What makes an investment "good?"

It seems like a straightforward question, but the answer is more subjective than most people realize.

Recently, my wife asked why I thought real estate was such a BAD investment when others she knows call it the BEST they've ever made.

Hearing it framed that way struck a different chord.

And rather than quickly defending my position with data and facts, I found myself reconsidering the question entirely.

In today's episode, I share how to evaluate investments in the real world, what separates good investments from bad ones, and why some popular metrics can mislead.

If you've ever wondered why an investment looks great paper but doesn't feel right—or why others swear by strategies you'd never touch—this episode will give you a clearer framework for thinking about your own portfolio.

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📆 BOOK A CALL:

For two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning.

The result?

Less stress. Lower taxes. More confidence about the future.

If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation.

👉 Click to Learn More and Schedule

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EPISODE RESOURCES:

→ Grab the Episode Show Notes

→ Join the Stay Wealthy Retirement Newsletter

→ Learn About the Total Retirement System™

After decades of filing taxes together, most couples assume their retirement plan will continue largely unchanged if one spouse passes away.

But for many surviving spouses, the first surprise is a higher tax bill, even when income hasn't changed much.

In this episode, I explain how a feature of the tax code can increase taxes after the loss of a spouse.

Using a real-world example, I show why tax brackets shrink, why retirement income often doesn't, and how that mismatch can quietly drive taxes higher over time.

More importantly, I share a planning framework couples can use while both spouses are still alive.

We'll cover common mistakes, why the "married window" matters, and how small, intentional decisions made years in advance can meaningfully protect the surviving spouse.

This isn't about fear or worst-case scenarios—it's about avoiding unnecessary surprises and making thoughtful, proactive decisions that support confidence throughout retirement.

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📆 BOOK A CALL:

For two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning.

The result?

Less stress. Lower taxes. More confidence about the future.

If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation.

👉 Click to Learn More and Schedule

***

EPISODE RESOURCES:

→ Grab the Episode Show Notes

→ Join the Stay Wealthy Retirement Newsletter

→ Learn About the Total Retirement System™

Every year, Wall Street rolls out its market predictions.

Targets get published, expectations get set, and the headlines make it sound like the future is just a spreadsheet away.

But markets have a long history of humbling even the most confident forecasts, and that creates a real problem for retirement savers.

Because, while short-term forecasts are usually noise, ignoring market expectations altogether isn't the answer either.

So in today's episode, I break down how to think about market outlooks the right way.

We'll cover why forecasts so often miss the mark, when long-term assumptions actually matter, and how market research can be used as a planning tool (not a prediction engine).

I also share key themes from Vanguard's Economic and Market Outlook for 2026, focusing on growth, inflation, and expected returns—and why all of that matters for your portfolio and retirement plan.

***

📆 BOOK A CALL:

For two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning.

The result?

Less stress. Lower taxes. More confidence about the future.

If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation.

👉 Click to Learn More and Schedule

***

EPISODE RESOURCES:

→ Grab the Episode Show Notes

→ Join the Stay Wealthy Retirement Newsletter

→ Learn About the Total Retirement System™