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.

Warda Youssouf

One of the most unexpected challenges I faced in my creative journey came earlier this year, during a one-month all-women and non-binary film challenge I joined in February. I entered it with the intention to have fun, I deliberately leaned into identity politics, cast women in all major roles, and ensured the rest of the cast were BIPOC. Most were white though, and the project was titled White Diet, a personal satire based on my immigration story to Canada. Read more>>

Kim Duncan

I got retired by covid in 2020. In 2022 I had a heart attack and in January of 2023 I had a stroke where I could not remember how to get home from a block away from a house I lived in for 36 years. When I could finally make decisions for myself, after almost 2 years in clouds , I found I could paint and now I am an artist that enjoys life after life. My wife divorced me after 46 years because of the dimensia l have from agent orange from Vietnam and Thailand. I realized, when I got 100 percent benefits because of the pact act, I get to strat my all over!!!! I’ve done a couple of art fairs and found a spiritual companion. Read more>>

DAngela Chase

One of the most unexpected problems I faced was actually finding clarity in my own voice—which is ironic, because that’s now the core of what I help other women do.

When I first started my business, I was doing “all the right things.” Posting, promoting, showing up—but it felt like I was building someone else’s brand, not mine. I was blending in, not standing out. And it wasn’t because I wasn’t capable—it was because deep down, I hadn’t fully owned my story yet. Read more>>

INSÉKTA

Having torn my ACL while rehearsing for a show on February 8th, 2025, left me no option but to sit with myself and radically accept my new reality—one that demanded patience, care, and real rebuilding. Not just of my right leg, but of my emotional and psychological landscape.  I’m grateful my husband/partner truly rode the wave with me—because fuck, what a ride—and so did many loved ones, both blood and chosen family, who uplifted my spirit when I saw no light. Read more>>

Chris Hiltz

Our business was on a path of explosive growth, expanding rapidly for years. But this success was built on a flawed foundation: we reinvested everything to avoid taxes, never truly owning our bottom line. The decision to scale brought it all to a sudden, grinding halt.

The fallout was brutal. The hardest moment of my career was letting go of half our staff—people I had personally hired during our boom years. In the wreckage of our old model, I confronted a hard truth: I lacked genuine financial ownership. Read more>>

Cindy Morgan-Jaffe

The unexpected challenge I faced as a dedicated and passionate entrepreneur was underestimating the power of money mindset. By age 40, after building several businesses but struggling to truly thrive, I recognized that a lifetime of unconscious beliefs and behaviors around money was holding me back from the success I envisioned. This realization led me to develop the 7 Principles of Positive Money and write my book, which now serves as the foundation for the Positive Money Club—a supportive community helping women 50+ get financially fit and align their money with what matters most. Read more>>

Lillia Sanders

My first company was founded when an angel investor provided my former husband and me with the funds to launch our home healthcare business. I had to produce forecasts and projections in my business plan that I presented to him. After receiving the funds, he asked for the financial statements to evaluate the company’s financial health and offer advice. Our company was starting to gain momentum, and I wanted to share the numbers with him. The only problem was that I couldn’t, and I felt ashamed. Why? Because my husband at the time was embezzling from the company. Initially, when starting a business, you have to figure out many things, such as taxes, payroll, and the appropriate charging rate. However, when you can’t explain your numbers because money is missing, that was something I didn’t anticipate. In that moment, I felt immense shame, anger, and a sense of irresponsibility, even though it wasn’t my own doing. Read more>>

Dre Olivas

For years, music was my creative outlet, a source of joy and therapy. But a few years ago, that changed. What once brought me peace began to cause stress. I felt unaccomplished, lost in direction, and uninspired. Eventually, I stepped away from music for months, unsure if I even wanted to continue. Read more>>

Derek Roura

Growing up, I lived in a tight-knit household with my two brothers, mom, uncle, and grandma. Although we couldn’t afford much as a single-parent household, my mom still encouraged my interests, and she invested in my music career by buying me a cheap upright piano on Craigslist—back when that was more of a thing. Of course, without enough money for music lessons, I turned to YouTube University to learn piano while in middle school and taught myself all my favorite pop, classical, and video game tunes; I wasn’t going to let any financial hurdle obstruct my path to realizing my dreams! Read more>>

Susan Hensel

Sometimes, the vicissitudes of living in a human body can overwhelm your creative work life.

Case in point: I had what I now refer to as “a series of unfortunate events,” spanning three and a half years that put me in a wheelchair for a while and forced a studio/home safety move! It started with spontaneous tendon tears, followed by a serious ice accident and a subsequent joint replacement to regain near-total mobility. Read more>>