Stress-Free Guide to Holiday Tipping

It’s tipping time again, and figuring out who and how to give a tip can bring on a holiday headache. So we’ve put together five tips from etiquette experts to help ease the dreaded end-of-year ritual. (You can also check out our handy slideshowthat breaks down who to tip and how much to give.)

Here’s what you need to know:

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Who gets a tip? Look at the people who are providing services for your every day life, says Mary Mitchell, author of “The Complete Idiot's Guide to Etiquette.” That means people such as housekeepers, hair dressers and babysitters, Mitchell says. “These are the people who are part of our daily lives,” she says. (See a full list of people to tip and how much in our slideshow.)

And the people who you tip should have worked with you for at least six months, says Mitchell, otherwise you can skip the tip.

Give what you can. “Certainly, you should not go into debt to tip,” says Diane Gottsman, etiquette expert and the owner of The Protocol School of Texas. “Tip what you can, and the amount that you can comfortably afford.”

If a job loss or budget constraints doesn’t allow you to the tip the people you would like to, Gottsman says the best thing to do is hand them some home-baked cookies and a note letting them know that they’re on your mind even though you can’t afford to give them anything this year.

Gottsman recommends writing something like this: “2010 has been both personally and professionally challenging, but I wanted to let you know how much I appreciate your wisdom, strength and support over the past year. I anticipate a much better 2011 and look forward to sharing my blessings with you! Happy New Year."

And if you weren't able to hand out tips last year, and this year you are able to, Gottsman says there is no reason to try to make up for it. “Just give what you are comfortable giving this year and move forward,” she says.

Write a note. “Don’t just stuff a $50 in some one’s hand. Write a letter,” says Mitchell. “It makes people feel special.”

A handwritten note is preferred over a pre-written card. In the letter, thank them and tell them you appreciate the work they’ve done over the past year.

Don’t forget the unseen workers. “People tend to overlook the newspaper delivery person,” says Mitchell. You may never see the person who delivers the paper or the garbage collectors hauling your trash at dawn, but that doesn’t mean they don’t deserve to be acknowledged. It’s worth waking up a bit earlier to catch them one morning and give them their gift.

Another often neglected group are postal delivery people. Although most have rules about receiving cash (see tip No. 5 for more on that) a small gift is a nice way of saying thanks.

Know the rules. Some organizations may not allow their employees to receive gifts or cash, so make sure to check. The United States Post Office prohibits their employees from taking cash or gifts over $20. Fedex also doesn't allow cash tips, but allows gifts under $75 and UPS discourages tipping, but allows employees to accept them if the customer insists. To be safe, give them something like chocolates or a coffee shop gift card.

Other people, such as an office assistant or a teacher, should not be given a cash tip. Assistants should be given a bonus and teachers should get a gift instead, as cash may seem like a bribe.