Leaping into IT contracting

I often get asked how do you know when you are ready enough for contracting?

Amazing picture

The contractor journey!

(BTW we are looking for a graphic designer to help us!)

This is my path, and it is shared with many others I now work with.

The early years

Fresh out of college, I was looking for a programming job. This was going to be a junior position, but they wanted degrees from University. I was the odd one out in my circle of friends by not going to Uni.

My search lasted for about 1 year, when a friend of mine told me about a Trainee Technician role at an IT hardware maintenance company. They wanted trainees to help move the ePOS equipment. When I say move, I mean remove and replace on site.

The promise? We will train you how to fix onsite and within 2 years you will be promoted. For me within 1 year I was able to pivot to PC support, a lot of printers and monitors, but also fixing configuration and provisioning Desktops and laptops.

As promised, in the 2 years I was promoted. If you have read the previous post, you’ll know I was made redundant a couple of months later. That’s for another post.


In the next 4 years, my technical experience grew from Desktop and Laptops, to include some Server configuration and setup. This included learning about virtual machines (yeah long time ago) and automated provisioning.

After 6 years of my IT journey, I was now working on Servers most of the time and then made redundant again.

So now the idea time to take my severance package as a cushion and leap into contracting with the skills and experience.

I didn’t really know what I was doing, but I found a contract, made a bunch of mistakes, which I will share with you.

Given my over 20 years as a contractor, I can guide you through this and other ‘features’ of IT contracting.

Come ask me and the community questions. You can find me on Slack.

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