There are always some people who present special challenges when it come to giving gifts.

Hardest of all are the people who buy themselves what they want, when they want it.  They have nothing on their wish list.  For folks like that, you have two good choices:  experiences and extremely unusual pieces.  Play or concert tickets, museum memberships, hot air ballooning, a cooking master class etc. are the sort of things they may not have already bought for themselves.  And if they have, a second class or concert is always nice. Many museums will let them extend their membership if they are already members and receive a second membership as a gift.  Museums are also a good place to find unusual pieces.  Many museums post their catalogs on the web, so you can choose one far away of you’d like.

What about business associates?  This will depend on how close folks are in your office and what the company tradition has been.  Some offices go out for a nice dinner and eschew gifts.  Some do Secret Santas.  In others, everyone buys everyone a gift.  In still others, bosses buy for staff but that’s it.  Unless you are personal friends with your colleagues, the gift should be businesslike, not personal.  Here’s a rule of thumb:  If you have to give the gift at work because you never socialize outside the office, don’t give a personal gift.   Good business gifts for colleagues include notebook portfolios to carry to meetings, business card cases, and travel accessories (like a talking digital photo frame for a parent who travels for business — she can hear her kids’ voices whenever she wants). If you are buying for your staff, I prefer gift cards for books, music, or electronics.  Avoid personal gifts like jewelry, fragrance, or clothing.  Also, keep in mind that any gifts purchased with corporate funds may be liable for taxation.  Talk to your corporate accountant for details.  (Gifts you pay for on your own are no problem.)

There are lots of questions about what to get teachers.  Trust me, they don’t want "World’s Best Teacher" tree ornaments, coffee mugs, T-shirts, license plate holders, statuettes, bumper stickers, etc.  The best thing you can do is write a letter giving specific details of a teacher’s skills and how these skills have helped your child to reach his potential.  Copy the letter to the principal and the school district.  If you do want to give something, make it something for the classroom.  Most teachers spend their own money on supplies.  A gift card to an office supply store, a craft store, or a big-box retailer means that the teacher can use her own money for things she wants.

Folks just starting out need most everything.  Try to focus on items that have multiple uses. A hassock can provide storage space as well as an emergency place to sit.  A toaster oven is more useful than a toaster because it is more versatile — it toasts, it broils a hot dog, it warms up leftovers, in a pinch it bakes cookies.  Basic kitchen utensils are terribly useful and can get expensive. Think can opener, corkscrew, wooden spoons, spatula, microplane, whisk, measuring cups and spoons.  A single good knife is more useful than a set of poor quality ones.  Decent sheets and towels, matching wine glasses, and throws for the sofa make a living space a bit more elegant.

On the other side, older folks on a fixed income probably don’t need any more tchotchkes.  They already have all the coffee mugs and candle holders and wall hangings they will ever need.  Give consumable things — like tickets to plays or concerts, fruit of the month, a box with attractive greeting cards and a calendar of family  birthdays.  Services are also great — lawn care, snow removal, window washing.  All of these things can eat away at the nest egg.  You can also give of yourself.  GIve a day to clean out a closet, organize a photo album, take down storm windows and put in screens, record them (audio or video) telling stories of their childhoods and burn the results to CD or DVD. 

The most important gift you give people is showing that they matter to you — and that you’ve bothered to notice what matters to them.