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.

Dr. Liz Wilson

One of the most unexpected and frankly, disheartening challenges I’ve faced in business was when a trusted client contact acted unethically and put my business and team in a deeply compromising position. Read more>>

The Fronks

In November ’23 we meet up for our first practice in our drummer’s basement as a four-piece band. Over the next year we added a sax player who soon moved away, we changed bass players a couple times, and added different lead guitarists to the lineup twice. The first of those lead guitarists left the band a week prior to what would have been our first show. In a bittersweet turn of events that show got cancelled 3 days before it would’ve happened anyway, which opened the door to us bringing on our current lead guitarist for our actual first show at Boxland. Read more>>

Kate Castro

Within the last year and a half, I was diagnosed with cancer. It was a complete surprise that catapulted surgeries and chemotherapy treatments for months. I decided right away that I was going to approach everyday with positivity no matter how I felt. My mindset got me through the darkest and most painful days of my life. I am grateful that I am very healthy, mind, body, and soul today! Sharing my story and perspective I believe, is a responsibility I have to help others through tough times. Read more>>

Carly Oishi

I have always understood the importance of reviews when it comes to running a business. The problem is, when you are new, if you receive one bad rating, it drags down your overall score, which in turn, affects your sales going forward. Honest mistakes can be made and some customers will never be satisfied. This was especially true for me as a reseller since almost all of my items were used. You can take photos and write accurate descriptions and someone will still find a flaw. Read more>>

Chachi Midencey

A lot of times when you’re doing underground, pop-ups equipment isn’t the best. It constantly goes out. Doesn’t run correctly. I mean, the list goes on. I ran my personal apartment oven into the ground from doing pop-ups out of my place. You basically resolve them by just being a MacGyver. Read more>>

Gregory Lewis

I took out two loans specifically for marketing and scaling my karate school. Shortly after doing this, my now ex-wife and mother of our son decided to leave the state without telling me.

I had the choice of proceeding as planned or using that money for finding my son and his mother.

Businesses come and go, I will always practice martial arts even if I don’t teach professionally anymore. Read more>>

Arastasia Rolain

If there’s anything I’ve learned in my journey as a creative entrepreneur, it’s this: life will absolutely throw the unexpected at you. Sometimes it’s exciting and full of momentum—those beautiful seasons where your ideas flow, clients are happy, and you feel unstoppable. But other times, life throws a curveball that knocks the wind out of you, and suddenly you’re navigating through overwhelm, anxiety, and self-doubt. Read more>>

Jesselynn Stegall

When I first moved to Los Angeles, the goal was to complete my graduate program at film school and dive straight into the world of acting. My mom was my manager in regard to making sure my marketing materials and everything I needed was up to par. We had a strategic plan. A few months after graduation, I had my first audition for my first independent feature film in Los Angeles. After I got the part, I received news that my mom had been spontaneously diagnosed with pancreatic cancer. Let’s just say that was the start of my breakdown. During school, I was very proactive and persistent in auditioning, attending acting classes outside of school, searching for agents, going to events… Read more>>

Roberta Levitow

I became a storyteller myself as an actor, singer, director, teacher and producer. For many years, I directed original plays that engaged with contemporary themes and events. I challenged myself to look directly at the outside world, no matter how frightening or crazy. My grandparents taught me to face the world with my eyes wide open, which can be energizing but also scary and confusing at times. Especially these days, real life can feel overwhelming. Read More>>

Taylor Jordan

For the most part, I’d have to admit that throughout my entire career, there have been a multitude of unexpected challenges and issues. The music industry can be a very turbulent place if you’re seeking structure. For example, one of the biggest pitfalls that we ever got stuck in as a band was the fact that we released our debut EP exactly one month before COVID hit, and it shoved everyone into lockdown for a very long time. Everything legitimately shut down during the pandemic here, and the music industry took, probably, one of the biggest hits of all. Read More>>

Craig Stewart

The project has been both a fulfilling endeavour and cruel mistress at once. While it is not my first attempt at designing a TTRPG (Table Top Role Playing Game), it has been the most challenging in both scope and goals. During the development, I would keep asking the playtesting group what they felt was missing, what needed to be covered. Even with their input, I still felt that something was missing.

One night, on the edge of sleep, it hit me. “If you have never played any TTRPGs before, what don’t you know?” This is the most difficult topic to cover, because its so difficult to remember what you didn’t know, way back when. Thus came a whole new chapter of the book – The Basics. Read More>>