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.

Paul Newman

When you have a unique presentation that can not simply be put into a category, genre, or checkbox; you have an interesting problem. How do you sell someone on a show that has to be experienced to be understood? I have been a musician/variety performer for the last 20 years. I am the man you hire to engage any audience who might not actually be ready to be engaged. I utilize a variety of circus skills, street performer intuition, and musical instruments to win over a room and connect with folks of all ages and backgrounds. I am up for the task of sharing in that unique transitional space with strangers and be the catalyst to inspiring everyone involved to collectively create the next moment. Read more>>

Brandon Smith

My ocd can get in the way one time I was playing a show then my ocd took over I had to play a song over and over and over again that was very embarrassing after that I was in a bad place after coming my self down I began to remix more I started to feel better you can hear all that stuff in my music Read more>>

Cynthia Grilli

Absolutely.  Like everyone else on the planet, when the pandemic hit there was an immediate need to adapt to an unforeseen, catastrophic event. For me, it meant finding alternative ways to teach classes that require in class participation. At first it was unfathomable, how one could teach figure drawing and painting without being in the same room with anyone. Teaching online meant trying to coordinate a with a model posing in their bedroom, and students huddled over their drawing boards in tiny spaces with little siblings zooming in the same room. All while drawing and demonstrating myself, hoping that the internet connection would be solid enough that I wasn’t freezing on screen every few minutes. Read more>>

Natalia Moscoso

When you’re on set you have to be prepared for any unexpected problems. It’s Murphy’s Law. No matter how prepped. you may feel, you must be prepared for the unexpected. Some unexpected problems that I’ve occurred on set have been things like, a camera no longer turning on, talent running hours behind or dropping out day of, rain, client changing shots, location change day of, and worst of all , no parking. Read more>>

Lynn Schwarz

While I certainly don’t want to suggest that the struggle of COVID-19 was my own personal mountain to climb, instead of acknowledging that it was a worldwide crisis that universally shut down everything and forced the whole human population to stop short and take stock of everything, all at once, I thought I’d describe how it specifically challenged me as the booker of a live rock & roll music venue. Read more>>

Victoria Pierce

As a producer, unexpected issues and problems arise all the time. I’d say that half of the job is pulling from past experiences where similar issues may have occurred, and the other half is encountering new problems and learning how to solve those. When I try to explain my job to people, I often tell them it’s like being a parent, but on a film set. Producers are in charge of everyone’s safety (hiring the right people and right crew members to ensure everyone will be safe, making sure the location is safe), you also hire all of your crew members and make sure you have a good team to carry the project, you pay and feed everyone, and more importantly: you have to manage everyone and ensure everyone is getting along at all times. With all of these moving pieces in mind, no wonder problems and issues arise quite fast! Read more>>

Marianna Israelyan

The most important step is to recognize that there is a problem, because any problem can cause anxiety. You’d be surprised at how many people will try to ignore it or put it off instead of dealing with it. I’ve gotten into the habit of writing down a list of problems that might reoccur. If you can, please find some benefit or opportunity in the problem; you have a better chance of working on it. For example, when I first got my real estate license, I agreed to host an open house for one of the experienced agents. He told me that all the buyers who came to view the property that day belonged to you. I, being naive, thought how great this agent was, but the truth was that when a house is on the market for a long time, the chances of a potential buyer are very slim. However, I, as a new agent, was enthusiastic, and I posted the open house all over my social media. Read more>>

Ashley St John

The most unexpected problem that I had at the very beginning of my business was the anxiety that came from posting my work publicly. I had a hard time sharing my work on social media because I was so scared that people would not like it. I would almost be in tears when I shared it and often I would delete it immediately if it didn’t get any likes or shares. Ironically, it was the overwhelming amount of support and people who liked my work that made me get over that. Now, I can’t wait to share my work with the world. Although I am still a perfectionist who pays attention to every painstaking detail, I guess it’s safe to say that my anxiety has been replaced with OCD. Read more>>

Dawn Brodey

I will share the story of how I graduated with a Theater Degree two weeks before 9/11. This means that I began my creative career at a time when the value of entertainment and humor was in total re-evaluation. My navigation of that terrain and commitment to continue to pursue a creative career, despite how different it was compared to what I had prepared for, is a big part of why I am where I am now. Read more>>

