If you’re careful with your money you probably face a frequent dilemma of how much to tip various people in service positions. Tipping ranges from the $3 slipped to a doorman who hails a cab to a couple of hundred for some guys who move your stuff cross-country.
Before I was married, I used to have a "local" in my neighborhood in Manhattan. That means there was a bar where I could drop by after work with friends and the bartender would have my usual drink set up before I even took a seat. The waitresses would stop by to chat, and I knew them by name. I would get the best seat in the house ahead of tourists waiting in line if I came in a group. The manager let me stay after hours, and invited me to special events.
If you have a situation like this, big tipping is tough to avoid. You get to know people and they provide wonderful, careful service on a constant basis. I never left less than a 15% tip even on rare occasions that I was dissatisfied, and 25%-30% was the norm. I got so many free drinks that often I would just take the amount I was given gratis and just hand it right back over to the waitresses or bartender.
Contrast this with stopping at a diner on an interstate trip. You get ho-hum service, perhaps, and ho-hum food. Do you leave a 15% or 20% tip like you would at a "local"? And if not, why? Would it make a difference if you knew that the cook got a fresh batch of salad out for your salad – and would it make a difference if it was just coincidence that he got it for you?
Tipping is an odd case of getting a service, then paying for it. If you hired a plumber to work on your house and said "you know what? I’ll pay you what I think it’s worth when you’re done" he would probably knock you over on the way out the door. Restaurant workers (and maid services in hotels, etc.) do the best they can to provide good service, not knowing if you’ll be the one-in-a-million person who leaves 10 $100 bills tucked under your check or the jerk who asks for 15 martinis and a steak done JUST SO before leaving a 3% tip. Imagine working at your job that way – if every payday you got a minimal base salary plus a "tip" depending on how happy your boss was with your work – or how annoyed he was that he dropped $1000 on the poker game last night.
It’s hard to balance tipping with being a frugal person. I don’t like tipping. I wish everything was a flat fee. I wish waiters and waitresses were paid minimum wage and I could write $0 for the tip without worrying about being a jerk. It’s easy if you’re a regular somewhere to be generous. If you live in Manhattan and have a super or a doorman, it’s easy to realize that you need their help, and they’ll give it whether you pay or not, so you SHOULD reward them for their help. It’s trickier when it’s the guy delivering the new couch. You’ll never see him again. He did his job. But it’s hard work, and maybe – just maybe – he could have dinged a wall or tracked in mud, but he took a little care not to.
I don’t know the answer. I generally tip generously at restaurants but not so generously when it’s "slipping cash" to someone, mainly because I’m embarrassed about it being too much (looking like a rube) or too little (looking cheap) so I often just pretend I "left my wallet upstairs." What I do know is that in general in life you’ll be a lot happier if you mentally price your tip BEFORE getting the service and then pay it that way after you get it. Think to yourself "I’ll tip the waiter 15% unless he ignores our table or gets an order wrong or forgets to bring us water," or "I’ll tip the housekeeping service $20 per day as long as the room is cleaned to a T," or "I’ll give that guy $50 to move the couch in unless he dings the wall or messes up the fabric," and so on. Tipping is an uncomfortable activity for most, and even more uncomfortable for someone who relies on them for a living.