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™

Every January, we go through the same routine.

Limits adjust, brackets shift, and most years it's just a quick refresh.

But 2026 is different.

Sweeping tax legislation passed last summer is introducing some of the biggest changes we've seen in a while.

And buried inside those updates are two new rules that have already caused widespread confusion (even among experts).

In this bonus episode, I walk through the most important tax updates for 2026 and explain why they matter for your retirement plan.

I also also break down those two unique rules, sharing how they work, who they apply to, and why they matter.

So even if you feel up to speed on the 2026 changes, I'm confident you'll walk away with at least one new and useful insight.

***

📆 BOOK A CALL:

For nearly 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:

→ Download the 2026 Tax Cheat Sheet

→ Grab the Episode Show Notes

→ Learn About the Total Retirement System™

After decades of saving and doing the right things, most people expect retirement to feel clear.

But for many, it doesn't.

Not necessarily because they didn't save enough, but because key financial decisions were made in isolation.

In this episode, I walk through the seven questions every retirement saver should be able to answer.

I also share the exact planning framework my team and I use to make sure those questions are addressed in a thoughtful, coordinated way.

By the end of today's episode, you'll have a clearer framework for evaluating your retirement decisions.

And more importantly, you'll understand what it actually takes to feel confident about the years ahead.

***

📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING:

For nearly 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 Here to Learn More

***

EPISODE RESOURCES:

→ Grab the Episode Show Notes

→ Join the Stay Wealthy Retirement Newsletter

→ Learn About the Total Retirement System™

It's that time of year again—time to step back from the complex tax strategies, Roth conversion debates, and retirement planning deep dives… and have a little fun. 😊

In this annual "surprising stats" episode, I'm sharing 7 counterintuitive facts about the markets and investing.

Some are counterintuitive.

A few might make you question things you've believed for years.

And at least one involves math that should make anyone considering complex insurance products hit the pause button.

By the end of today's episode, you'll walk away feeling more confident in the proven (sometimes boring!) academic approach to investing that we talk about so often here on the show.

And if nothing else, you'll have a few holiday-dinner stats to drop between bites of pie.

***

📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING:

For nearly 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 Here to Learn More

***

EPISODE RESOURCES:

→ Grab the Episode Show Notes

→ Join the Stay Wealthy Retirement Newsletter

→ Learn About the Total Retirement System™

→ Download the 2026 Tax Cheat Sheet

💥 Download the freshly updated 2026 Tax Planning Cheat Sheet (PDF): www.youstaywealthy.com/cheatsheet

***

Most year-end tax advice is generic... max out your 401(k), bunch your deductions, donate to charity.

But for diligent retirement savers with healthy nest eggs, the real opportunities are more nuanced.

In this episode, I break down three tax strategies that can help you avoid overpaying the IRS and reduce your lifetime tax bill.

You'll learn how to evaluate whether each move makes sense for your situation, so you're making informed decisions rather than chasing aimless deductions.

If you're nearing retirement or already there, this episode will help you close out the year with a clearer tax picture and a smarter plan for the years ahead.

***

📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING:

For nearly 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 Here to Schedule a Call

***

EPISODE RESOURCES:

→ Download the 2026 Tax Cheat Sheet

→ Grab the Episode Show Notes

→ Join the Stay Wealthy Retirement Newsletter

→ Learn About the Total Retirement System™

→ Careers at Define Financial

The Oracle of Omaha is officially "going quiet."

In a rare and deeply personal announcement, Warren Buffett published what appears to be his final press release to shareholders.

This episode isn't about taxes, investing, or the latest market headlines.

It's about how one of the most successful investors of all time is thinking about money, family, aging, and what actually matters when the scoreboard stops moving.

In this Thanksgiving special, I break down:

▶ Why he chose to say this now (at age 95!)

▶ What retirement savers and investors can learn from his message

▶ How his parting wisdom can change the way you use your time and wealth

If you've ever wondered what your future self might wish you'd paid more attention to today, this conversation is for you.

Tune in for the deeper meaning behind Buffett's Thanksgiving sign-off ("yes, even the jerks") and what it reveals about redefining success in the second half of life.

***

📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING:

For nearly 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 Here to Schedule Your FREE Strategy Session

***

EPISODE RESOURCES:

→ Grab the Episode Show Notes

→ Join the Stay Wealthy Retirement Newsletter

→ Learn About the Total Retirement System™

"Just buy the index." It's the simple advice that built your wealth and got you to the finish line.

But here's what often gets overlooked:

The strategy that got you to retirement won't necessarily keep you there.

When you switch from saving to spending, the math changes.

Suddenly, relying on a "simple" S&P 500 strategy exposes you to risks that didn't matter when you had a paycheck.

In this episode, we cover:

▶ The Simplicity Trap: Why "decision fatigue" lures smart retirees into risky, overly concentrated portfolios.

▶ S&P 500 Reality Check: Why the "safe" default option is actually dangerous for your retirement income.

▶ The "Flatline" Defense: How to build a retirement portfolio that protects your purchasing power during downturns.

▶ Beyond Investing: How to align your investments, taxes, and legacy for true peace of mind.

If you are approaching retirement and wondering if your "set it and forget it" strategy is enough to last a lifetime this episode is for you.

***

📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING:

For nearly two decades, my team and I 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 Here to Schedule Your FREE Strategy Session

***

EPISODE RESOURCES:

→ Grab the Episode Show Notes

→ Join the Stay Wealthy Retirement Newsletter

→ Learn About the Total Retirement System™