01 Adulthood — the first paycheck

~21–27

Secure your own foundations, in your own name

  • Your own hospital plan — don't assume your parents' arrangements still cover you, or still fit. Bought young and healthy, it's cheap and clean; every year of waiting risks an exclusion. ⏳
  • Emergency fund first — 3–6 months of essentials before any investing conversation.
  • Start the drip — even $300/month into something broad; time is the asset you'll never have more of.
  • CPF nomination — five minutes online, and your CPF stops defaulting to the Public Trustee.
  • One SRS dollar — locks today's withdrawal age for life, even if real contributions wait years. ⏳
  • Skip, politely: whole-life and ILP pitches from friends — read this first, and if you already signed, this second.

02 Marriage & the first home

~26–33

Two money stories become one

  • The money conversation — structure, autonomy amounts, and the monthly money date. The evidence says it matters more than the flat.
  • Redo your will and nominations — marriage generally revokes an earlier will, and insurance nominations don't update themselves. ⏳
  • The flat decision, priced honestly — BTO vs resale, the car test, and mortgage cover for the loan you just signed (HPS for HDB loans; term for the rest).
  • Term cover if someone now depends on your income — sized to the mortgage plus the years, not to a sales quota.

03 Trying for a child

before the news

The window that closes before the good news

  • Mother's hospital plan in force before pregnancy — cover bought after conception typically excludes this pregnancy's complications. This is the single most time-sensitive item on this page. ⏳
  • Maternity insurance has a purchase window — most plans are bought within a mid-pregnancy band, and each insurer's window differs. Tell me early and we'll time it right, not late. ⏳
  • Buffer for the first year — delivery, confinement, the run-rate — and the honest conversation about whose career flexes.
  • Review income protection now — a household about to depend harder on one income should insure that income first.

04 A newborn

first 90 days

Insurability is the gift

  • The baby's own hospital plan, early — a newborn insured before any condition is discovered is insured cleanly for life; wait, and any finding follows them as an exclusion. Some plans even start in utero. ⏳
  • Parents' term cover steps up — 9–10× income, now that someone truly can't do without it.
  • Will with a named guardian — the hardest conversation and the most important line. ⏳
  • CDA opened and matched — the dollar-for-dollar match is the closest thing to a 100% return you'll be offered.
  • The education drip, from birth — $230/month started now beats $695 started at eight. The maths.

05 The age-30 checkpoint

~30

Buy your future options while they're cheap

  • Full protection audit — income has grown; has the cover? CI (the 74% gap) and disability income matter more than more life cover.
  • CareShield supplement while young and insurable — the premium is set by the age and health you lock it at. ⏳
  • Will + LPA done — not because 30 is risky, but because they're cheapest to think about when nothing's wrong.
  • Savings rate over salary — run the freedom calculator; bank half of every raise before lifestyle meets it.
  • Single? The housing fund for 35 starts compounding now — the solo map.

06 The 40s and early 50s

~40–54

Peak earning — point it somewhere

  • SRS as a December ritual — peak income is peak marginal rate; the maths.
  • CPF cash top-ups — the 4% floor plus tax relief, for you and for parents. The double win.
  • Education fund vs runway check — enough years left to correct without drama; not enough to correct twice.
  • The parents conversation — their readiness is your exposure; the sandwich guide has the script.
  • Trim what's done its job — cover sized for toddlers can shrink as they near independence; premiums saved become retirement fuel.

07 Age 55

55

The Retirement Account arrives — decisions, not defaults

  • The FRS/ERS decision — how much to leave compounding at 4% toward lifelong income, versus what to withdraw. Deliberate, not default.
  • Spouse top-ups — evening out two Retirement Accounts often beats maximising one.
  • The drawdown map drafted — which pot pays 55–65, which pays 65+, where SRS's ten-year window slots in.
  • Healthcare priced to 85 — the ward-class decision made on purpose, before the premiums decide it for you.

08 60 to 65

~60–65

The CPF LIFE choice — one hour, thirty years of consequence

  • Pick the plan deliberately — Standard, Escalating or Basic; the choice effectively locks 30 days after payouts start. ⏳
  • The start-age decision — 65, or up to +35% for deferring to 70 if the bridge years are funded.
  • The "map" document current — every account, policy and password location on one page someone you love can find.
  • LPA if it's somehow still not done — free for citizens, and the last cheap year to think about it is always this one.

09 Retirement

65+

The maintenance years

  • Drawdown order reviewed yearly — cash bucket, portfolio, CPF LIFE working together so a red year never touches groceries.
  • Scam defences hardened — Money Lock and the family codeword; this is the decade the callers target.
  • Legacy documents refreshed after any family change — the will, nominations and LPA only work if they're current.
  • The home right-sized on your schedule — downsizing maths done unhurried at 68 beats forced maths at 80.

The honest fine print

Checklists age. Reviews don't.

Every ⏳ above marks a window that closes — insurability, nominations, purchase timing — and the exact rules shift with insurers and policy years. That's why the real checklist is one standing item: we look at the whole board together, once a year. How I help →

Notes

Timing rules — maternity purchase windows, newborn cover start dates, group-conversion periods, CareShield supplement underwriting — vary by insurer and change over time; treat every ⏳ as "ask before assuming", and I'll confirm the current rules for your specific situation. CPF milestones (RA at 55, CPF LIFE plan selection and start ages, top-up mechanics): CPF Board. Marriage's effect on wills: Wills Act — get proper legal advice for your documents.

General information, not financial advice. Jonathan Wong is a licensed financial adviser representative in Singapore, currently between firms — during that period he is not able to provide financial advice. You can check his registration yourself on the MAS Financial Institution Representatives Register at eservices.mas.gov.sg/rr.

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