Retirement
John Stoj · October 7, 2026
No, I’m not going to tell you your number.
It’s the question I hear most. How much do I need to retire? It’s a fair question, and it quietly assumes something that isn’t true: that retirement is one bill, due on one date, in one amount.
It isn’t. It’s several obligations wearing one trench coat, and each of them has a different life.
Take a made-up couple in their early sixties. They and their numbers are invented, and this is an illustration, not a recommendation for anyone. Their retirement holds at least five different obligations, and they don’t behave alike.
Essential living costs. Housing, groceries, utilities, insurance, healthcare premiums, and taxes. (With no more withholding, taxes become, “spending,” in retirement.) The timing is known, the amount is fairly predictable, inflation pushes it up every year, and there’s no flexibility. This is the paycheck that has to show up.
Healthcare beyond the premiums. Medicare brings its own complexity, including surcharges that rise with income. Part of this cost is known and part of it is a guess, and the guess arrives on its own schedule.
Extended care. It may never be needed. It may be needed for years. The timing is a coin flip, the amount can be enormous, and when the bill comes there’s nothing to negotiate. Low certainty, low flexibility, high consequence. That combination is why it earns its own line.
Travel and the fun stuff. The most flexible item on the list. It can slide a year, shrink, or wait for a better market. In a bad year, it’s the first thing to give, and that’s the point of it.
Gifts and legacy. Helping the kids, giving to causes, leaving something behind. There’s no deadline. Some of this money may never be touched, and in Asset Life Matching, that’s a legitimate life too: the money with the longest runway.
A single number, paired with a single allocation, treats all five alike. The market doesn’t. A decline in stocks is a nuisance to the legacy money and a threat to the paycheck money, and which one it turns out to be depends on what the dollars were matched to.
In a bad year, the trip can wait. The insurance premium can’t.
So the obligations call for different assets. The paycheck money wants stability and a known date, and the bond ladders piece shows one way to build that. The long-runway money can be invested for growth and inflation protection. Care sits in between, and it asks for liquidity and a plan rather than a forecast.
There is no universal definition of, “enough,” and I’ve stopped looking for one. A list of obligations does something a number can’t. Each one carries its own timing, certainty, flexibility, inflation sensitivity, and consequence, and together they give a way to decide what happens when something changes.
And things change. The kids stop costing money. Care shows up uninvited. A health scare reshuffles the list. When the list moves, the portfolio follows.
Retirement isn’t one liability. It’s a bundle of them, and each piece has its own life. I’d start by taking the trench coat off.
This resource is part of the Asset Life Matching library. Start with What Is Asset Life Matching? →
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Further reading
Christine Benz, Morningstar, July 2025. Benz treats long-term care as its own obligation, and shows that home-based care often costs more than people assume.
I chose these links because I think they’re worth reading. I have no financial relationship with the authors or their firms, and I’m not paid for them. Their views are their own.
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