Do all self employed out there, would you contribute to your CPF or do your own retirement planning via investment? Looking at semi retirement age at 55?

I would recommended using CPF life first to help plan for retirement. After that, you may also want to consider annuities or etf.

Self employed here. And I wouldn't use CPF as CPF Life is not flexible.

There are annuities with a better yield than CPF Life with the added flexibility to start payouts earlier or cancel at a later age if you're done with the monthly payouts.

And I'd rather invest as that's fully liquid as well. CPF top up is irreversible.