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.

Rebecca Klein | Co-CEO of TALLsmall Productions in Baltimore

I never realized how closed minded I was until Covid hit. Prior to Covid, my husband, Keith, and I led 99.9% of our communications workshops and private coaching sessions together in person. The personality of each session became fueled by the symphony of each person’s energy in the room playing off each other. We reserved Zoom for rare overseas or long distance private clients. We turned down most live and recorded webinar opportunities, casting them off as dry, impersonal and ineffective. Read more>>

Giselle Roca

Plenty of obstacles came my way when I started my small business, dealing with customers can be a big one. Some people see your work as easy and don’t expect to be charged accordingly. Sometimes when creating a custom piece for someone the materials you picked out don’t work well or you are stuck with a design they requested. I always have to remember to be honest and tell the customer I am having a hard time doing what they asked and if we can maybe modify it or I may suggest someone who can do it for them. Read more>>

Brandon Barber

We were an event driven company. We did 2 events a month for 19 years. Covid hit and shut everything down for events. We went from 9 employees to 3 in a span of 3 months because we didn’t need an events team. Our events stopped so the way we obtained coaching clients stopped. We had to let our coaches go. I made Covid, the government, society and life in general villains, which made me a victim. I went into FREEZE mode and couldn’t move. I felt paralyzed. Read more>>

Spirit Corley

I move by day in Workforce Development Program Initiatives, but I’ve always been creative. Ironically, it was a life-altering auto-immune diagnosis and its challenge and related health issues that drastically changed the trajectory of my life and my innovative career pathway. I didn’t know it at the time, but my illness was a blessing in disguise and an opportunity to dive deeper into what I’m here for as a maker and creative. Gem Scents Aromatics LLC was a manifestation of my life’s purpose, gift of scent, and passion for creating natural products. Read more>>

Laura Bladen

One of the first unexpected problems I faced as an emerging artist was when someone asked me to do a commission painting for them. This acrylic on canvas painting was a gift for this man’s son who had a small hot sauce business. I was asked to paint a representation of his bottles. I painted what I thought was a creative way to display the product. When I showed it to my client, he absolutely hated it! It wasn’t at all what he envisioned. Read more>>

Christian Allain

One of the toughest parts of being a creative/independent artist is staying motivated without seeing success right away. Delayed gratification is key. You can put hours and hours of time and work into something, and receive little to no reward for it. I’ve been in this industry for about five years. You have to develop a thick skin. Read more>>