My Checklist For Making The Self Employment Switch


self employment

Spidey’s got a plan…

Working two jobs is a pain.

Working two jobs is tiring.

Working two jobs is not something I recommend doing for very long.

But at the moment I’m actually enjoying it–a lot!

The reason for this is that I know what the possibilities are for me and my family this year, if we can accomplish some of the goals we’ve set for ourselves. And to be honest, that’s really the only thing keeping me on track at the moment, because as I look at my life over the first 2 weeks of 2014, I’m not very impressed with my work/life balance so far.

My goals for having this part-time job do NOT involve working long hours. As a father of two (with one on the way) I have a burning desire to spend quality, focused time with my wife and kids. Financial Independence is something I want to pursue for them, not in spite of them.

My goals DO involve transitioning from working 1.25 jobs to working around 0.75 jobs, and hopefully still being able to earn plenty for my family to live on. We’ve been working for the last 5 years to put ourselves in a position to make a move like this, but there are some things we still need to accomplish if we want to make our plan work.

Milestone #1: Pay Off Our House

In our last journey update I stated that we only have 14 more months of mortgage payments before we’re totally and completely debt free.

Well, sort of.

That estimate doesn’t include any of the part-time income from this side-job. If everything works out there’s a chance we could pay off our mortgage around December 1st of this year!

If that were to happen, it would be a huge milestone for us to reach. 5 years ago we decided to downsize our house in favor of living life a little differently, and paying off our mortgage would be a big step for us.

Not having a mortgage would mean that our annual expenses would drop by over $7500, which makes a job change much more forgiving, when you’ve got to provide for a family of 5. It would also mean that we would be instantly mobile in terms of location. We could rent out our house pretty easily if we needed (or wanted) to move somewhere else.

Milestone #2: Confirm that my side job could become my main job

Currently I’m planning to work around 4 hours/week at my side job, to help manage the IT projects that this company has going on. At the moment I’m working 8 hours/week, just to get them caught up and get myself acclimated to their way of doing things.

But if everything goes according to plan, and if they like my services as the year goes on, we plan to begin talking about the possibility of moving to 12 hours/week next year.

That means that I need to be going over and above the call of duty, when possible, to prove to this company that I’m worth the investment they are making. My limited amount of time right now makes this difficult, but I’m doing my best.

Milestone #3: Replace 75% of my current income

Obviously working 12 hours/week with no benefits does not a sound strategy make. Unless, of course, I can find some similar businesses that want to put my expertise to work. My hope is that I can either turn my current full time job into more of a consulting role, or else find another position entirely who could use me like this.

There are a TON of small businesses out there who need basic IT consulting, and since my rates are less than most I think I should be able to pick up a few clients in that arena if necessary. As I’ve stated before though, I love the company I work for and would love to continue to take care of them, just in a slightly altered arrangement.

Obviously there’s a lot here that has to be accomplished over the next 12+ months, but I’m very excited about it all! I’m working with people I enjoy being around and working in a field I love.

If I can tailor my work schedule more around my family over the next 12 months, even better.


Are you working extra to “get ahead” or are you happy with the level of work your job has? I’d love to hear what you think of my self employment goals for 2014, and if you have any for yourself!