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.

Sandy Levine

In the restaurant business, unexpected problems are an everyday occurrence. Roof leaks, POS systems crash, staff calls in sick, and thousands of other challenges pop up on a daily basis. At our places, we’re always trying to improve, which means we’re always looking for pain points to fix. Read more>>

Matthew de Bord

I will share 2 unexpected stories. First, people assume business owners are rich. I quickly stopped telling people I started my own business. I just tell people I work for a food manufacturer. This eliminates the assumption that I am rich. Read more>>

Jana Farrell

There are so many problems we face being a mobile business. My first event ever I was at a farmers market and I thought everything was good to go, lo and behold we are 15 minutes in and things start going awry. Read more>>

Brian Twitty

There are so many moments we encounter along the way that bring divergence and demand improvisation, but I am a thoughtful person regarding the verbiage I use and I rarely reference these as problems, but maybe issues sometimes. Read more>>

Jonathan Martin-Ives

Seeing as how I have taken a path to indulge in mostly sci-fi, horror and fantasy themes, the ability to create has been quite challenging. First of all, I work a regular 9 to 5 (well, actually 6 to 2:30) and only have an old laptop, old Nikon, and a very limited budget. Read more>>

Beau Sheil

I entered the entertainment industry during a period marked by unpredictability, mass-layoffs, and the rise of AI technology in the field. Many industry professionals in animation specifically have been struggling for quite a while. Read more>>

Freddie Crocheron

I am an illustrator with 8 years of professional experience under my belt. I started my career doing children’s books while in college at the Columbus College of Art & Design. At the time that I started finding clients, social media was at an early version of what modern social media is today. Read more>>

Latrell Carter

Diving into content creation is like stepping into uncharted territory; there’s a whole world of challenges waiting for you, some of them being ones you ever even thought about. Being a solo act in my podcasting venture brought its own set of hurdles. Read more>>