Gift Giving 101
It's the time of the year some of us love—and dread—most. The to-do lists are long, the tasks and pressure relentless. But the holiday grind isn't without reward. On the other side awaits the best stuff memories are made of: special time spent with family and friends. And that includes the loot we both give and get. Here are strategies to minimize stress while increasing the fun and meaning of holiday gift buying.
Decide how You Gift

Value doesn't only mean what things cost. Our set of values influence gift giving. So what types of conversations and associations about the holidays do you want for your kids after the gift frenzy? Sometimes it seems like the more there is of something, the less it's often appreciated. Not to say it's bad to just go for it, since some families might crave memories of abundance. But choose what you think is best for your family.
Set Priorities With Lists

To get organized and avoid feeling overwhelmed, Donna Sebastian, customer relationship director at Nordstrom, divides her list into five categories: Family, Friends, School, Business, and Charity/Social Groups. While doing so doesn't appeal to our best, most generous social instincts, creating a hierarchy of friends and family might be essential when it comes to holiday gift-giving. Even for those of us who aren't in the habit (or financial position) of buying gifts for a large circle of friends, there's always that person who loves to hand over a wrapped package come holiday season. Find some way to reciprocate.
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Set Your Budget

Start with a gross total amount and break it up into units. Create an Excel spreadsheet if need be or find other solutions. Jessica Jonas of MomciergeLA, a consulting service that helps new parents get organized, finds online tools useful. "We like to create a wish list on Amazon.com. Most of the members of our family with kids do this, so you can see what everyone is interested in and the price points." Such lists help eliminate the guesswork, too. For a different approach, getting crafty by making homemade gifts, cards, and even wrapping paper is both thoughtful and economically practical.
Make a Timeline

Don't wait until the last minute! Black Friday might not be the best starting time, but procrastination doesn't help either. Find some balance. Even the most seasoned gift givers have thought, "There'll be just a trickle of us foolish 11th hour shoppers," only to find a packed parking lot at the mall late in the afternoon on December 24th. A tip: Try to set a target number of gifts for each week, and pace yourself.
Shop All Year Long

It can be a wonderful thing to keep a gift closet to store those absolutely perfect gifts that practically jump off the shelf. So what if it's only March? If you have the budget and space, then stash it away for when the time is right. One downside to this tactic? Returns might be trickier or impossible.
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Decide Where to Buy

If it matters to you, this is the time to shop local or support alternative operations such as Etsy, where the options of handmade items seem to be limitless. Want to lower the amount of stuff that's being bought and sold in this world? Then either select a cause that deeply matters to you and your family, or make personal choices for family and friends based on their own cares and interests. With kids, encourage them to think about who they would want to help and why in a developmentally appropriate way, whether it's children who need clean water, families who need a place to live, or an endangered animal that needs saving.
Get Creative!

Large families carry a certain holiday gift burden. Tiring, even. If this is the case, time to better focus resources. Do a stocking swap with one family member, and don't worry about other presents. Alternately, have each person pick two names, and set a per-gift price cap. Or who says gifts need to come out of a shiny new package? A special experience or ritual can become a core part of any family's holiday observance, like an outing, or crafting DIY presents together. Or for family exchanges or holiday parties, suggest people bring a used gift and organize an exchange.
Be on the Same Page

Does a sister-in-law expect everyone in the family to get something of equal monetary value? Meanwhile, would you rather splurge on the kids while giving the adults something consumable yet special, such as fine teas, or artisanal chocolates? Or is this the year to do a White Elephant or Round Robin exchange? No matter what the approach, communicate ahead of time and set expectations.
There's An App for That!

Harness the power of technology to organize your holiday shopping. iPad and iPhone apps such as Christmas Budget, Shopper Pro, Gift Manager Pro, and mGifts Gift List Manager help through every stage, from setting an overall agenda complete with budget tools and recipient lists to ensure everyone is taken care of. These can also help with tracking coupons and discount offers, while keeping tabs on follow-up thank you notes.
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Remember to Say Thanks

Jonas doesn't always use snail mail to send thank you cards, but she makes an extra effort to personalize her kids' gestures of appreciation. “In our family, we do a thank you email to all our family members, including a photo of our kids with the gift they got," she says. If that sounds like too much, "my kids just hop on the phone and call whomever they received gifts from," she says. "Family members love to hear little voices on the other end of the phone."