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.

Dee Hilfiger

I would have to say Covid was one of the most unexpected and difficult issues that we faced in my businesses. fortunatley we were able to pivot and learned a lot of important lessons along the way Read more>>

Elana Jacobs

When I started my career as a choreographer/artistic director and Pilates instructor in 2011, it was very important for me to have balance between creating work and teaching Pilates. Having a steady flow of creative projects was vital for my sense of self. Productivity was defined by how many projects I created. I never considered that my idea of productivity would have to change drastically. Since becoming a mother, my life has become a balancing act of much more. I am no longer churning out as many dance performances per year. Between mothering two, owning a Pilates studio, and continuing to be the Artistic Director of a dance company, I have had to embrace my practice as interdisciplinary. If I try to hang onto that old version of success and trajectory, I end up feeling dissatisfied and not present in any of my jobs. Read more>>

Karma Lush

The most unexpected issue or problem that I’ve had is asking myself the questions: Where do I want to go with my art? Why do I create? What do I want to create? Questioning your own ambition and answering those questions honestly for yourself and no one else. Read more>>

Brittany Sallier

Unexpected problems I believe creatives face in this world is making our ideas strictly our own to share. What that means is, in this world of 8 billion people, ideas, thoughts and opinions have been done or created before. So when we come up with an idea, we try our best to make it original without making it feel like we are “copying” someone else’s idea. I just look at this world and the people in it as inspiration for when I create. I do create original works of art, but I will be the first to say I look for inspiration from those before me and thats okay. Read more>>

Kate Troyer

I already had a very successful home staging and design consulting business when I decided to pivot to my now, Feng Shui based business. I had done it before, I was already operating a successful business, I knew how to market, I had a large client list and a big network. I did it once, of course I could do it again, easily. I mean, I wasn’t even changing my business name, I was only pivoting… Read more>>

Kathleen Goldstein

Seeing the waist fast fashion contributes to landfills and the unhealthiness of synthetic materials drove me to open this little shop offering natural fabrics and biodegradable packaging while sourcing vendors who use ethical practices. The biggest unexpected problem is that the minute you mention sustainable fabrics and ethical practices the prices increase by about 2 00’s! My goal was to offer organic products at an affordable price which has proven to be so difficult. I have been a victim of “green washing” where I’ve been told the products were 100% cotton only to receive obviously synthetic fabrics then having to fight and tie up hundreds of dollars to return them! Read more>>

Camea Franklin

I started my career in the tax industry by being part of a franchise. I considered entering into this industry at a time when I was in transition. I had just been laid off for the second time and was looking for something that I could level up, control my own future and be able to support my family as I was a single parent. I only had myself to rely on, I was able to learn alot about the industry – how to setup your business, how franchise’s work, what the fees are, and the tax business life cycle. To make a long story short, due to the franchise fees that were required, I ended up owing the franchisor over $100,000 and had to exit the business. Read more>>

Danielle Kowal

Shortly after our 2020 flagship fundraising event, the Bleeding Hearts Ball, our home club, the Lizard Lounge, had the land it was on sold during the COVID-19 pandemic. We had worked with the owners of the Goth Night known as The Church for years both for that event and our annual KrampusNacht themed toy drive. Read more>>

Ashley Johnson Smith

As a woman, I am currently experiencing an unexpected issue. That issue is the toll that it takes for a woman to have it all in a competitive field. When I first started this career at 17 years old, I always knew it would take hard work to stand out and succeed. I always knew I would have to keep up with how fast the dance industry quite literally “moves”. However, I never worried about once I became a mother how the career I built would be so delicate.. Read more>>

Kemi Pavlocak

We currently operate two stores. One in rural desert of San Diego County and the other in Old Town San Diego. The location couldn’t be any different. We started out with the rural store five years ago. O’Shun’s Orchard was very much focused on agriculture and land development. I was slowly working on my bees. But we soon found out that the only store in town where our apiary was located was about to permanently close. My husband, also business partner, we went back and forth on whether we should step in. I really wasn’t interested because retail is not my thing and this community was foreign to me. I grew up in Brooklyn NY and Mike grew up in a New Jersey suburb. I felt someone who was a local resident should takeover. Read more>>

Travis & Whitney Washington

One of the most unexpected challenges we faced in our fitness studio was the abrupt COVID-19 shutdown in March 2020. Overnight, we found ourselves unable to operate in the traditional gym model, and uncertainty loomed over the future of our business. It was a seismic shift that demanded swift and innovative action. Read more>>

Joe Stafford

My wife and I purchased an existing iCode location from the Franchisor. The business is a school that teaches children ages 5 to 17 years old STEAM skills We were under the impression that it was a cash flow positive business and our focus would be on building relationships with local schools and organizations to further grow our enrollments. It turned out to be in a more challenging position than we had originally thought. Read more>>

Alfred E. Rutherford

As an artist there are always unexpected problems/issues from having to work a day job and find a way to go on an audition. That was when we had in person auditions, now it’s mostly self tapes which makes it a lot easier. I think one of the hardest parts of being an artist is to secure a job that will allow you to go away when you have a film project without fear of losing your steady job. Back in the day when I got my first lead in a Feature film I was working at the YMCA at the time and I had to take off for 1 month. It’s always a tricky situation because a couple of days is understandable but not many jobs will understand 1 month off. Fortunately for me it worked and they were very accommodating with my pursuit of my career but I know many of my artist friends have not been so lucky. Read more>>

Tiena Gwin

I believed that if you would create beautiful, well-made products, I would be successful. That is not the case. It takes more to running a business than just great products. Read more>>

Queen Sandruh

This time last year, I was eager to relaunch my brands BÈLPAK/BÈL BEAUTY, get back to doing my podcast Queen’S Table full time and finishing up my first published book “I Don’t Know It All, But I Know Enough”. Then life hit me in more ways than one and I couldn’t recover. I couldn’t ignore that I had to start all over again and didn’t know if I could do it all while emotionally, mentally, physically and financially being done and exhausted. This is something that I am still battling with and dealing with to this day. In a way I didn’t want to do this interview because then I HAD to put on paper and on record that from my last interview 2.22.22 till presently, I have nothing but my own memories to show. Read more>>

Ania Sari

Earlier this spring, I was involved in an car accident that redirected the trajectory of my plans as it pertained to music. I came out of the accident with a totaled car, a sprained neck and some. This was not too long after announcing I’d be working on more visuals, music, some big opportunities to perform, and dropping an EP later in the fall. I don’t think anyone could understand what I was going through because all of my pain couldn’t be seen, only felt. I had to focus on healing and completely detach from my plans for myself and curate a new strategy for overall wellness from the inside out. Read more>>