What are the perceived benefits of moving to a low-tax state in retirement? Is it all it’s cracked up to be?

We’re gonna cover a Wall Street Journal article by Debbie Carlson that delivers an important dose of nuance: “Don’t let the income-tax tail wag the total-spending dog.”

I also answer a very thoughtful question from Lynn about sequence of returns risk, as well as average returns vs order of returns.

Key topics from the article:

🏠 Real Estate & Insurance Can Eat Up the Savings
📊 For Middle-Income Retirees, Sales & Property Taxes Matter More
💵 Homeowners Insurance Is a Big—and Growing—Expense
📚 Don’t Forget State-Level Retirement & Estate Taxes
🧮 Ben’s Take: Look at the Whole Picture

Resource:
Article by Debbie Carlson: https://www.wsj.com/personal-finance/taxes/retirement-low-tax-rate-states-move-cabdb31b

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Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

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How do you stay calm and confident when the markets get messy? In today's Retirement Headlines we go through Cullen Roche's article from Discipline Funds - "Finding Certainty in a Sea of Uncertainty".

With tariffs, global uncertainty, and market volatility making headlines again offers nine practical steps to help you stay grounded, focused, and on track with your retirement plan.

The 9 Calming, Confidence-boosting steps the article lays out are:

1. Revisit Your Financial Plan
2. Update Your Estate Plan
3. Consider Tax Loss Harvesting
4. Dollar Cost Average Excess Cash
5. Think in Terms of Time Horizons
6. Stay the Course (If You Can)
7. Talk About It
8. Focus on What You Can Control
9. Go Do "Leg Day"

After that, I answer a listener question: “I’ve been paying $1,600 a year for a $500,000 level term life insurance policy, which runs through 2031. I have two financially stable adult children in their 30s, who are the policy’s beneficiaries, and two grandchildren. Should I keep making the premium payments—or let it lapse?”

Resource:

Article by Cullen Roche: Finding Certainty in a Sea of Uncertainty

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Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

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One of the biggest and often overlooked risks facing retirees is sequence-of-returns risk. The risk of experiencing investment losses early in retirement can have an impact on the sustainability of savings over the long term.

Morningstar researchers dug into this in their latest State of Retirement Income study. Their findings confirm what many retirement planners already suspect: the first five years of retirement are make-or-break.

I'll also answer a listener question: "Are there advantages to moving all your mutual funds into a brokerage firm such as Schwab? "

Resource:
Morningstar article: How to Avoid Outliving Your Retirement Savings? It’s All in the Sequence

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Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

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It’s no secret that market volatility can feel especially nerve-wracking when you’re no longer earning a paycheck.

But what if I told you that, historically, every single crash has ended the same way—with a recovery?

That's what happened after the Covid-19 market crash, the 2021 downturn, and even the Great Depression.

We're going to discuss an article titled "What We’ve Learned From 150 Years of Stock Market Crashes" by Emelia Fredlick. The article highlights some of the worst market downturns in history and, more importantly, the lessons they offer for long-term investors like you.

Takeaways:

Lesson #1: We Can’t Predict Recovery Times
Lesson #2: Every Decade Brings a Market Crash
Lesson #3: Staying Invested is the Only Winning Strategy

Then I answer question sent in from a listener: "What are some good ways to gift money to my children while I'm still living?"

All of this in less than 20 minutes.

Resources:

• MorningStar article by Emelia Fredlick: What We’ve Learned From 150 Years of Stock Market Crashes
• Book by Bill Perkins: Die With Zero
• How many annual exclusions are available? IRS website on Gift Taxes

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Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

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Is your 401(k) prepared for a market crash? With market volatility on the rise, many investors are wondering how to protect their portfolios.

In this episode, I share an article from Go Banking Rates on how to safeguard your retirement savings during turbulent times. I’ll highlight key takeaways from the article, share my own insights on where I agree or disagree, and explain why certain strategies may be more effective than others.

After that, I answer a listener’s question about long-term care (LTC) insurance. We’ll explore different types of LTC policies, discuss the ideal time to purchase coverage (such as around age 50), and consider whether self-funding might be a smarter financial strategy.

Key takeaways:

• Diversify, Diversify, Diversify
• Shift Toward Conservative Investments as You Near Retirement
• Rebalance Regularly—Not Just After a Crash
• Consider a 401(k) Rollover for More Flexibility
• Stay the Course—Don't Panic Sell

Resources:

Go Banking Rates article: How To Protect Your 401(k) from a Stock Market Crash

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• Subscribe to the newsletter: https://retirementstartstodayradio.com/newsletter
• Work with Benjamin: https://retirementstartstoday.com/start

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Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

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Most people assume their tax burden lightens in retirement, but what if I told you that some taxes are actually designed to creep up on you year after year—without Congress passing a single new law? In this episode, we expose the sneaky taxes that can quietly erode your retirement income, from Social Security taxation to Medicare IRMAA surcharges. These hidden costs don’t just affect the ultra-wealthy anymore; thanks to outdated rules and inflation, they’re hitting everyday retirees harder than ever.

