Crossword Genius

Endlessly regretting penury (4)

Ross

I believe the answer is:

ruin

I'm a little stuck... Click here to teach me more about this clue!

'penury' is the definition.
The answer and definition can be both states of affairs as well as being singular nouns.
Perhaps you can see an association between them that I can't see?

'endlessly regretting' is the wordplay.
'endlessly' means to remove the last letter.
'regretting' becomes 'ruing' ('rue' can be a synonym of 'regret').
'ruing' with its last letter taken off is 'RUIN'.

Can you help me to learn more?

(Other definitions for ruin that I've seen before include "Disaster, collapse" , "financial disaster" , "State of devastation and destruction" , "Dilapidated building" , "Destroy; downfall" .)

I've seen this clue in The Mirror.
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