Jack took a break outside then went back to work (9)

I believe the answer is:

restarted

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'went back to work' is the definition.
I can't judge whether this defines the answer.

'jack took a break outside' is the wordplay.
'jack' becomes 'tar' (both are informal terms for sailor).
'took a break' becomes 'rested' (resting is a kind of taking a break).
'outside' indicates putting letters inside.
'tar' put within 'rested' is 'RESTARTED'.

'then' is the link.

Can you help me to learn more?

(Other definitions for restarted that I've seen before include "taken up" , "Resumed" .)

I've seen this clue in The Globe and Mail.

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