I thought of the "tip in hand" as more of a "I see you, I know you're hustling in this gig economy to get by...or maybe working toward something bigger...or just to help make ends meet a little more. Either way, here's a little extra to say thank you for working hard and making my life just a bit easier."

And maybe the app doesn't have the same reaction in the moment - human connection missing.

Think of when you might've ordered something that came with a hand written "Thank You" vs a high gloss printed thank you card. You know someone designed the latter and it got mass printed. Kind of impersonal. But with the handwritten note, you know someone literally wrote that one. And even though the box was packed by hand and were many other parts of the process of getting thing from idea to your hand...think of how many people and hours were involved in that? There's something about a handwritten note that adds a closer connection to a person. A person you never saw but can somehow imagine writing the note, putting it in the box.

(I wonder if the connection is as strong if you've never handwritten anything)

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I love your stream of consciousness replies @Phil! The high gloss card vs a handwritten note is another good analogy similar to the tipping in-app vs in-person (with eye contact and all). Agreed.

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