Having to overcome unexpected problems is a hallmark of entrepreneurship. Almost every business owner, artist, maker, and creative we know has had to deal with countless unexpected problems that arise in the journey and so we asked some brilliant folks from the community to share their stories of the unexpected problems they’ve faced along the way.

Simone The Mastermind

My family and I (my two children and my grandmother stays with me) became homeless just two months before the expected launch of my marketing program. A marketing program that I have become so passionate about, that I decided to eliminate all other services that did not relate to it. Read more>>

Ashley Fajardo

I think some of the most unexpected problems I’ve faced has to have been during the entirety of the Covid-19 Pandemic. It was such an unknown and difficult time for us all as human beings losing loved ones, the fear and anxiety of the sickness and the challenges we would face as small business owners. We went through a chocolate shortage at one point, eggs were literally Bananas! Shortages and delays on supplies. Read more>>

Vincenzo Irrig

During my last semester of college, one of my professors asked the class if we were to adapt “A New England Nun” by Mary E. Wilkins Freeman into a movie, what changes would we make, what moments would be essential to include in the adaptation, and who would we cast. Like most people, I liked watching movies, but until then, I hadn’t thought about how to write one. Read more>>

Zhanna Kompaniiets

I have been a florist for 7 years now. As a purposeful and creative person, I always wanted to grow in my career. My husband and I decided it was time to start our own business. An idea was born and we started to act. The most important technical element in a flower shop is the refrigerator. Having designed it, we found a manufactory that will create it according to our drawing. We ordered everything we needed to start a business. Read more>>

Victoria Rios

“Success is not final, failure is not fatal: It is the courage to continue that counts.”- Winston Churchill. One of the biggest lies that our society tries oh-so-hard to ingrain into our brains from a small age is that success and prosperity is available to anyone who works hard. This isn’t true. I’ve learned this both through anecdotal experiences as well as from studying others. See, the thing about life it proves itself unforgiving time and time again. Life has no empathy, and it doesn’t slow down for you. Read more>>

Kemi Tijaniqudus

I rented a food truck from someone I found on Craigslist and the first month in, a few weeks later the generator got stolen. So I was forced to rent another generator from Home Depot until I could afford a replacement. Not so long after that experience ,the food truck started having issues , from major oil leaks, to having multiple mechanical breakdowns. Read more>>

Drew Smercina

When moving a boat several thousand miles everything is both unexpected and constantly changing. I am constantly adapting to changing weather, schedules, and mechanical breakdowns. The goal is always to keep the boat moving as efficiently as possible towards its destination. On deliveries my day-to-day is full of contingency plans and quick decision making to keep the boat and my crew safe. Read more>>

Barbara Claypole White

The author life is full of incredible highs and incredible lows. It’s impossibly hard to find an agent and snag that first pub. deal, and even harder to stay published. Within two weeks, my third novel, which I had written to contract, was dumped by one publisher and sold to another. My first publisher told me there was no interest in the story. Read more>>

Chuck Hailes

After 12 years establishing a brand, building a base of patrons and friends, then managing to survive a global pandemic, a founding member received an opportunity that would make him unavailable for the foreseeable future. The situation was existential to the project. Read more>>

Betsy Duffy

Part of being an entrepreneur is being nimble. Gezellig opened its doors in June of 2019. We were Read more>>

Noelani Getfield

Throughout my 3 years as a hairstylist, the most unexpected problem that I have faced is communication. Ever since I was younger, I was always the girl who loved to talk and I mean LOVED to talk. I attended every celebration, every gathering, and I can humbly say that I was the life of the party. Read more>>

Caroline Nikolaus

This issue might not be entirely unexpected, but I never seem to have enough money to produce music to the quality that I want. Hiring people to build an album (producing, mixing, mastering, distributing, paying session musicians) adds to a colossal amount of dough. I want to pay for these services because every creative deserves to get paid for their work. I know I have done my share of free or reduced-priced jobs because “it is for a friend.” Read more>>

Jessica Avery

As a small business owner in Tucson, Arizona, doing pop up markets is the best way to get your product and business name out there. I started doing pop up markets in April 2021 and instantly fell in love with getting to know other makers, entrepreneurs, and people in my town. I quickly bought a tent and got to work on my set up, ready to sign up for more markets. Read more>>

D. Tai Tai

My art making process crosses multiple media. It usually begins with a performance idea. The idea explores how texture and weight of the body parts interact with each other and the spaces around them. With my 15 years of movement training (contemporary dance, weight lifting and Iyengar yoga) the intricacies of those relationships and depth of emotional connection inspire a desire to solidify these ephemeral qualities into objects for others to project and contemplate on. Read more>>