Side Job To Self Employment – Could This Work?


side jobOne of the many benefits that come with writing a financial independence/personal finance blog is that you have your ear to the ground all the time when it comes to financial issues. I’m constantly exchanging ideas and philosophies with you, the reader, and with other writers that I follow. Then, when real life happens, I’m much more likely to be prepared to respond to it intelligently. Well, more intelligent than I would have otherwise.

So what the heck does that even mean?

In my previous post I discussed the option/possibility of taking less of a paycheck in order to become self employed. This was not a random topic, it’s something I’ve been mulling over and discussing with some folks since before Thanksgiving. The possibility of taking a part-time or self-employed position in order to have more flexibility in my life, and be able to allocate as much time as I like to my family. (If you missed it, I also revealed that we are expecting our 3rd child next summer.)

A couple of posts before that I talked about the two stages of debt that exist in the mind of the FIer. There is a pressure that exists inside me, a pressure to make as much money as I possibly can (and as quickly as I can) in order to escape this “time debt” and live in financial freedom. Obviously, this is the OPPOSITE scenario of the other post, because this prioritizes income potential ahead of flexibility.

So is there a happy medium? Is there a way to satisfy both desires? This is the question that I’ve been wrestling with for the last month.

My New Side Job

I have a friend who is looking for the exact sort of IT management that I currently provide in my full-time job, but he only needs around 12 hours a week instead of 40-50.

Now, 12 hours a week would be a full blown “hustle”, not just a side-hustle, and I’m not about to break away from a great company with a solid income in the year that I’m going to be paying for another child to be born. I turned down the offer, but suggested that we find a way for me to “keep my foot in the door” by giving them 4 hours a week of my time at a set rate, which I could do alongside my current job.

It looks like this plan is a go, and in January we’re going to give it a shot. I would work from 5-7pm twice a week in order to help them accomplish the tasks they are looking for, and would basically be billing them at a consultant’s rate, not just a part time employee’s.

So Where Does Self Employment Come In?

If everything goes well over the next 12 months we plan to talk about trying to get back to that 12-hours/week kind of schedule that they desire, in which case I could get paid around half of my current salary for performing 12 hours’ work per week! Unbelievable, but true. This firm doesn’t want to pay for a full-time IT Manager, but to be able to get one for 12 hours a week is exactly what they are looking for.

The key to this setup would be the flexibility. This arrangement would allow me the flexibility to spend the rest of my week as I see fit, which might be consulting for other customers, developing websites, day-trading, blogging, or spending the time with my family that I desire. They would even allow me to work out of their office for my other endeavors, so that I wouldn’t have to head to the coffee shop in order to “get some work done” from home.

It’s a dream scenario, but one that will take some careful planning and some hard work in the meantime to make it happen. And if it does happen, there’s the potential that I could earn just as much as I do now and work fewer hours in the process.

Then again, it may all blow up tomorrow! But even if it does, I’ve burned no bridges and lost nothing, and I’ve gained a valuable experience.

Going back to my first point, though. Reading about and discussing these topics will sharpen your sense of what you’re looking for in your financial future, what’s available out there to be pursued, and will give you confidence to go after them, because there are so many stories of people who have been successful in the past. Many other bloggers and commenters have given me the confidence to pursue this opportunity, and the wisdom to see how starting it as a side job (instead of my only job) could be the best plan.

Stay classy, blogosphere!