At some stage during the career of most IT pros the opportunity comes along to spend some time as a contractor.  The lure of high rates, fixed hours, frequent new challenges, and the idea of “working for yourself” are what draws most people towards contracting.  Each of those carries with it some truths and some myths that new contractors need to understand before diving in, otherwise they may find themselves learning a few harsh lessons during their first few contracts.

So you want to be an IT contractor?  Read on…

In this series I will discuss IT contracting from my own experience and from the experiences of colleagues of mine in the hope that it will help others as they enter what can be a very lucrative and enjoyable stage of their career.

Is contracting right for you, and are you right for contracting?

IT contractors usually fall into one of two categories:

  1. Low skilled labor, such as basic coding, call centers, hardware rollouts, and other menial routine tasks.
  2. Highly skilled specialists in high demand fields such as storage, virtualisation, messaging, security, and databases.

If you fall into one of those categories then it shouldn’t be hard to find contracting opportunities (they just won’t all be good ones).

The pros of contracting

There are some good things about contracting in IT, such as:

  • good hourly/daily rates available
  • opportunity to encounter new challenges and environments on a regular basis
  • working more than 40 hours per week much rarer than in permanent employment
  • easy to avoid office politics and just get on with the job
  • many good positions where your contract will be extended many times over
  • easy to walk away from the less enjoyable positions at the end of a contract

The cons of contracting

Despite all of the pros there are also some downsides to contracting, such as:

  • depending on how you set yourself up, can mean a lot of paperwork, tasks and costs associated with running your own business
  • no paid leave (annual leave, sick leave, public holidays, etc)
  • often responsible for own training and skills upkeep
  • often left out of strategic discussions and company social activities
  • can carry a higher risk of termination and/or unemployment during economic downturns
  • sometimes you need to take an unappealing contract when nothing else is available
  • work locations (and things like transport options and travel time) can vary wildly between contracts
  • have to deal with the recruitment sector on a frequent basis

If any of those cons bother you then maybe contracting is not for you.  If you’re willing to take some risks, do a bit of paperwork each week, month, quarter, and year, and are a good negotiator when it comes to dealing with recruiters and hourly rate discussions then most of those cons disappear.

In the next part of this series I’ll discuss the different ways that you can set yourself up for contracting.

About the Author

Paul Cunningham

Paul is a former Microsoft MVP for Office Apps and Services. He works as a consultant, writer, and trainer specializing in Office 365 and Exchange Server. Paul no longer writes for


  1. Andy Larin

    Love the tips on your site.

    We are a company that does this, we are all independant comtractors so you are in business for yourself, just not by yourself. Have a look.


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