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.

Dani Mccoy

Straight out of college and trying to build a creative career is already hard. Straight out of college and diagnosed with a chronic illness is even harder. The starving artist concept was what I was expecting for a few years out of college. I planned on working multiple jobs, networking, spending late nights on projects, and hustling until I “made it.” I did this for a little bit before I started getting sick. I was eventually diagnosed with an autoimmune disease and the bills started rolling in. I knew I would be off my parent’s insurance plan by the time I was 26 so the panic of affording insurance and getting the care I needed with the stability of a career felt needed. I remember sobbing to my partner feeling like I was abandoning my dream. Read more>>

Aliceson Bales

Owning and operating an agricultural business is unique in quite a few ways and in other ways, I suppose, it’s very much like owning and operating any other small business. There are good days and bad days. Times when everything (and everyone) works really well and times when it all seems like it’s falling apart. In early 2020 our processes were like clockwork. We had everything planned out to the day. And then. . . When the Covid quarantines hit they hit everyone. From big cities to small farms. We all remember those days and I’m not trying to rehash them! For example, from our perspective as farmers we went from harvesting animals as needed with a reliable processor we had a long-standing relationship with to delays and bookings up to four years. Yes. Four YEARS. Read more>>

Jen Carmiel

The most unexpected problem I faced while creating my art business is how much this journey would rely on some serious self improvement. When I sought out to turn my creative passion into a business, I thought it would be simple: make art, sell art. But turning my dream into a reality required something very different. It did not require me to “be the best artist who creates the best paintings,” required me to be the best, the most healed version of myself. I grew up in Ocala, FL, drawing nearly every day from the age of 11 years old (I still have the sketchbooks!) and attended West Port High School, a magnet school for arts. So much of my time was spent building the hard skills: learning to draw and paint, and eventually, learning to market and sell those paintings. About 7 months ago, I decided to take a risk. I quit my corporate 9-5, and dedicated myself solely to my art career. I scheduled coaching calls, and had something confirmed for me. I have the skills to succeed, but something was still holding me back. That something was myself. Read more>>

Abby Elise Baker

Unexpected challenges arise constantly in the life of a creative, and even more so when you add the responsibilities of running a business. When those two intersect, you often find yourself navigating some surprising and difficult situations. Creativity is naturally full of trial and error, whether it’s in perfecting your craft or finding effective ways to get your work in front of the right audience. One of the biggest hurdles I’ve faced in my journey has been identifying and applying for legitimate opportunities that can genuinely elevate my career, especially in a world saturated with scams targeting artists. A major issue I’ve encountered is the number of fraudulent ‘opportunities’ out there. Many of these schemes lure artists in with promises of exposure or career advancement, but in reality, they require hefty fees—first to apply, and then more to feature your work in their exhibitions, magazines, or books. It’s a predatory practice that preys on the hopes of artists, who are often some of the most underpaid professionals despite their hard work and dedication. It’s a topic that I feel should be discussed more openly within the creative community, but many artists hesitate to speak out, likely due to fear of missing out on that rare, legitimate opportunity. Read more>>

Terrence Nickelson

As a technical founder, I’ve come to realize that building a software platform is equivalent to being a full-time problem solver, much like a software developer. Every day presents new challenges—whether technical, business-related, or team-based—and it’s my job to figure out solutions. If you can’t solve the problem, your business won’t survive. I’ve faced countless issues, but each time, I’ve not only found a solution but often a better one than the original idea. One significant challenge we encountered was in forming partnerships with local Realtor associations to support the document section of our platform. We faced hurdles ranging from over-budget pricing to a general lack of interest from the associations. Since we were relying on these partnerships, this was a critical issue. However, we discovered a more dynamic way to manage Realtor forms on our platform that removed our dependence on these partnerships. We tested this new approach with real estate brokerages and found they preferred it. This pivot not only removed the overhead costs we would have incurred but also allowed us to scale more efficiently and offer more competitive pricing to our users. Read more>>

Elly Kalantari

Coming from a background in photography and painting, moving into sculptural work was like stepping into the unknown, full of unexpected challenges. When I started working on my life-sized sculpture “A Morphing Moment,” I didn’t know how to cast a full body, sit still for hours, or even what to expect. It was a frustrating and difficult process, but I wasn’t willing to compromise on my vision. I kept pushing forward, step by step, learning through failures and trusting that I’d figure it out. That craving for the unknown has always been a part of my life. In my twenties, I used to travel randomly to unplanned destinations just to throw myself into new situations and see where it would take me. I get bored with the familiar, so I’m constantly seeking out new challenges. That mindset naturally transferred to my art-making. I didn’t know how to sculpt, but I embraced the process, knowing failure was part of it. It’s fascinating how the mind adapts when you trust the process, stay flexible, and just keep going despite the obstacles. Read more>>

