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Mailbag: Renting, Dividends, and Social Security

Release Date: 08/14/2025

My Investments Underperformed the Market - Should I Fire My Advisor?

The Red Zone Retirement Program

We got a great question from a listener: "My investments didn't do as well in the last 12 months as the overall market has done. Should I be re-evaluating my advisor based on this lack of performance?" It’s a question a lot of people ask at some point in their investing lives, and John breaks down the answer today. Turns out, if your portfolio is doing what it was designed to do, that's the scorecard that matters. Here’s some of what we discuss in this episode: 📊 “The market” isn’t a single benchmark—comparison matters 🎯 Your portfolio’s purpose matters more than...

Volunteering: The Best Investment You Might Make In Retirement

The Red Zone Retirement Program

🏈 Don’t fumble your retirement - get your financial game plan at In honor of National Volunteer Week (April 19-25), let’s talk about why volunteering is an important part of life, especially in retirement. Retirement isn’t just about stepping away from work. It's an opportunity to step toward the things you've always cared about, with more time and freedom than you've had in decades. Here’s some of what we discuss in this episode: 🌟 Finding purpose after retirement through volunteering ⛹️‍♂️ Opportunities in sports (e.g., coaching, equipment management, and...

What People Really Google About AI and Retirement (and What’s True)

The Red Zone Retirement Program

🏈 Don’t fumble your retirement - get your financial game plan at AI headlines are everywhere right now, mostly bold predictions about how artificial intelligence will reshape the economy. Instead of reacting to the noise, John steps back and looks at what the data actually suggests about AI and the workforce. He also walks through the top questions people in their 50s and 60s are Googling about AI and retirement, giving clear, practical answers. The searches reveal what you’re worried about, but John shares what you should actually do about it. Here’s some of what we discuss...

Tax Season Hits Different When You're Retired

The Red Zone Retirement Program

🏈 Don’t fumble your retirement - get your financial game plan at Nobody likes tax season. But for new retirees, it can come with a few unwelcome surprises. The rules have changed, the income sources have shifted, and strategies that made sense during your working years may no longer apply. Today, John looks at some of the biggest tax mistakes retirees make as discussed in a recent Kiplinger article and whether these match what we see in the real world. Here’s some of what we discuss in this episode: 📊 RMD Rules: Required distributions can raise taxable income 🔁 Roth...

Should You Sell Your Business to Retire?

The Red Zone Retirement Program

🏈 Don’t fumble your retirement - get your financial game plan at Selling a business is one of the biggest financial decisions you’ll ever make. It’s not just about finding a buyer, it’s about structuring the deal correctly, minimizing taxes, and making sure the sale supports your next chapter of life. John coaches us through major considerations business owners need to think about before signing anything. A business sale can create tremendous opportunity, but only if it’s handled with intention and strategy. Here’s some of what we discuss in this episode: 📊...

Inheriting a House? Here’s What You Need to Know About Taxes

The Red Zone Retirement Program

🏈 Don’t fumble your retirement - get your financial game plan at Inheriting a home can feel like a blessing, until the tax questions start piling up. John walks through the playbook for handling inherited property the smart way. This big financial decision deserves careful thought and consideration, not quick reactions. When it comes to inherited real estate, you don’t want to move without a game plan. Here’s some of what we discuss in this episode: 📈 Step-Up in Basis: Resetting value at inheritance 💵 Fair Market Value: Why timing matters 🧾 Capital Gains Impact:...

Would You Trade $600 a Month to Protect Your Spouse?

The Red Zone Retirement Program

🏈 Don’t fumble your retirement - get your financial game plan at John tackles a listener question that feels like a red-zone moment: trade $600 a month now or protect your spouse for life. Using real-world examples and a coach’s perspective, John breaks down the tradeoffs, risks, and emotional weight behind pension elections. When the stakes are this high, understanding your options before you choose can make all the difference. Here’s some of what we discuss in this episode: ⚖️ Pension Tradeoffs: Income today versus certainty tomorrow 🏠 Survivor Reality: Why...

What’s Changing in 2026 (And Why It Matters To Your Money)

The Red Zone Retirement Program

🏈 Don’t fumble your retirement - get your financial game plan at What’s new in 2026 for retirees & pre-retirees? John covers several updates that could quietly impact your cash flow, taxes, and savings strategy. A quick review now can help make sure changes in 2026 work with your plan, not against it. Discover actionable reminders and why your next steps matter more than ever. Here’s some of what we discuss in this episode: 🧭 2026 Overview – Key retirement-related changes for the year 📈 COLA & Medicare – Social Security increases offset by premiums 🧾...

Year-End Mailbag: Your Biggest Retirement Questions Answered

The Red Zone Retirement Program

🏈 Don’t fumble your retirement - get your financial game plan at Join John as he wraps up the year and answers some of the biggest questions on listeners’ minds. This episode dives into real-world financial concerns, practical strategies, and tips to help you keep your retirement game plan on track. John cuts through the noise with straightforward answers that help you think clearly about the retirement decisions that matter most. Here’s some of what we discuss in this episode: 🎁 Holiday Gifting: understanding limits and smart giving strategies 💰 Excess Cash:...

I'm 62... Should I Claim Social Security?

The Red Zone Retirement Program

🏈 Don’t fumble your retirement - get your financial game plan at Celebrate our 100th episode as John tackles the ever-important topic of Social Security and retirement planning. In this milestone show, we discuss key considerations for deciding when to claim Social Security benefits and the common mistakes to avoid. Tune in for expert insights and practical advice to help you make informed decisions about when to take Social Security. Here’s some of what we discuss in this episode: 🚫 Don’t Rush at 62: the common arguments for claiming early 📊 Why Waiting Pays: the...

More Episodes

🏈 Don’t fumble your retirement - get your financial game plan at http://bookachatwithjohn.net

When it comes to retirement, the toughest calls aren’t always about the market — they’re about your life. In this episode, John takes a break from the playbook to field real questions straight from the audience mailbag. Big choices about where to live, how to invest, and when to start Social Security can feel like fourth-quarter pressure, and John’s here to help you call the right plays when it matters most.

John explores the pros and cons of renting in retirement, why relying on a “dividends only” strategy can limit your options, and the real story behind claiming Social Security after 70. With clear strategies, relatable stories, and a few laughs from the sidelines, he offers a winning game plan for finishing strong and walking off the field on your own terms. The choices you make today can shape your retirement for decades, so tune in to hear real questions and real answers that matter to people just like you.

Here’s some of what we discuss in this episode:
🏠 The surprising financial benefits of renting in retirement
📉 Why dividend-only investing may limit your flexibility
⏳ Taking Social Security after age 70
🐦 How “go-go, slow-go, and no-go” years impact choices

0:00 – Intro
1:56 – Renting in Retirement (Pros & Cons)
7:08 – Is Dividend-Only Investing Viable?
11:14 – Social Security Strategy at Age 70+

Get in touch:

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