The Encore — Monday, May 11, 2026

The Encore

YOUR SECOND ACT STARTS HERE

EDITION

Monday, May 11, 2026

Good morning. Here is what you need to know to start your retirement week right.

MONWEDFRI
Monday · The Week Ahead · 3 Sections · ~5 Min Read

The Encore — Monday, May 11, 2026

Good morning, friends. This week we're diving into something that trips up even the most careful planners: the hidden costs of getting your tax picture just slightly off in retirement. Let's get into it.

THIS WEEK'S NUMBER

20% — The effective tax rate many retirees actually pay when they think they're in the 12% bracket.

Here's something that catches people off guard: a single dollar of extra income in retirement doesn't just get taxed on its own. It can cause more of your Social Security benefits to become taxable, push capital gains into higher brackets, and even trigger Medicare premium surcharges. What looks like a modest 12% tax bracket on paper can behave more like 20% once these interactions stack up. This is why retirees often feel their tax situation is more complicated than expected — the system responds to combinations of decisions, not just individual ones. Understanding these "tax cliffs" before you hit them can save you thousands over the course of retirement.

Track all your accounts free with Empower

THIS WEEK'S SMART MOVE

Map out where your income "pressure points" are before year-end decisions pile up.

Mid-May is the perfect time to look at your tax picture for 2026 while you still have months to make adjustments. The key insight from this week's research: income doesn't increase your costs in a straight line. There are specific thresholds where crossing by even a small amount can trigger Medicare premium jumps, cause more Social Security to be taxed, or push investment gains into higher brackets. By identifying these pressure points now, you can make smarter decisions about Roth conversions, capital gains harvesting, or which accounts to draw from. The goal isn't to avoid all taxes — it's to maintain control over when and how they show up.

Get your estate plan started at Trust & Will

WHAT TO WATCH THIS WEEK

Tuesday, May 12: The Bureau of Labor Statistics releases the April Consumer Price Index (CPI) report. This inflation reading influences everything from Social Security COLA projections to how aggressively the Fed might adjust rates — both directly affecting retiree purchasing power.

Wednesday, May 13: Federal Reserve officials are scheduled to speak publicly this week. Watch for any signals about the direction of interest rates, which impact bond yields, CD rates, and the overall environment for retirement income planning.

Thursday, May 14: Second quarter estimated tax payments aren't due until June 16, but this week is a smart time to review your withholding and quarterly estimates. If you've had unexpected income from Roth conversions or investment sales, adjusting now prevents surprises later.

This newsletter is for informational and educational purposes only. Nothing here is personalized financial tax or legal advice. Always consult a qualified professional. Some links may be affiliate links.

This newsletter is for informational and educational purposes only. Nothing here is personalized financial, tax, or legal advice. Always consult a qualified professional before making financial decisions. Some links may be affiliate links — we may earn a commission at no cost to you.

The Encore

YOUR SECOND ACT STARTS HERE · SINCE 2026

AboutArchiveAdvertiseUnsubscribe

© 2026 The Encore · theencore.news
Smart retirement guidance — Monday, Wednesday & Friday at 5 AM.

Keep reading