This Week in Retirement: May 21st, 2026


Welcome to This Week in Retirement

The promise of This Week in Retirement:
If you only have 15–30 minutes per week to dedicate to learning more about retirement planning, I’ve got you covered.

Retirement planning is both my job and my hobby. Every week, I read dozens of articles and watch or listen to hours of podcasts and YouTube videos.
Every Thursday, I’ll share the best options from each category.

Pick a few. Skip the rest. You’re covered.

📰 Best in Retirement News

Survival is the Only Success - Nick Maggiulli

Nick Maggiulli argues that the ultimate measure of financial success isn’t how much money, fame, or short-term performance you achieve — it’s whether you can keep it. Using examples like Tai Lopez, Sam Bankman-Fried, Elizabeth Holmes, and overconfident investors who chase leverage, options income, or concentrated bets, he shows how greed can turn success into ruin. The big takeaway: survival matters more than maximum returns, because staying in the game long enough to compound is what builds real wealth.

Lifestyle Creep Isn't About Spending More - Derek Hagen

Derek Hagen discusses that lifestyle creep isn’t simply spending more money — it’s spending more without intentionally choosing why. As income rises, it’s easy for nicer vacations, cars, restaurants, or housing upgrades to quietly shrink the gap between what you earn and what you save. The goal isn’t to avoid improving your lifestyle, but to make sure those upgrades reflect your actual values instead of social comparison, habit, or autopilot.

📺 Best in YouTube


The 5 Levels of Retirement ROTH Conversion (From Basic To Advisor) - Ben Brandt

In this video I explain that Roth conversions get more valuable when they’re coordinated with the full retirement plan. Beyond tax brackets, good planning considers RMDs, Social Security taxation, IRMAA, widow’s tax risk, estate planning, and future flexibility. The big takeaway: Roth conversions are less about taxes alone and more about keeping control in retirement.

Exposing a $300,000,000 Scam - Coffeezilla

This is my favorite YouTube channel. This video details a multi-month investigation into Goliath Ventures, a private equity firm that was recently exposed as a $328 million Ponzi scheme.


Thunder Tube

This video features music created by one of my podcast listeners, Scott. His story is featured on our "Retire To Something" segment this week on my podcast. Scott is a retiree based in Texas, who is living out a lifelong dream of creating music after reaching financial independence.

Click here to listen to this week's podcast and hear Scott's story.

🎧 Best in Audio (Podcasts)

Decluttering for Retirement: It's More Than Cleaning Out Your Closet

Roger Whitney kicks off a new series on decluttering for retirement, explaining how the accumulation of “stuff”—from physical belongings to financial accounts to relationships—can unconsciously shape our decisions and limit our ability to envision a fulfilling next chapter. He reframes retirement as a rare opportunity to reset your identity, let go of what no longer serves you, and intentionally design a life aligned with who you want to become. The episode wraps with listener questions across a variety of retirement planning topics, including follow-ups on last week’s discussion around longevity.

Spotify | Apple Podcasts

Why Waiting Until 70 for Social Security Can Backfire (And the Question to Ask Instead) - Stay Wealth Retirement Podcast

This episode walks through a case study of a 62-year-old woman with a $1.5 million IRA and the question most retirees are wrestling with.

The math behind "wait until 70" for Social Security is real. Hold off claiming from 62 to 70 and your monthly benefit climbs by roughly 77%. So why would anyone walk away from a number that big? The short answer is that the standard break-even analysis only measures one variable.

And for retirees with healthy pre-tax savings, there are other factors at play that can make "waiting" a more expensive decision than it looks.

Spotify | Apple Podcasts

🧭 Other Business

Starting this year, I’m adding a short segment to the end of the podcast:

Retire TO something, not FROM something.

Each week, I’ll spotlight:

  • Volunteer opportunities
  • Part-time “fun” jobs
  • Creative or meaningful ways people stay engaged in retirement

Click here to share your ideas!

Additional resources:

Click here to order my book, Retirement Starts Today: Your non-financial guide to an even better retirement

Click here to get started on your retirement plan

Have a link you'd like to share with our audience? Reply with your best links & you might see them featured in an upcoming issue.

We'll see you next week for issue #21 of This Week in Retirement,

Ben 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).

Read more from Benjamin Brandt

Welcome to This Week in Retirement The promise of This Week in Retirement:If you only have 15–30 minutes per week to dedicate to learning more about retirement planning, I’ve got you covered. Retirement planning is both my job and my hobby. Every week, I read dozens of articles and watch or listen to hours of podcasts and YouTube videos.Every Thursday, I’ll share the best options from each category. Pick a few. Skip the rest. You’re covered. 📰 Best in Retirement News Retirement planning...

Welcome to This Week in Retirement The promise of This Week in Retirement:If you only have 15–30 minutes per week to dedicate to learning more about retirement planning, I’ve got you covered. Retirement planning is both my job and my hobby. Every week, I read dozens of articles and watch or listen to hours of podcasts and YouTube videos.Every Thursday, I’ll share the best options from each category. Pick a few. Skip the rest. You’re covered. 📰 Best in Retirement News The Hidden Problem with...

Welcome to This Week in Retirement The promise of This Week in Retirement:If you only have 15–30 minutes per week to dedicate to learning more about retirement planning, I’ve got you covered. Retirement planning is both my job and my hobby. Every week, I read dozens of articles and watch or listen to hours of podcasts and YouTube videos.Every Thursday, I’ll share the best options from each category. Pick a few. Skip the rest. You’re covered. 📰 Best in Retirement News Is It Possible to Invest...