Lyric discussion by petewillett 

"underline everything i'm a professional in my beloved white shirt/i'm going down among the saints"

-gets a new job, feels confident and excited and grown up

"Raise our heavenly glasses to the heavens, Squalor Victoria! Squalor Victoria"

-still goes out and parties every night because he feels so accomplished

"out of my league i have birds in my sleeves and i want to rush in with the fools"

-he's not equipped to hold down his new job, because he's not as grown up as he thinks he is - he still constantly thinks about getting out of work and partying with his friends

"3:30 in the last night for you to save this, zoning out, zoning out, zoning out"

-trying to finish a project for the next day that he's been putting off and he's just too damn tired to get it done

"this isn't working, you, my middlebrow fucker"

-could be him getting fired, but i really see it more as his own disgusted realization of his irresponsible and immature ways

I think the entire Boxer album, save for Gospel, is about struggling to find a foothold in the adult world during the mid-late twenties transition from carefree, young, partying to responsible adults, and this is possibly it's most direct song. I think it's a description of him in his early professional days, overconfident and having not yet realized that work has become a much more significant part of his life than he wants it to be

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