Jay Thompson

Medicare Open Enrollment is coming SOON. Confusion abounds. Here’s what can change for 2027, and why doing nothing may, or may not, be the right decision.

Heartbreaking loss and a move — finding my way back to the blank page. Retirement changes the calendar, but it doesn’t pause grief, upheaval, or new beginnings.

Nobody tells you this before you retire: unstructured time is harder than it sounds. The idea of having "nowhere to be" feels like the whole point ...

Ask most people whether retirement is good for your health and you'll get a confident "yes." Less stress. More sleep. Time to exercise. No mo ...

The word "retirement" implies a clean break. You work, and then you stop working. Full stop. But that's not how it plays out for a growing nu ...

Most people don't see this one coming. You spend 30 or 40 years building relationships at work — with colleagues, clients, managers, teammates. Some of ...

Most retirement planning focuses on the numbers — savings, income, Medicare, Social Security. And those things matter. A lot. But there's another side ...

Required Minimum Distributions are mandatory — but the tax damage isn't. Learn how RMDs work, when they start, and the strategies that can reduce what you owe.

Hire a financial advisor, or manage your own money? Here's an honest breakdown of fee structures, tradeoffs, and a middle path most people never consider

The debate focuses on consumers, marketing strategies, flexibility, privacy and even morality. But it’s really about who controls access to the housing market.

Roth conversion strategy explained in plain English—when to convert, how much to convert, and how to reduce lifetime taxes in retirement.

Choosing a Medicare Supplement plan? Learn how Medigap works, the differences between Plan G and Plan N, and how to pick the right coverage.

Every now and then, someone sends me a question that begins with refreshing honesty. Not the polished, carefully worded kind of question. The blunt kind. Th ...

When a longtime member lets their dues lapse after recalculating the value of association membership, that's worth paying attention to.

Retirement planning conversations usually orbit around money. Net worth. Withdrawal rates. Social Security timing. Medicare enrollment windows. All importan ...

At 51, I had a heart attack.Not a “maybe indigestion” scare. The real thing. The kind they call a widowmaker. Three cardiac stents later, I’m still here. Th ...

Bottom line: When you claim Social Security is one of the few retirement decisions that’s permanent. File early and you lock in a smaller check for life. Wa ...

Quick Summary: If you retire before 65, Medicare isn’t there yet — and health insurance becomes one of your biggest planning variables. ACA premiums are bas ...

Quick Summary: Retirement doesn’t automatically mean lower taxes. While earned income may disappear, taxable income often continues through IRA withdrawals, ...

Short version:Retirement income isn’t about “taking 4% and calling it a day.” It’s about building a repeatable system that manages taxes, market risk, Medic ...