Stay Wealthy Retirement Podcast

Most retirees have a general idea of which tax bracket they're in.

But that bracket doesn't always tell you what your next dollar of income really costs.

Cross certain income thresholds, and you could face an extra surtax, lose part of a deduction, or pay higher Medicare premiums.

These are often called stealth taxes.

And as year-end approaches, they can quickly change the math on a Roth conversion, a capital gain, or an extra IRA withdrawal.

In this episode, I'm breaking down 8 stealth taxes that are easy for retirement savers to overlook.

Here's what you'll learn:

→ Why some of the best years for Roth conversions can also create the most expensive planning trade-offs

→ Why some income thresholds deserve careful attention while others may be worth crossing intentionally

→ A simple 3-scenario exercise to run before you lock in your year-end decisions

Avoiding every one of these taxes isn't always the goal.

Sometimes paying more today can help you keep more of your wealth over the next 10, 20, or even 30+ years.

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📆 Book a Call With Our Team:

Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.

See how they fit together in one coordinated strategy built around your numbers.

👉 Learn More and Book a Call Here

***

Episode Resources:

→ Grab the Episode Show Notes

→ Get Your FREE Tax-Smart Retirement Toolkit

→ Learn About the Total Retirement System™

On Christmas Day, a woman picked up her 74-year-old mother's phone and found messages from someone she didn't recognize.

What she uncovered had been unfolding for nearly a year, cost her mom hundreds of thousands of dollars, and started with something millions of people do every day.

And to her mom, none of it felt suspicious.

That's what can make scams like this so difficult to recognize, even for careful, intelligent people.

But other financial threats don't require criminals to earn your trust at all.

In this episode, I'm sharing what her story can teach us about protecting our money.

I'm also sharing what you need to know about passkeys, a newer (and safer!) way to sign in to your online accounts.

Here's what you'll learn:

→ 4 simple habits that can make it harder for scammers to earn your trust

→ How passkeys work, the 3 places to store them, and what happens if you lose your phone

→ How criminals can sometimes access your accounts without needing your password, passkey, or verification code

The best protection is layered: stronger security on your accounts, a few simple habits, and someone you trust to call before you act.

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📥 Grab Your Free Retirement Security Checklist:

This 9-page guide helps you close the most common security gaps in about an hour.

Inside, you'll find family scam-prevention rules, passkey and credit freeze guides, and a plan for what to do if something goes wrong.

→ Download the Checklist Here

***

📆 Book a Call With Our Team:

Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.

See how they fit together in one coordinated strategy built around your numbers.

👉 Learn More and Book a Call Here

***

Episode Resources:

→ Grab the Episode Show Notes

→ Get Your FREE Tax-Smart Retirement Toolkit

→ Learn About the Total Retirement System™

Warren Buffett has shared exactly how the money his family inherits should be invested: 90% in a low-cost S&P 500 index fund and 10% in short-term government bonds.

It's simple, inexpensive, and recommended by the greatest investor of all time.

And if you've owned the S&P 500, your company's stock, or a single big winner for decades, it may be a big reason you're able to retire.

But once your portfolio has to provide a paycheck, that concentration can carry risks it didn't before.

In this episode, I'm sharing how to decide whether what got you here still fits the retirement ahead.

Here's what you'll learn:

→ Why the same portfolio can look very different once you start taking withdrawals

→ What you may give up by spreading your money around (and why it can still make sense)

→ A simple 5-step process for reducing a concentrated position while keeping taxes in check

If you were building your portfolio today, knowing what you need your money to do, would you choose the same mix?

***

📆 Book a Call With Our Team:

Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.

See how they fit together in one coordinated strategy built around your numbers.

👉 Learn More and Book a Call Here

***

Episode Resources:

→ Grab the Episode Show Notes

→ Get Your FREE Tax-Smart Retirement Toolkit

→ Learn About the Total Retirement System™

Last week, I explained why waiting until 70 to claim Social Security deserves a closer look, even when it makes sense on paper.

Weighing that decision depends on understanding how the program works.

And a few common assumptions can make that harder than it needs to be.

They can influence when you retire, how you plan for taxes, and what your spouse may receive down the road.

In this episode, I'm walking through 7 common Social Security myths and where the confusion comes from.

Here's what you'll learn:

→ What the trust fund's projected shortfall may (and may not) mean for your benefits

→ How your benefit is calculated, and why high earners often misjudge it

→ 3 options that may still be available if you've already claimed early

Whether you're years away from claiming or already collecting, a clearer picture of the rules can make it easier to choose an approach that fits the rest of your retirement plan.

***

📆 Book a Call With Our Team:

Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.

See how they fit together in one coordinated strategy built around your numbers.

👉 Learn More and Book a Call Here

***

Episode Resources:

→ Grab the Episode Show Notes

→ Get Your FREE Tax-Smart Retirement Toolkit

→ Learn About the Total Retirement System™

If you've researched when to claim Social Security, you've probably heard to wait until age 70.

And there's good reason for that advice.

Waiting means a larger monthly benefit for life, which can be especially valuable if your retirement lasts several decades.

But while you wait, you'll need to cover your expenses from other sources.

That means considering how comfortable you are drawing from savings, how a market downturn could affect your plan, and how many healthy, active years you have ahead.

So, how do you weigh those trade-offs?

And when might claiming earlier make sense, even if you can afford to wait?

In today's episode, I'm exploring 6 overlooked considerations that could influence your claiming strategy and help you decide whether the advice to wait fits your retirement plan.

We'll look at how they might influence your claiming strategy, and why a recommendation that sounds sensible on paper may need a closer look in your own retirement plan.

***

📆 Book a Call With Our Team:

Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.

See how they fit together in one coordinated strategy built around your numbers.

