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.

Jim Lippens

I worked 15+ years in production environment. My boss asked me if I wanted to become a plant manager of 108 employees. That time I had 1 direct report. I agreed. On my first day I was asked to fire 27 employees, and the plan was to fire them all in max. 3 months, as the department was loosing money since 30 years, there where accidents, violence, quality problems, absenteeism … etc. When I had to bring the message to the first 27, I saw the fear in their eyes. I could not live with this (abuse of power and injustice) and decided to do all I could to save these people’s jobs. Read more>>

Cristall Harper

Burnout is a devastating situation for a creative person. I recently came out of the longest burnout period I’ve ever had as a painter. It was both unexpected and stressful. I resolved it by leaning into rest. Even if I wasn’t actively painting, I was storing feelings and experiences away that come out later as art. I also talked to a trusted friend and my husband. I slept. I cleaned my studio. I went through references. And I started with a small, play project. Then I did a big painting, another big painting, and I feel like I’m back in the groove. Read more>>

Aaliyah Nelson A.

On the road to success, I been faced with many challenges . I was forced to fight for trademark rights against with one the biggest names in the fashion industry. I was so scared and confused. Why would they think I’m a threat to them ? LOL . But they so the potential of my business and how big it could become. I learned right then , Intellectual properties are so important . You have to invest in your business . After I won the case, I knew God had put this calling on my life to to dress and impact others. I am focused on creating generational wealth for my family. My only regret is not trademarking my business sooner. Read more>>

Theo Preiswerk

Dealing with people in the creative industry can indeed be challenging due to the presence of egos and poor communication. Managing these dynamics requires a delicate balance of understanding and effective communication skills. It can be a challenge to navigate through different personalities and ensure everyone is on the same page. One specific instance that stands out is when I transitioned from Germany to the US. The cultural differences and communication styles posed initial challenges. I had to adapt to a more direct and assertive communication approach, which was different from the more indirect and consensus-driven style I was accustomed to in Germany. Read more>>

Diana Griffin

Well, COVID was a big one for everyone and then trying to get back into the sellers’ market was difficult so I transitioned into teaching. I currently teach at San Diego Oasis (55+ community) at Grossmont Center and Rancho Bernardo. It is incredibly fulfilling for me to instruct on a medium that I love and sharing that with other students. I have quite a few regulars that attend my classes and I enjoy watching them put their glass pieces together, everyone so different, creating their own art pieces. Read more>>

Honesty B

Navigating the entertainment industry as an attractive Black woman presents its unique challenges. While beauty can come with its advantages, it becomes problematic when individuals fail to see beyond appearances. This issue extends to the persistent unwelcome advances, unprofessional behavior, and a lack of proper channels for recourse. Unfortunately, such behavior has become normalized within the industry, making it even more challenging to address. Moreover, the presence of women who are willing to compromise their integrity to advance further perpetuates this problem. It’s disheartening that talents, intelligence, and potential contributions often take a backseat to one’s physical attractiveness. Refusing to succumb to these pressures can sometimes lead to the withdrawal of support from those in positions of influence. Read more>>

Meghan Jaskinia

My most unexpected problems, or speed bumps, were my own obstacles of life. I had an idea of what I wanted my business to look like, then life happened. I continued to go through these experiences and they would guide my to a completely different path. A spinal cord lesion brought me out of the career I went to school for, a detour in a different career path led me to taking the leap to creating a wildly different life purpose than planned. Read more>>

Jesse Blount

One of the most unexpected things that I came across when I started podcasting was that I didn’t know I was going to be a podcaster. My very first idea for an entrepreneurial adventure was to be a karaoke DJ and a music DJ. When I started that adventure, I had nothing. I had no music, no speakers, no microphones, nothing. So I decided to open a GoFundMe page and hope that people would just give me money. Obviously, that didn’t work out the way I hoped. I think I only got a couple hundred dollars in a couple of months, and that was probably my mother giving me a few dollars just to make me feel better about what I was doing. Read more>>

