I'd been bumming around for a while, hesitating. I quit my job in the heat of the moment, but really I should've gritted my teeth and stuck with it — that's what I kept wondering.

Literal

For-a-while bum-was-doing, was-hesitating [explanation-んです]. Momentum [with-で] resignation-letter put-out-[regrettably-ちゃった] [but-けど], really [topic-は] endure continue [should-べき] [copula-だった] [wonder-のかな], [quot-って].

プータロー is casual/slang for 'unemployed person / bum / shiftless layabout,' sometimes used ironically for someone between jobs. 勢いで 'on momentum / in the heat of the moment' is a set phrase for impulsive action. 辞表 'resignation letter' is the formal term. ~べきだった 'should have done' is the past form of the modal ~べき. のかな trails as a musing question. って at the end reports the whole preceding clause as a quoted thought — the speaker is reporting what they were thinking.