Oy Vey. It’s that time again. The time when we’ve got to open our wallets and dole out a fistful of hard-earned cash to the service workers who make our lives run smoothly all year round. The postal carrier. The building superintendant. Your kid’s babysitter.

But what if you make less than they do?

The building where I live has 14 tip-hungry employees. I know because they send around a card to all the tenants, carefully listing all of their names – and their job titles – so we’ll know who to remunerate and at what level on the tipping etiquette hierarchy to do so.

I’m lucky to live where I live, and I wholeheartedly appreciate the work done by the building crew. They’re some of the nicest, most responsible and hard-working guys around. Yet, paying a decent gratuity to each of them takes a huge chunk out of my funds just when I need money most to treat my own family to a pleasant holiday. Honestly the whole practice makes me – and I’m not proud of this – just a bit resentful.

After all, I pay a monthly maintenance fee to cover their salaries, and that is difficult enough for me to scrape up. The economy’s hit hard, and I know for a fact that I earn roughly half of what the building guys do. So, do I still have to cough up the cash? And if so, how much, and how do I do it with panache? 

Emily Post’s website has some great etiquette for holiday tipping. Or you can find more concrete adivce on holiday tipping (including suggested amounts) at MSNBC or a whole host of other sites. But here are my own ideas for tipping with an ethical slant:

First, ditch the Scrooge attitude. Tip generously and tip freely, or don’t tip at all. Whoever instituted the practice of paying holiday gratuities may need to be taken out back to the shed, but now that it’s here, it’s here to stay. People expect it, they consider it a snub if you don’t do it, and may wonder if you think they’ve given bad service if you don’t acknowledge them in some fashion. Plus, some folks really rely on their holiday bonuses – since the system is institutionalized now, a lot of times salaries are adjusted lower with the expectation that employees will receive an end-of-the-year bump. So, when I’m feeling resentful, I just need to suck it up and deal. Being ungracious or stingy will only make me feel small and petty – and BE small and petty – whereas tipping with an open heart as well as an open wallet will spread goodwill.

Second, get creative. If you’re low on moolah, why not make something like cookies or holiday ornaments that don’t cost a lot but may be appreciated (nearly) as much? Each year I set aside a day to bake huge batches of my famous gingersnaps and package them all up carefully into holiday gift bags, with ribbons and all. Maybe my doorman would prefer $50, but if I can’t swing that, maybe $20 and a side of yummy treats will still show I appreciate his work. 

Be thoughtful. My husband and I usually spend a good amount of time composing cards to all the folks on our tip list. Who knows if they can read our crappy handwriting or if they even care what we have to say, but I like to think it means something to thank them individually and personally, and let them know I noticed the special attentions they’ve shown me over the year. 

Relax. A lot of people tip out of fear (as a great New York Times article from a few years back discussed), believing their super or plumber or massuese (yeah, right!) or garbage collector will retaliate with bad service or a sullen attitude if they don’t. Being held hostage to today’s tipping expectations is no fun, but it’s my belief that most people aren’t that sinister. Also, you’re free to tip year-round, for individual services, rather than handing out one lump sum at a time when it’s tough to scrape up that much cash for multiple recipients.

Lastly, ride the good karma. Research the going rates, crunch the numbers, and see what you can afford and what you WANT to afford. Consult your gut as well as your finances, and act accordingly. But in the end, just know money’s never as important as making people happy and ensuring a smooth transition into the coming year. Enjoy the feeling of having done the right thing, rather than focusing on what it costs you. It’s advice I’m taking. Maybe in the process, my too-small heart will grow a size or two.

How do you handle holiday tipping?

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