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For Valentine's Day, you can offer a choice of 3 or 4 love songs. For Christmas, you can work up several Christmas carols. And the same goes for all the other holidays. Even on non-holidays you can come up with some songs that people might need. Perhaps you could learn the song "I'm Sorry" for people who need to apologize, or "Happy Birthday" for people who want to send birthday greetings to someone they love. You could offer small cards, like florists do, that your customers can sign their name to and you deliver when you sing your song.
If you don't play an instrument, you could take along a recorder that will play the music and you can sing to that. You could charge up to $25.00 per singing telegram! It's a great way to make money using your talents.