Retire Today

By Jeremy KeilBusiness Investing

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Typical duration
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per episode

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Retire Today episodes

August 13, 2025 True Retirement Story: How a Plan Salvaged an Unexpected Early Retirement with Anthony Napolitano
Jeremy Keil interviews Anthony Napolitano about how he managed to adapt his retirement plan after an unexpected end to his career.
40 min
August 06, 2025 “Retirement Revealed” is Now “Retire Today”!
Introducing the next chapter of the "Retirement Revealed” podcast as “Retire Today”
8 min
July 30, 2025 Trump’s One Big Beautiful Bill: What It Really Means for Your Retirement
Jeremy Keil explores the incoming changes resulting from the “One, Big, Beautiful Bill” and how they might impact your retirement.
26 min
July 23, 2025 Are These the 11 Best Low-Risk Investments for 2025?
Jeremy Keil breaks down the Investopedia.com list of the 11 best low-risk investments for 2025.
26 min
July 16, 2025 5 Social Security Traps That Could Cost You
Exploring Heather Schreiber’s 5 costly Social Security traps and exploring options of how to handle them.
I’ve seen it time and again throughout my career: the intricacies of navigating Social Security can trip up just about anyone. So when I saw the headline “5 Sneaky Social Security Traps” in Heather Schreiber’s newsletter, I knew right away this was going to be something that deserved a closer look on the podcast.
Let’s dive into these 5 Social Security traps–and these aren’t just random quirks—that can lead to unexpected gaps in income, tax surprises, or permanent reductions in your benefits.
1. The Entire Month Rule
You might think that turning 62 means you're automatically eligible for Social Security that month. Not quite.
Social Security has a quirky rule: you have to be 62 for the entire month to receive benefits for that month. If your birthday is on June 15, you don’t qualify for June’s benefit. Instead, your eligibility starts in July, and your first payment doesn’t arrive until August.
What’s even weirder is that the SSA counts your birthday as the day before you were born. So if you're born on June 2, you're considered 62 starting June 1 and therefore eligible for June benefits (which are paid in July).
If you’re planning on your Social Security check arriving the month you turn 62, you could be left waiting an extra month or two—potentially throwing off your cash flow.
2. Rest in Peace, Now Return to Sender
Just like you must be alive the entire month to earn that month’s benefit, if someone passes away mid-month, they don’t qualify for that month’s Social Security payment—even if it’s already been deposited.
This can be a shock to surviving spouses or family members when the SSA takes that money back. If a loved one passes away on June 14, and the June payment was already deposited in early July, that money must be returned. It wasn’t “earned” under SSA rules.
So whether you're filing for your own benefit or helping a family member, remember: Social Security is earned month-by-month—and only if you’re alive for the full month.
3. Lump Sum FOMO: When Free Money Isn’t Always Free
When you file for Social Security after your full retirement age, you have the option to take up to six months’ worth of benefits retroactively. That sounds great—who doesn’t like a lump sum?
But here’s the catch: taking that lump sum means your official filing date is backdated. So if you file at age 68.5 and take six months retroactive payments, SSA treats you as if you filed at 68—reducing your benefit by 4%.
That “free” $18,000–$20,000 could cost you thousands more over the course of your retirement. Sometimes it’s worth it, but many people take the lump sum without realizing the long-term cost.
4. Under-Withholding Today May Lead to Regret Tomorrow
Here’s a situation I see far too often: retirees who start taking Social Security, forget to set up federal tax withholding, and then get a surprise bill come tax season.
Unlike pensions or employer paychecks, Social Security doesn’t automatically withhold taxes unless you fill out a separate form (Form W-4V). If you don’t do this and your Social Security income is taxable, you could owe hundreds—or thousands—at tax time.
Take the time to set up appropriate withholding levels. SSA allows you to choose from 7%, 10%, 12%, or 22%.
5. Medicare IRMAA and the Two-Year Lookback
When you hit age 65 and enroll in Medicare, your premiums for Part B (and possibly Part D) can go up significantly if your income from two years ago was high.
