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.

Roilda Medina

In the early days of our business, everything happened from home. It was just my husband and me. Two dreamers, a couple of laptops, and a handful of small clients. Budgets were razor-thin, but our faith was unshakable. When things finally began to look up, we decided to take a leap and rent our first office, a 100 sq ft executive space. Read more >>>

Danielly Kaufmann

The most unexpected challenge I faced was trusting my instincts when logic said otherwise. In the beginning of 2023, while visiting Luxembourg to finalize citizenship documents, I heard an inner voice repeatedly saying ‘you are not going back.’ I abandoned my return ticket to Brazil with no concrete plans, limited resources, and no close connections. Read more >>>

Sofia Moreno

The food & beverage industry is not for the weak. If your not worrying about rising food costs, new innovative food concepts, social media and equipment breaking down during a rush. You are trying to keep a fun and productive work crew. Unfortunately this career is not for everyone (even though everyone should work in a service industry job at some point in their lifetime). Read more >>>

Shaunna Phillips

One of the most unexpected problems I faced in my business occurred earlier this year and was a very transitional phase for me as a person and entrepreneur. From January-April 2025 I was behind the scenes working with FashionBar Chicago, preparing to execute my first runway collection of vintage pieces/outfits styled by me. Read more >>>

Carrie Blackwell

I started out in the travel business in late 2022 after my husband and I completed a 10 month road trip around the United States. I didn’t know anything about being a travel agent but all my friends were raving about the things we did on our trip, wanting to repeat it. I happened to see an ad on LinkedIn one day. Read more >>>

Matthew D. Hughes

The most unexpected problem I have faced is being a blocked artist. You always hear about how writers and artists get blocked and just can’t think of what to create, but you think it will never happen to you. Read more >>>