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.

Kay Nine Tha Boss

I remember when I went on my first independent tour. I only had enough money for gas in my car and food. I didn’t have enough money for a hotel, so the plan was to sleep in my car. I ended up getting into a car accident and totaled it just days before my tour was scheduled to start. I had no way to get there and nowhere to sleep even if i did. I decided I would use my gas money to catch the train and sleep in the streets after each show. I was willing to do whatever it took to continue with my tour. The day before I planned on leaving. One of my homies sister allowed me to use her car. I always look back at that time and it reminds me how hungry I was. I was willing to make whatever sacrifices necessary to get my name out there. Fast forward to the present me and I am still just as dedicated. Read more>>

Devony DiMattia

Working in an artistic field professionally often leads to a lack of clarity when it comes to addressing issues as they crop up. It can be difficult to know who to bring those concerns to or, if you’re dealing with a personal dilemma, it may be a challenge to hold yourself accountable to solve it. I think we can all look back and find moments where we wish we had a better support team or strategy in place for solving those problems. For me, I love to work on the creative elements of my business, but I tend to struggle when it comes to the more logistic side of things. Like, how do I correct this page error on my blog’s website? Or how do I optimize this post with the right SEO that Google wants to see? It can be easy to fall into the trap on the other side too- being overly detail-oriented or perfectionist to the point that you’re not able to finish anything! Done is better than perfect. Read more>>

Kelsey Hunter

Like a lot of people in the entertainment industry, the double strikes had a big impact on my employment this year. I was fortunate to have many months of work with a production that did not have writers, but when our show wrapped I was in the same boat as many others. Being in this turbulent industry as a freelancer made me feel out of control and worried for my future. However, the time I’ve had to myself has given me the opportunity I needed reprioritize my time to work on my personal goals, my art, and strive for new career paths. Read more>>

Shiheng Xu

In the creative industry, the client services aspect and the personalities involved truly constitute a significant 80% of the business, and this realization took me by surprise! In the midst of a world that values technical skills and personal artistry, especially in the vibrant creative hub of Los Angeles, I’ve consistently found myself navigating the delicate balance between my artistic endeavors and mastering interpersonal dynamics. Read more>>

Shayna Blass

I don’t recall one particular problem, but living in New York as an artist is what I like to call, Daily Mental Olympics. If you don’t have someone paying your rent or supporting you financially, it’s definitely a different experience. My biggest struggle has been figuring out how to balance a bunch of different jobs while also performing and creating shows. There’s really a constant thorough process around what’s better; having more flexibility to take performing opportunities or taking the job that pays more but needs more of your time. Still working on figuring out that balance, but if you’re going through that daily, you are not alone!! Read more>>

Susie Sharpe

Growing up in Korea, art was my first love, and my dream was to become an artist. When I was 16, my family immigrated to the U.S. Without speaking any English, I felt I needed to find a different career than art that offered security to support myself and help others. I decided to become a physician, although it felt like an impossible dream. After many grueling years schooling, while also learning English and supporting myself, I received my M.D. and residency training from Yale. I have had a very successful and fulfilling career as a physician. Read more>>

Zeina Elchanti

looking at all those successful influencers, the idea of social media seemed very easy. A person can post stories, posts or videos and will be famous. However, after u start with your page, you realize that it is so hard to get famous. When I first started it was so hard for me to get views on my posts. I started looking at other influencers and learning from them. I even took a course that teaches all about social media in order to learn how to deal with such a problem. Read more>>

Heather Cardwell

When I first started taking photos, I thought someone simply knowing photos were occurring, that they’d be prepared for them, I’d arrive, capture the work or subjects and be on my way to another Google review. Not once before starting a business did I consider that people needed to be coached through a process for the best experience overall. Read more>>

Connor Ek

The biggest thing that sets me back really is the feeling of not knowing where I want to be. I had a large period of time where I was just in limbo genre-wise and not sure how I would perform. I had a ragtag set of songs that I’d play but most of the time, I was so unsure of where I stood that these songs fell on deaf ears. Playing songwriter-esque songs for a spot more suited for rock, and too soft for a honky tonk. I felt that I didn’t know what I wanted to do with the skillset I had, bouncing from a different live backing band at every show, I was really just unsure of everything, and if I had the cajoǹes to be a legitimate solo performer. Read more>>

Johnny and Dorothy Chau

A few years back, we were working on an annual report. While creating a file, designing and layout, a section was accidentally left off. Despite going through two rounds with the client’s proofreaders, the report went to print, not catching the oversight. After the report went to print, the client then realized the section was missing. Even though the proofing stages fell on the client’s responsibility, we decided to absorb the cost of the reprinting of the report. Have to admit, when this unexpected issue arose, there was a little bit a of panic. It was a huge cost to reprint this report – but it was the right thing to do. Read more>>

Ash Darq

I didn’t realise I wanted to be an artist till I was 28. Subconsciously I probably knew, but I only dabbled, but always put it on the back burner. Once I acknowledged it, it was like I was on fire trying to make up for lost time. At first I thought I could just quit my job and be an artist full time straight off the bat. Many artists make this mistake, and I became just another statistic. However this only lasted as long as my savings held out, and then I realised I needed a job to SUPPORT my journey as an artist, so I could set everything in place, build up a fan base and a community. Actually take a lesson or two in my vocation. Read more>>

Nicole Beal

The journey to where we are today business-wise has been interspersed with successes, but also many lessons along the way – there is always a learning curve when growing a new brand. But we describe the process as a “labor of love!” We have enjoyed every step, bump, peak and valley because our business is aligned with our purpose, and we have seen the positive impact it is creating. As the saying goes, “if you do what you love, you’ll never work a day in your life”. We have found that to be true! There have been challenges along the way, but more importantly, there were extremely beneficial lessons that came out of them. Some of the key ones are: Read more>>

Danielle Sheree Brown

One unexpected business problem I had at DSB Solutions was terminating a client. It was unexpected because 1) The Client PAID very well, 2) it had an incredible mission, and 3) The Client PAID on time. I would say a “perfect” client. Here is the story, DSB Solutions worked with the Client for several years, providing annual tax preparation services. Read more>>

Laura Mijangos

Loss of husband and parents within a short time of each other and it’s affect on my art and life. Read more>>

Dylan Berry

How the fear of criticism debilitates your forward progress in life, carer and pursuit of happiness. Read more>>

Heidi Clinite

Hi, I’m Heidi Clinite. I’m a multimedia artist. I’ve been drawing and painting since I was a kid. When adults asked me what I wanted to be when I grow up, I answered, an artist! After college, I studied figure drawing and painting at The Art Students League of New York. Read more>>