If the original speaker didn't mean "一擔擔", then I believe he meant to say "兜踎". I do not know its word origin, but I always think of it as a reference to the posture of a beggar. It is used to describe someone who is poor and not doing well in life.
I think "一兜踎" is probably "一樣兜踎" if the you didn't write down every word of the conversation.
I think "一兜踎" is probably "一樣兜踎" if the you didn't write down every word of the conversation.