Best Retirement Podcasts (2025)

1
Social Security Benefits, IRMAA, and QCD Timing: Q&A #2517 1:05:39

1h ago1:05:39

1:05:39

Jim and Chris discuss listener questions relating to Social Security spousal benefits, IRMAA relief, suspending Social Security for tax planning, and QCD timing with RMDs. (3:00) A listener enquires whether her 85-year-old mother, who recently remarried, must remain on her ex-spouse’s record for one year before switching to spousal benefits on her …

1
496: Claiming Social Security Early: Is it the Right Strategy for You? 22:46

24m ago22:46

22:46

Conventional financial wisdom encourages you to delay collecting Social Security benefits until age 70, but in certain cases, your “optimal” claiming age might actually be to pull benefits early. In this episode, we discuss: Factors that benefit filing early Your “breakeven” number of filing early vs. later How your rate of return should factor int…

1
403(b)/457(b) Basics: Asset Allocation 35:51

5h ago35:51

35:51

In episode two of our new pod series: 403(b) & 457(b) Basics Scott and Dan look at asset allocation. They describe what it is, why it's important and they go over several strategies for allocating a 403(b) and a 457(b). Importance of Asset Allocation by Barb O'Neill The Price of Peace: Why diversification is difficult, but necessary by Nick Maggiul…

1
453 The Barbell Strategy: How to Be a Pessimist and Optimist at the Same Time 15:31

1h ago15:31

15:31

In today’s episode, I’m sharing a time-tested strategy that can boost your confidence when it comes to withdrawing money in retirement—the barbell strategy. Also known as the two-bucket approach, this method is designed to help you navigate market volatility while staying focused on long-term growth. I'll walk you through the who, what, when, where…

1
4 Warning Signs That You Might Be Receiving Bad Financial Advice 47:06

7h ago47:06

47:06

Folks reach out to Keen Wealth for all sorts of reasons, at all different points in their lives. We talk to young couples just starting out who want to put themselves on a path towards financial security. New retirees want to feel secure about transitioning away from work. Older seniors come to us looking to secure their legacies and make life a li…

1
Transition Period Strategy and Positioning: EDU #2517 1:18:00

3d ago1:18:00

1:18:00

Chris’s Summary: Jim and I are again joined by Jacob as we continue exploring transition period strategy—the years just before retirement when you’re not yet withdrawing but want to prepare. We cover how near-retirees can manage emotional reactions to volatility while positioning assets to support early retirement spending. For those using our Mini…

1
When Does Sequence of Return Risk Go Away? 16:24

2d ago16:24

16:24

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 ret…

1
930 Risk It 1868:34:25

3d ago1868:34:25

1868:34:25 icon

Retirement itself involves a degree of risk. We don't know if we will be happy or not. We don't know if we will have enough income to live comfortably. We don't know if we will have enough income to last until our death since we never know how much time we have yet to live.By Del Lowery

1
How to Handle Stock Market Downturns, Ep #258 20:05

4d ago20:05

20:05

Do downturns in the stock market inevitably lead to down years? On the show this month, I’m walking you through an analysis of U.S. market trends over the past two decades, illustrating how downturns, even severe ones, often don't spell disaster for annual returns. I’ll also share what savvy family stewards can do to weather these turbulent times a…

1
Tax Planning, Minus-One Method, Inherited Roth RMDs, and Early Social Security: Q&A #2516 1:37:30

4d ago1:37:30

1:37:30

Jim and Chris discuss listener questions relating to tax planning at full retirement age, the minus-one method for RMDs, inherited Roth RMDs, and early Social Security. (9:10) A listener jokes about the state trivia and offers a suggestion for Chris’s benefit. (11:10) Another listener shares a PSA about delays in online Social Security applications…

1
495: Freedom After 50: The World is Ending… What’s Next? 34:58

5d ago34:58

34:58

If you saw the amount of time you had left to live—whether it was one day or one year—how would you spend it? What would you worry about? In this episode, we discuss: How to let go of always trying to control your narrative Why the pursuit of contentment is greater than the pursuit of happiness 5 questions to help you find pure contentment in the p…

1
Spring Cleaning Your Personal Finances (#370) 34:22

5d ago34:22

34:22

Barbara O’Neill, PhD, CFP, AFC, owner/CEO of Money Talk: Financial Planning Seminars and Publications, and a monthly columnist for 403bwise talks spring cleaning your personal finances. Spring cleaning is more than deep cleaning and decluttering. It is a great time to neaten up your finances. Spring Cleaning Your 403(b) and Personal Finances The Tr…

