IT Contracting: Is It for You?

By Donald Sears  |  Posted 2009-05-15 Print this article Print

It feels like the question of these times for a technology pro: whether or not to become a self-employed, "for hire" technology contractor.

For those of you used to the stability, benefits and opportunity for growth of full-time positions at technology or other companies, is becoming your own boss something you would even consider?

There are a ton of things to think about and know, but for some, it may be one of the best options out there. For others, it could easily be the only option out there right now.

After reading up on what contractors and those who own contracting businesses have to say, I think I have it boiled down to a few key things to know. It's not necessarily a slam dunk, but then again, nothing really is these days, so the thought of working for yourself could have some appeal.

I've broken things down in to thumbs-up and thumbs-down, but some of this is really going to depend on your own personality or how much of it you are willing to change.


  • Freedom to make your own hours, and say yes or no to a manager, job or project
  • Flexibility to take time off if you make enough to survive, pay your bills, mortgage, support family, put money away, etc.
  • Potential to work at many different companies, types of projects and with many different colleagues and peers
  • Chance to avoid petty office and work politics--you're there to work on a project and get it done (and hopefully do not get pulled into the fires that inevitably happen)
  • Potential to keep more of the money you make as your own company

  • Issues about benefits like health insurance, retirement and the accounting of all of these things
  • Work travel, and potentially lots of it, could keep you away from spouse and children (or simply where you live) for longer than you'd really like (though aren't many of you already doing this anyway?)
  • Paying for skills training (though I don't know too many tech shops doing much of that in this recession, but it's more about the time off and no one is going to pay for it--this is skill-level dependent)
  • Having to always be working (time away could be difficult if you live somewhere where your monthly expenses are high or if there are other factors such as debt)
  • Have to work when the work is there (work can be cyclical--both busy and dry times will occur)
  • Stress of worrying about all these things

Here are a few links I used to get a sense of what it's really like for those in the trenches, and how some are adapting to career changes in contracting or starting their own businesses.

From InformIT: Now What? - The Advantages and Disadvantages of Being an IT Contractor

From What It Means to Be an IT Contractor

From Starting Over--as an Entrepreneur |

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