Forest Hill's Jeff Judge featured in Kiplinger: The calmest retirees aren't the richest ones

By Jeff Judge, CFP®, AEP®, ChFC®, CLU®, Managing Partner, Chesapeake Financial Planners, Forest Hill, MD.

After almost two decades of sitting across the table from people about to retire, I've noticed something that surprises them: the ones who feel calm about spending are rarely the ones with the biggest accounts. They're the ones with the clearest rules.

I wrote about this for Kiplinger recently. Financial anxiety doesn't end when the paychecks stop. For a lot of people it gets louder, because every withdrawal starts to feel permanent. What changes that feeling isn't a bigger balance. It's structure, decided before the stress shows up.

A few habits do most of the work. Separating your money by when you'll actually use it, so the cash you need in the next couple of years isn't riding on this year's market. Picking one withdrawal approach and sticking to it instead of guessing month to month. And putting a real healthcare number on paper. Fidelity has estimated a 65-year-old retiring in 2025 may need roughly $172,500 for healthcare in retirement, not counting long-term care. That figure is far less frightening once it's written down with a plan behind it.

For Harford County retirees, none of this requires more wealth. It asks for decisions made in the right order. The question I put to clients is simple: if the market dropped 20 percent this year, how much of your next two years of spending is already set aside? If the answer comes quickly, the rest of the portfolio can be managed with a longer view.

This piece builds on "7 Money Habits of Retirees Who Never Stress About Spending," in Kiplinger (June 2026)

Jeff Judge, CFP®, AEP®, ChFC®, CLU®, is Managing Partner at Chesapeake Financial Planners in Forest Hill, MD. Book an intro call.