1
Making Sense of Social Security 1:04:48

6d ago1:04:48

1:04:48

In this episode of Boldin Your Money, host Steve Chen sits down with financial advisor and YouTube creator Devin Carroll, the mind behind Social Security Intelligence and the book Social Security Basics. Devin shares his journey from tire salesman to financial planner, and how a curiosity about Social Security turned into a mission—and a media plat…

1
Women’s Month Special - Money, Mindfulness & Mastery 51:43

9d ago51:43

51:43

In this episode of Boldin Your Money, host Steve Chen welcomes Leisa Peterson, a financial coach, author of The Mindful Millionaire, and advocate for financial mindfulness. Leisa shares her personal journey from growing up in a financially unstable household to becoming a successful financial expert, entrepreneur, and coach. She discusses the impac…

1
Asset Positioning in the Transition Period: EDU #2516 1:24:55

7d ago1:24:55

1:24:55

Chris’s Summary: Jim and I are joined by Jake and Jacob to discuss listener emails related to asset positioning for retirement and the transition period leading up to it. We break down how we think about asset allocation across account types, what a liquidity account is and why we use it, and how we handle year-end tax planning. It’s all part of ho…

1
494: Beyond the Headlines: How Retirees Can Navigate Investment Risks with Larry Swedroe 1:08:36

9d ago1:08:36

1:08:36

Today, I’m speaking with Larry Swedroe. Larry is the former Chief Research Officer at Buckingham Strategic Wealth, an accomplished author with 18+ books on investing, and a true pioneer in evidence-based investing. He’s also a well-known advocate for cutting through the financial media noise to focus on strategies that actually work. In Larry’s lat…

1
What We’ve Learned From 150 Years of Stock Market Crashes 18:44

9d ago18:44

18:44

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 art…

1
929 Murder Trial 8:25

10d ago8:25

8:25

Retirement allows us time to expand our horizons. New experiences may be closer than we think. You might want to check out your local courthouse and find out what trials are scheduled to start soon. Here is the story of our experience.By Del Lowery

1
Social Security, RMD age, Tax Planning, and Inherited Roth IRAs: Q&A #2515 1:13:29

11d ago1:13:29

1:13:29

Jim and Chris discuss listener questions relating to Social Security, origins of the RMD age, the tax planning window, and RMDs from Inherited Roth IRAs. (11:00) Georgette asks how to qualify for child-in-care survivor benefits if her ex-husband, who has been missing for seven years, is legally declared deceased. (23:00) A listener wonders when to …

1
493: Chaotic Markets: A 4-Point Checklist to Safeguard Your Retirement Savings 27:45

12d ago27:45

27:45

Are you feeling uneasy right now? If market turmoil is causing you stress, it’s time to determine if your retirement plan is truly built for the unexpected. In this episode, we discuss: How a process can give you greater investment and financial control How to assess your liquid/safe reserves Tax and inflation protection opportunities brought by ma…

1
Father & Daughter Educators: Partners in 403(b) Advocacy (#369) 48:12

12d ago48:12

48:12

Nicole and Larry Dubill, two Buffalo, NY area educators, share passion for education, music, and 403(b) advocacy. Cleveland Hill School District 403(b/457(b) Vendor List Hamburg Central School District 403(b)/457(b) Vendor List The Truth About So-Called "No Fee" Products Meridian Wealth Management 403bwise.org Nothing presented or discussed is to b…

1
How Tariffs Actually Work (And Why They're Shaking the Market) 58:08

13d ago58:08

58:08

Today I'm diving into the tariff-induced market mania that has been dominating every news headline. Specifically, I'm joined by Cullen Roche, monetary economics expert and founder of Discipline Funds, to discuss three important things: ► How tariffs actually work and why economists across the political spectrum overwhelmingly agree they are bad ► W…

1
Tariffs, Markets & The Macro Story 51:58

17d ago51:58

51:58

In this episode of Boldin Your Money, host Steve Chen and guest Mike Himmelfarb unpack the newly announced "Liberation Day" tariffs and their sweeping impact on global markets, economic strategy, and personal finance. Recorded just days after a sharp market correction, the discussion blends macroeconomic insight with practical, real-world investing…

1
Should Tariffs and Market Volatility Change Your Retirement Timeline? 38:50

14d ago38:50

38:50

"Jim" (66) and "Karen" (64) both retired in the last six months. Jim has an IRA with $900,000, and Karen has a Roth IRA with $300,000. They inherited a brokerage account with $600,000 and a cost basis of $500,000. They have $100,000 in an emergency cash fund. Jim is receiving his Social Security benefits of $2,600 per month. He also has a pension o…

