Sense with Cents

There is a version of this story I hear more often than I would like. Someone has been using the same software for fifteen or twenty years. It still opens. It still does what it always did. So why change it?

Then the computer fails.

I had a customer contact me recently in exactly this situation. They had been using accounting software since the late 2000s — installed from a CD they still had in a drawer. The computer they had been using finally gave out. They had a backup of their data. What they did not have was a path forward. The software had gone through multiple major revisions over nearly two decades. The data structure had changed significantly along the way. There is no upgrade path that spans that kind of distance. The data was effectively stranded.

This is the cost of “if it ain’t broke.”

The software was not broke. It opened every morning and did its job. What was broken was the assumption that nothing would ever go wrong — and that if it did, there would be an easy way out.

Keeping software current is not just about getting new features. For most people, the new features are beside the point. It is about staying within reach of a recovery when something goes wrong. Software companies change data structures over time. They drop support for old formats. They stop building migration paths for versions that nobody should still be running. When you skip updates for long enough, you eventually find yourself on an island.

This applies to any software that handles something important to you — accounting, payroll, medical records, legal files, tax history. The longer you let the gap grow between the version you are running and the version that is current, the harder that gap becomes to cross.

Updating software is not free. It takes time, sometimes money, sometimes relearning things that changed. It can be inconvenient. But that inconvenience, spread out over time in small doses, is far cheaper than the alternative — which is to pay it all at once, under pressure, when something has already gone wrong. Staying current is itself a form of not declining. The software you depend on is only as current as the last time you updated it.

There is a footnote to all of this that still surprises us. It has been more than thirty years since Medlin last used our own DOS-based software internally, yet we still get a question or request about it every year or two. Honestly, there is a nerdy nostalgia to it — we still have people here who were involved in building that software and are happy to reminisce. But the situation is not a good one for either side. The customer, who may have been running what started as trial software all these years, is unhappy because we cannot help them. And we are unhappy for the same reason. Nobody wins when the gap gets that wide.

It is a lesson we know firsthand. At Medlin, we learned this too, about a decade ago. Computers are no longer tools used only by experts — they are more like appliances now, and people expect them to just keep working. Customers do not always keep current on their own, and we could not assume they would. So we adapted. Every time you open Medlin, it checks to make sure you are running the current version. Ignore enough reminders, then warnings, and you will reach a point where you can no longer move forward without updating first. We did this on purpose. For payroll software specifically, staying current is not optional — tax tables change, laws change, forms change, and we average at least 50 updates in a single year. We would rather you never find out what too far behind looks like, so we make sure you never get there.

Take a few moments and think about every piece of software you use for something that matters — your finances, your records, your business. If any of it is more than a year or two out of date, contact the developer and get current. There is no good reason to let your software go stale. The same goes for your computer hardware and your operating system. None of it should be left to age quietly in the corner. The cost of keeping up is small. The cost of falling behind has a way of arriving all at once.

If you would like to discuss your own situation, I am happy to do so by email. I will share what I do personally, both software and hardware. On the hardware side, I replace my computers on a regular cycle — at least every four years, to avoid the trap of aging in place. The one thing that changes that routine is a new operating system. When that happens, I get a new machine with the new OS preinstalled rather than upgrading an existing one.

I also keep my former computer at the ready, unplugged but not forgotten. Every few months I connect and power it up, install any updates, and restore my current backups to it. That way I have something ready to go if the worst happens. My main backups are online, so I do not have to worry about local backups being damaged or misplaced — though I still keep local backups current for those moments when I need to recover from my own mistakes. Fat finger recovery, as I call it.

See also: Do You Really Have a Backup? and Help Me Help You.