I’ve been keeping a small list of humorous personal finance faux pas from my circle of family and friends that easily qualify for the old Penny Wise, Pound Foolish idiom for a while now.

If you’re not familiar with the phrase, it’s generally defined as:

Being frugal or cautious with small amounts of money, but being gullible or wasteful with larger amounts of money.

I enjoy this phrase simply because it brings a sort of Three Stooges vibe to the discussion, and since public humiliation is generally a successful way of teaching one not to do dumb things, you just know I would have to list a few here.

1. Cutting coupons from the Sunday paper to save money, but knowingly paying a front load mutual fund fee for years because your financial planner said you should keep doing so. (My personal favorite)
2. Not taking your daily medication at $1 per pill per day, but having serious medical complication and racking up a $5500 hospital bill.
3. Being too cheap to water the lawn, but spending hundreds of dollars on expensive shrubbery that requires copious amounts of water. Shrubbery dies soon after planting.
4. Buying a new netbook computer, but never using it because your 56k internet connection is irritatingly slow.
5. Taking the Home Depot “weekend warrior” experience too far by attempting to fix a plumbing problem, only to cause a separate leak and require the replacement of your basement ceiling.
6. Insisting on driving across town to the get the cheapest gas possible, but flooring the accelerator at a stop light just to hear the turbocharged engine do its thing.
7. Repeatedly buying small quantities of any product, instead of buying in bulk where the cost per unit ratio can be lower by as much as 10% to 25%.

Perhaps I’m being overly critical since much of my life revolves around the financial world, but I can’t seem to figure out why someone would worry about saving a few bucks here and there, only to pay out way more in the end when the final expenses are tabulated.

Then again, I guess that’s why some people like to play Chess and others like to play Checkers… sometimes people just don’t like to think more than one or two moves ahead.