1
Defining Unicorn Status in Retirement: EDU #2515 1:12:15

14d ago1:12:15

1:12:15

Chris’s Summary: Jim and I are joined again by Jacob as we discuss listener emails about “unicorn” status—our term for retirees whose Minimum Dignity Floor and Fun Number are both covered by secure income. We clarify what qualifies as secure income and explore whether a very low withdrawal rate from a conservative portfolio might serve as a substit…

1
How To Protect Your 401(k) from a Stock Market Crash 23:35

16d ago23:35

23:35

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 ag…

1
928 Road Trip: The Vehicle 8:39

17d ago8:39

8:39

We wanted a rig that was relatively safe. We wanted airbags and all of that other fancy stuff. And as well as safety we wanted a bit of comfort. When one decides to take a road trip that could last a few months, comfort becomes important.By Del Lowery

1
Social Security, Roth Conversion Tax Strategy, and Identity Theft PSA: Q&A #2514 1:43:11

18d ago1:43:11

1:43:11

This week’s is a bit of a non-traditional Q&A episode where Jim and Chris address two listener questions on Social Security but then move into Public Service Announcement mode. For the first PSA they discuss a listener email about a potential state-level Roth conversion tax saving strategy. Then, to wrap up the episode, Jim shares a continuation of…

1
452 Buckle Up: Navigating Market Volatility 13:08

18d ago13:08

13:08

If you're feeling stressed about what's happening in the market right now—you're not alone. Market volatility never feels good, but there is a better way to invest: one grounded in planning, discipline, and long-term thinking. In today’s episode, I’ll share 8 important things to consider as you navigate this market, so you can make confident decisi…

1
492: 3 Levels of Retirement Readiness: Where Do You Stand? 23:07

21d ago23:07

23:07

How would you rate yourself on the retirement readiness scale? When you understand where you are and how to proceed, you are more likely to feel elevated confidence to and throughout retirement. In this episode, we discuss: Financial vs. non-financial retirement readiness Why your income strategy is key Considerations for long term care insurance H…

1
Equitable Threatens Educator (#368) 33:05

19d ago33:05

33:05

Teacher who sought to educate colleagues about the 403(b) gets threatening email from Equitable. We read and discuss correspondence. Read the letter The Truth about Structured Investing Options (SIOs) Meridian Wealth Management 403bwise.org Nothing presented or discussed is to be construed as investment or tax advice. This can be secured from a vet…

1
Weathering Market Downturns: EDU #2514 1:05:05

21d ago1:05:05

1:05:05

Chris’s Description Jim and I talk about how market downturns—like the one we’re seeing now—can cause people to second-guess their plans, even when they’re well prepared. We walk through how our Secure Retirement Income Process is designed to provide structure and clarity during volatile times, and explain how proper positioning can help you mainta…

1
Sneaky Retirement Taxes (The Tax Traps You Never Saw Coming), Ep #394 19:51

23d ago19:51

19:51

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. …

1
927 Road Trip USA 8:17

24d ago8:17

8:17

Deciding to see America from the road is an easy choice to make when one enters retirement. It’s a big country and to drive around it takes a lot of time; time that most folks don’t have until they retire.By Del Lowery

1
Identity Theft, Spousal Benefits, RMD Taxes, IRA Withdrawals, and 401(k) Contribution Limits: Q&A #2513 1:16:40

25d ago1:16:40

1:16:40

Jim and Chris discuss listener questions relating to spousal Social Security benefits, RMD tax withholding, IRA withdrawals, and 401(k) contribution limits. Jim also shares a PSA about a recent attempt at identity theft. (20:15) Jim shares a PSA about a fraudulent payday loan application attempted in his name and what he learned about credit freeze…

1
491: Freedom After 50: 8 Reasons the Month You Retire Matters 32:28

26d ago32:28

32:28

Before you make your transition into retirement, it’s important to dial in the ideal timing not just for your money, but your mind. In this episode, we discuss: Irrational reasons to not retire The “3 Cs” of retirement timing Family, health, and social considerations in retirement Listen in as Casey Weade is once again joined by Les McDaniel to exp…

1
Captain America of Consumer Protection (#367) 46:45

26d ago46:45

46:45

Erin Witte, Director of Consumer Protection for the Consumer Federation of America, discusses the work she does protecting consumers in the face of a very anti-consumer climate. Erin Witte Meridian Wealth Management 403bwise.org Nothing presented or discussed is to be construed as investment or tax advice. This can be secured from a vetted Certifie…

1
451 The Risk You're Not Getting Paid For 10:46

26d ago10:46

10:46

I recently came across a fascinating paper by Hendrik Bessembinder titled “Which U.S. Stocks Generated the Highest Long-Term Returns?” The research is based on nearly 100 years of stock market history, and it delivers some surprising and important lessons for retirees.By Jason Parker

