Start with a list of everyone you'd like to acknowledge in some way. Then, find ways to make your tips personal.
Focusing on the word "tip" makes people think more of money, Weiss says, rather than a gift. But a personal note means so much more and conveys your appreciation when used along with something more personal.
"It doesn't have to be monetary," Weiss said. "A simple thank-you note or bottle of wine can go a lot further than $20. It is more meaningful and has true impact."
If you know the recipient likes wine, you can pair the note with a wine shop gift card. "These personal touches go a lot further than cash," Weiss said. "If they don't remember the tip, what is the point of giving?"
Another way to make sure your gift isn't lost in a flood of holiday tips: Give it earlier or later than the December holidays. "People remember it," Weiss said.
Don't feel obligated to do all your tipping at the end of the year. If you're tipping someone whose work is seasonal, such as yard work or pool cleaning, it makes sense to tip in the summer.
Don't tip your kid's teachers. "While holiday and end-of-year gifts for teachers are traditional in many places, tipping is not," said Randi Weingarten, president of the American Federation of Teachers.
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Instead, Weingarten says personal gifts from students and parents can be very meaningful. Always appropriate: a heartfelt, handwritten thank-you card. Many school districts have regulations on what teachers can't receive. Many allow for class gifts and group donations from families.
As a cash guideline, Weiss says he uses a simple rule. Either give someone a cash amount equal to their regular service – whether a monthly dog groomer or weekly landscaper – or a flat $100.
Keep in mind the real purpose behind tipping: a way to acknowledge someone's efforts during the year.
It's also OK to shorten your list, Weiss said. "Find the people you have a meaningful relationship with and give a personal gift that will have more impact."