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.

Daniel Kupakwashe Sithole

The main problem a lot of digital artists face is that in my country, the entertainment industry does not cater to the digital artist. We do not have mainstream content that is in need of a digital artist. In order to make a living, you either work remotely as a freelancer or find really niche studios that offer such services to companies and organizations wanting to advertise. Read more>>

Liz Perry

The biggest, and most surprising, hurdle in my art career has been the amount of internal growth and self-development it demands. I used to think that once I learned how to paint, I’d just paint, people would buy my work, and it would all be that simple. But the reality of creating art professionally has been a deep journey through self-doubt, constant comparison, perfectionism, and sometimes the urge to give up altogether. I have a tendency to compare my success to others’ and let that turn into self-criticism. As a self-proclaimed perfectionist, every painting brings up this inner “dance” with myself—a mix of second-guessing, striving for flawlessness, and resisting the urge to just walk away. Eventually, I reached such a low point that the stress and self-talk actually began showing up in my health. Read more>>

Shirley-may Soong

When I decided to transition into full time coaching and build my own business, I planned on working with tech leaders and founders- similar to the space I came from. As word spread through my circles, I started getting introduced to early entrepreneurs in the creative space. I would have introductory calls with them and even though most of them couldn’t afford my services, I saw the potential to help and gifted sessions here and there as well as did some trades. Read more>>

Louis P. Author

When I first decided to become an independent artist full-time, it was never an expectation to become “rich and famous” over night (if ever). My interest towards the music industry came with the knowledge of it’s new found independence. No longer having to audition for big producers like P. Diddy, or even having to deal with collaborating with other local artists, who may not share my vision 100%, just for the hopes of being “discovered”. With new distribution companies like CD Baby, Distrokid and more, It was basically a “no brainer”. I simply use the ability to produce,write and record, to release some of the most timeless music this generation has ever heard. Of course, nothing in life is that simple, and there are a few unexpected issues I’ve come across in 2024. Read more>>

Steven Pullin

I have been on this beautiful planet for 36 years, and played music for 33 of them. As long as I can remember, music has been such an important part of my life. From my mother singing to me when I was a baby, to the many musical influences I had in my life as a young child. At five years old, I found my true love with guitar and drums. Over the years, I got the chance to record on a number of albums, as well as create and play live with the number of talented musicians. Read more>>

Rachel Mullen

All of the expected hurdles, I’ve cleared. I think networking, and finding places to play, and even learning how to use my equipment have all been difficult and challenging, but I’ve completed those tasks and they are done. What is ongoing, and what I think a lot of people in any field can relate to, is self doubt or imposter syndrome. I know I belong. I like the way I sound. And yet, sometimes, before a gig, I think of how my music probably isn’t the right vibe for this venue. Or, I wish I played guitar. That’s probably what they are looking for. This never ending thought process, that is so difficult to check off my list, because deep down: I LOVE my music. But I always second guess myself going to a new place. Read more>>