A Good Mistake: Leave the Wallet Home
I forgot my wallet on a July 3rd grocery trip. (I'm the designated shopper in the family.) When I got to the grocery store—22 miles from home, the closest—I discovered I'd left my wallet behind. Luckily, I had a secret cash stash in the glove compartment, just for this sort of eventuality. Boy, did I ever empty that stash out in my 5 or 6 stops around town!
So I, doubtless like you, pay for stuff with plastic. There is many an "ouch" in the process. But the credit-card "ouch" is a far cry from peeling off $138 at the grocery store, $37 to fill a ... Subaru, $77 at one of my "ordinary" stops at the book store, and a couple of others. One's sense of the true cost of living goes up by an order of magnitude.
I'm not sure exactly how to translate this into my or your professional life, but I am (very) sure it would be a damn good idea. For those who are solos or in a small professional office or a small retail operation, I'd urge you some month to repeat my adventure in some form or other; after paying the office supply bill in $20s, I'd bet a pretty penny or 10 that the next month would inaugurate an era of tighter purse strings.
In BigCo world, if you've got departments reporting to you, what about invoicing the dept head in the old fashion way (yes, I know the perils of cost allocation—so what) for services rendered—and demanding that he-she pay the bill by writing a check; not quite as powerful as my deal, but perhaps a start.
The bigger point is obvious, if elusive—bringing reality home in some high-impact way. Not that "work as a clerk for a day" crap—which is just a rather fun game—but something somehow realistic.
Many (many) years ago I did a stint in the Pentagon, working on military construction—Navy bases, etc. One day the Admiral in charge called a few of us into his office. We mostly worked on translating the needs of the field into Pentagonese. The sums were, even then, in the billions—and we abbreviated with $2.3B, etc. The Admiral said we were all too careless with taxpayers' money (an extraordinary statement in the Big 5-sided Building), and that, starting immediately, we'd be required to put in all the zeros; hence $2.3B would now be $2,300,000,000. I can't promise you that this little drill in the end benefited the taxpayer; but I can tell you that it did, as the Admiral intended, make us think twice. A trivial story—or not. You be the judge.