I recently have been pushing myself to sing and play when I feel like it at the dog park, a park, by the river, on a corner. I got about 60 songs memorized, I'm used to playing and singing alone, in relative privacy.

I know that sometimes it's not appropriate to sing in public, or sometimes I feel that way, sometimes it feels super weird, and I have refrained from it in the past during those times. By really weird I mean that the people there just seem like the kind of people that would get annoyed or irritated by my playing or singing, or at the dog park there might be twenty people standing around looking at their dogs and for me to grab my guitar and start singing might feel like a cry for attention. Awkward.

Don't get me wrong though, the reason is not fear necessarily but rather worry about loosing my stoke to play and sing, not from criticism but because of weird vibes, bad feelings, soul leaching feelings, generated from lack of judgement about where and what to play. Or just playing in a place that feels off.

I like going to the beach at the bay, there's usually a little breeze, people spread out, maybe a few couples forty feet away or so, small waves lapping at the shore. I'll sing something mellow like tamborine man, rivers of babylon, landslide, redemption song, man who sold the world etc... seems right, feels right.

on the other hand it would feel really weird to go to a crowded park with little natural noise, and sing loud rocky songs like got me wrong, simple man, far behind, bobby magee, ball and chain, plush...

So I know that there is some decision making involved with what to sing where, but about where to sing, I'm still hung up on that. Should I just sing anywhere and everywhere, or would it be wise to pick and choose carefully? I'm not trying to make money off this, I love the feeling I get sometimes from playing and singing, for me it's all about keeping that love.
Last edited by nylonbeater at Jul 8, 2014,
It's a great way to hone your craft but... respect others space. Pick a spot that is good for singing but leave about 10-20 yards between you and them. Start softly and work up gradually. If you begin to attract a crowd, you got somethin. If the crowd moves away, you don't. Woodshed and reflection time. Learning to gauge audience response and being able to adapt is a big part of live music.
"Your sound is in your hands as much as anything. It's the way you pick, and the way you hold the guitar, more than it is the amp or the guitar you use." -- Stevie Ray Vaughan

"Anybody can play. The note is only 20 percent. The attitude of the motherfucker who plays it is 80 percent." -- Miles Davis

Guthrie on tone: https://www.youtube.com/watch?v=zmohdG9lLqY