How does CPF Life payout work?

What you must understand is that CPF Life is a public annunity that is compulsory in nature whose payout is based on premiums that you contribute into the Lifelong Income Fund, and the plan you choose: Basic/Standard/Escalating.

For the basic plan, 10% of your RA is deducted at age 55. The rest – about 90 per cent – of the Retirement Account savings is untouched and can continue to grow and compound with interest. Near 65, two months before your birthday, there will be a second deduction. This time, it will be approximately 10 per cent of the new money that has built up between your 55th and 65th birthday. The rest of your Retirement Account savings will stay put until your payout eligibility age.

In comparison, for the standard and escalating plan, for those who join this plan at age 55, there will be two installments deducted as annuity premiums just at 55 and near 65, just like the basic Plan – but the percentage of deductions differs.
Members who join this plan at age 55 will have the Retirement Account deducted for their CPF Life annuity premiums in two installments – at age 55 and near 65. The first deduction is up to the current Basic Retirement Sum of $80,500. The premium goes into the Lifelong Income Fund.
Two months before you reach 65, the balance Retirement Account savings will be deducted as the second installment of your annuity premium and channeled into the Lifelong Income Fund. This will include any new money, including interest earned or refunds from sale of property or investments that you have built up between your 55th birthday and 65.
For members who join the Standard or Escalating Plan on their payout eligibility age or after, there will be only one annuity premium deduction, which is all the sum in their Retirement Account, made at the time of joining.
CPF Life is structured such that 3 out of 4 people will only “obtained" what that has been put into the amount.

Yes if you don't calculate the interest earned from 55 to 65.
So it's 11 years to break even from the 55 yr old figure and 16 years from the 65 yr old figure.

Anything after that is "profit".
But note that the bequest drops down to 0 after 16 years on the standard plan, so you're just literally paying yourself till that age and only "earn" if you live longer than that.