Sadly try hard to pen fresh clues (5,4)

'sadly try hard' is the definition.
I don't know anything about this answer so I cannot tell whether it can be defined by this definition.

'to pen fresh clues' is the wordplay.
'to' becomes 'work' (I can't explain this - if you can you should give a lot more credence to this answer).
'pen' indicates putting letters inside.
'fresh' is an anagram indicator (a fresh re-ordering of the letters).
'clues' anagrammed gives 'seluc'.
'work' enclosing 'seluc' is 'WORSE LUCK'.

Can you help me to learn more?