my American husband. I was so young and had such little life experience but knew in my heart I had to take the leap and leave safety and wealth for love and new opportunities. Looking back, I can now see 12 years later how BRAVE I was. From the outside in it looks a lot more different than it felt when I decided to go. It wasn’t an easy decision because my parents felt sad and offended in some ways, but I know this opened up so many doors for me in figuring out my identity and purpose in life. Read more>>

Christopher James

I worked in corporate America for a great company but after awhile I started feeling unappreciated by upper management. Read more>>

magda lopez

I feel like if there is no risk, there is no reward. I have had a lot in my life so far, thankfully. And I have lost more, thankfully. Both of these experiences, have enriched my mind, body and soul. I made a business out of it. I am beyond grateful for the highest of highs and the lowest of lows. I wrote my first book, I opened a very aggressive business. I swore I would never fall in love again. All of this happened in one year.  Read more>>

Brian Hook

The risk I’ve taken from the beginning was having faith in myself and ignoring as much negativity as I could. Read more>>

Trey Phillips

How did an award winning physician and retired SWAT team leader leave their traditional professions to end up leading the cannabis market in Dallas-Fort Worth? Read more>>

Cameron Ball

Title: “If you don’t try, you’ve already failed.” My Dad once said “if you don’t try, you’ve already failed” which continues to push me to take risks and pursue dreams. My passion for craft beer started with home brewing while I was studying engineering at Cal Poly San Luis Obispo. I was brewing 5 gallons of beer in a small pot on the stove and cooling it down by leaving it in bathtub full of water while hitting the night bar scene with college buddies. Read more>>

Aleasa Word

Several years ago I was going through a tough divorce. I had two young children at home and a teenager. Finances were tough but I was tougher. I woke up on a monumental birthday and made a choice. I didn’t want to wallow in self-pity or fear so I decided I was going to enroll in a certified coaching school. Now, I was BROKE!!! I mean I was so broke I couldn’t afford lint in my pockets. Somehow the lights were still on and we had a roof over our heads, food and transportation. I knew something had to change and I had to go from the blame game to the hustle game. I had to regain what I call my “financial gangsta.” Read more>>

Jamice Bentley-Terry

I took a risk with moving my business from a $250.00 a month rent payment to moving into a larger space, different vity, changing to a sole proprietor, and my rent increasing to almost 5 times it’s original rate. During this experience, it pushed me into an even deeper relationship with God(as you can imagine lol), because it’s definitely not an easy task. I’ve learned to trust the people that God has assigned to your life, with what He has designated them to help you with. Read more>>

Patricia Edwards

As an entrepreneur, every idea and vision is a big risk. The risk is great because you have to evaluate if your idea is going to be received well by others. You have to consider the time and financial investment that is poured into your business idea in hopes that you will see a positive return. Flawless Belle was an idea brought to life and one of the lowest points in my life after losing my mom to Lupus. It definitely has its’ ups and downs, but I’m grateful for the connections I’ve made, the opportunity to share my talents with others, and most of all helping my clients feel Flawless. Read more>>

William Lyday

The biggest risk I ever took was just after I decided to quit my job after being passed up for a promotion, just fresh from a bad breakup, and my landlord in Portland Oregon wasn’t going to renew the lease. I had sold almost everything and packed my bags for mexico. I was living with a childhood friend who happened to get deported, in Puerto Vallarta. I made that jump and was able to live off of commission and freelance work. It was scary at first but also a real confidence booster. Read more>>

Connor Lock

“Oh, look. A pandemic is sweeping across the globe” “This would be a great time to start up a second branch of my company out west!” (warning, I suck at grammar things and I just write with emotion so hang on) Yup, I did that. Talk about a risk. My creative business in Charleston, SC was running perfectly smooth but I knew that I needed to shake things up out of my comfort zone to grow as an artist, designer and above all as a human. Read more>>

Sarah Buchanan

I was once very focused on a path: bachelor’s degree, master’s degree, clinical licensure and then PhD happened one right after the other. I worked as a staff social worker for a couple of agencies throughout, returned to one after taking a couple of years off to complete PhD coursework and became Director of a county-based program while finishing my dissertation. I then moved on to a role as Director of a new state-wide program that I’d been advocating to initiate. Read more>>

Elizabeth Marie

Every stroke of my brush is a risk. A risk on my reputation, my finances, my ego and my fragility. I like to think I’m the kind of person who can step off the cliff and know, just know the crystal bridge that is invisible to my eye is there to welcome my foot and guide me across. The joys of fantasy verse reality! Read more>>

Susanna Wilson

Susanna – Anyone who has ever started a theatre company knows that doing so comes with huge risks. Even before the pandemic, audience numbers and funding for nonprofit arts organizations were on the decline, making it very difficult to successfully launch and maintain a new one. And the existing organizational model for nonprofit theatres, with a dedicated building, subscription-based programming, educational offerings, and a governing board of directors largely made up of wealthy donors, has proven to be unattainable for most artists. In my experience, the proliferation of small, all-volunteer community-based theatres came about because emerging artists, finding that the existing structures did not work for them, decided to start companies of their own. Read more>>

Mardell Rampton

My post secondary education is in computer science followed by a long career in the telecommunications industry in Canada. While there was definitely accomplishment in building systems and being part of a corporate team, I felt like something was missing. I wasn’t exactly sure what I was looking for, only that it needed to be creative in a grounding, nurturing way. Read more>>

Libby McGowan

I’m generally not a risk taker. I like to make sure when I land from whatever leap I make that there are several layers of mattresses to catch me when I fall. Read more>>

