This is not very nice, and you will need to add to $(INITIALS) until you are happy, but:
INITIALS := abcdefghijklmnopqrstu vwxyz U := $(strip $(foreach a,$(INITIALS),$(if $(USER:$a%=),,$a))) DIR = /user/$(U)/$(USER)/
Perhaps a sensible approach would be to take into account the use of := in the above and change your simple version to DIR := ...$(shell ...)... so that the shell command is called only once.
source share