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.

Christina Bjorklund

Packaging has been our biggest obstacle and resulted in a lot of trial and error. We tried various jars and lids and some would leak or didn’t meet the look we were aiming for. We finally invested in aggressive seals for our products to prevent spillage. We also tried many packing boxes before we could determine the size we would need the most of. It’s been challenging but I feel like a packaging expert now! Read more>>

August Bleu

Well, it’s not the issues I had with business, but more of what I went through while pursuing my career as a recording artist/songwriter. I was shot 7xs and paralyzed, so that kind of slowed down the process. I was able to recover from that situation mentally, due to having an amazing support system. Read more>>

Brynn Brdar

I think the most daunting thing about identifying as an artist, and choosing to attempt to make your living as such in this world, is the balancing dynamic of acting as a creative architect, while simultaneously having to self-promote and act as your own PR and media agent. This is a conundrum I’ve dealt with outside of the arts and within the artistic field for some time. This conundrum is the acknowledgment that holding all human beings to the same standard of performance glazes over our fundamental differences as individuals, as well as forces conformity on people who may shine in some areas, but have difficulties performing in the socially upheld standards. Read more>>

Abby Monroe

The biggest unexpected setback that I ever faced came towards the end of my time in undergrad. I went to college in San Francisco, which is a notoriously expensive place to live, so all throughout college, I had to work a series of non-musical jobs to get by. I worked mainly in a coffee shop, which was a lot of fun for a college side-hustle. However, as I started to get more established in the Bay Area as a working musician, having the coffee shop job on top of playing gigs and performing was incredibly hectic. There was a turning point right before my last year of college where I realized that my music schedule was becoming too unpredictable, and I was making enough money doing it enough to get by, so I decided to quit the coffee shop and focus on music entirely. Read more>>

Melissa Minh Truex

Sometimes things don’t go according to plan. That’s why I’ve made it a habit to always have a backup plan ready. I approach challenges with a problem-solving mindset. Forging ahead is the only option, particularly when you’re your own boss. Over time, I’ve discovered that such challenges can often lead to unexpectedly positive outcomes. Take, for instance, the experience with a floral ceiling project. The client wanted a feeling of abundance with no ceiling showing through the dried florals. We were working within a strict timeline as the store opening date had already been set and the remaining florals would not be delivered in time for installation. Rather than waiting for post-opening to finish the installation, we opted for an alternative solution. Read more>>

Meghan Hogrefe

One of the most unexpected issues/problems is that you must prepare for the unexpected. When I launched my clothing line, it happened to coincide with my husband and me launching multiple businesses in another state. While we didn’t initially expect that we would be so entrenched and involved in as many businesses as we came to launch, it just made sense to keep the ball rolling or bouncing! This unexpected endeavor taught me be to be able to embrace the process of change and to relinquish my expectations. Especially in regard to everything operational, i had to realize that my dreams may always be there yet sometimes, you will have setbacks or delays. That it is ok to not do it all, all at once, It is easy to get pulled into so many directions and feel torn between what you dream to do ( my clothing line) and what makes sense to do. Read more>>

Quantez Harper

I was recently commissioned for an exterior art installation at a local school. After a few meetings and finalizing the idea with a 3D model my first big project started. This is where the first issue appeared, equipment. As I began to gather things I realized the additional items and heavy-duty equipment I was going to need in order to pull this off with a great level of craftsmanship. I knew I had the ability to complete the project but I only had 10% of the equipment. Renting or buying the tools was an option but that meant using contingency funds and I wanted to avoid that if possible. Thankfully, I was able to borrow most of the things from a neighbor. Later this neighbor would say that he was “amazed by the number of people with talent and vision who simply do not have equipment”. Read more>>

Marquita Miller Joshua

Losing a spouse while managing a business can be an overwhelming journey. Navigating the complexities of grief and maintaining business goals often prove to be an intricate balancing act. In my case, my late husband passed away in May 2017 after a 23-year marriage. His integral role in the business was undeniable, serving as the foundation upon which our business idea was built. Read more>>

