It seems to me that you would be more properly employed as a chimney sweep, or maybe a newsie.
Well, we haven’t determined if he’s plucky yet. Surely you’ll concede that in order to do those jobs with any degree of literary consanguinuity, he must be plucky.
Alternatively he could also be plucky or spunky, although people with the latter trait often find successful careers in quite a different area of work.
You forgot shoe-shiner.
He would also need to exhibit a lot of gumption. And a little bit of moxie.
Asked and answered. Closed. samclem