Good morning, Retirement Starts Today Community. Welcome to "Every Day is Saturday," the newsletter reminding us that in retirement, every day is Saturday (including Thursday mornings).​​​

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We often think of taxes as something that only changes when Congress passes a law—but what if I told you some retirement taxes are designed to quietly grow more painful every year… without anyone lifting a finger in Washington?

In this episode, we unpack Four Sneaky Retirement Taxes that could quietly bite into your retirement income. From the outdated Social Security taxation thresholds to hidden Medicare penalties, these stealthy tax traps can cost retirees thousands. Click here to listen​

Even if you’ve got a solid plan, it’s worth knowing how the tax code (or lack of updates to it) can work against you.

And in our listener question, we dive into a heartfelt (and very familiar) topic:

It’s a powerful question that hits close to home—and I share why it’s one of the reasons I became a financial advisor in the first place.

Outline of This Episode​
(0:00) Intro: Why this topic matters (and a personal backstory)
(1:45) Sneaky Tax #1: Social Security taxation
(5:10) Sneaky Tax #2: Capital loss deduction limits
(8:33) Sneaky Tax #3: Medicare IRMAA penalties
(12:45) Sneaky Tax #4: Net Investment Income Tax (NIIT)
(16:18) Listener question: Preparing your spouse & executor for your legacy

Four Sneaky Retirement Taxes

1. Social Security Taxation​
Back in 1983, Congress added income limits to tax Social Security—but those thresholds have never been adjusted for inflation. Today, more than half of retirees are affected, even though the rule was meant for only the wealthiest in the '80s. That $44,000 threshold? It used to mean “top 10% income.” Today, it’s practically middle class.

2. Capital Loss Deduction Limits​
The IRS lets you deduct capital losses—up to $3,000 per year. But that cap hasn’t changed since 1978! If it were inflation-adjusted, it would be more than $13,000 (or double that for married filers). Instead, a $100,000 loss might take 30+ years to fully deduct. Ouch.

3. Medicare IRMAA Penalties​
The “birthday penalty” kicks in at age 63—even though Medicare starts at 65. If your income was high at 63, you may be surprised with surcharges later. And like everything else on this list, IRMAA brackets haven’t kept up with inflation.

4. Net Investment Income Tax (NIIT)​
Married couples get penalized here too. The income threshold for this 3.8% tax hasn’t changed since 2013—and unlike other tax rules, it doesn’t double for married couples. Two working spouses can get hit with this “marriage tax” even if their combined income is modest by today’s standards.

This week’s theme? These taxes may be quiet, but they’re not small. Understanding them helps you build awareness and avoid costly surprises—because no one wants their retirement plan eaten alive by outdated rules.

Listener Question of the Week​
“I’m a 69-year-old retired engineer. How can I make sure my wife is financially secure if I pass away first—and how much should I set aside for our executor?”

This one hit home. It reminded me of my grandparents—the inspiration behind my own financial journey.

Here’s what we covered:

• Consolidate and simplify multiple accounts to reduce complexity
• Automate income and bill pay so she doesn’t have to manage daily finances
• Pre-select a trusted advisor as her financial “fire alarm” if help is needed
• Prepare a ‘When I’m Gone’ guide with passwords, contacts, and instructions
• Set aside 2–5% of your estate in a POD (payable-on-death) account for final expenses
• Avoid safety deposit boxes for key documents—seriously, they’re a legal nightmare

If this resonates with your situation, you’re not alone—and this segment is packed with practical tips for leaving a legacy of confidence, not confusion.

Retirement Starts Today (the book) is Available!

My new book, Retirement Starts Today: Your non-financial guide to an even better retirement, is available! To order click here​

That's it for our three hundred and seventy-third installment of "Every Day is Saturday." As always, reply to this email with your retirement questions and you might hear them featured on the show! I read and respond to (almost) every email.

Have a great "Saturday",
- Benjamin Brandt (your humble host)

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