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.

Priye David

Let me talk about two problems I faced running my business. In the spring of 2021, I went to a different city (Kelowna) for a friend’s wedding. I wasn’t the photographer for the event, but I went with my gear. Cameras, lights, lenses… the whole nine yards. Read more>>

Bianca Fitzpatrick

When we experience professional problems in our careers, although sometimes challenging – we learn to pivot. But when we experience hardships in our personal lives that bleed into our “professional” lives, it feels a lot more challenging to conquer. Read more>>

Ashleigh Valero

In pretty much every business book I’ve read, especially in starting a physical products business is to expect delays, and that the process will take twice as long as you plan. Read more>>

Jermaine Clark

I wouldn’t consider this a problem as much as a learning curve. In the initial stages of transitioning to a full-time artist, I found myself lacking structure. Having previously balanced a corporate job with my artistic pursuits, my time was meticulously planned. Read more>>

Tammie Lowe

The biggest unexpected problem I faced was building my business during COVID-19. At the beginning of 2019, I had only closed 3 real estate deals and thought to myself that I had failed myself. Read more>>

Steven Johnson

As a management consultant with several years of experience guiding businesses through the murky waters of growth and change, I’ve encountered a myriad of challenges that many companies face. Read more>>

Jimmy Wildcat

At the beginning of 2015, I had just turned 29 and I was beginning to feel stuck in my life. Six years earlier I had earned my bachelor’s degree in Radio, Television, and Film, moved to Austin, and spent the next few years building a modest career as a songwriter and live performer on weekends and evenings, outside of whatever day jobs I could find that would indulge my requests for time off to tour and play shows. Read more>>

Akos Gabossy

The COVID-19 pandemic marked the most unforeseen challenge in my business career. Our stores were forced to close for an entire year, leaving us grappling with the daunting task of surviving without any revenue. Read more>>

Theresa Carpenter

I believe we all must learn how to navigate challenging relationships. I grew up in an environment that I now understand as “toxic” so when entering the workforce, I was not prepared to handle particular challenges. Read more>>

Anais Timm

I haven’t had unexpected problems yet, but as an entrepreneur I have some challenges. Therefore, it is not easy to balance responsibilities such as being a balloon artist photographer, senior caregiver, nurse student, wife, and take care of 3 adorable german shepherds that demand attention. Read more>>