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.

Jenni Hardnett

One of the most unexpected challenges I’ve faced in my career didn’t come from a lack of opportunity, it came at the exact moment everything was working. I was part of a business partnership that had grown rapidly. What started as something modest turned into real traction, real revenue, and real visibility in a short period of time. On paper, it looked like success. Read More>>

Brian Cook

The one that hit hardest came in 2018. I’m in a hospital bed in Pennsylvania — Army War College — staring at medical reports telling me everything I’d built over 33 years is finished. Not winding down. Finished. My body had done something my adversaries never could: it stopped me cold. Here’s the backstory. Five combat tours. Desert Storm through Afghanistan. Read More>>

Angie Misailidou

One of the most unexpected problems I’ve faced in my creative journey is definitely time management. Being both an artist and a student is very challenging, you have lots of homework, need to stay on top of your musical growth, take care of yourself, and maintain a social life. I can’t imagine how much harder it must be for even more successful artists out there. Read More>>

Coya Cager

I would say one of the biggest challenges I may have faced throughout my course of owning businesses is being okay with change. Growing up I loved fashion, I pursued and received my degree in fashion business management. While in my degree I did not realize how much math it would be and it was not as hands on as I thought.  Read More>>

Nick Good

The biggest unexpected problem I’ve ever faced was both professional and personal. I lost my brother, Austin, to suicide on October 6, 2021. Austin wasn’t just my brother; he was my best friend and my business partner. We started The Good Home Team together back in 2009, and then in 2010, we got into real estate investing. That became his thing. Read More>>

Sen Ho

I had always thought I was running out of time, especially while being on a visa I was afraid that if I didn’t get my ‘dream job’ by graduation that I was essentially done for. Read More>>

Marcus Drones

That’s a great question. Since I’m a private Chef and caterer, so many unexpected issues can happen. Since I cook, I usually cook at the venue and prep at home. A few years ago, I was hired to cook for a birthday party. If I can remember, it was for a 75th birthday dinner. Read More>>

Marie Thouvenot

When I launched my business, I was focused on everything you’d expect: training, administrative work, building the website. I thought I was prepared. But nothing really prepares you for your first paying client. The most unexpected challenge wasn’t technical or strategic. It was the wave of anxiety that hit me right before my first paid hypnosis session. Read More>>

Kristin Calhoun

When I started my online business in 2017, I just knew that it was the perfect career for me because it allowed me to work from home, (painting art and shipping it all over the US, and creating video tutorials to sell online), it didn’t require certain set business hours, no structure imposed on me, freedom to structure my day the way I wanted, Read More>>