Tim and Lindsay Ellis

[Let’s just say….things will not always be as they seem when it comes to owning a business and being business owners. We believe it’s the attitude of “making it work” no matter what, that elevates one in the face of adversity. From the start of our journey, we have had an uphill battle with our station’s tower signal. A quarter million-dollar investment to reverse our said issues isn’t exactly a walk in the park for small business owner. Instead of hiding behind an ongoing issue, between engineering obstacles and financials, we own the situation we are in and talk openly regarding our signal with listeners as well as prospective and active advertisers. Instead of allowing defeat in our business, and to ourselves personally, we’ve became about ‘flipping the script”. Read more>>

Tyler Chronicles

The ups and downs of being an entrepreneur can sometimes be overlooked. You have to have some type of fortitude to be way up top and down at the bottom, sometimes in the same week. Looking ahead can bring anxiety. But planning ahead can bring peace. Read that again. Read more>>

Kevin Breeze

The most significant challenge I’ve encountered as a full-time social media influencer and content creator is determining which platforms and projects merit the majority of my attention. Given that time is a limited commodity, I must prioritize activities that will most effectively push me towards my goals. Instead of trying to maintain a constant presence on every major social media platform, I’ve chosen to concentrate on just a few. This strategy allows me to produce the highest quality content for my audience. I’ve also come to realize that it’s perfectly acceptable to decline certain opportunities, even if they seem tempting at first glance. Read more>>

Mikey Boss Dog

I think managing the dichotomy our society has between artist and “business owner” I’m a full time artist. I run my design and apparel company full time. I have two full time employees and two part time employees who work at our brick and mortar. But I am an artist. No different from the artist who produces posters and sells them on Etsy to an extent. I identify as a business owner because I don’t know many artists personally who aren’t business people. Being taken seriously, successfully making a living, having the savvy to make the right calls — those are all attributes of a successful artist in 2023. The problem I encountered was realizing the world doesn’t like to work like that. From Instagram to life itself, people don’t see artists as having agency typically. Read more>>

Diana bribiesca

I would say that the biggest unexpected problem for my company would be the shutdowns due to COVID-19 in 202. I was unable to plan or execute any wedding or event. The way I resolved it was to offer to postpone any wedding on the calendar at no charge. During 2020, our company also created elopement packages and offered those to couples who were still looking to get married without a large guest count. We as a team were able to navigate through the next year of regulations by offering these elopement packages. We still had challenges though with a limited amount of marriage license appointments being released for San Diego County. Read more>>

Stability X

When being discharged early from a 9 year career in the U.S. Army due to issues related to work based disabilities (traumatic brain injuries from jumping out of military aircraft as a paratrooper ) as a single mother my safety net vanished. Collecting $500 a month in disability from the Veteran Affairs left me and my daughter homeless and with a reposed car. This gave my ex husband credibility to walk into Family Court and Petition for custody of our daughter after I had been Primary care giver for the last 6 out of 8 years. Once losing custody in August of 2021 I begin using Art full time to voice my pain and frustrations but to also be a form of visual therapy for me. Read more>>

Shina Lee

Honestly speaking, many of the challenges I’ve faced in my career (both as a graphic designer and art director) often boiled down to me not being American, and thus feeling super stuck whenever I had to come up with or tap into insights about the local market–all of which is essential in creating ads or designs that resonate with people. Beyond that, I felt I couldn’t often even relate to many of my coworkers, which was pretty isolating. Interestingly enough though, a few years in, this same struggle that constantly held me back also ended up propelling me to new professional heights. Read more>>

Sakeisha Hylick

Dr. Sakeisha’s Journey: Overcoming Obstacles and Helping Marriages Win Dr. Sakeisha has defied the odds, both in her personal life and her professional journey. Raised in a single-parent household, she and her husband made a firm commitment early in their marriage that divorce was not an option for them. Their shared passion and determination led them to create the ‘Vows to Victory’ virtual summit, a platform where bold couples could openly share their truths and triumphs, fostering transparency and growth. Read more>>

