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Take a cue from the rich: Do a midyear financial check-in

Beth Pinsker at MarketWatch wrote about why wealthy families do a midyear financial check-in with their advisers, and why everyone else should copy the habit. She asked me what those meetings actually accomplish.

Summer is the right window for financial planning. Not because the markets are quiet, but because you are. There is no year-end deadline pressure, which leaves time to look at savings rates, estate documents, beneficiary designations and what has changed since January.

What I keep seeing is that the clients who make the worst decisions in summer are almost always the ones who skipped their last review. Six months of avoiding their numbers turns every headline into a warning sign, and a social media post about a market reset is enough to send them toward cash. My most important midyear work is often not a portfolio adjustment at all. It is talking someone out of a panic move they would regret by October.

The proactive version is worth something too. Rebalancing after a strong first half, checking whether a concentrated position has grown past its limit, harvesting losses while there is still time to use them, and confirming the withdrawal plan still fits the spending.

If you have not done a midyear review, especially within ten years of retirement, it is worth 30 minutes now rather than a scramble in December.

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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