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Plain-English articles from Jeremy Shipp, CFP®, on the decisions long-tenured professionals face on the way into retirement. He writes about when to stop working, how to cover health care before Medicare, how to turn a lifetime of savings into dependable income, and how taxes follow every one of those choices.

Friday, October 2, 2026

The beneficiary form you signed on your first day may control more of your money than your will. What to check after a long career, and the tax bill your heirs could inherit.

Thursday, October 1, 2026

Many professionals keep working until 65 because of health insurance. Here's how the bridge to Medicare works, and why the income you report at 63 can set your Medicare premiums at 65.

Thursday, October 1, 2026

Thirty-one wolves changed Yellowstone. One missing piece can throw off a retirement plan too. Why 30 years of savings in one tax bucket ripples into Social Security, Medicare and required withdrawals.

Thursday, October 1, 2026

Your pension election is a one-way door. How survivor options and lump sum offers really work, and why the best answer isn't always the biggest check.

Thursday, October 1, 2026

The skills that get you to the summit aren't the ones that get you back down. Six questions to ask before you hire a retirement income planner, and how I answer each one.

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Thursday, October 1, 2026

Your tax return works like a financial X-ray. What it shows about your income, your investments, and your retirement taxes, plus the segment from ABC7 Good Morning Washington.