1
Could Tariff Turbulence Create Opportunities for Your Financial Plan? 46:27

28d ago46:27

46:27

Tariffs are nothing new. They've been implemented at several points in U.S. history, including as recently as 2018. But there are a confluence of factors surrounding President Trump's current round of tariffs that make it worth discussing. On today's show, we round up questions we've been receiving at Keen Wealth about tariffs to provide a comprehe…

1
Roth 5-Year Rules and the Tax Planning Window: EDU #2513 1:16:49

28d ago1:16:49

1:16:49

Chris’s Summary Jim and I continue our review of interesting and sometimes confusing retirement planning facts, mostly drawn from Jim’s recent Ed Slott conference. We focus on the two Roth five-year rules and how they apply to Roth IRAs versus Roth 401(k)s. I explain the key distinctions between tax-free earnings and penalty-free access. Jim goes f…

1
Fiduciary Duty Meets Stewardship: Aligning Compliance with Care 58:55

29d ago58:55

58:55

In this episode of 401(k) Roundtable, Rick Unser is joined by Todd Solomon, ERISA Attorney and partner at McDermott Will, & Emery Law Firm, for a timely conversation on the evolving fiduciary landscape. They explore trends in ERISA litigation, the impact of the current administration on the Department of Labor, and the shifting expectations around …

1
Five Key Retirement Challenges (and Solutions), Ep #393 18:46

1M ago18:46

18:46

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…

1
926 More Questions Than Answers 7:17

1M ago7:17

7:17

"Why" has to be among the first words we learn. Little children have a way of repeating it over and over until we just wind up saying, "It just is. I don't know why.” It is strange how this simple exchange seems to hold over the years.By Del Lowery

1
Social Security Benefits, Roth Conversions, and Annuities: Q&A #2512 1:15:07

1M ago1:15:07

1:15:07

Jim and Chris discuss listener questions relating to Social Security strategies, spousal benefits, Roth conversions, and annuities. (8:15) George asks whether a widow who was widowed before age 60 has two Social Security claiming strategies available based on the FRA benefit of each spouse. (20:30) The guys address a question about how spousal bene…

1
490: Retirement Withdrawal Strategies in Down Markets: Should You Shift Yours? 27:11

1M ago27:11

27:11

Market volatility is inevitable. Whether you’re 10 months or 10 years into retirement, it’s vital to ask: is your investment strategy prepared? In this episode, we discuss: Why market volatility is necessary When down markets no longer become an opportunity How to avoid sequence of returns risk 4% withdrawal rule flaws Today's articles are from The…

1
Inside the NTSA Summit Conference (#366) 46:21

1M ago46:21

46:21

Anonymous attendees dish on remarks made at a recent conference by leaders of lobbying group working to keep broken multi-vendor, sales agent-driven K-12 403(b) market in place. Audio + Transcript of Brian Graff LAUSD Appearance Video of Brian Graff LAUSD Appearance NTSA Puts the Tax in the K-12 403(b) Vanguard Meridian Wealth Management 403bwise.o…

1
450 Margins Of Safety 20:00

1M ago20:00

20:00

When markets get wobbly, people panic. It’s natural. We’ve all seen it—headlines screaming recession, market crashes, and doomsday predictions. The fear can be overwhelming. But what if I told you that you could structure your retirement investments in a way that makes all of this noise irrelevant? That’s what today’s episode is about—building Marg…

1
ESG Investing: The Hidden Costs, Real Impact, and How to Avoid the Hype 35:35

1M ago35:35

35:35

ESG investing is exploding in popularity—but it's also a giant, confusing mess. Over $35 trillion in global assets now follow ESG guidelines. 🤯 But despite the rapid growth, most retirement investors still don't fully understand ESG investing... ...or how to spot legitimate ESG strategies from clever marketing hype. To help break through the confus…

1
Things That Make You Go Hmm – RMD Rules, IRA Mistakes, and Tax Court Surprises: EDU #2512 1:09:21

1M ago1:09:21

1:09:21

Chris’s Summary: This week’s EDU show is a throwback to an old favorite—things that make you go “hmm.” Jim brought back a list of oddities from the latest Ed Slott training, covering everything from RMD rules the IRS only recently addressed to real-world court cases involving bankruptcy, lottery tickets, and IRA self-dealing gone wrong. Turns out, …

1
Top 3 Retirement Mistakes - An Interview with Mr Retirement, Ep #392 21:50

1M ago21:50

21:50

Click here to work with us! 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 fi…

Podcasts Worth a Listen

Retirement Podcasts

Podcasts Worth a Listen