If you're relying on Social Security, investment income, or Medicare in retirement, you may already be on the IRS’s radar—without realizing it. We break down the four biggest tax traps, explain how they’ve changed over time, and why they’re pulling more retirees into the tax net each year. Whether it's the frozen thresholds for Social Security taxes or the stealthy Medicare penalties that kick in just because you had a good income two years ago, these sneaky policies can add up fast.

By the end of this episode, you’ll have a clearer picture of how these taxes work, why they exist, and what—if anything—you can do to soften the blow. If avoiding unnecessary taxes in retirement sounds like a smart move, you won’t want to miss this one!

• (0:00) Sneaky Retirement Taxes
• (3:20) Sneaky Tax #1: Social Security taxation (how frozen thresholds trap retirees)
• (5:10) Sneaky Tax #2: Capital loss deduction limit (unchanged since 1978!)
• (6:55) Sneaky Tax #3: Medicare IRMAA (tracking your income before you even retire)
• (08:45) Sneaky Tax #4: Net Investment Income Tax (how it quietly pulls in more taxpayers)
• (09:40) Wrap-up – Why these taxes persist & what you can do about them

• The Retirement Podcast Network
• Social Security Administration’s Taxation of Benefits
• IRS Q&A on Net Investment Income Tax

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Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

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Most people focus on saving for retirement, but what happens when you actually get there? Retirement isn’t just about having enough money—it’s about managing risks that can threaten your financial security and lifestyle.

In this episode, we explore Five Key Retirement Challenges (and Solutions), inspired by a Kiplinger’s Personal Finance article by Walt West. From unexpected market downturns to rising healthcare costs, these challenges can catch retirees off guard if they’re not prepared.

We break down each challenge—financial instability, healthcare expenses, taxes, inflation, and estate planning oversights—and discuss practical strategies to navigate them. Learn how to structure a flexible withdrawal plan, prepare for long-term care costs, use tax-efficient strategies like Roth conversions, and ensure your estate plan protects your loved ones.

Plus, we tackle a listener question about using a MIGA ladder strategy to bridge the gap until Social Security—offering insights into the pros and cons of annuities in a retirement portfolio.

If you want to retire with confidence and avoid costly missteps, this episode is a must-listen. Whether you're years away from retirement or already in it, understanding these key challenges and their solutions can help you make smarter financial decisions for the road ahead.

• (0:00) 5 Key Retirement Challenges (and Solutions)
• (1:17) Retirement headline: Kiplinger’s article on retirement challenges
• (1:42) Challenge #1: Financial instability
• (4:09) Challenge #2: Healthcare and long-term care costs
• (6:33) Challenge #3: Taxes in retirement
• (7:33) Challenge #4: Inflation’s impact on retirement income
• (8:32) Challenge #5: Estate planning oversights
• (10:25) Listener question: MIGA ladder strategy for retirement income

• The Retirement Podcast Network
• Kiplinger’s Personal Finance “Five Key Retirement Challenges” by Walt West
• Fidelity’s Healthcare in Retirement Report

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• Subscribe to the newsletter: https://retirementstartstodayradio.com/newsletter
• Work with Benjamin: https://retirementstartstoday.com/start

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Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

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Most people plan for retirement by focusing on their savings and investment returns—but what if some of the most important decisions happen after you stop working?

In this episode, I sit down with Jeremy Keil, also known as Mr. Retirement, to discuss the three biggest mistakes retirees make—mistakes that can cost them financial security, tax savings, and peace of mind.

From misunderstanding the best time to take Social Security to underestimating how long retirement will last, we break down the key oversights that can derail even the best-laid plans.

Jeremy and I dive into why retirement age and Social Security claiming don’t have to go hand in hand, how to accurately gauge your longevity to avoid outliving your money, and the crucial difference between optimizing for next month’s income versus planning for a lifetime of financial security.

Whether you’re a few years away from retirement or already in it, this conversation will challenge the way you think about your financial future and equip you with strategies to make smarter decisions.

• (0:00) Intro
• (1:19) Mistake #1 – Tying retirement to Social Security
• (4:05) Mistake #2 – Underestimating longevity
• (8:41) Planning for an earlier retirement than expected
• (13:50) Mistake #3 – Optimizing for short-term income over long-term security
• (19:20) Where to find more from Mr. Retirement

• The Retirement Podcast Network
• Mr. Retirement YouTube Channel
• Longevity Illustrator Tool

• Connect with Jeremy Keil AKA Mr Retirement on LinkedIn

• Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com
• Subscribe to the newsletter: https://retirementstartstodayradio.com/newsletter
• Work with Benjamin: https://retirementstartstoday.com/start

Get the book - out now!
Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

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Apple Podcasts, Spotify, Overcast, Pocket Casts, Amazon Music, or iHeart