Danielle Vinson

Opening a creative community studio in the midst of a pandemic was one of the biggest risks I have ever taken in my life. I always had this dream to open up an art and yoga studio, but that dream felt like just that – a dream, a fantasy, or at best, something perhaps, maybe, possibly I could do much later in life. After being laid off from my job in travel in April of 2020, Read more>>

Jess Parker

The risk I took in 2019 has made me the fearless person that I am today. From 2017 to 2019 I worked in various salons and spas, throughout that time I worked for incredible and influential professionals in the beauty industry. Because of this, I always had a burning desire to be my own boss, I wanted to set my own schedule, have my own clientele, and call my own shots. In 2019 a salon that I was working at the owner decided to sell it and I found out the last day that employees could work there, to say that I was livid was an understatement. Read more>>

Jamela Carter

I worked in healthcare for the last 4 years. While photography has always been a passion of mine, I always enjoyed helping people and providing care and just being a positive light for my patients. I was in school as well as working during covid and I remember like the rest of the world I was getting burned out. My business however continued to grow and that gave me peace and a sense of purpose outside of work. June 2022, I decided to walk away from healthcare and put 100% into my business, I realized I couldn’t go another day without pursuing my passion. Read more>>

Carlene Levy

Hair extensions, wigs, sew-ins, and relaxers are hairstyles that have been around for years. Growing up in New York, I love seeing different hairstyles which bring your fashion style and outfit together. I wore protective styles and tried new hair extensions and wigs that were trending. I could not take care of my natural hair, so I got a relaxer. During those periods when I was switching up my hairstyles, I fell in love with naturally curly hair. I wore lots of loose and tight curly wigs and hairstyles like my natural hair texture. Read more>>

Christian Euzarraga

I had been collecting vintage since my freshman year of high school in 2011. During my later college years I found myself missing classes and hanging out in thrift stores, even setting up my own stand in the middle of the college campus to try and make money. I had seen a setup before during my freshman year of college while attending The University of Houston right outside of the Cougar Village dorms. Read more>>

Caitlin Jenco

Back in 2020, I was working full-time managing a gym and I was in school on an accelerated track to obtain my law degree. I had been in college for 2 years and transferred 3 times in desperation of trying to make college feel right for me. At all 3 schools, I felt too big for college and I felt that there was something else I should be doing but I didn’t know what that was. Once Covid started, the gym shut down immediately and I found myself with 3 months of down time to explore. Read more>>

Kym Ali

When I decided to pivot from nursing to becoming a DE&I consultant, I was taking a huge risk. The pandemic had caused healthcare facilities to be inundated with patients, and I knew my expertise could be put to better use elsewhere. Read more>>

James Carson

I am a Board Certified Orthopedic Surgeon working at Next Generation Orthopedic & Spine Institute. I have been in this position for about 10 months now. Before that I had spent about 4.5 years as an employed orthopedic surgeon. The position was very comfortable and paid well, however I still felt stifled as a medical professional. When employed, one has to follow certain rules of employment which aren’t great for entrepreneurial pursuits. I even had a job offer from a longer established practice in the area. Read more>>

Amanda Anderson

In August of 2021, I had the opportunity to test my faith. I left my family, friends, business, and other business opportunities in Michigan to move to California. I still grieve everything I left behind but I grieve in a positive way. A’Rae Photography and Caffeine My Life are the 2 businesses I put on hold for my big move. Along with wanting to start a dance non profit. Since my move I’ve been spending time getting acclimated and figuring out what chess piece to move next. My mind is always coming up with creative ideas; rather it be with writing, dancing, or photography. Read more>>

Jay Byers

I knew for months that I was going to quit my teaching job, and I finally did during a solo-trip to Cancun last June, but I didn’t know then that I’d be calling myself a full-time entrepreneur right now. Read more>>

Ashleigh Gray

When I was growing up I have always been in the restaurant industry. At 18 I was serving/bartending outside of my family’s restaurants debating on what I should do. In my life at first, I started business school at Northwest Community College and I ended up not finishing, (life hits you) but that wasn’t where my true passion was so I eventually started cosmetology school at Goulds Academy after having my daughter. Thankful enough to have a good support team who helped me while I began cosmetology school and finished. Read more>>

Dusty Gannon

I took a huge risk this year leaving the Fire Department as a firefighter and paramedic to go full-time in music and content creation. I had been working in that field for the last 5 years, and I truly loved it, but the band was growing at a pace that became incompatible with the schedule, so I decided to take the leap of faith and focus my efforts on my greatest passion in life, which is creating art. Read more>>

Keshawn Johnson

The biggest risk that we’ve taken to this point is starting our first business. Going into in the fall of ’21 Devin and myself both knew we wanted to be business owners and have our own line of clothing but we had no experience in anything business and very limited funds to support our business. We knew it would take a lot of hard work and dedication so we put our heads down and started grinding, trying to gain as much information about the whole world of clothing in as little time as possible. Read more>>

Meg Schenck

So I have always loved singing, writing, and performing, and knew, at a very young age, somehow that it was going to be part of my life forever. But until recently I have also worked a side job in addition to pursuing my music career. However, early this fall I got the opportunity to quit my waitress/bartender job and was able to perform on stage full time! It requires a lot of work but if you want it more than anything else, you will find a way. Sometimes the universe just lines everything up for you, and sometimes you just have to risk it and see what happens! Read more>>

 

Michelle Thigpen

“Living with fear stops us from taking risks, and if you do not go out on a branch, you’re never going to get the best fruit.” This quote from Sarah Parish shows that taking a risk is a major key to getting us through life, and this view of overcoming that fear may look different to everyone. In my opinion, a risk requires going out on a limb and taking a stab at a certain predicament where the probability of failing miserably is higher than the odds of taking a win. Read more>>