The biggest mistake I made with my small business is not starting it sooner

Kara Monroe
3 min readJun 17

Photo by Arnel Hasanovic on Unsplash

Being my own boss was always in my plan for my life. I’d tried to make a go in multi-level marketing (MLM) sales through Creative Memories and Longaberger, which is a story of a financial mistake I’ll save for a future article. However, even as I toiled away as a more than “full-time” employee for more than 20 years, I also picked up side gigs where I thought I could do good work for the client. And, I loved those opportunities to be my own boss. To do the work in real partnership with the client, but on my time and by my means.

When I left traditional employment in early 2022, I quickly formed Monarch Strategies LLC and signed agreements with my first few clients. As I walk down this path, though, I realize how silly I was to not create the LLC years ago and begin building my “side hustle” as an active business.

First, not having at least two years of business income on my taxes has caused me challenges in two areas thus far. We’re still another year and a half out from the last time a W2 will show on my taxes. I have no doubt this may come back to grab me again.

The first time this came up was filing as a woman owned small business in my state. This type of certification — available in many states — can take eons to get through. It takes even longer when you don’t have “traditional” business history to show for your past work in the form of tax returns for the business.

The second time this came up was buying a house. My income doesn’t exist according to the bank, since there aren’t two years of W2 free income. Are there ways to get around this? Yes. But essentially, until you’ve been in business for two years, as standard practice, your income doesn’t matter. This is made even more complicated since I’m buying this house with a friend. Our partnership really should resemble a business deal. It would have been cleaner for our estates to buy it as an LLC. Unfortunately, that makes the already complicated financial nature of this proposed purchase even more challenging.

Second, it feels unethical to me to refer to clients I had before I incorporated Monarch Strategies LLC as past corporate clients. This is a very fine line of ethics…

Kara Monroe

I am a world traveler, part-time road warrior, and home body all wrapped up in one gadget-loving package. Writer, photographer, chef, and aspiring artist.