👉 Learn More and Book a Call Here

***

Episode Resources:

→ Grab the Episode Show Notes

→ Get Your FREE Tax-Smart Retirement Toolkit

→ Learn About the Total Retirement System™

📥 Grab Your Free Charitable Giving Planning Resources:

Charitable giving can be simple, but the tax and planning decisions behind it often are not.

Get four practical resources to help you make more informed giving decisions:

A QCD guide, a donor-advised fund guide, a breakdown of which assets may be best to give, and an overview of the charitable-giving vehicles available when your planning gets more complex.

→ Download All 4 Resources Here

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🎙️ Episode Description:

Earlier this year, the U.S. Tax Court threw out a $665,000 charitable deduction.

The donors had an appraisal, the required IRS form, and a signed letter documenting the donation.

And yet the court denied the entire deduction... because of ONE missing sentence.

And that same requirement can apply when you write a check to your church, give from your IRA, or buy tickets to a charity gala.

In this episode, I walk through what went wrong and what it can teach the rest of us.

Here's what you'll learn:

→ Why a canceled check alone may not be enough to back up your deduction

→ How QCDs, appreciated stock, and new 2026 rules can change the tax outcome of the same donation

→ The 4 questions I'd ask before making your next charitable gift

The charity gets your gift either way. The question is whether you get the tax benefit, too.

***

📆 Book a Call With Our Team:

Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.

See how they fit together in one coordinated strategy built around your numbers.

👉 Learn More and Book a Call Here

***

Episode Resources:

→ Grab the Episode Show Notes

→ Get Your FREE Tax-Smart Retirement Toolkit

→ Learn About the Total Retirement System™

Once required minimum distributions begin, the IRS decides how much comes out of your IRA each year.

But it doesn't decide when...

You can take it all in January, wait until December, or spread it out across the year.

At first glance, the choice seems almost meaningless.

The required amount is the same, and the distribution still lands in the same tax year.

But the timing can matter in ways that aren't always obvious.

And even if you're years away from taking RMDs, this is a decision you'll eventually need to make if you have money in pre-tax retirement accounts.

Here's what you'll learn:

→ The 3 things RMD timing can still affect (and how much each one really matters)

→ Why the order of your RMD, charitable gifts, and Roth conversions can matter more than the month you withdraw

→ When taking your RMD early, late, or throughout the year makes the most sense

By the end, you'll have a simple framework for thinking about RMD timing before it becomes another retirement decision you're forced to make on the fly.

***

📆 Book a Call With Our Team:

Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.

See how they fit together in one coordinated strategy built around your numbers.

👉 Learn More and Book a Call Here

***

Episode Resources:

→ Grab the Episode Show Notes

→ Get Your FREE Tax-Smart Retirement Toolkit

→ Learn About the Total Retirement System™

One multi-decade study suggests nearly half of working households may be at risk of falling short in retirement.

But another respected study found that fewer than 20% were actually behind.

So which one should you believe?

The answer reveals a weakness in the way we typically measure retirement progress.

Here's what you'll learn:

→ Why 2 respected studies reach such different conclusions about who's really at risk

→ The 3 ways the "save a percentage" rule can break down for families

→ Why the years when saving feels impossible may be more normal than you've been told

→ How your 50s and 60s can become the most important saving windows of your life.

By the end, you'll have a better way to judge whether you're truly behind and a clearer picture of the opportunities that may still be ahead.

And if nothing else, you'll understand why a difficult savings season today doesn't necessarily define where you'll end up.

***

📆 Book a Call With Our Team:

Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.

See how they fit together in one coordinated strategy built around your numbers.

👉 Learn More and Book a Call Here

***

Episode Resources:

→ Grab the Episode Show Notes

→ Get Your FREE Tax-Smart Retirement Toolkit

→ Learn About the Total Retirement System™

Most retirement planning treats the transition like a single event.

But in reality, you're navigating THREE different shifts at the same time.

And while traditional planning is well-equipped to handle the first, it spends far less time on the second and almost none on the third.

Here's what you'll learn:

→ Why 50% of retirees plan to spend little or none of their savings

→ Why even a well-funded retiree can treat every withdrawal like a threat

→ 5 questions that work better than "Can I afford it?"

By the end, you'll have a clearer picture of which transition your plan may be overlooking, why that matters, and what it can take to close the gap.

And if nothing else, you'll have a better answer for why spending your own money can feel so difficult after decades of doing everything right.

***

📆 Book a Call With Our Team:

Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.

See how they fit together in one coordinated strategy built around your numbers.

👉 Learn More and Book a Call Here

***

Episode Resources:

→ Grab the Episode Show Notes

→ Get Your FREE Tax-Smart Retirement Toolkit

→ Learn About the Total Retirement System™

You've spent decades building a nest egg large enough to fund the retirement you want.

The next challenge is making sure it can support that same lifestyle for the next 30 years.

At 3% historical inflation, the $100,000 lifestyle you retire on could cost $240,000 a year by age 90.

And the assets that feel safest — cash, CDs, and money market funds — have historically done the least to keep up.

In this episode, I'm simplifying a century of market history into 8 numbers that shape how long your money lasts.

Here's what you'll learn:

→ The hidden cost of playing it safe with money you won't need for decades

→ The 2 bond numbers that look nearly identical, and the risk hiding between them

→ How they all fit together into a simple framework for making confident decisions

My hope is that when we're done, you have a small set of reference points to return to, and a lot less noise competing for your attention.

***

📆 Book a Call With Our Team:

Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.

See how they fit together in one coordinated strategy built around your numbers.

👉 Learn More and Book a Call Here

***

Episode Resources:

→ Grab the Episode Show Notes

→ Get Your FREE Tax-Smart Retirement Toolkit

→ Learn About the Total Retirement System™