You’ve probably had an item of clothing that seems to fit better, feel more comfortable and just “sits right” on you. Maybe it’s a sweater, a pair of jeans or a leather jacket. I’ll bet you wore it until it literally fell apart, and if it hasn’t yet fallen apart, you’ll still wear it – even if only while gardening.

Many people do the same with their accounting software. The version of the software that they implemented in 1998 worked well then, and still feels good to “wear”. So they’ll keep using it, forsaking all upgrade offers, because it’s comfortable.

But just as that old shirt will eventually unravel, or develop holes, your old accounting software will eventually “fall apart”. Assuming for the moment that the feature set is still fine, and you truly don’t need the functionality provided by newer versions (a stretch, but bear with me) – you’ll start running into problems when you try to install it on a new computer running Windows 7, or when you need assistance and no-one working for the software publisher even remembers how that old version works.

The difference, of course, is that when that item of clothing unravels, you just change into something else. But when your critical business and accounting software fails, or the computer it was running on dies, it’s not that simple to replace or upgrade.

Case in point: last week my company was asked to help a customer running a 1998 version of our software. Yes, that’s not a misprint – 1998! They tried to install it on a new computer running Windows 7, and not surprisingly the installer failed (having been written 11 years before Windows 7 existed). Turns out their only choice was to format the drive of their new computer, install Windows XP, locate and download all the device drivers and patches needed to get Windows XP running on this computer, and then re-install their 1998 software.

I suggest you don’t let this happen to you. Keep your key business software at least relatively up to date.