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.

Taiane Bozzay

When I started my cake business I thought that I just needed to focus on making delicious and beautiful cakes to be successful. I was wrong! Just like other entrepreneurs, I had to learn (and I am still learning) about marketing, sales, building relationships with customers and so much more. Some weeks I spend more time on administrative tasks than baking. Read more>>

Kimberlee Centera

Not long ago, I was completely blindsided as I read a 13-page letter of criticism and complaint from a member of our team. We had met just days before, and I asked whether there were any issues or concerns to address, but none were expressed. Seemingly out of nowhere, I received a massive written litany of problems. Suddenly, I was confronted with lost revenue and legal challenges, which occurred during the COVID lockdowns, when we could least afford it. I felt devastated, betrayed, and angry. Wasn’t it enough that we’re in the middle a pandemic…and now this? Read more>>

Jenna Spencer

I wouldn’t say it has been a perfectly smooth road, but the bumps are what kept me going. Facing challenges is a huge part of being an entrepreneur and growing a business, and these challenges move us forward. The biggest challenges I have faced were always around people. I hired someone whose vision was not aligned with mine, and ultimately learned that in this life, people come for a reason, a season, or a lifetime. I had to dismember my leadership team and reassemble a new one which was very hard for me. Read more>>

Autumn Grant

The most unexpected problems and issues I faced happened throughout the duration of 2022. I had been sick for most of the fall in 2019 with little to no answers as to why I was feeling the way I was. I was going through various tests and scans and ended up in the hospital twice. My doctors referred me to a neurologist and scheduled an appointment a few months out for March 5th, 2020. I continued to work hard on my business and try to keep it running smoothly during the waiting period. Read more>>

Julie Russell

I have always wanted to be a singer! From my earliest memories as a young child, I can remember writing songs (one of the first songs i wrote consisted of only one word,,,, AWAY), and performing them for anyone who would listen. At the age of four, I was singing solos in the church choir, and by the age of 10, i had landed my first paid studio session as a vocalist. This was just the beginning of the kinds of opportunities I was hoping to land. I continued to train and pursue opportunities to perform. Little did I know how my dreams would be hijacked. Read more>>

Franchesca Davis

As an artist, I not only like to be involved in projects but I also like to create stories for myself. Back in 2019, I had moved back home in Kansas City from New York. At that time, I was flooding in debt and I needed to go back home to recuperate. At the time, I was more focused on trying to survive rather than thrive within, creatively. It is important to not let something like that disappear. Read more>>

Ryan Himmel

The most successful people are the ones that solve the biggest problems. Every time I’m dealing with a client there is always a problem that they have and if I can be the one to solve that problem for them then the relationship will go that much further and will pay off much more in the long run. Read more>>

Ariel Carrillo

There arent too many problems I’ve faced, but I’ve definitely had negative experiences in the modeling industry. I’ve been scammed out of money thinking I was hiring a reputable agent to manage me when it was really a con artist trying to get money out of me. I’ve also been put in uncomfortable situations in the beginning of my career. All of my problems stem from me being too trusting of people. Read more>>

Aliyah Fisher

As a first time business owner, i ran into many issues and problems. Many of which causes issues within my Marriage. I personally chase instant gratification and when my business took off I developed tunnel vision. This ultimately lead to me making several decisions that negatively effected my business and my marriage that I deeply regret. Read more>>

Tiana Taylor

The entire journey of being a content creator has been unexpected for me. I didn’t realize how much work and time it took. I wasn’t a social media person prior to content creating. I mean, I would scroll and like but I’d hardly ever post. The most I knew about hashtags was to use them to search for things. It never looked that hard when I saw other content creators posting. I would think to myself “Oh that’s easy. I could post everyday”. Read more>>

Oluwatoyin Adetunji

Branding! Creating a brand that already had existing presence was difficult to navigate. We wanted to be different. Authentic and pure. We sought out the beans and we were sure it was going to break into the already coffee market.
Truth is, coffee is a universal beverage. Creating Kilimanjava was not an easy task because we were ploughing an existing market where any regular coffee beans would still be okay. Read more>>

Kiara Hicks

The expected errors and issues I faced was running into trials and errors . I wasted so much material day by day until I continued doing my own research and perfecting my craft . I was so frustrated and wanted to give up , but I knew I couldn’t give up because I knew customizing things was my thing and my passion . Once I focused and sat down to deeply learn the details and researched throughly , you couldn’t tell me nothing . I was getting better and better at it and was able to learn many different things . I had the mindset that I know I can do anything else I put my mind to . Read more>>

Gabriella Martucci Jones

The most unexpected problem I have faced so far in my journey as a creative who started a brick-and-mortar music school was getting married to an Air Force officer. That meant I would be moving out of state, changing time zones, and possibly even changing countries. It meant life would never be routine and lifestyle and life plans would be constantly changing and flexing. How was I going to run a brick-and-mortar when I couldn’t be physically present? How was I going to carry on with my dreams if I also want to marry into a military lifestyle? Read more>>

Cabell Rhode

I think that anyone who says they have it figured out is missing something. I have always found obstacles and sometimes you can work around them other times you have to find a new path. For example for many years during my career I could not find a local studio. I had to work around it by doing home made production. This limited the sonics and overall quality of my earlier large scale projects and songwriter albums. Read more>>

Darnell Rice

Embrace is a service based organization and I’ve been building for the pass 3 years and it been tough. Not understanding the funding part obtaining and building business credit. I was under a 5013c and was trying to secured funding. The organ went a different direction. I really need some guidance and just so clarity. Read more>>

Dan Honig

One of the biggest challenges that we faced in starting Happy Valley Meat Company was partner alignment. A year into starting our business, there were four partners, each one of us had a different vision of what success at company should look like, what our responsibilities were going to be and what was expected from each of us. Read more>>