Why You Should Tip Big

I once heard somebody say, “Everyone needs to work a season of retail during the holidays so they know not to be disrespectful,” and I respectfully say, “F*ck that.”

Not because I don’t think people need better manners on the whole, mind. In fact, most definitely the opposite – all too common nowadays is it for people to feel insanely entitled – I just really don’t want to work a season of retail. Rather, I don’t want to work any retail, if I can help it, precisely for the above reason.

But that’s one of two occupations that experience a ton of entitled crap from a largely unforgiving public. The other, of course, being restaurant staff. (And yes, yes, before we go any farther, clearly there are other jobs that have to endure this too, but let’s focus here for today.) From complaints, to demands, to unreasonable privilege-seeking, Martha who grooms dogs or Bruce that manages a car lot seem to suddenly find a gem-crusted crown atop their domes the moment someone shows them to a booth at an Applebee’s.

And even setting those cultural, societal, (dumb) norms aside for the moment, working for damn-near free/”grovel wages” would be reason enough for the title. So yes, tip big if you find yourself able.

I tip between 20%-30% on average regardless of the bill for a number of reasons that will soon make painfully clear that those figures are in no way some sort of ‘humble brag.’ The first being that I can never remember what’s proper: Is it 15%? 18%? Is that with gratuity, or without? Was there a gratuity this time? I don’t want to leave 15% when 18% is the norm, and now that person thinks I’m stiffing, them or making a negative comment about their help, or something. So, if for other reason than laziness, err on the side of a touch more than a touch less.

Another shade to that reason too, actually, is embarrassment. Not at my powers of retention regarding customs, but at…hmm, expectation? Let me put it this way, if it’s Valentine’s Day and your classmate (pretend for a moment we’re in grade school, it makes the mental exercise work) gives you a Valentine’s Day card that states simply “Will you be my Valentine?” is that a sincere gesture, or just witnessing the fulfillment of a perceived obligation? Right? So if you’re given that card, it doesn’t say anything special and isn’t really even for you, it was just done out of tradition, but now you have to thank them or you’re the turd; but if you aren’t given a card, oof, well now you’ve been snubbed. Ouch.

But if you get a card from a classmate that goes a little above a beyond…? Oooo, that’s kind of sweet. That card has some hand-drawn glitter art? Got a little chocolate that comes with it? A personalized note? Oh, lawd, well now it’s kind of touching.

I don’t see how tipping is really all that different in form from the above situation with Valentine’s Day cards. It’s a win-win, too. If the service was great, the bonus tip sends the message, “Hey, you there, for real, thanks for taking care of me today.” And even if the service was awful and the person was kind of a butthole about the whole thing, you leave with the satisfaction that that person is probably going, “Aw, jeez. Well now don’t I feel like a rube…”

Moral victory secured.

But really, even all of that is just because I enjoy crafting a torturously long wind-up to my real point. And what I really draw from when I press this, is the following experience.

There was a time I went out to lunch with a friend (shocking, I know – I have FRIENDS), and I covered the bill. My memory’s a little fuzzy on who it was with, I don’t quite remember where we went, what we ate, or even clearly how many years ago this was, but I do very clearly remember what happened as we were leaving. I left a pretty sizable tip for all the above reasons (maybe closer to 30-35% this time; I was doing alright), and did so in cash just because it was what I had on me. As we were walking to the door, the fellow who’d served us ran interception and asked me if I’d made a mistake. Honestly perplexed, I just raised an eyebrow, smiled, and said, “No. No mistake, that’s yours.”

Now, there were no tears. No heart-pouring tales of hard times. But there was an indescribable look in his eyes that I didn’t know at the time I would one day understand intimately well. On the surface, he was just really grateful, and a bit surprised, so I took it that way. It was nice. Put a pep in my step, and I got to be That Guy (the good kind, not the bad kind) to somebody that day.

Fast forward a few years to Fall 2019, life’s gotten pretty hard. I’d left my job somewhat ambitiously only to wind up pouring most of myself and my worldly goods into a family emergency (Don’t regret it, do it again in a heartbeat only smarter), dropped classes I’d promised myself I’d finish that semester, had maxed out credit cards, and had $1.63 in my checking account…

It was rough.

I had a job lined up, but it didn’t start for another week. So I was taking a walk to a local deli, and I was going to put that last dollar and sixty-three cents to work (technically, I also had a paper dollar and two quarters in my pocket, as there’s a debit card minimum set above $1.63 at most places) on a cheap roll and a mini cup of salad dressing, which I knew to be a $1.25 in total. I get to the counter, and I guess prices had gone up, because the register rings me in at $1.89.

I stare at the numbers. My stomach drops out, anxiety and embarrassment prickle my scalp in turns, and I start muttering to myself about how it’s okay, I’ll just put the cup of dressing back. The fellow behind the counter waves it off after a moment with a smile. “You’re in here all the time,” he jokes. “Let me cover this one.” He presses a button on the machine and the balance goes to $0.00. I don’t know precisely how I must have looked to him, but in that moment it occurred to me with a painful lucidity that I must be giving him the same stare that waiter had given me years back. I choked out the same, whispered “Thank you.”

I barely made it to the door before I was bawling my eyes out.

So there you have it. You never know where someone’s at, and there’s no risk in being kind. Not just nice, but kind. Really, it’s a “There but for the grace of God go I” type of tale, a reminder to be kind in all those ways that can help even if you aren’t around to see it and it costs you next to nothing, because you could very well at some point wind up desperately grateful to be on the receiving end of a token like that.

Throw in that extra two bucks, Money Bags. You could make someone’s day, or leave an impact so deep and meaningful someone will preach about it online years later.

Ciao, everybody.