This may be a metaphor that doesn't mean a lot to you southern and California people, but Idealware's based in Portland, Maine, and up here we give a fair amount of thought to snow. I was shoveling out the driveway from our first big snow of the season (maybe 6") yesterday, and while I did it, I was giving a fair amount of thought between the overlap in shoveling and technology planning. Bear with me here.
While you're shoveling out your driveway, you plan how much room you'll leave for the cars. Maybe you're feeling lazy, and you shovel out a passageway with just an inch or two to spare. Or maybe it's an easy shoveling job, and you shovel out generous room to turn in from both sides of the street.
It doesn't feel like a decision of much importance, until you've lived somewhere where it's below freezing most of the winter. Here, you build some serious snow dunes with what you've removed from the driveway. And soon those dunes thaw a little, freeze a little, and there's a little rain, and a little more snow on top of them... and within a few days your casually shoveled banks of snow become impenetrable blocks of ice. Which may well be with you until spring, unless you have an unseasonable thaw or invest a lot of backbreaking labor.
Okay, so here's where the metaphor comes in. There's a lot of technology decisions that we as nonprofits approach just as casually. But just as often, our decisions can be with us for much longer than we thought they would. You decide to just throw up a temporary website without a lot of thought to the structure... but then between one thing and another, you're still using it two years later. You decide to use a particular piece of software mostly because you need something in a hurry, but then your staff is used to it, knows how to use it, and doesn't want to change.
Change is hard, whether it's chipping through the ice to widen your driveway, or trying to move off something you've been using for a while. It's worth giving a little extra thought when you're making those "temporary" decisions, to consider whether they're likely to make your life a misery if you need to try to maneuver though between the barricades they've imposed for much longer than you planned.