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.

H. E. Thompson

In the early days of my entrepreneurial journey, I was still working a 9-to-5 job. A difficult situation arose when after being on a new job for 2 years I was laid off. Read more>>

Matthew Heffelfinger

We took nearly 6 months to negotiate our lease. It took so long because the property manager would take 4-5 days to respond to every edit we gave them. Read more>>

Marina Dell’Utri

I was 24 years old when I decided to open Mantra, the first raw and vegan restaurant & cold pressed juice production company in Milan, Italy. Read more>>

Laura H. Rubin

One of the most unexpected challenges I’ve encountered in my business has been dealing with the capabilities of AI. AI image generators like Midjourney can produce stunning artworks with just a few clicks, based on paintings by real artists,(without their consent). Read more>>

Mr Dark

The journey I’ve undertaken has been far from smooth. For over seven years, I remained distant from my homeland, immersed in solitude during my time in the USA. Read more>>

Matt Drayton

When I first started my speaking business, I thought it would be easy because I had many years of experience talking in front of audiences during my military service. Read more>>

Octavia Grant

I subscribe to Murphy’s Law; Anything that can go wrong will go wrong. Though I am an independent author, I rely on other businesses’ services to ensure that my business runs smoothly. Read more>>

Quynn Red Mountain

When I was 17 I came up with an idea about how to blend my photography skills with a way to bring me some money, but I felt overwhelmed with the details of how to manifest it, so I gave up on the idea. Read more>>

Eric Weninger

I started bringing salted maple syrup out of the kitchen and onto big adventures & endurance races in the late 2000s. At the time I was using little flip-top plastic bottles, which were not ideal but better than fragile glass, and the maple was way more delicious & digestible than commercial gels so I made due. Read more>>

Drew Davis

If anyone is considering a career in standup comedy or other kind of field as an entertainer I would say, it’s an amazing experience, but you really need to be aware of your mental health and how you deal with all emotional aspects of this job. Read more>>

Ceres (Diaja)

Out of all the unexpected things in my life that have altered the trajectory of my business, I would have never thought homelessness would be one of them. Read more>>

Chelsea Warren

Running my clothing brand has been quite the adventure, with unexpected challenges cropping up along the way. One of the toughest hurdles? Read more>>

Tina Afiqah

No one ever tells you at first, that (albeit of where you’re from) the creative industry is a cutthroat, competitive scene. For instance, you constantly have to adapt to the ever-changing needs and demands of your consumers and clients to sustain the hype (while also trying to find new ways on how to stay fresh). Read more>>

Eva Pohler

I earned my Ph.D. in English in the mid-nineties, specializing in twentieth-century British and American narrative strategies. Ever since, I have taught writing and literature–full time for twenty years and part-time in more recent years–at a university in San Antonio, my hometown, where I live with my husband of nearly thirty years, two of our three adult children, and three rescue dogs. Read more>>

Evie King

One of the most surprising challenges I encountered while growing the team at InDependent was the issue of digital communication across time zones. Read more>>