Name your files so you can find them again without resorting to private detectives.
Use full, meaningful filenames
Use names that let you tell files apart just from the name. Be specific, and be bold! Computers let you use long names. "Letter inviting Schmoopy to Aspen" and "Xander coaching proposal" would have been much better names. And just in case you've changed Schmoopies over the years, you might event want to use specific names. Like, "Letter inviting Jules to Aspen."
Of course, your next Schmoopy might also be a Jules. Or a pair of Juleses, so you might even want to include a last name.
But wait, it gets better.
After our Aspen retreat, Xander wanted to move forward. I banged out a proposal. The response? "Not expensive enough. I need to impress people with how much I pay for my coach. Triple your fees." How could I refuse? I created "Xander proposal 2." But it still wasn't enough. "How much would you charge to visit me in New York on my private plane?" Xander sounded in such pain, I just had to help. I created yet another proposal, called "Newest Xander proposal." Then went to lunch.
After lunch, though, I had "Letter XXX," "Newest Xander proposal," and "Proposal 2 for Xander." Yikes! Which was which?