Listlessness even now needs upgrading into headings (5)
I believe the answer is:
ennui
'listlessness' is the definition.
(I've seen this before)
I can't explain the remainder of the clue.
Can you help me to learn more?
(Other definitions for ennui that I've seen before include "Boredom, tedium" , "Weariness with life" , "Lack of interest" , "Boredom, listlessness" , "bore" .)