Every Day is Saturday: May 8th, 2025


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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This week, we’re digging into one of the most common retirement myths out there:

“If I move to a no-income-tax state, I’ll save a fortune!”

Well… maybe. But the Wall Street Journal says not so fast. We break down the full picture—property taxes, insurance premiums, HOA fees, and more—in our Retirement Headlines segment.

After that, we tackle one of the most thoughtful listener questions we’ve received all year:

If two retirees are the same age with the same portfolio, why is one at greater risk than the other just because they retired five years later?

It's a brilliant exploration of sequence of returns risk, order of withdrawals, and why five years can make a huge difference in retirement.


Episode Breakdown
(0:00) Why financial independence gives you permission to live in any state—even an expensive one
(3:10) Retirement Headline: Moving for taxes? Count the other costs first
(14:45) Listener question: What’s the real risk in your early retirement years?
(24:00) Minefields, back pain, and what the Army taught me about risk

Listen on Spotify, Listen on Apple Music


Retirement Headline: Will Moving to a No-Tax State Actually Save You Money?
Source: Wall Street Journal by Debbie Carlson
Key Idea: Don’t let the tax tail wag the retirement dog

It’s a common retirement dream: sell the house in Indiana, move to sunny Florida, skip out on state income taxes, and bask in all that extra cash.

The reality? Your tax bill may shrink, but your overall costs might jump off the page. Here’s why:

Higher Real Estate + Insurance Costs

  • Florida’s average home insurance = $5,300/year
  • National average = ~$2,200/year
  • One couple now pays $35,000/year for insurance + taxes + HOA fees on their condo
  • Surprise hurricane repairs? Yep, those too.

Sales & Property Taxes Matter More Than You Think

  • Tennessee has no income tax… but a 9.56% sales tax
  • Texas skips income tax… but property taxes run 1.58%—double Florida’s rate
  • Retirees with less income may feel these taxes more

Estate & Retirement Income Taxes

  • Illinois: doesn’t tax retirement income
  • Colorado/New Mexico: do
  • Oregon: estate tax kicks in at $1 million vs. the federal $14 million

Buying a New Home = Higher Property Taxes
Many states reassess your home at purchase price, so you’ll owe more than the previous owner did—another surprise expense.

Bottom Line:
Taxes are just one piece of the puzzle. Add up real estate, insurance, sales taxes, inheritance taxes—and don’t forget your happiness. Financial independence means you don’t have to make every decision for the lowest cost.


Listener Question of the Week

“Why is the first 5 years of retirement called the danger zone for market risk? If two retirees are the same age, with the same portfolio and life expectancy, why does it matter when they retired?”

Meet Lynn. She just asked one of the best sequence-of-return questions we’ve ever heard.

Let’s say:

  • Mary just retired at 65
  • Jane retired 5 years ago at 60
  • They’re both 65 now
  • Both have $1M portfolios
  • Both withdraw $50,000/year

They experience the same returns, just in a different order.

  • Mary’s order: -15%, +5%, +10%, +20%
  • Jane’s order: +20%, +10%, +5%, -15%
  • Mary ends up with ~$923k
  • Jane finishes with ~$1,028k

Even though their average return is the same (~5%), Mary’s early losses during withdrawals lock in damage Jane avoids.

This is sequence-of-returns risk. It’s not about age. It’s about when you take withdrawals during a market downturn.

That’s why the first 5 years of retirement—when you start drawing income—are so critical. A bear market early on can be like hitting a landmine in a minefield. (Yes, we went there. And yes, I was trained to clear minefields. Seriously.)

Pro Tip:
Measure your retirement runway—how many months of income you can generate from your bonds and cash (not stocks). That buffer can make all the difference when markets get choppy.


Resources & Mentions

  • WSJ: Retirees Who Move to Lower-Tax States May Not Save as Much as They Think by Debbie Carlson. To read click here
  • 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-eighth 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)

Benjamin Brandt

Want to spend more money & pay less taxes on your way to an even better retirement? Then you'll definitely want to check out our newsletter and podcast! Our weekly newsletter helps to remind us that in retirement, every day is Saturday (even Thursday mornings).

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