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Insights


When Should I Sign Up for Medicare and How Do I Enroll?
Medicare enrollment is one of those topics that tends to get put off. The rules are specific, the terminology is unfamiliar to many, and there are enough moving parts that most people are not sure where to start. The good news is that once you understand the basic timelines and what drives them, the process is quite manageable. This post outlines the enrollment periods you need to be aware of, the consequences of missing them, and the process for signing up when the time arr
May 6


May 4, 2026
Wall Street continued to rally with equities ending last week on a strong note. The S&P 500 and the NASDAQ closed at record highs, driven by robust corporate earnings, a potential end to the U.S. military involvement in Iran, and easing crude oil prices.
May 4


April 2026
What's Inside: What Do Americans Do with Their Tax Refunds?; How AI Is Helping Modernize the IRS; Be Storm Smart: How to Prepare for Extreme Weather; The Evolution of Retirement Savings; Don't Overlook the Value of Social Security Survivor Benefits; and Federal Student Loans: How Much Do Borrowers Owe?
Apr 29


Why Your Tax Bill Going Up Might Be a Good Thing
For pre-retirees in their 50s and 60s, a higher tax bill is sometimes the smartest move you can make. Here is why the conventional wisdom of always minimizing taxes may be working against you.
Apr 28


April 27, 2026
Stocks continued to rally for the most part last week, fueled by cautious investor optimism that U.S. involvement in the Middle East may be nearing an end. In addition, cooler inflation data (see below) along with the start of what is hoped to be a resilient earnings season also contributed to the rally.
Apr 27


What You Need to Know About Taxes on Your Social Security Benefits
One of the most common surprises retirees face is learning that their Social Security benefits may be taxable. Many clients come to me with the assumption that Social Security is simply a return on a lifetime of contributions, money they already paid taxes on, and therefore should be tax-free. Unfortunately, that is not how the IRS sees it.
Apr 21


April 20, 2026
Stocks surged last week with the easing of geopolitical tensions that had weighed on equities for weeks. The S&P 500 crossed the 7,000 point barrier, while the NASDAQ achieved its longest winning streak (12 straight sessions) since 1992.
Apr 20


Q1 2026 Review: Markets Confront Pressure from AI Disruption, Geopolitics, and Private Credit
The market backdrop has shifted quickly in 2026, with AI disruption, rising oil prices from geopolitical tensions, and growing concerns around private credit replacing earlier optimism.
Apr 15
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