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(1) Do you plan to continue working?
(2) Do you plan to continue to work? (both are from Webster's Learner's)
Can I understand each of the two examples as below?
(1) Do you plan to continue the work that you are doing now?
(2) Do you plan to continue the repetition of working what you are doing now?
(gerund is used for actual present; to-infinitive for repetition - CGEL,p.p.1242-3)
No, Listenever, the sentence
Do you plan to continue working?
bears no reference to some particular work. The asking person merely inquires whether the other person plans to still be engaged in work of any kind in the future.
Check by googling for "continue working into": you will get instances like
By contrast, only 5 percent of people questioned in Brazil thought they would have to continue working into old age.
These Brazilians do not necessarily plan to continue working at their present jobs.
The sentence
Do you plan to continue to work?
seems equivalent to the first.
