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.

Charlie Michael Baker

Transitioning from a teenage social media personality to a business owner brought unforeseen challenges. First and foremost, managing the shift from a more casual, youthful online persona to a professional one was a delicate balancing act. Maintaining credibility and trust with my audience while engaging with corporate partners required adaptability. Additionally, I encountered the complexities of business operations, such as financial management, legal obligations, and team leadership, all of which demanded a steep learning curve. Navigating the changing algorithms and trends of social media platforms added further unpredictability, affecting my reach and engagement. Read more>>

Ashley Marcial

One of the biggest unexpected problems I’ve faced in my business was getting robbed after my first t-shirt release. One day in October 2022 someone robbed my car of my first collection drop. It felt like “why me?” because I’m a small business owner, not a big brand like Gucci, Yeezy. I came to my trunk rummaged through, leaving me with only under 10 shirts. It was very heartbreaking because I saved up throughout the year for it and it was my first collection officially for my brand. With so much thanks & support from outsiders, I was able to raise & gain enough to revamp my logo to start fresh with a new collection. I am very blessed and I appreciate the support that I have gained and can receive from outsiders and those who follow my business on social media. Read more>>

Alex Ferrara

As a creative, it’s important to not be too attached to timelines – though that’s often much easier said than done. For instance, in 2020, as an actress and a model in NYC, it was so hard to see all the projects I had lined up for the spring go away in an instant, and watching the business and New York City shut down overnight made it feel like everything I had been building toward came grinding to a halt as well. Then, more recently, when I found out I was pregnant, it was such great news… and then, when I got unexpectedly really sick with hyperemesis in my first trimester, it pushed back the launch of my new podcast, “Glow Up And Speak Out”. Looking back on these two chapters of my life, what I’ve learned is that you can and SHOULD have intentions and goals, but you absolutely canNOT control the timeline in which they happen. And in the end, things really do come to fruition when they’re meant to! Read more>>

Jenna Skipworth

I chose to be a dancer when I was just two years old, and I’ve been obsessed ever since. It’s no surprise that the dance world is filled with twists and turns (to put it kindly) that my two-year-old self could have never foreseen. As I continue onto my second decade as a professional freelance dancer, I’ve noticed problems and obstacles that have consistently appeared. These are things that no mentor mentioned or prepared me for. I don’t think it is typical to talk about these things, which is why I make it a priority to guide younger dancers and athletes and prepare them for the darker side of pursuing such an intense career. Read more>>

Janna Yotte

I previously worked as a freelance photographer, graphic designer and art director. When I decided to pursue my career in contemporary arts, I assumed it would be a similar kind of hustle in which I was comfortable – and it’s not. Looking back, I stepped into it knowing nothing about it. Here are some things that unfolded as different challenges: – Solitude. Read more>>

Jon Passow

One of the biggest lessons I’ve learned in life is that failure is our greatest teacher. Failure will happen multiple times along the road to success, and you are going to make mistakes, that’s just how life works. The trick is to always learn from the experience, get back up, ask “How can I make this work”, and then try again. Read more>>

Keisha Manijean

One of the most unexpected problems I faced in business was covid. In 2019 I was awarded best artist of the year and best concept for my universal love series from a international world-renowned magazine called destic magazine out of London. Do to covid I was unable to go to London and receive My awards or tour with the magazine.. The following year, I was also awarded best artist of the year with the same magazine and once again covid. I was devastated to say the least It seemed Colvin would never end. So like they say when you’re given lemons. Read more>>

Orin Abrams

By far, the most unexpected challenge I’ve faced in my professional career, was the COVID-19 shutdown. As ‘lease operator of the food & beverage concessions at the Anaheim Hills Golf Course, +80% of my revenue was derived from pre-booked event services (‘mass gatherings’), weddings representing the lion’s share. Weddings and other special events tend to be high stress for clients without this added dilemma, and one of the things which I prided myself in, was my ability to provide a level of calm, via expertise, experience, compassion, empathy and integrity. I had the foresight to have had an ironclad contract, which anticipated and provided for such possibilities as pandemics. Read more>>

Kris Martinez

There will always be little issues or problems that pop up, especially when getting ready for a big event. It can be something as little as forgetting to bring the straps to hold up my banner to forgetting the display for a particular piece. In the heat of the moment, issues like these can make me feel like the world is going to end, but really, I can easily fix these issues by improvising and moving certain pieces around. Read more>>

Bryant Portwood

Insecurity is a huge issue in the arts. Whether you are just getting started or already at a professional status, artists will always compare their work to others. I think that insecurity as an artists is inevitable. We create original works, pouring hours of heart and effort into every project. It is a very vulnerable thing to do, and of course, we want that work to be noticed and admired. I still constantly compare myself to other artists I have looked up to and focus on what could still be improved in my own work. It wasn’t until very recently that I experienced a shift where now I can still focus on how I can constantly improve my craft, but at the same time have a lot of confidence and pride in the work I produce and share with the world. Read more>>

Kumar Patel

At Omnidya, we faced several unexpected challenges as we sought to revolutionize the insurance industry. One of the most significant was the traditional mindset of the sector. For years, insurance had remained largely unchanged and was not in sync with modern technology. Introducing a model that combined AI, data transparency, and a focus on customer experience was met with skepticism. Moreover, as we evolved into offering hyper-personalized insurance with IoT devices, we had to ensure that our technology was robust, secure, and user-friendly. Read more>>