This IRMAA (Income-Related Monthly Adjustment Amount) surcharge can sneak up on you—especially if you had a one-time event like a Roth conversion, large capital gain, or business sale.
If you had a significant drop in income due to retirement, job loss, or other life event, you can appeal your IRMAA using a life-changing event form (SSA-44). I’ve helped dozens of clients successfully reduce their IRMAA—and save hundreds each month on premiums.
Plan Smart, Prepare for Surprises
Social Security can be a crucial part of your retirement income. It’s not just about “when” you file—it’s about “how” you plan around it. Whether it's making sure you're eligible for your first check, avoiding tax pitfalls, or preparing for Medicare surprises, proactive planning may give you more options to address situations as they arise.
Don’t forget to leave a rating for the “Retirement Revealed” podcast if you’ve been enjoying these episodes!
Subscribe to Retirement Revealed to get new episodes every Wednesday.
Apple Podcasts: https://podcasts.apple.com/us/podcast/retirement-revealed/id1488769337
Spotify Podcasts: https://bit.ly/RetirementRevealedSpotify
Additional Links:
Heather Schreiber, HLS Retirement Consulting
Extra Medicare Cost IRMAA Appeal form SSA-44
Social Security Withholding form W-4V
Supercharge your Social Security Benefit with These 5 Tips - Mr. Retirement YouTube Channel
How Social Security Affects Your Retirement Taxes - Mr. Retirement YouTube Channel
When is the Right Time to File for Social Security? - Mr. Retirement YouTube Channel
How to Use the Social Security Quick Calculator (and Why It Matters If You Retire Early!) - Mr. Retirement YouTube Channel
Social Security Earnings Limit 2025 - Mr. Retirement YouTube Channel
Average vs. Maximum Social Security – Where Do You Stand? - Mr. Retirement YouTube Channel
Social Security and Work: How Much Can You Make in 2025? - Mr. Retirement YouTube Channel
WHEN Will You Get Your Social Security Benefits Each Month? - Mr. Retirement YouTube Channel
Connect With Jeremy Keil:
Keil Financial Partners
LinkedIn: Jeremy Keil
Facebook: Jeremy Keil
LinkedIn: Keil Financial Partners
YouTube: Retirement Revealed
Book an Intro Call with Jeremy’s Team
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Disclosures
Videos/Podcasts/Blogs (media) published prior to June 30, 2025, were recorded and approved while the advisor was affiliated with Thrivent Advisor Network. These media reflect the advisor’s views and interpretations at that time. The information and disclosures contained in those media were believed to be accurate and complete as of the date of recording, but may not reflect current market conditions or Alongside, LLC, policies.
All content is provided for educational purposes only and does not constitute personalized investment advice. Read below for current disclosures and potential conflicts of interest.
This media is provided for informational and educational purposes only and does not consider the investment objectives, financial situation, or particular needs of any consumer. Nothing in this program should be construed as investment, legal, or tax advice, nor as a recommendation to buy, sell, or hold any security or to adopt any investment strategy.
The views and opinions expressed are those of the host and any guest, current as of the date of recording, and may change without notice as market, political or economic conditions evolve. All investments involve risk, including the possible loss of principal. Past Performance is no guarantee of future results.
Legal & Tax Disclosure
Consumers should consult their own qualified attorney, CPA, or other professional advisor regarding their specific legal and tax situations.
Advisor Disclosures
Alongside, LLC, doing business as Keil Financial Partners, is an SEC-registered investment adviser. Registration does not imply a certain level of skill or expertise. Advisory services are delivered through the Alongside, LLC platform. Keil Financial Partners is independent, not owned or operated by Alongside, LLC.
Additional information about Alongside, LLC – including its services, fees and any material conflicts of interest – can be found at https://adviserinfo.sec.gov/firm/summary/333587 or by requesting Form ADV Part 2A.
