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.

Brandon Lavorgna

My biggest client went under basically two weeks before I was going to add to the team. It was 5 days before their next contract would kick in with me. That was THOUSANDS of dollars just poof up and gone. I felt bad for them because I had worked with them for a year. I was obviously frustrated because the timing couldn’t be worse. Read more>>

Jalynne Geddes

More often than I’d like, my anger is what gains traction. I’m not an angry person but like a lot of people, I get frustrated at this world. I get frustrated at the systems that continually work against us. And as a form of expression, I’ll write or create something that is born from that anger, and it seems to gain the most traction. I think it represents where a lot of us are right now, emotionally, and have been for the past few years. It’s not a bad thing to feel and express anger, but I don’t like how anger can turn into currency. That’s not a currency I want to invest in all the time. It’s not sustaining or life-giving. It’s good to feel and release those real and uncomfortable emotions, but I don’t want to live there all the time, so it’s troubling when people gravitate to my anger and not to my hope. Read more>>

Nicole Fae

One of the most unexpected challenges I faced was realizing that talent alone isn’t enough to build a sustainable career in the beauty industry. Many artists struggle with pricing, contracts, marketing, and financial literacy, which leads to burnout or lost opportunities. Read more>>

Doug Paul

One of the most unexpected challenges I faced as a freelance artist wasn’t the creative process itself, but the struggle of marketing my work. Creating art is one thing, but getting people to notice and buy it is another battle entirely. The question is: how do you make your presence known in an already saturated market? Social media offers a platform, but simply posting isn’t enough—you have to navigate algorithms, engage with audiences, and build a brand over time. The key I’ve found is perseverance and patience. Consistently sharing my work, experimenting with different approaches, and learning what resonates with potential buyers are all part of the long game. Whether through Etsy, social media, or word of mouth, I continue to refine my strategy, knowing that success in marketing is just as much an art form as painting itself. Read more>>

Rondré “key” Brooks

Last year, I entrusted a General Contractor to oversee the project management of three fix-and-flip properties my company, Property Rush, had acquired. Unfortunately, despite presenting himself as a reputable professional, he misappropriated funds, overcharged us for materials and labor, and ultimately derailed our timelines. His negligence and dishonesty forced us to hold onto these properties much longer than anticipated, costing us thousands in carrying costs and missed opportunities. Read more>>

Navid Amini

The convoluted process of opening a cafe in St. Paul. The rules, regulations and processes are difficult to understanding which impedes people’s abilities to turn to entrepreneurship as a career. Read more>>

Carrie Dietze

Lets face it, starting a business isn’t easy and more than likely will come with issues. First, we had to learn to sew! Neither me or MaryClair’ had ever sewn nor did we own a sewing machine! So we signed up for a private lesson on MaryClairs’ husband’s, grandmothers machine! Our sash pattern is very easy so we pretty much mastered it right off the bat thank goodness! Hurdle #1 check! Read more>>