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.

Patrick Welsh

One of the most unexpected problems was having to large of a team and all the drama that was associated with it. I also would have never of guessed a friend for over 30 years would stab me in the back and secretly plan a departure while lying to my face. It was a very difficult and painful lesson that I learned. Read more>>

Justin Kesheneff

As an entrepreneur in the entertainment industry, it goes without say that ensuring your business has a strong online presence with rich, engaging content that looks and sounds great is paramount to success. I chose to enter this space in mid-2022 just as the wedding and event industry was slowly starting to emerge from the COVID pandemic. What many vendors found was a completely new world and competitive environment nearly unrecognizable to the one they had become accustomed to over the past two decades. Gone were the days of huge bridal expos and weekly “live showcases” to win over interested couples. Instead, the industry had taken almost completely to social media, Google Ads, and popular wedding sites like The Knot or WeddingWire virtually overnight to try and gain a competitive edge. This disruption and market shift is precisely how I knew it was the right time to enter the market. Read more>>

Kexin Zhang

It hasn’t always been a smooth road—like most journeys, mine has been filled with challenges that shaped who I am today. Early on, I faced doubts about my ability, the pressure of people around me who engaged in the same work, and doubts about the theme I want to express, which taught me resilience and the importance of staying focused on my goals. Read more>>

Johnny Hu

Most people see the final wedding film—the beauty, the emotion, the seamless story. What they don’t see are the behind-the-scenes moments when things don’t go as planned.

At one summer wedding in Pasadena, less than 30 minutes before the ceremony, my main camera completely shut down. No warning. No quick fix. I was shooting solo, and it was the first time something like that had ever happened to me. My heart was racing. There’s no pause button on a wedding day—you either capture the moment, or it’s gone forever. Read more>>

Morgan Boyer

One of the most unexpected and difficult challenges I’ve faced in my creative journey came last year, on June 26th, 2024 which was the day my mom was diagnosed with grade 4 brain cancer, glioblastoma. As I sit here writing this, we’re just 22 days away from the anniversary of that day, and without a doubt, it was the beginning of what has been one of the hardest chapters of my life. Watching someone you love go through something so devastating, knowing there’s nothing you can do to stop it … that kind of helplessness is brutal. It makes time feel both frozen and relentless. Read more>>

Brandi Hines-Lee

Expectations vs Reality! As my business was growing, so was my ambition. I had been teaching classes, and my students were needing supplies. Stained Glass supplies are not easy to find. So, I decided to go all in for it and open a brick-and-mortar-Stained Glass Studio to teach, create, and sell supplies. I signed a lease that was 3 times my current rent and moved into a 1,500 square foot space in a town near my home. We had painted, ordered our inventory and was ready to open. I had never sold goods before, so I had to learn how to make a barcode, how to set up inventory, pricing and all the sales tax and so forth. Not everything I tried worked, it took a lot of trial and error. That was not anything I had considered and what would happen next would have me standing in a territory I had no idea how to manage. Read more>>

William Ernster

My biggest challenge has been marketing myself and actively getting new clients. When we first started, we were already firmly rooted in our local gym community in Flagstaff, Arizona. When we started the business and began taking on clients, there was immediate interest and we didn’t have to work very hard to get clients. When we left Flagstaff and moved to the Phoenix area we quickly realized how much local connections drive business, as we had very few in the new area. We also, much more slowly, began to realize how different the world of online fitness coaching was to the personal training side of things. Being predominantly online, most of our energy was going to social media. We didn’t run ads, only relying on organic media and the occasional in-person workshop we would host in our garage gym to generate leads and clients. Read more>>

Pamela Bergmann

I have made the mistake over and over of listening directly to a client and taking their word as law. In many cases, there are more than one client because most often I’m serving a couple in their home or for a special occasion with two sets of opinions and fuzzy idea of what they like at best. Most people who hire a designer don’t have the ability to visualize the end result without experiencing examples because if they did they might not hire me at all. They’d manage just fine with Pinterest, Instagram and their own imagination. Read more>>