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.

Jenna Matlin

As a psychic tarot card reader and medium, I’ve encountered many problems due to misperception or outright bias against my actions. From banks refusing to service me, to businesses expecting that I should work for their events for exposure, to being tested by clients it can be hard to navigate. Read more>>

Ross Theisen

For me, one unexpected problem or reoccurring issue I’ve dealt with in my creative journey, really is just learning that burnout is real, and inspiration can come and go in waves. I’ve realized my creative brain, while always thinking, is not always working when I need it to, for something specific I may want to do. I would often beat myself up over this, thinking I always needed to be “on the grind” and hustle constantly. Read more>>

Antonio and Amber Hall

When working on trying to get the business going and going continually, the two things we thought were the hardest were: 1. Lack of knowledge, 2. Doing it yourself, without help. Since my husband was single handedly taking care of the business in producing a whole size run of one of the items from the collection. Without the proper knowledge to get through the full process of designing and producing a garment it makes a breeding ground for a lot of mistakes. Read more>>

Alexa Colyer

What I originally thought would be the “easy” tasks of launching, hosting, and running a podcast turned out to be some of the hardest – and vice versa. When I first started Virtual Coffee, I figured it’d be fairly easy to keep up with posting on Instagram, Facebook, and other social medias. Since I already did that for my personal accounts, how difficult could it be to do for a second account? Read more>>

Sheila Wysocki

Wysocki became a household name in the private investigation world after she helped solve the cold-case murder of her college roommate, Angie Samota, more than 25 years later. Only wanting to figure out Angie’s case, Wysocki was ready to close the case on her PI career. However, that’s when letters from around the world came pouring into her inbox begging her to help their families who had mysteriously lost a loved one. “I just couldn’t say no,” recalls Wysocki, “these families were in the same position I was after Angie’s death and I knew I had to at least try to help them.” Read more>>

KingDarius TheGreat

In this industry, unexpected problems are almost expected. You learn that rather quickly in this business and the most successful individuals prepare themselves for it mentally because it is inevitable yet makes you a stronger person and business based on your troubleshooting abilities. With that being said, I’ve had my fair share of unexpected problems in the music industry, but one definitely stands out because it hurt me personally beyond the business standpoint. Read more>>

Nick Nikkhah

Just like most businesses around the world, the COVID pandemic was an unexpected problem for our business. Until that moment, our key business was scanning humans and pets and then turning that scan into a 3D file which would then print in full color creating a lifelike figurine of the person or pet. Once everything was shut down, that basically ended that portion of our business and all of our prospects as most of what was on our calendar was related to that business.  Read more>>

Zenobia Williams

I’m an officer during a time where when you turn on your tv we are headline news. The biggest struggle? Being a black police officer in today’s society! The biggest problem is wanting to remain true to who you are, be proud of what you are, and effectively do your job. This is tough when you know you are a good officer and you wear this uniform for all the right reasons. I have asked myself over and over again, is it all worth it. It’s a feeling of having the weight of the world on your shoulders. How can you positively impact those around when you are looked as the enemy? Read more>>