This Is Terrible, But: The Pain of Tipping People Richer Than Me

by Erica Taddeo

I try to be a good tipper. I tip at restaurants, because I’m not a monster. I tip cab drivers, and some of them seem confused when I do, which I assume means that they don’t get tipped often enough. I drop my change in the tip jar at the sandwich shop where I pick up lunch, even though all of the suits trying to cut in line don’t even seem to notice that there is a tip jar. I’m generous when my budget allows it, or when the service is especially good, or at places I go to regularly. This is, in part, because I appreciate having friendly waitstaff who find me a table on a busy night, or a cab driver who gets me home safely and quickly so I can sleep off a hard day’s work or a few shots of whiskey, and because I know that not every sandwich shop would give me bacon instead of cheese. It’s also because I know (or assume) that the bartender, cab driver, and sandwich shop owner have lots of expenses that their salaries might not cover.

My past life as a retail employee has provided me with a lot of empathy for people in similar jobs, people who might be seen by others as a means to an end. My tips may not help them with everything, but they’ll be at least a bit of financial help, and certainly a symbolic show of thanks to people who deserve it. I have at least some knowledge of how hard it is to spend an entire shift making sure that customers or guests get more than their money’s worth. It’s also widely known that people in the service industry are often grossly underpaid.

But what about when they aren’t depended on? And am I placing too much weight on whether or not my tips are “deserved”?

I ask myself this question mostly because of two hairstylists I’ve been to. The first one gave me a really great haircut when I was in university. Not long after, she was hired by a pricey salon that didn’t offer a student discount. It was located a block away from campus and the experience felt luxe, so despite a sharp increase in price, I followed her there. After some time, I noticed that she often over-booked appointments, working on two haircuts at a time, tried to upsell me on pricey hair products and cosmetics, and that eventually I just didn’t like the haircuts she was giving me anymore. To top it off, she would occasionally talk about how she wished she was making more money, even though to me she seemed to be doing just fine financially: going to nice dinners, getting great tickets for concerts, that sort of thing. (I had no evidence that there was something awful going on in her private life, like legal or medical bills, that would require supplemental income.) Ultimately I just stopped going to her salon. Spending a lot on a haircut, being unhappy with it, and feeling guilty when I thought about leaving a smaller tip just wasn’t worthwhile.

The second stylist is someone I go to for blowouts from time to time. She’s very nearly some kind of blowout wizard, and I can’t make my hair look anything like Connie Britton’s without a lot of help. It’s just that she doesn’t help as much as I ask her to. I can get a blowout, but once my hair is straight, any other requests for styling are politely turned down. Full disclosure: I know enough about her personal life to know that she doesn’t rely on tips, or even her salary, as much as most service workers do. She is better-off financially than I am. That, combined with her chorus of “But it looks so nice like this! We shouldn’t do anything more to it” just doesn’t motivate me to tip generously. I have absolutely no problem paying for the services rendered, but I always tend to wonder if my tip money will buy her a designer purse that’s out of my price range, or drinks on a vacation I could never afford.

Sometimes it just seems a little harder to part with my money than others, even though I know I can’t control where “my” money goes once it has been spent.

Should I really feel differently about tipping people who have more money than I do? Does that make me a terrible person?

Erica works as a subtitle editor and moonlights as a hockey blogger. She’s still learning how to do money.