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.

Benjamin J. Burton

When I kicked off my adventure of penning my first novel, I was blissfully ignorant, wrapped up in a fairy tale where simply creating the book would be enough. I imagined it soaring off the shelves, effortlessly landing in the hands of eager readers, like some kind of literary magic trick. But oh, reality came crashing down faster than a bad plot twist. I quickly realized that the real mountain to climb in the publishing game wasn’t just about spinning a good yarn; it was all about marketing that baby and getting it into the hearts of those who would actually enjoy it. The noise out there was deafening, and cutting through it felt like an uphill battle. Read more>>

Benedetto Manzella

The primary problem I continue to face is one that almost all creatives struggle with, and it concerns the perception of my work. Oddly enough, the worst perception of my work often comes from fellow artists and creatives but that encourages me to keep working in order to defiantly hone my work while others waste their time and effort putting down another artist. Documenting live performances by bands is a chosen craft taken for granted by far too many people. Read more>>

Ashleigh Schuellerman

So when I started my real estate career last May (2024), I filled all of my time with real estate related things. I was hosting open houses across San Antonio every single weekend, and sometimes even during the week during after school hours. I was actively trying to make myself known and talk to as many people as I could. I pushed myself out of my comfort zone and started going out of my way to talk to people outside of real estate related things. Read more>>

Radel Rosin

One of the most unexpected challenges in my creative journey came with the expansion of the Performing Arts Center at AuSable Artisan Village. It was a huge step forward for our organization—transforming an old, underutilized space into a thriving hub for live performances, workshops, and community events. The vision was clear, but the reality of working with a 100-year-old building was anything but simple. Read more>>

Sailynn Doyle

I started my entrepreneurial journey to reclaim control over my time, money and flexibility after working 5 jobs in 7 years due to a short-term contract and 2 layoffs!

I opened my first business in 2007 by purchasing a senior home care franchise. In just 3 years I had achieved the million dollar revenue level but was completely burnt out because it required me to work 80+ hour weeks! Read more>>

Justin Cobb

When I was growing up in Pennsylvania I was raised in a fundamentalist, conservative Protestant home. At a young age I started questioning the theology I was being raised in and I started challenging it. Also around the same time I was going through moments where my sexuality was awakening and I felt so awkward as a teen. I told my father one day that I supported gay rights and he got violent. The trauma that I sustained would change me forever. Read more>>

Helena Mace

I am.a.full time singer songwriter and.in 2020 i had to have emergency radiotherapy on my brain for a benign brain tumour. This treatment has.made.me permanently deaf in one ear. Read more>>

Paul Harrison

Early on, when I was just trying to push my own creative projects, I lacked confidence in my own abilities. For this reason, I looked as much as I could to collaborate – with writers, other creatives and the like. This often meant my ideas were watered down and eclipsed by the others I worked with. At one point I found an animation company who loved my Urban Squirrel idea and wanted to work with me on it. They wanted me to work with their in-house writers and illustrators to develop Urban Squirrel as a kids’ show. Initially I thought this was great and threw myself into it, until they sat me down with a ‘global marketing expert’. He informed me that in order to tap the Chinese market we would have to lose the squirrel as a main character and opt for a dragon. Read more>>

Brina

Music is an evolving industry. Over the last couple of years, we’ve seen the music industry change completely. The demand for the amount of content you have to put out is at an all-time high. Not only is recording costly, but you also have to factor in videos, styling, choreography, and any props you may need. The good part is that as artists, we now have more control in marketing ourselves through social media. On the other hand, this access does not omit the cost it takes to produce the product in the first place, which in this case is the music. When I put out my EP “Bonjou,” I completely underestimated how much time and money is required when releasing a body of work. Read more>>

Alison Browne-ellis

As a woman leader, my personal experiences have taught me that garnering the respect of both leaders and peers is paramount to your success. The level of competence in my subject area is not the only leadership attribute that I need to consistently display as a woman leader. My level of success is collectively defined by my confidence, assertiveness yet display of humility while commanding the spaces I occupy, while leveraging my voice to influence people and desirable outcomes. Read more>>

Levi Moore

One of more challenging unexpected aspects of being a full time artist, and in my case, musician, is the amount of time that is required outside of performing. It takes many hours of practice to hone our creative skills to a level that they are worthy of being displayed, but also to make sure that they are marketable skills, and that they are an accurate representation of who we are as creatives. Read more>>

Jonathan Duff

I would say for sure, things going wrong on stage. Playing a concert is one of the most wonderful experiences ever. But things aren’t always going to go as planned. On my latest Christmas Tour, it felt like every night something else would go wrong. Whether in ears (which I use to hear myself) randomly cutting out. Or confidence monitors, or my voice going. Learning to keep your cool and rely on your instincts is one of the most crucial parts of playing. No matter what situation you face on stage. You should just breathe in and know at the end of the day it doesn’t really matter. I’ve heard it said fans are there to see you, mistakes and all. Sometimes you gotta laugh it off and push through. Read more>>