The content of this media should not be reproduced or redistributed without the firm’s written consent. Any trademarks or service marks mentioned belong to their respective owners and are used for identification purposes only.
For important disclosures visit: https://keilfp.com/disclosures/
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15 min
July 09, 2025 The Hidden 401(k) Costs You’ve Never Heard Of – And What To Do About Them with Paul Sippil
Forensic consultant Paul Sippil explains little-known costs for business owners and plan participants and what you can do about them.
34 min
July 02, 2025 How Can You Protect Your Retirement from Market Volatility Right Now?
Jeremy Keil explores Barron’s 5 strategies to respond to market volatility with your retirement portfolio.
Are you feeling nervous about what today’s market volatility could mean for your retirement? You’re not alone. A recent Barron’s article titled “Market Anxiety Is Running High. How to Secure Your Retirement Portfolio” caught my attention—not just for the headline, but because it echoes what I hear from so many of you. Retirement can already feel uncertain, and when the stock market adds another layer of unpredictability, it’s natural to start asking: “What should I be doing with my investments?”
Let’s explore five strategies—based on that Barron’s article and my own experience as a retirement-focused financial planner—that you can use to help protect your retirement income from the ups and downs of the market.
1. Be Realistic About Market Returns
The last decade has seen significant growth for the stock market. From 2009 to 2024, returns were some of the strongest in history. But expecting this trend to continue indefinitely could lead to disappointment.
In fact, projections from Morningstar suggest that U.S. equities could return just 3.4% to 6.7% annually over the next decade. Compare that to the roughly 20% growth we saw in 2023 and 2024, and it's a sobering reality check.
Being realistic doesn’t mean avoiding stocks altogether—it means adjusting your expectations and preparing for a range of outcomes.
2. Get Your Asset Mix Right (Based on When You Need the Money)
While it may be tempting to invest based on how the market is performing at the moment, Barron’s suggests that your personal needs with your investment should be high on the list of drivers in your investment strategy.
Your short-term money (needed within 1–3 years) could be in short-term, stable investments. Long-term money (needed 10+ years out) could go toward growth-oriented investments like stocks. Too often, I see people keeping everything in the market when they’re just a year away from retirement, hoping for “one more good year.” And sometimes it backfires—just like it did in early 2020 when COVID hit, and the market took a steep dive.
Plan ahead. By adjusting your retirement investments 3 three years before your retirement date, you could have more of a buffer, just in case you retire earlier than expected.
3. Diversify and Rebalance
It’s tempting to stick only with what’s worked recently—especially U.S. stocks, which have produced strong returns since 2009. But diversification means having exposure to different areas of the market, including international stocks. And while international stocks have lagged in recent years, 2025 has shown a surprising shift: as of early June, international indexes are up nearly 19%—ahead of the S&P 500's 2% gain.
You never know when one part of your portfolio will outperform. That’s why it’s important not just to diversify, but also to rebalance—systematically adjusting your investment strategy to maintain your target allocation.
4. Maintain a “Goldilocks” Level of Cash
Cash can earn some decent interest—around 4% as of 2025. That doesn’t necessarily mean you should pile all your money into savings, but it does mean you have the option to keep a portion of your retirement funds in cash or high-quality bonds for short-term needs.
How much cash is enough? Many financial advisors recommend keeping 1 to 5 years’ worth of withdrawals in cash or short-term investments. The right number for you depends on your retirement timeline, expenses, and risk tolerance.
5. Bolster Other Sources of Income
One of the most underappreciated strategies for navigating market volatility is increasing your guaranteed income. That could include:
Delaying Social Security to maximize your benefit
Maximizing your pension payout, if available
Exploring annuities to create additional income streams
I know the word “annuity” often brings up mixed feelings. But the reality is, with stock prices high and bond yields strong, there could be an opportunity to convert some of your portfolio into income—if that fits your retirement plan.
And remember: it’s not about finding the one perfect solution. It’s about combining different tools—stocks, bonds, cash, annuities—into a balanced, well-designed retirement portfolio.
