Every Day is Saturday: September 25th, 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).


I wanted to share something exciting: I’ve been quietly building a YouTube channel. You might be wondering—why didn’t I mention it sooner?

Simple: YouTube works best when the algorithm introduces your videos to people who are already browsing for that kind of content. It gives the channel a better shot at organic growth and reaching the right audience. Announcing it too early (especially before the algorithm has a chance to do its thing) can actually limit long-term performance.

Your support means the world! If you enjoy the content, please like, subscribe, and share your thoughts in the comments, it helps us grow and reach more people.

Click here to view a recent video from my channel about The 59.5 Iceberg Most Retirees Don't See Coming.


Click here to work with us!


Episode Breakdown:

  • (0:00) Claim Social Security early & invest? The 6 obstacles you can’t ignore
  • (18:45) Listener Question: 60/40 vs. alternatives (gold, REITs, Bitcoin, managed futures)
  • (34:10) Practical Planning: Guardrails + Retirement Runway—boring portfolio, exciting retirement

Listen on Spotify | Listen on Apple


Retirement Headline

Claim early, invest the checks—can you “beat” delaying Social Security?

Morningstar’s Christine Benz and Social Security expert Mary Beth Franklin recently unpacked this strategy. My take: while tempting in theory, it runs into six big obstacles:

  1. Permanent benefit reductions (and survivor cuts)
  2. Extra tax drag
  3. Lost growth + bigger COLAs
  4. Short, risky investment horizon
  5. Missed Roth conversion years (plus widow’s tax exposure)
  6. Behavioral risk—can you stick with it in a downturn?

Social Security is often the only guaranteed, inflation-adjusted lifetime income stream—making it too valuable to gamble with.


Listener Question

“Should retirees stick with 60/40—or add gold, REITs, Bitcoin, etc.?”

For my clients (and my own money), I keep it boring: globally diversified stocks + bonds. Here’s why:

  • Opportunity Cost: Every % in shiny objects comes out of proven strategies.
  • Risk Management: Behavior > products. Guardrails + 6–10 years of “retirement runway” in bonds/cash work better than chasing alternatives.
  • Trust the Foundation: The best companies in the world adapt for us.
  • Boring Portfolio → Exciting Life: Keep attention on retirement, not babysitting investments.

Practical Planning Corner

  • Guardrails: Pre-set rules to raise/cut spending when your portfolio crosses thresholds.
  • Runway: Multiply your monthly draw by the years you want “covered” (e.g., 7 years). That fixed-income cushion helps you ride out bear markets calmly.

Resources Mentioned

  • Click here to view my YouTube channel, Even Better Retirement
  • Click here to order my book, Retirement Starts Today: Your non-financial guide to an even better retirement
  • Click here to read the Morning Star article, Does It Make Sense to File Early for Social Security and Invest in the Market?

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-eighth 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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