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.

Marlena Shepherd

When I first had the idea to start my own Life Coaching business, I was elated. I had finally found my soul’s passion and mission! I couldn’t wait to get started. I did all of the things people tell you to do: I created a website. I built a funnel to get clients. I created an Instagram page and learned how to use Canva to create marketing materials. I learned who my ideal client was and how I could help her. Read more>>

Adam Sliger

As a music focused business person, one of the biggest problems you can face is lack of funds. When you’re on tour, things can go wrong. Vans can break down, gear can break, shows can fall through for myriad reasons. When these things happen, you have to find ways to make it work and push through. Read more>>

Krysia Badass

Not too long ago, about two weeks ago, I was at a low point, and I hadn’t felt that low since my eighth grade year of life. I was feeling as though I was alone in this world, struggling to tell what was my destiny versus what was my own mind. I felt like my mind was playing tricks on me, and I couldn’t decipher between my brain and my spirit. Read more>>

Julian Stanz

The past 4 years I’ve had constant migraines. It hasn’t been until relatively recently that I’ve gotten them under control. I was unable to work, write music, perform, record in studio, and struggled with basic functioning. Moreover, I was an inconsistent person. I couldn’t be relied on because I was always in such pain. I had 5 to 6 migraines a week, was on 3 medications, and was an absolute wreck. Read more>>

Melian De Carolis

The biggest problem was starting. I always wanted to have my own bakery but I was always financially on edge and unable to gamble with a business. When Covid hit I lost my 9-5 job like many others did. Ans as many have experience there was not much hiring going on at that time. So with the support of my husbands I took things in my own hands. That is how I started my company. Read more>>

Shana Regenhardt

Covid was an issue no one was prepared for. To have entire Industries shut down for months at a time, had never occured before. like we all experienced in 2020. My showroom had just parted ways with vendors I had been representing for years, due to changes in buying patterns. I decided to go in a new direction with a fresh curated package of products. Read more>>

Mitch CK

Look, posting videos of yourself online for the world to see takes guts. Even those out there that don’t have large followings, but are still making content. It’s not easy to do, and I commend all that do it. For me, all of that was fortunately made easier by my presentation skills and my ability to mentally compartmentalize my life. Read more>>

Kj Fraser

A challenge that I faced early on was learning how to separate business from personal relationships. I’ve always loved bringing people into my plans, however I learned it’s not always the best move. I have come to realize not everyone deserves access to what I hold dearly to my heart. That’s still something I work on improving everyday, which goes beyond the art and into my daily life. For me, the only solution is breaking ties and moving on. Read more>>

Jen Friel

My biggest “problem” or “issue” was technically something I was born with. I spent 37 years thinking I was “neurotypical” only to one day literally wake up and realize I’m not only on the spectrum, but I also have the gift of synesthesia. Synesthesia is a neurological condition that you are either born with, can receive via a blunt trauma to the brain, or by doing psychedelics. (Spoiler alert: I’ve done all three!!!) Read more>>

Patrick Goss

Something that is unexpected about pursuing a career making music is how much non music related activities go into building yourself a viable career. Like any other creative profession you get into it because of the love of the craft and the personal need to create. I thought that my passion and love for music production would be enough to build a career off of i.e. make a lot of music -> get better -> once my music is good enough I will start to build a following naturally and find success. This is sadly not the case. Read more>>

EZ Duzzit

One of the biggest obstacles of my career was figuring out what kinds of people to keep around me, as well as which ones to stay away from. Often times we have connections to people we feel are “close” such as family or long-time friends and unfortunately in this business you begin to realize that many of these people are more “in the way” rather than being “supportive”. Read more>>

Lyric Abbott

There’s a reason why so many people stay at their 9-5 jobs because when owning your own business you never know what’s going to happen next. When you have a business that provides digital products there will be unexpected issues. One of the first common issue I faced is Chargeback’s. For those who may not know A Chargeback is when a customer call their bank and basically state they did not complete a transaction that’s viewed on their statement then the bank will mark the transaction for that product as fraudulent and then the money will be returned to the customer’s debit or credit card, Read more>>

Kim Berkley

One unexpected issue I’m still learning to navigate is the difficulty of saying “no” to opportunities and increased workloads. Freelance life is freeing, but the cost of that freedom is a lack of stability and job security. Some writing gigs are temporary; the workload in others may fluctuate from week to week and even day to day. Read more>>

Alexandra Calvo

If there’s one thing I’ve discovered, it’s that nobody is as invested in your business as you are. Out of all the individuals I’ve collaborated with, only two individuals stand out for genuinely caring about every aspect of the business and conducting research whenever problems arose. I believe we are all guilty of this. It’s incredibly easy to clock out at the end of the day and simply forget about the issues that are impacting the business’s profitability or customer satisfaction. Read more>>