Tried sending a bill with a hand-drawn cartoon and the client actually paid faster

So last month I had this small roofing job for $350 and the guy kept ignoring my emailed invoices. Out of frustration I drew this silly cartoon of a sad roofer holding an empty wallet and scanned it into the invoice. He emailed back laughing and paid within 6 hours. I mean it probably only works for certain clients but maybe adding a little humor helps. Has anyone else tried something weird to get a slow payer to cough up cash?

3 comments

3 Comments

the_elizabeth5d ago

Is it weird that I used to roll my eyes at the idea of putting jokes on invoices? I always thought it was too unprofessional, but this honestly changed my mind. Getting a laugh out of someone makes them feel more human about paying, you know? That sad roofer drawing is genius because it makes the client see you as a person instead of just another bill. I bet it works even better for small jobs where the amount isn't huge, kind of like a friendly nudge instead of a demand.

miaprice5d ago

Oh man, this is so true! @the_elizabeth nailed it when she said humor makes people feel more human. I've noticed the same thing in all sorts of small interactions, like leaving a silly note on a parking ticket or adding a smiley face to a reminder text. It's like breaking that formal wall just reminds everyone we're all regular people dealing with money stuff, and that little shift can make all the difference. Your sad roofer cartoon is a perfect example of that whole vibe working in real life.

johnson.eva5d ago

You ever try that with a check? I wrote "please" in tiny letters on one guy's invoice once. @the_elizabeth is right, humor makes it feel less like a fight. That sad roofer cartoon probably worked cause it was so simple. Sometimes you just gotta remind them you're human too.