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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8th Annual Listener Survey​
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This is your chance, as a listener of the podcast, to influence the show for the next year. This quick survey takes less than five minutes and gives you the opportunity to anonymously share what you love, what you’d change, and what you'd like to hear more (or less) of on the show. I’d love your input. Thank you in advance!

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Episode Breakdown:​
​Only 5% Are “Living the Dream”… What the Other 95% Can Learn

• We unpack Deb Boyden’s Yahoo Finance piece: why just 5% of retirees report “living the dream,” 19% are “living the nightmare,” and—most importantly—the three lessons you can use to stack the odds in your favor.
• Plus, Listener Question: The pro-rata rule and Roth conversions—when it applies, when it doesn’t, and the simple step that keeps things clean.

​Listen on Spotify | Listen on Apple​

Retirement Headlines:

“Only 5% of retirees say they’re living the dream, 19% are living the nightmare.”

Here are the three big lessons I pulled out—and how to apply them:

1) Start anyway (even when life isn’t “perfect”)

• The survey notes only 40% of retirees feel they saved enough and 45% say expenses are higher than expected. Translation: the “perfect” time to save never arrives.
• Your 20s/30s bring loans and car payments; your 40s/50s bring tuition and home repairs; retirement brings healthcare and longevity costs. Problems don’t vanish—they evolve.
• Action: Automate saving now (even small amounts). Compounding is the only way to experience that “my portfolio grew more than my salary this year” magic.

2) Expect the unexpected (and plan for inflation)

• Inflation whipsaws: it’s spiked before, calmed down, and can do it again. That’s why 92% worry about inflation, 85% about healthcare, 80% about the next market drop.
• De-risking by abandoning stocks can feel safe—but it often trades market volatility for inflation certainty. Long retirements likely require your income—and portfolio—to double (or even triple) over time just to keep purchasing power.
• Action: Manage market risk without surrendering growth:
  • Keep a Retirement Runway (cash/bonds) so you’re not forced to sell stocks in a downturn.
  • Use Retirement Guardrails to temporarily trim spending when markets fall, then resume.
  • Stay invested enough to outpace inflation.

3) Winging it won’t cut it (get a real plan)

• 64% of retirees don’t work with an advisor, 44% don’t have a plan for expenses/income/investments, and 62% don’t know how long their money will last.
• DIY can be excellent (tools like NewRetirement/BOLD are powerful), and some advisor “plans” aren’t plans at all. The right litmus test: TAXES.
• Action: Whether DIY or with an advisor, make taxes a core pillar: review returns annually, map multi-year Roth conversions, coordinate RMDs, Social Security timing, and charitable strategies. Confidence to spend comes from a written, tax-aware plan—not vibes.

Bottom line: With a savings habit, an inflation-aware portfolio, and a written, tax-smart spending plan, you’re far more likely to land in that “living the dream” 5%—and stay there.

• This avoids tracking basis on Form 8606 forever and makes annual Roth conversions straightforward.

Measure twice, convert once. A 15-minute call today can save years of spreadsheet gymnastics.

Listener Question

“If I don’t have any after-tax money in my IRAs, does the pro-rata rule still apply to my Roth conversions?”

Short answer: No. If all of your IRA dollars are pre-tax, every converted dollar is taxable—clean and simple—and the pro-rata rule isn’t an issue.

Where people get tripped up:

• Pro-rata kicks in when any after-tax basis exists anywhere across your IRAs (Traditional/SEP/SIMPLE). Conversions must then be a proportional mix of pre-tax and after-tax dollars.

Pro tip to keep things clean:

• Before rolling assets at retirement (or when doing in-service rollovers), call your plan/custodian and separate pre-tax from after-tax dollars wherever possible (e.g., roll pre-tax back into a 401(k) if permitted; move after-tax to Roth).
• This avoids tracking basis on Form 8606 forever and makes annual Roth conversions straightforward.

Measure twice, convert once. A 15-minute call today can save years of spreadsheet gymnastics.

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Resources Mentioned

• ​Click here to order my book, Retirement Starts Today: Your non-financial guide to an even better retirement
• ​Click here to read Only 5% of retirees say they’re ‘living the dream’ and 19% are ‘living the nightmare.’ Here are 3 lessons to protect your future

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I need your help...

I will be starting a new segment on my podcast: Retire TO something, not FROM something.

The segment will be brief at the end of the show and will share a fun retirement idea, along with links to learn more. Volunteer work and part-time “fun” jobs will be a common theme.

​Click here to share your ideas!

That's it for our three hundred and ninety-sixth installment of "Every Day is Saturday." As always, I read (and usually reply to) every listener email. Got a question? Hit reply—you just might hear your name on the show.

Enjoy your “Saturday,”
​Benjamin Brandt

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