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The biggest risk to your retirement isn’t a market crash — it’s a crisis you probably haven’t planned for

Morey Stettner at MarketWatch wrote that the biggest risk to retirement is not a market crash but a health crisis nobody planned for. The median private nursing home room ran $11,294 a month in February 2026, and about 70% of people turning 65 today will need some long-term care.

My experience matches the headline. Most people think of retirement risk in terms of market crashes. Healthcare is the one that actually derails the most plans I have seen. A bear market recovers. A five-year care need does not.

I told Morey how I model it for pre-retirees. Three scenarios: the most likely base case, a future with accelerated or historically high healthcare inflation, and a catastrophic scenario in which one spouse needs extended care. If the plan survives all three, the client can stop worrying about it. If it survives only the first, we have work to do while there is still time to buy coverage or earmark assets.

The story I shared was about avoidance. A client told me that if either he or his wife needs long-term care, they will move to Vietnam, where his wife is from, because for $200 a day he can live like a king. But what if he cannot travel? He is avoiding the reality. The plan has to work in the scenario where the person who needs care cannot get on a plane.

Model the crisis you do not want to think about. That is the whole job.

Read the full article at MarketWatch →

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Jeff Judge Managing Partner
Jeff is one of Chesapeake’s founding partners and a go-to advisor for professionals navigating complex transitions like retirement, business sales, or sudden windfalls. With nearly two decades of experience, he’s known for delivering calm, clear guidance when it matters most. Clients say working with him feels like talking to a longtime friend, if that friend happened to be an award-winning financial expert.
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