Make a list (check it twice!). Know for whom you are shopping and pull together holiday gift ideas for everyone before you hit the stores or Internet. Organizing your approach in advance will save time and money.
Shop for whole families or do gift exchanges. How about a museum membership for your sister’s family rather than buying gifts for each person? Or, maybe chip in with another sibling to get your nieces and nephews one expensive gift from both of you. Organize an exchange in which you draw names and only shop for one family member rather than all. You can up the spending limit, so you’ll all be giving (and receiving) a nicer gift.
Buy the same gift for multiple people. Of course, take care that they all have similar interests or tastes. Every gift does not have to be individually chosen for the recipient. A client gift that your sister-in-law would love is a twofer! If you find good toy for your son, give it to his same-age cousin. They’ll play together.
Ask people what they want. Not exactly a revolutionary idea, I know, but sometimes the intent to surprise someone can really make your holiday shopping a lot more complicated. And if people suggest two or three items, then they’ll still be somewhat surprised.
Shop online. This is perfect for work-at-home moms. You’re home to accept packages, but not necessarily available to leave the house for a shopping trip. Shop online early in the season so there's time for delivery and dealing with out of stock items. You probably can’t do all your shopping online, so what you can’t get online will likely mean a trip to the mall.
Utilize “strategic strike shopping” (as my husband calls it) at the mall. Go to the mall with a reasonable list—be it a list of gift recipients or actual items—and don’t leave until you’ve accomplished that list. If you see something, buy it. Don't spend a lot of time debating whether it's exactly right. This is how you talk yourself out of a perfectly good gift. If someone is so difficult to shop for that you can’t find anything, then just get them a gift card. Don’t figure that next time shopping for this person will be any easier. Don’t prolong the job by leaving the mall empty handed.