Hi anon, As a self employed, I did 2) first. The reason is because I want CPF to be a safety net for my retirement. And since I am self employed and no one is going to contribute to my CPF other than me, I had better do something for myself. Of course, the tax relief helps as well. Once that was done, then I did 1) up to the annual limit, for reasons similar to the above, just that I now take into account the fact that I would need money for a house downpayment, as well as to ensure that my MA has money for medical insurance and long term care insurance premiums. Lastly, I would do 3), but I didn't do it this year. As I am still more than 20 years from 62, I'd prefer to leave SRS as another layer of tax relief when I no longer have the ability to do 1) due to reaching the FRS. Thus, in your example, I'd just do $7K to 1) and then $13K to 2).