Looking ahead to 2019....
* I've already decided to increase monthly savings by about 8% (ex-CPF) since I feel that's a new, higher, sustainable savings flow. No change to portfolio allocations.
* January is CPF top-up month(*), including my spouse. January 1 or 2 for any MediSave top-ups (as the Basic Healthcare Sum rises, to beat employer contributions, and they must fit within the CPF Annual Limit). Same thing if/when there's a MediSave withdrawal, e.g. for Integrated Shield base plan premiums -- some MediSave "gap filling," if able and if allowed, with tax relief. Late January, but credited within January, will be the Special Account top-ups, with tax relief.
* January 31 is the deadline to file any 2018 medical claims against employer-provided insurance. (Employers vary, but that's a common deadline.)
* Keep transferring surplus CPF Ordinary Account dollars into the Special Account, every month in 2019 and beyond.
* February and March tend to be tax information collection and reporting months, since I try to get those tasks out of the way reasonably early (U.S. person here).
* March: The Integrated Shield carriers will all have announced their rule compliant riders by this point, ready to be in force no later than April 1, 2019. I'll probably take a look at the new riders and premiums, then review our coverage to see whether the new rider makes sense.
* At various points in 2019 there will be a few annual insurance premium notices and renewals to consider. I don't think there will be any major changes, but we'll see.
* Once a year it's a good idea to update "digital will" instructions.
* Get your annual medical check-ups, go to the dentist, etc., etc.
....And past that is too far into the future.
(*) Now is CPF top-up month if you haven't done your 2018 top-ups for tax relief yet.