Sarah Harris

When running your own business you will have unexpected challenges. There is a risk of failure and that fear is what can keep us in the safe zone, in the comfort zone and can sometimes even paralyze us. Taking on short term rentals as my new business comes with many challenges as I like to say instead of problems, I like to say challenges to change mindset to conquer that challenge and create a solution base outcome. Everything is about how you look at it. How do you envision yourself worth, your business ability to solve the services you offer. You have to critically think about these things to really know what type of service you will provide for your company. Read more>>

Casey Anderson

There are always challenges in business from finding your next client to being prepared in handling negative press. When I first started out, I had a large client that made a mistake and was receiving some pretty bad press. These situations can be difficult to navigate and balance as any comment could be spun in a negative context. To resolve this, the first thing I advised was to remove emotion from the equation and admit the mistake. We then devised a feel good PR campaign moving forward. It took a lot of dedication, time and investment for the client but ultimately we overcame the challenge. Making mistakes happen and knowing how to work through them can make all the difference. Read more>>

Jamez Geiger

The one unexpected problem that stands out the most when I think about it would be the very first one I’ve experienced when getting into the camera field. Basically, I curated an event for artist of all different mediums, and it was going well up until I noticed that somebody stole my camera right out of my bag, well actually they stole my whole camera bag & the equipment I had it in. It was my first camera That I ever owned, & that camera was a gift from the person who even taught me how to use a camera, let alone take a picture. So it was very discouraging, & just very personal. I felt betrayed, & violated… but it also awoke something very important inside me, and taught me an important lesson. It made me even more determined to keep on pursuing the craft! Literally about 2 weeks later I had an even brand new camera with more equipment & a new bag. I used all of my savings at the time plus a couple of dollars from some family members and got right back in business. Read more>>

Charles Brantley

The problems that I face in my artistic journey, I can honestly say, are not unexpected. As a matter of fact, I am surprised when things go easily or smoothly. I studied architecture at the University of Houston in 1999 through 2004. I didn’t finish, but I learned a great deal of design theory and history. The most important thing I think I became aware of is being surprised with criticism in jury judgments even though I thought my design was great. I anticipated flaws in design as soon as I began sketching from that point on. Read more>>

Nina Marcelo

As an actor you kind of go into the industry expecting the unexpected. Things in this field are incredibly unpredictable, that’s a big part of the excitement from it! However, no matter how “prepared” I thought I was I definitely experienced some large unexpected problems. My last year at my acting school was 2020 and of course nobody expected a global pandemic, but it happened. Graduating during that time was absolutely one of the biggest challenges I’ve faced and I know many people feel the same. I had finally reached my moment of living in Los Angeles with good training under my belt and the ability to go out and work, and then everything shut down. Not much was happening which also made my search for representation difficult and also maintaining life in LA with no job was basically impossible. Read more>>

Tk Art

Navigating unexpected problems is a crucial skill I had to learn quickly. Going on the entrepreneurial path, whether in art, media, music, design, or any other field, demands a mastery of handling unforeseen issues. It’s not a question of “if” but rather “when” hurdles will arise. As both an entrepreneur and an artist, I’ve come to understand that when these unexpected problems occur – whether during a gallery exhibition, vending at an event, conducting an interview, or orchestrating my own event – they are inevitable. Read more>>

April Walterscheid

For this interview, I mainly want to talk about how Hollywood TV shows and films have used (possibly) thousands of human beings likenesses without permission for decades. And how Artificial Intelligence is just a new version of that… Both are unacceptable. Read more>>

Barbara Poole

I retired from Mesa Superior Court at the age of 66. I had recently brought home a small Pug, six months of age from a pet store. The little pugs eyes were weeping and infected within days of bringing her home. We found out that she had been born in a puppy mill, inbreeding had caused her to have ingrown eyelashes. Ingrown eyelashes are very common, very painful and a health issue from inbreeding. I named my puppy Liberty, she was a very sick little girl. We took her for surgery to have the eyelashes removed. The surgery was $10,000. Liberty survived, but unfortunately, her eyesight could not be saved and Liberty was blind for 14 1/2 years. Read more>>