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.

Arianne King Comer

Two Unexpected problems/issues:

One: Creating a line of Wearable Art for the National African American Museum that was ‘one of a kind items that sold out quickly but yeilded low compensation.

Two: Family funds for a IBILE Artist Sanctuary dissipated due our naive consciousness to unchartered territory for a 1031 Exchange that did not happen. Read more>>

Karli Sherman

After much back and forth I decided to listen to the advice of those in my own speaking industry and start my own business. Worried with thoughts like “what if I fail” I was met with messages of “but what if you FLYYY!” So I launched my business publically in February of 2020. Then I quit my full time job at a university leaving a decade long career in higher education. My last day with the university was March 2, 2020. …And the world shut down 2 weeks later. So there I was with a fledgling business in a global pandemic. Read more>>

Renato Lerner

One of the most unexpected and challenging problems I faced in my business occurred during my time in Angola. This situation tested my problem-solving skills, resilience, and adaptability in a high-stakes environment.

The Backstory: The Crisis in Angola
In 2008, I was invited to manage a construction company in Angola. At that time, the country was recovering from a long civil war, and the construction industry was booming due to the demand for infrastructure and housing. The business potential was huge, but the challenges were equally formidable—logistics were complicated, bureaucratic hurdles were extreme, and the workforce needed extensive training. Read more>>

Dasia Janea

As a creative most of us use our gifts as a coping mechanism to process the hardships of life. Creativity as a form of release. I know i did all throughout middle and high school. It kept me sane through my raging ever changing hormones and severe mental diagnosis before my college career. Read more>>

Mariela Batista

Emigrating is like jumping into the unknown with one suitcase full of dreams and another packed with uncertainty. When I arrived in the U.S., I knew I wanted to start my own business, to build something from the ground up. What I didn’t know was how many obstacles I would face. Read more>>

Melina Finkelstein

As an owner of a boutique rug brand that spanned decades I was used to dealing with supply chain issues that arose by way of trade sanctions. In 2011 I traveled to Vancouver, Canada with my family to look for an alternative distribution country after Obama placed trade sanctions on Iran that would force my rug business to close in the US. Shortly after we visited Vancouver we moved to Konya, Turkey to change the manufacturing country instead. When those same sanctions were lifted we reopened our workshop in Iran and returned to the Bay Area. Any small business person can imagine the anxiety of the struggle to remain in business when it feels like the rug is being repeatedly pulled from underfoot. Read more>>

Ameia Mikula-noble

The biggest and most unexpected challenge I faced in dance was learning how to create and show my own work. Stage fright was not something I struggled with, I have always loved performing in front of people. As a child, I would put on shows for my friends and family; playing the piano, singing, and dancing. The caveat was that everything I performed was already made. Famous composers, pop artists, and even friends had laid the groundwork for my performances. Read more>>

Femme Future Perfect

Starting out in Hollywood over the past 5 years, there was so much talk of gender inclusivity that it came as something of a surprise that genre — specifically horror, action, and sci-fi — is still seen as a largely male space. As female/non-binary screenwriters, we came up against an industry that wanted us to give them rom-coms or low-budget women-in-peril thrillers for streaming. None of us are interested in that route. We love watching genre stories, so we want a chance to tell them! Read more>>

Olander Wilson

Falling behind on rent for YEARS! Literally. It was only through the grace of God that we were able to stay in that Hamilton Terrace apartment in Harlem on 145th street for that long. After literally 2 years behind on rent, being in housing court almost bi monthly, we were finally evicted. NYC had my possessions of all our valubles and I was homeless living on the streets, gym, trains and after 3 weeks – I lived in my girlfriends (at the time) car. She still does not know til this day that I slept in her car. Moving to NYC to pursue a dream and being derailed by homlessness was the biggest, most unexpected issue that occurred during my early transition in nyc. Read more>>

Suzanne Cook

I’ve always been a fan of having a website, so when we got into breeding high quality Frenchton Bulldogs, an amazing website was TOP of my list.

Years ago, it was fairly easy to sell puppies – many websites allowed you to post info on your litters, and 12 years ago when we bred boxers, I had a waiting list with 50 names on it. Read more>>

Aundrey Jackson Jr

Two and a half years into business, my five year old daughter was diagnosed with leukemia. At that point my whole life came crashing down. It was hard for me to work, let alone have the mental capacity to be around other people besides my daughter. I wasn’t sure what would happen with my business and honestly didn’t care. Thanks to the support from my staff, clients, and community, I was able to keep things afloat. Read more>>

Karen Exemar

One of the most unexpected problems I faced in my business was when my boutique’s Instagram page suddenly stopped growing after months of steady engagement. In the beginning, I was seeing great traction—my audience was engaging, sales were coming in, and my posts were getting shared. Then, out of nowhere, the engagement dropped significantly. It felt like I was posting into the void, and no matter what I did, the algorithm just wasn’t pushing my content. Read more>>

Jeremiah Conley

One of the biggest challenges LuckyMoonRecords has faced in the Arizona music scene is music-based discrimination. Many venues and promoters associate rap and hip-hop with violence, despite the genre’s rich history and cultural significance. As a result, some venues refuse to book hip-hop acts while favoring genres traditionally associated with the Western U.S., such as rock, punk, grunge, and metal. Read more>>

Honey The Model

With me being a nontraditional model, my height and weight has caused issues. I’ve met with some designers that cater to all sizes and some that only work with taller/thinner models. I’m more on the medium height and curvy side of Fashion. Read more>>

Brandon Rivera

This question is somewhat difficult to answer because not only have I experienced many unexpected problems, but to this day, I still do! So it’s hard to pin-point a single one, but one thing I tell newer entrepreneurs, or just people in general who are curious, is business (for me, at least) feels a lot like a show called Silicon Valley. I highly recommend it to everyone, as it’s a hilarious show about ‘tech-bros’ in Silicon Valley, but I particularly recommend it for people who want to start a business, or have recently started a business. Read more>>

Kim Duncan

One of the most unexpected challenges we faced came just as our dream was coming to life. My significant other of 16 years, Bretton, and I had always wanted to own a small business together. With his fine art background—having studied fine art and art history—we envisioned creating a space where we could bring artistry and craftsmanship into people’s homes through fine art printing and custom framing. We spent 1.5 years meticulously planning, saving, securing a retail space, investing in top-tier equipment, and building out our studio store. Finally, in December 2019, our doors opened, marking the beginning of what we hoped would be a thriving business. Then, just 2.5 months later, everything changed. Read more>>