TraMel

In the beginning, I believed that those closest to me like family and friends would automatically be on board. In the beginning I believed that someone would recognize my “greatness” and want to sign me or basically rescue me by guiding*   through the process and be encouraging when I wanted to quit. None of these things were true. Some family and friends have supported me from day one, but ultimately I had to prove my worth to everyone. Read more>>

Santiago Echeverry

Technological changes! I started work g with technology back in 1988, when cameras were attached to backpacks, and 3/4” tapes ruled the professional world. The first creative computer I ever used was the TI994A, followed by the Commodore Amiga. The first interactive tools I used were Authorware, HyperCard and Director. I created plenty of projects that I can no longer access because those technologies became obsolete. Some of my most complex projects were created for the web on Flash, and now I can’t even see them. This has forced me to adapt constantly to change, and have no attachments, it’s a zen practice that allows me to enjoy the moment and be open to upcoming challenges. Read more>>

Jasmine Cain

When you’re a touring artist, breakdowns and malfunctions are going to happen. If it’s electronic, it’s going to fail. If it’s mechancial, it’s going to fail. If it’s human, it’s going to break down. Throughout the years of touring, I’ve realized the importance of having back-up plans for back-up plans. It takes some time to put those safety nets in place, but realize that when you have something that fails, there is nothing more satisfying in knowing that you have a contingency plan. Obviously it costs a lot of money and takes time to buy more than one wireless pack for your systems and have a stockpile of batteries, strings, straps, tuners, and all the little parts that might break on your instrument. Read more>>

Rick Wilkinson

There are lots of problems we faced. Insurance is a big one. We have commercial insurance on the vehicle as it is required to go to events. Your personal vehicle policy clearly states your vehicle cannot be used for commercial purposes. By definition, once you have an item in your vehicle for delivery, it is a commercial run/ use. It can be voided and will be in the event of a collision. Making candles in your house goes against your home policy as well. Commercial. A business also has higher risks for torts (slips and falls). Your house was not set up commercially, and you can be sued personally. It is not worth the risk. We have commercial space for that purpose. Read more>>

Chris Limeres

Well, an interesting story on this subject is that when I began to get into the clothing design world and I started to implement graphic elements from my illustrations on to clothes, everything was going well, but I took time to really plan out how I was going to make this work. What printer and software would allow my elements to pop in certain areas of the clothes? That was the challenge. I chose inkjet printers, which, when combined with transfer paper and heat presses, allowed me to transfer my art onto the clothes. For starters, many challenges resulted in my chosen paper type. I used sublimation ink, which doesn’t work with regular ink, and I kept heat pressing with the right temperature and pressure settings, but still nothing. Read more>>

Jae Vonne Teague

I decided to launch a magazine as the first introduction to my Faith-based media company back in 2020 when all of the pandemic and socio-economic challenges was at it’s peak. I wanted to be a bridge of hope to women who were struggling during that time. Due to the pandemic, most local vendors that I needed to properly launch my magazine and get help with content, was either unavailable, had limited work hours, or was completely out of business. This included local print shops, other local magazine companies, previous mentors, etc. Read more>>

ALEXSORCIST

Growing up in poverty and in a culture that never openly discussed their emotions or mental health, I always leaned on art to express myself. The unexpected issue that I began to face during my creative journey was differentiating the part of my work was business, while also navigating which parts of my work were personal. As an artist who was using art to self express, I found myself burning out a lot and dealing with chronic depression to a point where I no longer wanted to create; I was overwhelmed with the industry and not seeing results I wanted in order to “succeed”. I couldn’t understand why everyone seemed so great at networking and constantly working on their art, while my brain felt like it was on fire. My anxiety had gotten so bad, I stopped all together. Through that hiatus and years of self discovery, I had to question: who was I making art for? Read more>>