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.

Dale Fielder

I entered 2025 with hope and optimism for a new life. For over 40 years, in addition to a full-time career in music, I worked full-time as a corporate office worker, primarily to finance my independent jazz label, Clarion Jazz. In my last 10 years, I began working for myself, contracting as an ADP Payroll Specialist. Read More>>

Billie Asmus

As I was building my company and launching my product into the market, I faced numerous unexpected challenges that I wish I would’ve had more knowledge around when first starting out. For example, when I first started Repaint Studios, I decided to partner with some business advisors that had experience in the product industry, manufacturing, wholesale, etc. Read More>>

Jordon Alexander

This isn’t unique to us, and it certainly isn’t unique to food trucks, but it shows up in very specific ways in this industry. Food trucks are often viewed as simple, flexible, or low-overhead by nature — a kind of “just show up and sell food” model. Read More>>

Abigail Schimke

A very unexpected problem that our agency faced was one that arose the month of our Grand Opening in January 2020…the COVID pandemic. During a time that we anticipated to be planning many new exciting trips, we were instead cancelling them. Read More>>