Forest Hill's Jeff Judge in Kiplinger: What the wealthiest retirees actually do differently

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

Most people assume the retirees who feel financially secure simply saved more. That is not what the data actually shows. In a piece I wrote for Kiplinger this week, the pattern across the wealthiest retirees is not a bigger balance. It is a set of habits built years before retirement day arrives.

They keep two to four years of spending in cash so a market drop never forces a bad sale at the worst possible time. They convert traditional retirement accounts to Roth in the low-income years before Social Security starts, paying tax now at a lower rate to avoid it later. They delay claiming Social Security to age 70 when the math supports it, even if it means drawing from other assets in the meantime. And they treat their estate documents as a living plan, reviewing them every three to five years instead of filing them away once and forgetting them.

For families in Kingsville, retirees commuting into Towson, or longtime residents of Cockeysville, this matters more than a national statistic suggests. Harford County and Baltimore County have plenty of households who did the hard part, built the savings, paid off the house, raised the kids, without ever building the sequencing plan that protects that work from a bad five years in the market or an avoidable tax bill.

The takeaway is not that you need millions to adopt these habits. Most of them scale down proportionally. What matters is starting the plan years before the decision, not the week you retire.

This piece builds on "10 Things the Top 10% of Retirees Do Differently With Their Money," in Kiplinger (September 2026).

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