As almost any entrepreneur or creative will tell you, unexpected problems are to be expected. Below, you’ll hear some incredible stories that highlight and illustrate the kinds of issues and problems entrepreneurs and creatives are dealing with everyday. It’s not easy, but the silver lining is that dealing with unexpected problems is one of the best ways to develop antifragility.

Jon Remmel

I call unexpected problems or issues ‘curve balls’ and I have come to expect them daily. I even call them out loud when they occur so I can remind myself, “this too shall come to pass.” This morning, it was a server related issue and the Court cancelling a last minute hearing. Curve balls are inherent in any business. Learn to hit the curve ball. Read More>>

Samantha Wilkerson

One particular issue we are currently maneuvering at Annapolis Marine Art Gallery is the ongoing construction taking place on our street. It is part of a large plan to mitigate coastal flooding, implement a park, and build a new welcome center in Downtown Annapolis, Maryland. Read More>>

Cecilia (CeCe) Lehman

One of the most unexpected challenges I faced was acquiring my salon in 2019. At the time, I was content working as a commission-based employee, focusing solely on my clients and routine cleaning responsibilities. When the opportunity to purchase the salon arose, I was the only person in a position to take it, and I decided to step up. Read More>>

Maria Englehardt

One of the most unexpected challenges I’ve faced came during a season of growth — which, ironically, is when I thought I had finally “made it.” My business was busy, referrals were rolling in, and I was saying yes to everything because I wanted to help everyone who came my way. But behind the scenes, I was drowning in emails, projects, and late-night admin work. Read More>>

Shawn Satterfield

One of the most unexpected challenges we faced at Shine Music was the disconnect between the impact we were making and the financial infrastructure needed to sustain it. As our festival grew, so did the expectations around our three core pillars: Accessibility, Innovation, and Community. Each year, we pushed ourselves to expand accessible design, integrate new technology, and deepen our partnerships with disability organizations. Read More>>

Joshua Crawford

So there are two that really stand out back in June 2020 I hit 75,000 subscribers on YouTube after that I received an email to do a product review of a software one of the biggest mistakes I’ve ever done in my career after upon opening the software, I was signed out of my YouTube channel automatically password has been changed and a space X live stream was running on my channel. Read More>>

Dee Bowden

One of the most unexpected problems I’ve ever faced happened early in my career, and it became the moment that shaped everything I do today. Years ago, I worked part-time as a collections specialist for a small IT company just outside of Boston. On the surface, everything looked fine — the company was making sales, delivering great work, and serving its clients well. Read More>>

susie st john

Ugh. Hiring a general contractor (GC) is like giving birth. You’re excited & scared to death. One project (I’m not telling you which project), there was a GC I had hired before who was a new kid on the block, learning their ways, doing great work & committed to client satisfaction. But something went wrong. Everyone wanted to hire him. Read More>>

Rebecca Yates

When COVID hit, everything we thought we knew about running a health insurance brokerage went out the window. Overnight, people were losing their jobs — which meant losing their income and their health coverage at the exact moment they needed it most. The phones never stopped ringing. Read More>>