Looking back, contributing to CPF was one of the main deterrents to applying PR back when I first started out here. When you earn less than $6,000/mo, that 20% really bites, especially when are on your own (no parents to live with), and you don’t have nearly enough for a downpayment, so owning is not an option.
In my particular case, I was getting 6.2% deducted for SS and 1.45% for Medicare, and 6% deducted for ESPP (voluntary, but necessary to get the employer match). Imagine deducting another 20% on top of all that… I don’t think I would have had enough left to pay the rent, let alone anything else.
I guess I’m the square peg. But I feel as though things have worked out in the end. My employer has a CPF substitute program that I don’t need to contribute to, so I haven’t really lost out versus what I would have collected in employer contributions to CPF. That is the main reason I’m still on an EP after all these years; switching now would actually set me back financially.