Every Day is Saturday: August 28th, 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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8th Annual Listener Survey

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:

Why Retirees Underestimate Longevity & Claim Social Security Too Early
(0:00) Why planning for a long life is good retirement planning, not pessimism
(7:45) Six cognitive biases that push retirees toward claiming at 62
(23:10) Practical steps to apply for Social Security online, by phone, or in person
(31:30) How widows can claim survivor benefits without reducing their own
(38:50) How spousal benefits work—and what happens if you apply first

Listen on Spotify | Listen on Apple


Retirement Headline:

The Psychology Behind Claiming Social Security Too Early
Source: Advisor Perspectives via Rick Kaler

We all know the math says most retirees should wait to claim Social Security. But many don’t—and the reason isn’t financial, it’s psychological.

Six Biases That Trick Us Into Claiming at 62

  1. Availability Heuristic – We remember tragic deaths more vividly than long lives.
  2. Optimism/Pessimism Bias – We assume either we’ll live forever or not make it past 70.
  3. Present Bias – The marshmallow test: we want benefits now, even if they’d be bigger later.
  4. Anchoring Effect – Once we hear “62,” it feels like the default.
  5. Status Quo Bias – Once we’ve decided, it’s hard to change—even with better info.
  6. Death Avoidance – If we don’t think we’ll reach 90, we don’t plan for it.

The lesson? Plan for a long life—because chances are, you’ll live one.


Listener Question:

This week’s listener had three excellent Social Security questions:

  1. How do I apply for benefits?
    • Create a “My Social Security” account at ssa.gov.
    • Takes 30–45 minutes online—usually faster than waiting months for an appointment.
  2. How can a widow claim survivor benefits without triggering her own early benefit?
    • Be crystal clear: “I am applying for survivor benefits only.”
    • Handle this by phone or in person for fewer mistakes, and keep documentation.
  3. If I apply before my husband, do I automatically get spousal benefits when he files?
    • Not always automatic.
    • Spousal benefit = up to 50% of your spouse’s full retirement age benefit.
    • If you claimed early, that amount is reduced.

Final Thoughts:

Math and psychology both point to the same solution: plan for longevity. A flexible income plan with guardrails, growth, and tax-smart Social Security timing protects not just you, but also your spouse.

Claiming early might feel like a win in the moment—but waiting often wins over decades.


Resources Mentioned

  • Click here to order my book, Retirement Starts Today: Your non-financial guide to an even better retirement
  • Click here to read The Psychology of Early Social Security Claiming from Advisor Perspectives

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-forth 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


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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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). Click here to work with us! Episode Breakdown: The Danger of Inflammatory Social Security Headlines (0:00) Why financial media doesn’t always have your best interests at heart (6:55) Breaking down the misleading “$18,000 cut” claim (18:45) Why claiming early out of fear can backfire (25:20) How to be a “Prudent...

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). Click here to work with us! 8th Annual Listener SurveyThis 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...

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). Click here to work with us! 8th Annual Listener SurveyThis 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...