Chufei Yang

I once created a group of art jewelry and sculptures made from eggshells for a short-term exhibition. These pieces were fragile but held deep symbolic meaning. During the exhibition, the staff took extra care to secure the works with museum wax and clearly placed “no touching” signs throughout the space. However, towards the end of the exhibition, I was informed that one of the jewelry pieces had been damaged due to a visitor’s accidental touch. At that moment, I felt a wave of mixed emotions—shock and anxiety, especially because the fragile eggshell material required meticulous attention. Despite these feelings, I quickly regained my composure and decided to repair the piece myself. Since I knew every detail of the work intimately, I carefully examined the damaged area and used the appropriate tools and materials for the restoration. The process tested both my technical skills and my patience in managing an unexpected challenge. Read more>>

Chiachen Wang

I began painting in 2016 after moving to California while working full-time in marketing. To explore whether art was the right path for me, I initially started taking Saturday classes at a community art center. After two years of balancing weekend and evening online classes with my job, I made the decision to switch to part-time, which allowed me to pursue art more seriously. A significant part of this journey has been the support of my spouse, who has been instrumental in making it possible for me to juggle work and the cost of living in the Bay Area while dedicating time to my artistic development. With this support, I’ve been able to continue learning, creating my own art, and entering shows and competitions. It’s been a gradual process of balancing work and my passion— not easy, but with this foundation, I’ve been able to navigate both worlds more confidently. Read more>>

Janet Lyn Boswell

The most unexpected problem I have faced in my business is helping trauma survivors to understand that they have indeed experienced trauma because we don’t tend to describe it that way. For many of us, it is “just life.” But we don’t understand how the adverse experiences we have survived continue to affect us – spirit, soul (mind, emotions, and will), and body. Early on, it became clear to me that I needed to explain two things: what trauma is and how it affects how we show up in the world and function. So, I began to share this simple, yet comprehensive definition of trauma: “a deeply distressing or disturbing experience” (Oxford). I stress the word “deeply” with clients, workshop attendees, and podcast viewers/listeners to help them understand the scope of how trauma affects our souls – mind: how we think about ourselves, God, and others; emotions: how we feel about ourselves, God, and others, and will: how we make decisions. So often, we are not aware of what is truly motivating our behaviors. Read more>>

Quincy Harding

As a new, young, illustrator and designer, I sometimes feel overlooked, especially in a market that’s so saturated with voices and amazing artwork. There’s a tendency for people to put you in a box or make assumptions about your work and who you are, whether it’s based on your appearance, your background, or the content they expect from you. In this fast paced world I think sometimes people see the beautiful finished pieces, but they don’t always understand the time and energy put into each piece of art. It can be frustrating, especially on social media where the competition is so fierce, and it often feels like you have to work twice as hard to be seen or taken seriously. It’s also difficult to keep an audience when the content you create changes, especially if people followed you for one particular style or type of work. The algorithms often reward sticking to a formula, so when you deviate from that, there’s a risk of being overlooked.  Read more>>

Nina Hernandez

Last summer workin a wedding in sheer panic my camera would not focus I took the camera completely apart cleaned the lenses, did the WORKS. Still nothing. I prayed over the situation, contacted my great friend Marissa who is also a local small business photographer. She came running to the rescue with her camera for me to borrow. I learned, never to be good to ask for helps and invest in that back up camera. Read more>>

Selena Owens

Well, in 2020-2023 I became fully homeless. I was living in hotels, moving from state to state and even stayed outside once. I was scared, depressed, and just feeling completely defeated. My mental, emotional, physical, and financial lives were crumbling down. It was hard to really live. One day, I was on YouTube watching Street Dance Videos and came across a show called Battlefest. It was an underground street dance battling competition. I was so excited about it after I watched it, I decided to change my whole IG page into a Street dance blog to share the videos and show how excited I was about the artists that I just saw. I started researching different dancers, following, and sharing their dance videos on my page. Doing this really made me feel amazing especially when the dancers would personally thank me for sharing their videos. It was a way to escape my reality and focus on something that I personally enjoyed. Read more>>