Last week I was driving and on a phone call (with my coach), and I went through the drive thru at Starbucks. I apologized to Tim, placed my order, and then continued the conversation with him. When my Chai Latte arrived, the barista needed me to physically take the credit card holder from her, so I could – with my own finger – indicate that I didn’t want to leave a tip. I found the exchange needlessly frustrating, mostly because I’m an over-tipper and recent tipping requests are taking away my joy.

Jason and I are believers in a concept called WAM, Walking Around Money. We budget $100 per month which we carry around in smaller bills. When someone goes above and beyond, we like to give them cash reinforcement and thank them for providing excellent service. I like to do this for retail workers, teenagers working the drive thru (not at Starbucks, not ever if they ask), or the random service worker who isn’t normally tipped. 

I love Jimmy John’s, and particularly love their Freaky Fast delivery. When we order for delivery, we add the tip to the electronic bill, and then pull out a $5 bill. If they can get from order to door in under 13 minutes, we call it Freaky Fast and give the driver an additional $5 on top of the 20%+ tip on the bill. And we think it’s fun. The surprise on someone’s face when you over-tip is worth WAY more than the couple of dollars extra.

We’ve also been known to play a game to see how many times in a month Capital One can send me a text message that says, Did you mean to tip 40% at dinner? Yes, in fact, I did. I think the algorithm is learning because we keep over-tipping, and the emails are slowing down. It’s a game which organically keeps getting more difficult.

We all know what to tip the server, the bartender, and the person who gives us a massage (20%+ for excellent service.) But what are we supposed to do with all the new people, sometimes aggressively, asking for tips?

First, let’s look at how this shift occurred. With Covid and the massive increase in food delivery services, we’ve now been asked to tip before the service has been completed. I don’t know about you guys, but I always feel like if I don’t tip well upon ordering, my food will arrive cold. I’m not sure if that’s accurate, but it’s a constant concern, and one causing a little resentment.

I don’t expect the dog groomer, my mechanic, or the clerk at the supermarket to hold out their hand and ask me for more. We already over-tip but the ask feels classless to me. If you’re not sure what to tip, check out this guide for current tipping best practices and this global tipping infographic. Then, do whatever you feel is right.