Having to overcome unexpected problems is a hallmark of entrepreneurship. Almost every business owner, artist, maker, and creative we know has had to deal with countless unexpected problems that arise in the journey and so we asked some brilliant folks from the community to share their stories of the unexpected problems they’ve faced along the way.

Aleya Harris

One of the most unexpected and soul-shaking problems I faced in my business came after the birth of my daughter, Ruby Coral. I was hit with a wave of postpartum depression so intense that I didn’t recognize myself anymore. For 11 months, I was in survival mode—barely treading water, lost in a fog, and unsure if I’d ever feel like “me” again. It wasn’t just the sleepless nights or the hormonal rollercoaster. It was the crushing weight of trying to rebuild a business while wondering if I was fundamentally broken. Read more>>

Daniel Dyer

So while keeping it anonymous my wife and I moved here just over 3 years ago with a plan for me to potentially work in podcast editing for a ministry in Nashville. Soon after moving my mom passed away, then our vehicles were broken into and stolen and then and then. I applied for a ministry working with the unhoused and whiled the man said I was full of the gospel, I wasn’t hired. Even with 4 years of experience a local mission turned me down as well as warehouse positions, I applied for that I had qualifications for. While we could not understand it seemed like every door we tried to walk through for provision and direction was locked. Read more>>

Debra Sheffer

The suicide of our 22 year old son marked the redefining of my life.
With that tragedy my husband fell into a depression which, in a few years, was accompanied by so many health issues that he was forced into early retirement. For me this meant that our plan for me to leave full-time employment to pursue painting was shelved. My income as the Director of Graphic Design at a private college was critical. The challenge was that, though I was highly motivated to paint and be recognized professionally, it became a tough juggle. Read more>>

Thorsten D Meier

When I created and launched KICKit World, I encountered a variety of unexpected challenges—both during the initial launch and while working to scale this festival for underserved communities.
One of the biggest surprises for me was just how difficult it can be to do good and give back. Finding sponsors was a significant hurdle. As this was a first-time event, many companies were hesitant to support us. We created an unique concept: a sports festival combined with RiseAbove masterclasses tailored for underserved children. Unfortunately, without a track record, many potential sponsors declined to get involved. Read more>>

Shannon Turner

In 2007 I had begun my journey as a professional actor/performer. I was living in nyc and booking work. My community was growing -my audience was growing- and then I suddenly became very ill. 2007-2008 marked the beginning of what would be s LIFETIME of navigating illness and disability. In 2007 I was working for a theater in Rochester NY and I began to experience health problems. After lots of testing, I was diagnosed with HCV that was determined to have been brought on by a blood transfusion at just a day old. I was born 4 months premature and a blood transfusion was necessary to save my life. Autoclaving did not exist in 1985, meaning there was no way to screen the blood I received. Read more>>

Edson Choi

Industry changes. In my opinion, there’s few industries more volatile than the music biz.
It’s always been a strange and shady industry, but once streaming took over both the big labels and small artists have shifted strategies many times.

And then COVID hit and sent the shifting models in the industry to even more unexplored territory. Putting an even bigger emphasis on social media presence and following. Read more>>

Jordan Sanford

In October 2021, I became General Manager of Kantishna Roadhouse, a beloved destination 90 miles into Denali National Park. For almost 15 years, I had been part of the Doyon Family of Companies, but this new challenge felt like the next big step in my journey. When I first accepted the position, there was a sense of excitement and anticipation and a cloud of uncertainty. The Denali Park Road had been closed in August 2021 due to a landslide – a situation still very much up in the air at the time. Read more>>

Casi Denton

When I started my wedding and family portrait photography business in 2008, fresh out of college and eager to create, I was completely unprepared for the harsh criticisms that would come—not just from the outside world but also from other business owners and even my own family.

One of the most painful challenges came in 2013, when I learned firsthand that family doesn’t always support your dreams. That year, I had photographed my cousin and her fiancé in a historic district of Baltimore City. It was a drizzly, slightly chilly day, which gave the photos a moody, “Rainy Day in Paris” vibe—something different from my usual work at the time, but I personally loved them. At the end of the session, as a wedding gift, I offered to photograph their wedding at a steep discount. Read more>>

Samantha A. Morrison

When the current SAG video game strike regarding AI protections first started, everyone was in a tizzy! Actors, clients, financiers, you name it… and it suddenly became my job to assure them that not only would things still be able to continue on time & on budget, but also ethically with the actors, as a collaborative team. Traversing the varying social circles and intricacies (particularly during an industry strike) takes not only a certain finesse, but also will challenge your moral center a business owner. Remaining steadfast in your choices is vital during these times. You can never take back what has been done, you can only keep working towards that new & better tomorrow. Read more>>

Victoria Mendoza

My husband is in the military and while moves are inevitable, I underestimated the amount of work some of our quicker moves would require. We don’t typically get to pick where we move and the vast differences between cities across the country makes moving a location-based service business challenging. We moved from Georgia to Mississippi in July of 2023. In October of 2024, we were sent to Illinois for two months and then Little Rock. Our assignment here also has a short turnaround and we’ll be moving again before 2025 is up. Our move in 2023 also came with a new baby and the challenges of learning how to care for 3 children under three years old, while my husband worked an extremely demanding schedule. Read more>>