One definition of the phrase "pennywise and pound foolish" is to "describe something that is done to save a small amount of money now but that will cost a large amount of money in the future."

I think of this a lot when working with my clients, especially when they are making decisions about technology. (And if I'm being blunt, I see it most among those in the finance area.)

The "price to entry" for a lot of technology can be (perceived as) very high, especially if the organization has been spending little to no money on technology for a long time. I've had more than a few clients who, having not paid much of anything for technology for years, have sticker shock when they find out how much a modern AMS is going to cost them.

But often what they're not taking into account is the incredibly high indirect costs of spending so little on technology. For example, I once had a client tell me that she had staff actually resign from their jobs because, as the staffer put it "our poor technology makes it almost impossible to do my job."

So when you're investing in technology, you really need to think of it as an investment, not just an expense. The money you think you're saving now will likely have to be spent later, and quite possibly even more.