Wading Back Into Freelancing

At some point around the end of 2019 I made the decision to wind-down the freelancing side business and focus on something different for a while. Unfortunately, that "something different" turned out to be just more time spent working for the day job. While this did result in earning more money than I would have through freelance contracts, the range of work was not nearly enough. One of the many things that I've come to enjoy when working with clients is learning of new ways to solve common problems, and codifying that in some sort of system, digital or otherwise. Last year was a wash for so many people, but 2021 is looking up. I've already had two former clients reach out to carry on with some projects, and I'm putting out feelers for more projects to see what opportunities might exist. Despite always feeling there's never enough time, I cannot help but feel the need to create new things that reduce friction in people's lives. It's pretty much the only thing I've ever been remotely capable of.

Working on the side often comes with a number of pros in the long run and cons mostly up front. There's the need to register a business with the government1, hire the services of an accountant twice a year, hire a lawyer within 90 days of registering to go over various legal expectations, obtain licenses and permits, and track financial data. All the things I grew tired of doing when freelancing last time. However, I do plan on being a little smarter about the legal requirements this year by making use of a company in town that specialises in these tasks for small businesses. I'll let the experts do what they do for a reasonable fee so that I can do what I do for slightly more than I used to charge … mainly because of the fees.

What I hope to achieve with this new foray into freelancing is a sense of accomplishment. While there are a lot of benefits to working with teams of smart people around the globe, I much prefer working with small businesses. People are just as focused on solving problems, but there's much more attention paid to efficiency and effectiveness. If something takes a little bit longer to get right, then the time can usually be accommodated with a small entity if it means saving money in the long run. I appreciate this approach a great deal and, by working with a smaller number of people, it's much easier to get answers to questions. Getting information from a company with 5 employees is much easier than a department with 50.

Of course, I do worry that I might once again bite off more than I can chew. As the years go by this body is much less forgiving of all-nighters. Perhaps some hard rules will need to be put into place again, like I did five or so years ago when it became taboo to look at anything with a glowing screen past a certain hour. If I force myself to put everything away — including the phone and tablet — by midnight, then it should be relatively easy to get into bed before 1:00am. With six hours of sleep every night, I generally wake feeling refreshed and ready to go the next morning.

This is wholly dependent on whether I can earn some freelance contracts, though. Right now everything is still in the early stages of discussions with former and potential clients. Once someone agrees to get started, then I'll put in the legwork to re-register Matigo Solutions with the local and federal governments.


  1. If I earn more than $2,000 per year, I will need to declare it on my income tax statements and collect tax from domestic clients.