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Vanguard’s Advisor’s Alpha research found that good advice can add roughly 3 percentage points of value a year, on average — some years more, some years less. Most of that doesn’t come from picking better investments. It comes from things like not panicking during a downturn, choosing the right accounts, and drawing money out in the right order. It’s an industry estimate, not a guarantee.
Without one, transition deadlines pass silently: a Medicare enrollment window closes, a pension survivorship election locks by default, the withdrawal order gets set by whichever account was easiest to tap. With one, someone whose job is watching your deadlines catches these while they’re still movable — and keeps your CPA, attorney, and accounts working from the same plan.
What the relationship actually looks like, decision by decision →
Retiring is not one decision. It is a cluster of them, and several run on deadlines that are set by someone else and pass without a reminder.
Medicare has an enrolment window. It opens before you turn 65 and closes a few months after. Miss it without qualifying coverage from an employer and the late penalty can attach to your premium permanently. The window is the thing to diarise, not the birthday.
A pension election is usually irrevocable. If you have one, the form asks you to choose between a lump sum and monthly payments, and to choose a survivor option that determines what your spouse receives if you die first. Most plans treat that choice as final once payments begin. Your plan has to give you a written relative value comparison — the document that shows what each option is actually worth. Ask for it before you sign, not after.
Social Security timing is a trade, not a right answer. Claiming earlier means smaller payments for longer; claiming later means larger payments for less time. Which one is better depends on your health, your spouse’s earnings record, and whether you need the income to stop working at all. It is one of the few retirement decisions that can be modelled honestly in advance.
The order you spend accounts in changes what you keep. Taxable, tax-deferred and Roth accounts are taxed differently on the way out. Drawing from whichever is easiest to reach is a decision too, just an unexamined one — and the years between finishing work and starting required withdrawals are usually the widest window you will ever have to move money deliberately.
Health coverage before 65 is its own problem. If you stop working early, something has to bridge the gap, and the cost of that bridge often decides the retirement date rather than the other way round.
None of these are hard once someone is watching them. They go wrong when nobody is — when the enrolment window closes quietly, the survivorship election defaults, and the withdrawal order gets set by whichever account was easiest to tap.