Descend means decend.
Descend when ready or pilot discretion means just that.
The addition of a restriction to be level by *** is usually there to constrain the profile to a particular sector or to provide separation from another standard profile, vis a vis descend FL140 level 40 before OCK on G1 keeps the profile separated form the KK inbounds from the north which come through WOD at FL150.
Hence the instruction descent FL140 level 40 before OCK can be thought of in two parts
a) descend (now)
b) make FL140 40 DME before OCK
The one thing I agree with is if in doubt ask. I would rather have the R/T "cluttered" up for a few seconds than be writingincident reports because of a mis-understanding!!!