As almost any entrepreneur or creative will tell you, unexpected problems are to be expected. Below, you’ll hear some incredible stories that highlight and illustrate the kinds of issues and problems entrepreneurs and creatives are dealing with everyday. It’s not easy, but the silver lining is that dealing with unexpected problems is one of the best ways to develop antifragility.
Charlie Gillette
One of the biggest challenges I’ve had to overcome—one that I think so many artists and creatives struggle with—is limiting beliefs and self-doubt. It was unexpected because I didn’t even realize how much I was holding myself back for so many years. Only recently, after doing some deep inner work around my creative and life goals, did I start to see it clearly. Read more>>
Kaycie D.
In my late twenties, I was working a full-time job illustrating at game studio, and I had just started production on my webcomic, “B-SIDE You”. I was drawing and working approximately 10-12 hours a day, seven days a week. Turns out, the body is not equipped to work for that long, and my elbow tendon gave out. Several weeks of no drawing, some occupational therapy, and lots of misery later, I was back at work. I invested in some ergonomic solutions, but did not lessen my workload. I blew out the same elbow AND my wrist three months later – one week after putting in my notice at my job to pursue freelance and comic-making full-time. Read more>>
Sitong Liu
When I first started my freelance illustration career, I realized that being ignored or passed over by potential clients was completely normal. As a recent graduate entering the industry, I found that securing a steady stream of clients was much harder than expected. Even after sending hundreds of cold emails, I often got no response. This harsh reality isn’t something we were taught in school—where good work seemed like the only thing that mattered. But what students see as ‘good’ doesn’t always align with market demands. The only way to change that is by researching industry trends and emphasizing what makes our work unique. Read more>>
Danicea Woods-mcswain
The most unexpected problem I’ve faced in my creative journey is not being able to listen to myself fully. For a while I thought that I knew myself, that I knew what I wanted, and that I was following my true path. However, during that time, I was working in a career that wasn’t satisfying to me, in friendships and relationships with people who didn’t really love me, and allowing myself to be treated in ways that didn’t align with how I truly felt about myself at the core. Coming from an emotionally and physically abusive background, it becomes very difficult to hear yourself. You may not realize it, but you begin to hear and listen to the voice of your abuser. The people you love even share that voice; discouraging you from achieving your dreams, making jokes about your interests, or swaying you to partake in activities that don’t align with your personal values. When I began to realize that I had difficulty listening to myself, I began to strip down to the basics and start from the beginning. This meant I had to begin to viscerally listen to what my body was saying to me at all times. I used to be the type of person who would hold it for hours “until I felt like” going to the bathroom, rolling over and falling back asleep in the middle of the night when I was clearly woken up to relieve myself. I stopped that. I started to question all the things I had been told or had believed about myself prior to this realization, and I’m continuously working to assure myself that only I know who I truly am at the core, what I want to experience in this life, and the extensiveness of my capabilities. Read more>>
Jennifer Von Stauffenberg
One of the unexpected problems I have recently overcome is taking that journey from doing the work and working your brilliance to becoming a business owner and running your business. I didn’t know it would be such a difficult transition and I wasn’t exactly sure how to do it with grace. As a public relations and marketing professional, I rose in my career because of my skills in those areas specifically, so I have had to really step into my business shoes and learn even more in order to achieve my own business goals. Read more>>
Naama Levit
My process is deeply rooted in problem-solving, as is common in many art and design practices. The challenges I create for myself often revolve around understanding and reinterpreting materials—pushing their perceived limits to achieve what seems impossible. I explore how materials can connect, transform, and behave beyond their assumed characteristics, using a method of systematic exploration and analysis. By deconstructing them conceptually and physically, I uncover new meanings they carry as well as new ways of working. Read more>>
Sage Hickam
In 2017 I was involved in a shooting as a police officer. I was the first officer on scene (Deputy technically) and confronted an armed subject breaking in to a home. He unfortunately held the homeowners hostage and eventually lit a fire in the home after the shoot occurred. He killed two occupants in the home and the suspect burned to death in the home. We were able to get one party out. This was the beginning of the end of my law enforcement career. Read more>>
Kiazer Sylve
I can remember the first time I quit my job to paint full-time. Initially it started out great. I was doing pop up art markets, taking commissions and it seemed as if the art Gods embraced me. Then something very unexpected happened. Art became my job, I was now dependent on art financially. It put a terrible strain on my creative process and mind set. The fear of not making money, the competition with other artist, doubt in self became regular. I never wanted art to take on that much responsibility at least not so fast. So I went back to work and now I have a healthy relationship with art making while working a 9-5. Read more>>
Devyn Akers
Once I graduated from SUNY Purchase with a BFA (bachelor of fine arts) in Acting, I realized that there aren’t any more tests or assignments that I have to wake up and prepare my mind for out of wits end. This is the time where all of the countless hours, studying, practicing and training for theatre, goes into full effect. Time flew by in the blink of an eye. Tick tock tick tock. It was, and perhaps still is, overwhelming to hear the clock ticking, staying true to the righteous path of what the true tangible goals are of being an actor, for me. To aspire. To inspire. To be an all time Great actor. Read more>>
Karen Borne
One of the most unexpected and challenging issues I faced in my business happened early in my career when I encountered a high-profile client whose horse had an extremely atypical back shape. No matter what adjustments were made, no off-the-shelf saddle—or even traditional custom options—seemed to provide the right balance and comfort for the horse. The stakes were high, as the client was a competitive rider who needed a solution quickly, and I was determined not to let them down. Read more>>
Joohee Oh
Like many nonprofit festivals, PrideFull has encountered its fair share of hurdles. Specifically, for me as a festival director, one of the most challenging yet fulfilling tasks is crafting the film lineup. While we receive submissions through platforms like FilmFreeway, I also dedicate significant time to exploring international film festivals, seeking out hidden treasures—films that may not have been shown in the U.S. but are a perfect fit for our audience. Deciding which films make the final lineup is never easy, but our programming team thoughtfully curates selections that are powerful and deeply resonate with our community. Read more>>