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.

Daniel Wakefield

an attitude about getting clients. I assumed that if my portfolio was good enough, I could just put out a nice looking website and people would start booking. Wrong. My first full month in business, I made $60. It was truly a wakeup call. What those early months taught me is that I can’t wait around for clients to find me. I need to get out there and find them. I started to do this through in-person networking and LinkedIn. I began focusing on building relationships with people instead of just selling them on my services. And over time, this proved to be one of the secret sauces for an increasing number of referrals and growing a thriving business.

Jaime Rubio

One of my clients wanted me to build some windows. It was my first time making an estimate for merely windows, as I mostly worked on plastering, fencing, deck, etc. As the project went on, I realized that there were many unforeseen factors that took more time and money than anticipated. First, the plexiglass in the size that we wanted was much harder to find than we thought, so we spent a whole day calling all material stores around hoping we could have some luck. None of the stores had the materials in stock, so we had to pay a much higher price to purchase a bigger size. Since I wasn’t as experienced in window projects, I failed to consider my time to paint the woods, accurately quote for the plexiglass, and ran into a shortage of another material — rubber weather strips. All the unexpected issues had lengthened the project from an estimated duration of 2 days to ultimately 4 days. Fortunately, my girlfriend helped me throughout the whole project, and hence I only had to hire 1 employee instead of 2. We were working overtime till around 8pm for a couple of days to make sure we didn’t pass the deadline.  Read more>>

Kathryn Gawrych

The biggest most unexpected problem of my entire life was being forced to shut down my business that had only opened 9 weeks prior. I had just left the start to a very successful career at one of the big four accounting firms and put my entire life’s savings into this business. It had taken about 2 years between securing a 7A governmental loan, permits, build out, fire marshals, fire marshals, and fire marshals from getting the idea for my business to actually opening the doors. So the anticipation was incredible. When the facility opened there was about 600 children at the grand opening!!! Amazing! Couldn’t have asked for a better turn out. Flash forward 9 weeks later……..COVID-19 hits. This was supposed to be a 2 week shut down max. Gyms were closed 4 months minimum and forced to stay at a limited capacity even when reopening 4 months later. During those 4 months of full closure and about 3 more months of limited capacity my landlord had no mercy on me. With a 9,533 sq/ft facility on long island my rent was in the 5 digits per month. It felt like I would NEVER in a million years be able to survive this. I wasn’t eligible for any of the government relief due to the fact that the facility was not in operation at all until 2020. Read more>>

Lori Maney Lentini

My stepmom, Karen Juckas opened our horseback riding stable in 1965 and ran it until she died in 2020. Her and my dad were known locally as Prominet people in the horse business in New York. I rode growing up but had not ridden much since i was 14, I’m now 62. I never dreamed of owning a horse farm or even riding again. But then……. In May of 2020 my dad passed away and three weeks later Karen joined him in heaven. She left her estate and the farm to her daughter who lived in California. Her daughter ran it for a few months then put it up for sale. Karen had talked my entire life about wanting to leave her farmland and all 117 acres as a land preserve. Because of Covid we couldn’t have a funeral for Karen, but several months later we had a memorial service outside on the farm. My, Nephew, Brian who lived in Lake Placid came down (Karen was his grandma and my dad had mostly raised him). After the ceremony he came back to my house and spent the night. We opened a bottle of wine and shared memories and discussed the fact that her daughter told us she had a cash offer from a buyer who was probably going to develop the land. We knew Karen would hate this! We opened another bottle. When it was finished, Brian looked at me and said here is an idea – you cash in your retirement plan, and I will go home and sell my house and business, and we will make an offer and keep Karen and dad’s legacy alive. The next morning over coffee, Brian looked at me and asked so are you in?  Read more>>

Keith Smith

In my creative journey, I’ve faced several unexpected challenges that, while difficult, became pivotal in shaping who I am and the work I do. One of the earliest turning points was my divorce. Suddenly, I was starting over as a 34 year old parent with three young children, struggling to make ends meet. The dreams I had for my writing and creative work felt out of reach as I focused on providing for my three daughters. Yet, I clung to writing, filling notebooks, scraps of paper, anything I could get my hands on, scribbling on paper ideas, poems, and thoughts that kept my creative spark alive. It was a silent, personal stand against the overwhelming demands surrounding me. Years later, after my children were grown, I went through another formative moment—the unexpected end of a twelve-year relationship. I was at a crossroads again, but this time as a 52 year old with no money or job, and the failure of a new business I had started only months before. Looking back over my life, I began to see how the common denominator in the repeated “crash and burn” events of my life was me. I needed a change and the change had to begin within me. Read more>>

Jody Dimitruk & Johanna Loke

We sold a very high end condominium and the night before settlement, we were notified by the management company that there was going to be a special assessment in excess of $700,000 for this small building. Neither the buyer nor the seller wanted to pay the unit portion of this amount. On the morning of settlement, the buyers hired an attorney and the situation got resolved with the seller paying a flat amount in excess of $40,000 which the buyers accepted and which was one of the largest credits a seller has every given in our careers. To add insult to injury, the buyers ordered a home warranty and prior to settlement, confirmed that their HVAC unit would be covered. Shortly after settlement and in the heat of the summer, their air conditioning stopped functioning correctly. The home warranty company denied responsibility for the repair although they had the complete home inspection report prior to issuing the warranty. This was a huge second hurdle that the buyers had to resolve with the home warranty company. Needless to say, this transaction was extremely stressful for our buyers and for us and we hope we never run into these situations again. Read more>>

Vernon Vanderwood

The catalyst for my most successful works is often unexpected problems. My art practice is really materially involved and often resides in biomaterials and performance based installations. For example, my sculptures are made up of growing natural mediums such as SCOBY and mycelium. Because of this i’m constantly confronted with the unexpected variables of another living thing! This journey of learning how to collaborate with these mediums has shifted my perspective to not take the unexpected always as an “issue to resolve” but a spontaneous moment for innovation or action. A recent example is my journey with mycelium casting, which is the process of growing fungus in the shape of a mold. In this case I had grown fungus in the shape of my torso, yet the first try grew a lot more than fungus…it started to rot! This unexpected and some might say disturbing sight of my own form falling apart really evoked the themes of self critique and growth that I was writing and working through for this project. I ended up installing the unexpected first iteration alongside the more successful finished cast. I feel as though I seek out materials and a practice where the unexpected flourishes, I tend to learn a lot more that way. Read more>>

Mark Tuggle

My computer crashed two years after I started writing my book. I lost everything. Everything. I was depressed, despondent, devastated and disgusted for several months. I had zero positive energy flowing through my body. I became isolated, unhappy and withdrawn. I struggled with suicide ideation. I was unable to focus on my vision. I questioned my sanity. I wondered if God had, yet, another plan for my semi-charmed life. My improbable journey of becoming a first-time, independent, self-published author – 61 years old – seemed doomed to fail. Why is this happening? Who can help me? What are my options? I was flooded with conflicting thoughts, feelings, judgments, opinions, etc. I saw no way out. My dream of becoming a published author who can serve humanity felt empty, shallow and untenable. Sadly, it appeared this would be just another disappointment in my life. My family and friends would never understand my emotional compass. Why should I tell anyone how I felt? Read more>>