My Side Hustle is Turning into a Fumble

The realities of small business ownership and general chaos

Jenna Goldsmith
4 min readFeb 19, 2022


Photo by Garrhet Sampson on Unsplash

As much as I preach mindfulness, rest, and a simple life being a millennial means I’ve fallen into the trap of Hustle Culture™️ and opened my own small online business. In June of 2020 — right smack dab in the middle of the first wave of this pandemic — I opened “The Littlest Online Bookshop,” a teeny tiny online used bookstore.

The reasons why I made the plunge into business ownership are muddy and complicated, but in its essence, it was about my love of books and my desire to bring that love and passion into my local community. Of course, I was hoping it would be successful and make some money, but that wasn’t the top priority.

Once it was up and running, I felt the surge of pride in my own accomplishments. I was no longer Jenna, sometimes writer, I was now Jenna, sometimes writer and business owner. It seemed by taking this step, I’d added some value to my life in some way.

Though, when I think of it with some hindsight, it seems a little superficial.

I wasn’t a better person or a more valuable person because I opened my own business and basically had to work all the time to keep it running. Though, I felt less guilty for my “downtime” after my day job because it was now spent working on my online business instead of, well, relaxing and enjoying my evenings.

At first, though, it was quite rewarding; building up my inventory, my social media following, and my customer base. When I started getting repeat customers, I felt so elated because people actually cared enough to come back!

I seemed to be on a slow but steady upward trajectory. Of course, I never expected or had ambitions for massive growth, so anything was fantastic.

Just over a year after I’d opened, I even did a very rustic mildly successful pop-up shop.

But in late 2021, after a mediocre holiday season and an even more mediocre winter, it hit a plateau and a plummet. And I don’t know how to fix it.

To be completely honest, I started this business on a fairly tight budget. But, I worked with what I had and did everything myself. I don’t have swaths of family money to…



Jenna Goldsmith

Writer || INFJ || Wellness junkie and chronic oversharer.