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.

Jessica Qian

As an art director, unexpected problems are almost inevitable in the creative process. One of the biggest challenges I’ve faced is managing last-minute changes and unforeseen circumstances, such as an artist needing to reschedule or the weather not cooperating with a planned location shoot. Read more>>

Laura Kendrick

The most unexpected problem I ever faced? Hating my job from day one. And that’s saying something, considering I’ve always been a word nerd. My high school heroes were Sam Seaborn and Toby Ziegler from The West Wing. Yep, I was that kid. Naturally, copywriting felt like the perfect fit. I mean, I love writing. I’m obsessed with the sheer power of words. And buyer psychology? That’s my version of a beach read—can’t get enough of it. Plus, I was good at it. So why did I hate it? Read more>>

Jeff Vande Zande

One thing I didn’t really think about while working on my first novel was the significance of marketing and promotion. I don’t know if I was naive, but I guess I assumed that either people would naturally find the book or the press would be responsible for marketing. In my mind, writing the book and finding a publisher would be the biggest challenge, but I soon learned that marketing was the biggest issue. I never was able to get an agent for any of my six novels and, as a result, all of my novels have come out from small presses. Read more>>

Hady Mendez

I had been thinking about starting a speaking side hustle for years. When I got laid off in early 2023, I finally decided, “This is the moment.” Despite having no entrepreneurial experience, over 25 years in corporate had taught me the basics: I needed a product or service, potential customers needed to know I existed, and every customer interaction had to be an opportunity to deliver. Read more>>