Market anxiety is real. But it doesn’t have to derail your retirement. If you understand when you need your money, build a diversified and flexible plan, and bolster your guaranteed income, the volatility that comes with investing may feel less overwhelming.
Don’t forget to leave a rating for the “Retirement Revealed” podcast if you’ve been enjoying these episodes!
Subscribe to Retirement Revealed to get new episodes every Wednesday.
Apple Podcasts: https://podcasts.apple.com/us/podcast/retirement-revealed/id1488769337
Spotify Podcasts: https://bit.ly/RetirementRevealedSpotify
Additional Links:
“Experts Forecast Stock and Bond Returns: 2025 Edition” - Morningstar.com
“Market Anxiety is Running High. How to Secure Your Retirement Portfolio.” - Barron’s
What Can I Do When the Market Goes Down? 3 Investment Options - Mr. Retirement on YouTube
Ideas to Build Your Cash Position in a Down Market - Mr. Retirement on YouTube
If the Stock Market Crashes While I'm Retired, What do I do? - Mr. Retirement on YouTube
Connect With Jeremy Keil:
Keil Financial Partners
LinkedIn: Jeremy Keil
Facebook: Jeremy Keil
LinkedIn: Keil Financial Partners
YouTube: Retirement Revealed
Book an Intro Call with Jeremy’s Team
===
Disclosures
Videos/Podcasts/Blogs (media) published prior to June 30, 2025, were recorded and approved while the advisor was affiliated with Thrivent Advisor Network. These media reflect the advisor’s views and interpretations at that time. The information and disclosures contained in those media were believed to be accurate and complete as of the date of recording, but may not reflect current market conditions or Alongside, LLC, policies.
All content is provided for educational purposes only and does not constitute personalized investment advice. Read below for current disclosures and potential conflicts of interest.
This media is provided for informational and educational purposes only and does not consider the investment objectives, financial situation, or particular needs of any consumer. Nothing in this program should be construed as investment, legal, or tax advice, nor as a recommendation to buy, sell, or hold any security or to adopt any investment strategy.
The views and opinions expressed are those of the host and any guest, current as of the date of recording, and may change without notice as market, political or economic conditions evolve. All investments involve risk, including the possible loss of principal. Past Performance is no guarantee of future results.
Legal & Tax Disclosure
Consumers should consult their own qualified attorney, CPA, or other professional advisor regarding their specific legal and tax situations.
Advisor Disclosures
Alongside, LLC, doing business as Keil Financial Partners, is an SEC-registered investment adviser. Registration does not imply a certain level of skill or expertise. Advisory services are delivered through the Alongside, LLC platform. Keil Financial Partners is independent, not owned or operated by Alongside, LLC.
Additional information about Alongside, LLC – including its services, fees and any material conflicts of interest – can be found at https://adviserinfo.sec.gov/firm/summary/333587 or by requesting Form ADV Part 2A.
The content of this media should not be reproduced or redistributed without the firm’s written consent. Any trademarks or service marks mentioned belong to their respective owners and are used for identification purposes only.
For important disclosures visit: https://keilfp.com/disclosures/
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19 min
June 18, 2025 Health Savings Account (HSA) Tax Breaks Incoming?
Exploring “The One, Big, Beautiful Bill” and its proposed changes to HSAs.
18 min
June 04, 2025 Age 60 is a New Beginning, not an Ending | Allison McCune Davis
Author Allison McCune Davis shares her insights on why turning 60 can be a powerful new beginning.
32 min
May 28, 2025 Are You Headed for Retirement Heaven or Hell? with Mike Drak
Retirement author Mike Drak shares his story of emerging from the hardships of retirement to finding his own satisfaction.
34 min

About Retire Today

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In the Retire Today podcast, Jeremy Keil, CFP®, CFA® shows you how to turn your retirement savings into retirement income. Listen in as Jeremy and his guests guide you towards making smarter…