Having to overcome unexpected problems is a hallmark of entrepreneurship. Almost every business owner, artist, maker, and creative we know has had to deal with countless unexpected problems that arise in the journey and so we asked some brilliant folks from the community to share their stories of the unexpected problems they’ve faced along the way.

Emmy Tran

Censorship is a problem I face often with the content of my artwork. I create paintings that highlight queerness and liberation for marginalized communities, both of which are considered ‘political’ even though they are simply my identity and lived experiences or the existence of the closest people in my life. Read More>> 

Ashley Mangum

The most unexpected problems I was faced with was a lack in sales. You have an idea and you start that business but no one tells you what to do when you don’t have any costumers. Full transparency, I had to shutdown everything and work for someone else during that time. Read More>>

Italia Giulia

In 2017 I fell off of a bike and hit my head suffering a concussion. From their I dealt with post-concussion syndrome and still deal with it to this day. Back in July/August I went through a big mental health crash related to my concussion while I was weaning off of my medication. Read More>>

Mallory Moss

As a self-published author, I’m also the marketer, the copyeditor, the publisher, the communications team, the website designer, and the financial backing. This, I was prepared for, and I spent seven years polishing my first two books, slowly making all the payments needed for developmental edits, character art, cover design, proof copies, and copyright to ensure that when launch time arrived, I was ready. Read More>>

Sunghoon Chung

I used to believe that investing a great deal of time and effort into creative endeavors was the surest path to improving my work; however, I discovered that this was not necessarily the case. I observed instances where I would fall into a creative rut or become so completely immersed in the work itself that I would lose my own critical perspective on my pieces. Read More>>

Nicole Mitchell Colley

One of the most unexpected challenges I faced was stepping into leadership of an organization that had to be rebuilt from the ground up. We didn’t just inherit operational gaps—we started with no usable funds, limited access to prior accounts, and a damaged reputation from the previous employee association. At that point, we were starting from zero—financially and relationally. Read More>>

Zach Riley

You’re always gonna face unexpected problems in this industry. They’re inevitable. But you just gotta adapt as best you can and keep moving forward. I’ve definitely faced my fair share already and I’m only a few years into it. Probably the biggest unexpected hurdle that I’ve faced so far in this endeavour would be bands splitting up. Read More>>

Kevin Dickson

As an adult living with undiagnosed ADHD, it was getting increasingly difficult to cope with the strenuous effort of writing novels. This was compounded by the fact that I set myself a very difficult goal with my Vampire State novels: I set out to write a trilogy, in three years. Read More>>

Jessica Dion

One of the most unexpected challenges I’ve faced hasn’t been the operational side of the business, it’s actually been putting myself out there and talking about it. Going into this, I assumed the hardest part would be things like finances, managing expenses, ordering supplies; more of the traditional “business” side of things. Read More>>

Claudia Martin

Some of the most unexpected problems/issues I’ve faced in my business were salon closure, and unexpected caregiving roles simultaneously. My grandmother became severely ill, not long before the 2020 Covid pandemic. I became her caregiver alongside a few family members during that time. All while I was navigating this new season in my life of caregiving I received an alarming phone call. Read More>>

Celina Go

One of the most unexpected challenges in my career has been learning how emotional real estate can be, not just for clients, but within the dynamics of the people involved. At the end of the day, I’m not just in the business of property, I’m in the business of people. And people are unpredictable. Read More>>