April 8th, 2014 or April 15th, 2014 – which date is worse?

If you are prone to procrastination then you can appreciate why April 2014 is a month that will make you a little cranky. If you have not done proper tax planning, you will wind up teary eyed with your hand shaking writing a fat check to the IRS.  If your company has failed to properly plan for its desktop migration for the last, oh 12 years or so, then you will be budgeting some fat numbers to pay Microsoft’s extended support ransom note.

Now, although you should have been planning your migration years ago, you can opt for an extension, but, like your tax return, it does not relieve you of your obligation to pay.  So, for those who have chosen to wait, it is a “pay me now and pay me later” scenario. And you’ve got no one to blame.

So, if you are of the mindset that hackers aren’t gathering at some virtual Churchill Downs, sipping mint juleps, just waiting for the April 8th post time to fly out of the gates on their way to exploiting Windows XP’s all to public vulnerabilities, then just carry on with what you have been doing.

I suppose you can do your best to quarantine vital systems, bone up on security, be hyper vigilant and virtualize XP systems and create your very own lost world, but it really should only be bridge solution. I would expect hackers already have little treats in store for XP laggards, so it will be interesting to see how this all plays out.

Who knows, maybe Microsoft will bend a little.  There is a fine line between support and enabling.  If you are expecting (or worse, hoping) for Microsoft to extend the olive branch to you, I would advise you that is probably poor thinking.

Let’s face it, nobody likes doing their taxes or doing an upgrade.  It is just a cost of doing business.  However, it is generally better to do both a little early, than face the consequences of doing it late.  Rushing to finalize either a tax return or migration will usually end up with costly oversights, errors and missing out on ways to reduce the burden (or increase the benefits) had you taken a more proactive approach.

Now, where is my checkbook…