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.

Debjit Mukherjee

Switching from Engineering to Management was a significant career shift, and there were several unexpected challenges that I faced during the transition. One of the most surprising problems I encountered was the need to shift my mindset from a technical, problem-solving focus to a broader, strategic thinking approach. Read more>>

Nadia Nimalan

When you attend a fashion show, there is so much excitement and enthusiasm for when the clothes finally hit the runway. What many people do not realize, is that a great deal of stress and uncertainty occurs before this beautiful moment takes place. Truly Debonaire debuted it’s first runway collection at New York Fashion Week in 2024 and although it was such an incredible experience there were a few bumps along the road to success. Read more>>

Kimara Nicholas

Some of the most unexpected problems I’ve faced so far in this new creative journey of mine is finding people who are willing to have the Paint Parties. Living in Clayton County, there are very limited spaces that are available to rent at affordable prices for a start up business. Another problem is that if I do find an affordable venue, I am worried about paint spillage and damage to the space. I don’t have the space to have events outside of friends and family in my home. Read more>>

Brianna Brown Keen

The most unexpected problem I faced in my creative journey? Realizing that for my career to change, I had to change. It was a tough pill to swallow, but wow—what a game-changer! Looking back, I’m actually thankful that as a kid, I was usually pretty good at things but not exceptional. Why? Because it meant I had to hustle. I had to go from the C team to the A team in soccer through practice, determination, and grit. Read more>>

Kelsey Albro Itämeri

I started my winery, itä wines, in July of 2019. For those of you who are unfamiliar with the winemaking process – it takes some time! My first harvest was that fall, and I made 6 wines, with production skewed a bit toward my two white wines and rosé, since those are able to get to market with less aging than red wines. My winery is in a small incubator building in Walla Walla, WA and we don’t see a lot of visitors in the winter, so my big plan was to make the wines in the fall, fix up my tasting room and bottle the whites and rosé in the winter, and then open the tasting room in Spring of 2020. March of 2020 was going to be our big entry onto the wine stage – I’d go to Taste Washington in Seattle in mid-March, where thousands of people would have the chance to see the brand and try the wines before returning to Walla Walla and having the grand opening the following weekend. As we all now know, 2020 had other plans for us. Taste Washington was cancelled due to COVID, and the Washington State lockdown was enacted the following weekend. Read more>>

Austen Marr

When I started to pursue a professional artistic career in earnest, I knew that I needed to work very hard. I threw myself into my work completely for many years and made a lot of sacrifices. I think this paid off in growing my skills and acumen as an artist, but I didn’t allow myself to be anything OTHER than a hard worker. This led to issues surrounding balance in my life. Family, friends, health, and leisure took a backseat to my work, which led to repetitive stress injuries and isolation. Read more>>

Kaymi Butler

High turnover within my organization was a challenge I hadn’t fully anticipated. As someone passionate about serving youth, I initially assumed that the job would be easy—after all, who doesn’t love kids? But what I failed to acknowledge was that people are ultimately driven by their own needs and priorities, which is completely understandable in certain circumstances. Read more>>