Pioneer somehow crossing Poles — he may get income for life (9)
I believe the answer is:
pensioner
'he may get income for life' is the definition.
'pioneer somehow crossing poles' is the wordplay.
'somehow' indicates anagramming the letters.
'crossing' means one lot of letters goes inside another.
'poles' becomes 'ns' (North and South poles).
'pioneer' is an anagram of 'peioner'.
'peioner' enclosing 'ns' is 'PENSIONER'.
(Other definitions for pensioner that I've seen before include "One past retirement" , "retiree" , "beneficiary of fund" , "Former worker" , "One is older and paid so they don't have to work" .)