I think it's related to the period where he recorded the Born&Raised album.
"We pick up in New York City. I'm tryin' to find the man I never got to be. But when I push down on the pavement, find the whole thing so much harder than it seems."
He recorded it at Electric Lady Studios, which is at NY. It's about his mind-changing after that media boom about him. He decided to be a new person through his music. Or, as he said on some interviews, he only wanted to be a singer and songwriter. Well, I think every Mayer fan knows what he was been through. And, yeah... not easy to change or even throw away some beliefs. Old habits can die hard.
"The only deal I ever signed, no devil drew a dotted line. The stage was set, the words were mine, I'm not complaining"
The record deal he signed gave him complete control on his content. He was free. Whether it's good or bad words (and consequences of it), it's all about him.
"Whiskey, whiskey, whiskey, water, water, water, sleep.
Whiskey, whiskey, whiskey, wake up, shake it off and repeat.
It's just a phase, it's not forever, it's just a phase but I still might have a ways to go..."
He developed this habit of drinking whiskey. Plenty of it. It could help him on keeping sad thoughts away, I guess. And he knows it's an issue if mantained for long time, but he hopes he can quit it.
"Every night around this time, my friends and I we treat it like a race. But when I really start to break it down, I wouldn't trust a girl who knew about this place"
Or a man, either. It's numb for me, but I think it's about drinking with friends, relaxing a little, and even having a "race", a competition with the glasses. But anyone who literally knew the best places for drink or figuratively have reached the “place” of alcoholism already has some issues going on.
"Walking on with no one left, speak softly underneath my breath: 'Hey world you ain't seen nothing yet!'. -Great, now it's raining"
I didn't get the raining part, but about the rest, while no one was around (Mayer asked the sound engineer to cut off his (engineer) headphone volume, and the man would say "ok, do your thing, text me when you're done") he was walking around the studio, which was nice and quiet, saying "Just watch. I’m gonna redeem myself and show the world that I am a better person".
"Dreamed somebody missed me... wake up, shake it off and repeat it, repeat it, repeat after me"
Now I don't know if it's exactly his thought, but I guess it's again about escaping the world, kind of making the people forget about him (and making himself forget about overthinking what other people think about him).
"...Cuttin' me off and pour me in the street"
Would this be about his routine? It's in the same place of "Wake up, shake it off and repeat". I'm not sure.
Well, there it is, it's my interpretation of this great song. It's my favourite album, also.
(First of alI, sorry for my bad english.)
I think it's related to the period where he recorded the Born&Raised album.
"We pick up in New York City. I'm tryin' to find the man I never got to be. But when I push down on the pavement, find the whole thing so much harder than it seems."
"The only deal I ever signed, no devil drew a dotted line. The stage was set, the words were mine, I'm not complaining"
"Whiskey, whiskey, whiskey, water, water, water, sleep. Whiskey, whiskey, whiskey, wake up, shake it off and repeat. It's just a phase, it's not forever, it's just a phase but I still might have a ways to go..."
"Every night around this time, my friends and I we treat it like a race. But when I really start to break it down, I wouldn't trust a girl who knew about this place"
"Walking on with no one left, speak softly underneath my breath: 'Hey world you ain't seen nothing yet!'. -Great, now it's raining"
"Dreamed somebody missed me... wake up, shake it off and repeat it, repeat it, repeat after me"
"...Cuttin' me off and pour me in the street"
Well, there it is, it's my interpretation of this great song. It's my favourite album, also.