Cryptic crossword clue
Short career on cash register’s over, followed by year of fun!

The most common and most likely answer to this crossword clue is the 7 letter word JOLLITY

I've seen this crossword clue in The Guardian
J
O
L
L
I
T
Y

Buddy explains!

The straight part
We know that "fun" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case fun = jollity.
The cryptic/wordplay part
In cryptic crossword there's often an wordplay/cryptic part as well.
This part involves a more complex hint, such as an anagram, homophone, hidden word, etc.
Sadly, We don't have an explanation for this specific crossword clue yet.

What does JOLLITY mean?

JOLLITY noun
  1. The state of being jolly; cheerfulness.
  2. Revelry or festivity; a merry or festive gathering.
  3. Things, remarks, or characteristics which are enjoyable.

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