Mimi Botscheller

After many years as both an artist and educator I became seriously sensitive to the oil paint materials I used both in my personal artwork as well as while teaching painting. The college I worked for had inadequate ventilation and I developed debilitating headaches from the paint and mediums I used. This caused me to seek medical attention and the Dr took me out of the classroom to see if the headaches persisted. They in fact stopped as soon as I distanced myself from the source of the migraines. Read more>>

Donata DeNicola-Barrett

I’m sure my story resonates with many people in the food industry, regardless where you are positioned in the food chain. I was out of the country and had just returned on March 15, 2020, when my children called to tell me to close our family business asap. Although I had been following the news and covid related articles, this was a new phenomenon for me. I had never closed for more than a snow day in the last 42 years. What could they possibly know that I didn’t. I chose to stay open until then gov Kate Brown ? shut us down on March 17 only to be told we could still have take out and delivery on March 18. My head was spinning. What would this new business model look like, and how could I make it profitable, keep my many employees known to me as my pack. Read more>>

John Vilardi

In the summer of 2001, a car accident changed my life dramatically. It resulted in serious injuries, requiring back surgery and prompting me to reevaluate my future. The aftermath of the accident was physically and emotionally demanding, forcing me to confront my limitations and face an uncertain future. Despite these challenges, I refused to be defined by adversity. I returned to school, discovering my passion for 3D animation and modeling, marking the beginning of my journey towards innovation. Read more>>

Arielle Zadok

While Intimacy Coordinating has become a bit of a buzzword as of late (for good reason), it wasn’t until 2017, after the #MeToo movement, that anyone was giving real thought to the process, power dynamics and vulnerabilities that exist when creating scenes involving nudity and / or simulated s*x. Actors were left to advocate for themselves in an atmosphere where “no” wasn’t truly an option, and other crew members (mostly Assistant Directors and Costumers) were left to do what we could to support the actors, handle the additional needs and keep the day on track. I was one of those crew members. Read more>>

Ryan Walters

I was working full time as a theater technician. I had the chance to work with all sorts of performances, music, theater, dance, and more. In 2020 I was working as the technical director for an internationally touring dance company. When the pandemic began, I lost all prospects of work, and lost my sense of home on the road, and the family I had created with that company of creatives. Read more>>

Lori Escalera

Whew! Retirement age sure rolled around quickly! Not much chance of that happening anytime soon… but I have switched from taking “all” work to the projects that feed my soul and those that contribute to the well-being of others. Grateful, to continue maintaining my optimism in the face of difficult circumstances. Read more>>

Will Jackson

One of the biggest problems I’ve encountered as a freelancer and business owner is managing my time. I used to find that certain tasks would consume me. I would often obsess over certain details that often were not worth the time investment. One of the primary reasons that I’d allow my self to delve into this was because (I think mainly subconsciously), I assumed I had more time in my day to day than I did. I would often think ‘ahh that other task can wait, I’ll probably tackle it tomorrow”. Read more>>

Kyle Mayfield

In November of 2022 after battling more and more health issues I was diagnosed with a rare condition called EDS and it changed everything. There are so many problems that come with this diagnosis, but it finally explained why my joints are painfully shifting around at their own pace. I have to wear several different braces to keep them in place- wrists, knees, shoulders for while I sleep, neck, and my lower back. It is so bizarre to me that I will experience 10/10 pain and have to my hand and actual hold my discs in place. I am no longer able to drum, I currently cannot hold anything remotely heavy, so I cannot play guitar. Read more>>

Brit June

Gather ’round, dear reader, for I’m about to regale you with a tale of entrepreneurial misadventure that’ll make you laugh, cringe, and applaud our tenacity all at once. Picture it: a few years back, my business partner and I found ourselves in the clutches of what we now fondly refer to as the “Threads of Fate F*ck Up 2018.” You see we’d birthed two distinct, yet eerily similar products. Imagine twins separated at birth, only with packaging instead of cribs. These items were our babies, born from the same creative womb but dressed in wildly different outfits. We couldn’t contain our excitement as we sent a massive order hurtling towards our e-commerce site and international brick-and-mortar pals. Read more>>