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

​Your 12 Good Years - The Retirement Manifesto​

In this article, Fritz Gilbert introduces the idea that retirement often comes with a limited window of “go-go years” — roughly the first 10–15 years when your health, energy, and ability to fully enjoy life are at their peak. He argues that too many retirees underspend during this period out of fear of running out of money later, only to find themselves with fewer opportunities as aging sets in. The key takeaway is to intentionally plan for higher spending and meaningful experiences early in retirement, while you’re still able to enjoy them, rather than saving everything for a future that may not look the way you expect.

​4 Expert-Backed Tips for Choosing the Best Healthcare Proxy - Advisor Perspectives​​

Choosing a healthcare proxy isn’t about picking the closest person—it’s about picking the right person. This article walks through four key tips: choose someone who can handle stress, communicate clearly with doctors, follow your wishes (even if they disagree), and is willing to advocate for you. The big takeaway is that this role is less about relationship and more about capability—because in a crisis, clarity and decisiveness matter most.

📺 Best in YouTube

​Once Retirees See This, They Claim Social Security Late and Convert Early - Ben Brandt ​

The video explains a retirement strategy where you delay taking Social Security (often until age 70) to get higher monthly payments, while using your early retirement years to do Roth conversions—moving money from traditional retirement accounts into a Roth IRA and paying taxes at a lower rate. The idea is to live off savings first, reduce future tax burdens, and lock in larger guaranteed income later, though it emphasizes that this approach depends on personal factors like income needs, health, and overall financial situation.

​If You Can Answer Yes to These, Retire Now! - Kevin Lum​

This video breaks down why a rigid retirement plan can quietly fail—even if the math looks solid on paper. The core issue isn’t necessarily how much you withdraw, but when and how you take it. Early negative market returns (sequence risk) can do lasting damage if you’re pulling the same amount regardless of what the market is doing.

🎧 Best in Audio (Podcasts)

Why Even the Best Retirement Calculator is Wrong - Retirement Answer Man

Roger Whitney explores why retirement planning software—especially Monte Carlo simulations—can give a false sense of confidence if misunderstood. He explains what these tools actually measure, the hidden assumptions behind them, and why retirement is a complex problem that requires judgment, flexibility, and resilience—not just a high “success rate.” Roger shares how to properly interpret results, avoid common traps, and use software as a guide rather than a decision-maker so you can build a retirement plan that supports a great life.

​Spotify | Apple Podcasts​

​Estimated Taxes Are a Pain. Let's make it Easier - Ben Brandt

In this episode, we tackle one of the most frustrating parts of retirement—estimated taxes—and why you could pay everything you owe and still get hit with an IRS penalty. A new piece from Laura Saunders at the The Wall Street Journal highlights how these penalties are rising, especially for retirees. We’ll break that down, then answer a listener question on what happens when you lose faith in fixed income as the foundation of your retirement plan, and wrap up with “Retire to Something,” where listeners share what they’re actually doing in retirement.

​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 #15 of This Week in Retirement,

Ben Brandt