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How to Keep Client Couples’ Simultaneous Retirements From Going Wrong

Rob Burgess at ThinkAdvisor wrote about what goes wrong when couples retire at the same time, and asked me what I have seen. I frequently work with dual-income couples in their late 50s who want to retire together, and the plan is usually about money when the problem turns out to be about something else.

I told him about a couple, both in corporate roles, who delightedly retired the same week. Six months later, one of them regretted not considering part-time work. The adjustment had nothing to do with money and everything to do with identity. Two people who had built their days around being needed at work suddenly had all day, every day, together, with no structure and no title. That is a conversation I now start early, not after the papers are signed.

There are financial reasons to stagger as well. Losing two incomes in the same year compresses the tax planning window: the low-income years where Roth conversions and capital gains harvesting work best get shorter when both paychecks stop at once. And health coverage before Medicare is often the most underestimated expense; a couple that retires at 60 and 61 is buying two policies on the exchange for years.

My advice to couples is to talk about what each of them wants a Tuesday to look like before they talk about the date. Then decide whether the dates should be the same. Often the better plan is one leaves first and the other follows a year or two behind, financially and emotionally.

Read the full article at ThinkAdvisor →

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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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