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Keep your portfolio firing on all cylinders for the rest of 2026 using these steps

Darla Mercado at CNBC asked advisers what investors should be doing with their portfolios at the midpoint of 2026, with the S&P 500 up nearly 8% for the year and futures markets pricing a 62% chance of a September rate hike. My answer focused on taxes, because that is where the midyear window is worth the most.

If you have been riding the AI trade or any concentrated winner, your portfolio is probably more skewed than you realize, and this is the time to rebalance. Pair that with tax-loss harvesting. Sitting on losses from the volatility earlier this year and waiting until Q4 is leaving money on the table. Trim the position that has grown too large, sell the one that is underwater, offset the gain with the loss, and stay clear of the wash-sale rule by waiting 31 days before buying back anything substantially identical.

The piece of this most people miss is on the other side. For investors in a low-income year, it can make sense to harvest capital gains rather than losses, especially if they can do it at the 0% long-term rate. Retirees and semi-retirees qualify for that bracket far more often than they use it.

Knowing your bracket in June is the difference between planning and scrambling. Tax work done in December is almost always more expensive.

Read the full article at CNBC →

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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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