The U.S. remains at relatively low individual income tax rates. Many of us are thinking about Roth conversions and other ways to minimize our lifetime tax bite. 2026 brings meaningful changes to U.S. tax policy that open up new planning opportunities. From updated retirement savings rules to higher deduction limits, being aware of these shifts can help you make smarter financial decisions.

For executives, retirement rarely happens in a straight line. You step away from a high-income role… but you’re not 65 yet. Your paycheck and your employer-based healthcare coverage stops, but Medicare hasn’t started. Suddenly you’re exposed. This gap, typically between ages 55 and 65, is what I call the “Executive Healthcare Bridge”.

For restaurant industry executives, owners, multi-unit operators, general managers, or senior leaders, approaching retirement in your late 50s or early 60s is a pivotal moment. Here’s a checklist to get you started.

For restaurant industry executives, owners, multi-unit operators, general managers, or senior leaders, approaching retirement in your late 50s or early 60s is a pivotal moment. Here’s a checklist to get you started.