Best Socialsecurity Podcasts (2025)

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088: The Importance of Retirement Planning for Women and Widows with Alina Osokhovska, CFP® 23:03

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8h ago23:03

23:03

Losing a spouse is one of life’s most painful experiences, and in the midst of grief, surviving partners are often faced with overwhelming financial decisions. From settling estates to adjusting to changes in income, the process can feel like an impossible burden to carry alone. Without a plan in place, surviving spouses may find themselves vulnera…

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Is Financial Software Giving You False Retirement Confidence? - 548 47:56

22h ago47:56

47:56

Wendy and Joe in Colorado ran the numbers, and their financial planning software says they'll have over $10 million when they pass. Wendy's wondering if they should continue converting to Roth while working, despite their high tax bracket. But has the software lulled them into a false sense of security? That’s today on Your Money, Your Wealth® podc…

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Why So Many Americans Are Claiming Social Security Early in 2025 24:48

2d ago24:48

24:48

So far in 2025, early Social Security filings have jumped dramatically compared to last year. Nearly half of those filing early say they’re doing so because they’re worried about cuts. But will filing early really help? In this episode, we talk about what the data shows, what most people get wrong about Social Security cuts, and how to think about …

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Roth Conversions: When to Make 'Em, When to Take 'Em - 547 43:20

8d ago43:20

43:20

A YMYW listener from Missouri and his wife are retired at 69 and 67, with less than $2 million dollars. Should they continue converting retirement savings to Roth for the tax-free growth? What should they do about long term care insurance? More importantly, is our listener’s name (Cousy) pronounced "Cuzzy" or "Koozy"? Speaking of Roth conversions, …

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087: How Death Doulas Help Families Navigate End-of-Life with Love & Compassion with Aimee Yawnick 38:35

14d ago38:35

38:35

Death is one of life’s certainties, yet it remains one of the hardest subjects to talk about. Many families avoid end-of-life conversations out of fear, discomfort, or superstition. Unfortunately, this avoidance can lead to increased stress, resentment, and regret when the time comes to make critical decisions. So how do we make the process smoothe…

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How to Accomplish Your Retirement Goals - Even Without a Fat Wallet - 546 51:07

15d ago51:07

51:07

We heard your feedback, and today on Your Money, Your Wealth® podcast number 546, Joe Anderson, CFP® and Big Al Clopine, CPA are spitballing retirement for the not-so-fat wallets: Joe and Masako in Washington state and Reid in Indiana have less than a million saved. Can they still accomplish their retirement goals in their 60s? Mr Buckeye in Ohio a…

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What The New Law Means For Your Roth IRA! - 545 38:04

22d ago38:04

38:04

One Big Beautiful Bill is now law. How does it impact your Roth conversion strategies and other financial decisions? Plus, you may have seen or heard other advisors talking about their strategies for getting your retirement savings into tax-free Roth accounts. How are these different from a good ol’ Roth conversion, and what do Joe and Big Al think…

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Three Priorities That Should Shape Your Social Security Decision 25:58

23d ago25:58

25:58

When should you claim Social Security? For high-net-worth retirees, this is not a simple decision. In this episode, we explain why Social Security is not just a monthly check but a strategic part of a well-built retirement plan. Devin begins by challenging the common belief that wealthy retirees do not need to think about Social Security. In realit…

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What's the Tax Triangle and How to Find Out if Yours is Lopsided - 544 28:35

29d ago28:35

28:35

You’ve heard Joe and Big Al talk about the benefits of tax diversification in retirement. That is, having money in tax-deferred, tax-free, and taxable accounts. But what should you do if this tax triangle of yours is lopsided? Joe and our special guest co-host, Marc Horner, CFP®, spitball on this quandary for Rae and Roy in Central California, toda…

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What Millionaire Retirees Fear Most (But Rarely Talk About) 41:22

1M ago41:22

41:22

For many affluent retirees, the biggest financial fear isn’t market volatility or rising taxes. It’s this simple question: What happens if I’m not the one here to manage the plan? In this episode, we talk about a deeply personal concern shared by countless couples. When one spouse manages the investment strategy, the tax planning, and the long-term…

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086: Career Insights for New Grads Aspiring to Become Financial Advisors with Raphael Hanna 31:18

1M ago31:18

31:18

Graduation marks an exciting new chapter for young professionals, but for those eyeing a career in financial planning, the path forward can feel uncertain. What are the skills that investment firms are looking for? Which licenses and designations matter most? And how do you land that first opportunity in a highly competitive field? Today, Matthew P…

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Can You Retire at Age 57 and Spend Big? - 543 38:58

1M ago38:58

38:58

Is it possible, common even, to spend a lot early in retirement to celebrate your financial freedom? How do Roth conversions and withdrawals work if you do plan to call it quits around age 57, and spend big early on? Should you convert retirement funds to tax-free Roth after you stop working? Joe Anderson CFP® and our special guest co-host, Marc Ho…

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Private Equity Meets Your 401(k) 24:07

1M ago24:07

24:07

Should everyday investors be allowed to hold private equity, venture capital, or even crypto in their 401(k)s? A new executive order suggests it might soon be possible. In this episode, we walk through the real implications of this move, especially for retirement savers who may not be equipped to handle the risks. We start with a quick quiz that hi…

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Are You Cutting Retirement Too Close? - 542 35:49

1M ago35:49

35:49

"Rubble and Skye" in Minnesota want to spend $65,000 a year in retirement, and they’ll have $67K in annual fixed income. Are they cutting it too close? "Atouk and Tala" in New Jersey will have retirement money, Social Security, and “Lumpy,” their lump sum pension - will they be okay? We’ll find out today on Your Money, Your Wealth® podcast number 5…

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085: How Donor-Advised Funds Simplifies Charitable Giving And Maximizes Tax Benefits with Kyle Casserino 43:15

2M ago43:15

43:15

Many retirees want to give back—but aren’t sure how to do it in a way that’s financially savvy and tax-efficient. If you’ve ever wondered how to streamline your charitable giving, take advantage of smart tax strategies, or leave a lasting legacy without the administrative burden, we have the perfect guest to help with those important decisions. Tod…

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Are These Millennials Saving Enough to Retire Before 60? - 541 49:29

2M ago49:29

49:29

Pam and Jim in Phoenix are 38 and 41 and want to retire at 59 and 62. Matt and his wife in Pennsylvania are both 39 and want to retire at 57. Are these millennials on the right financial path, or have they brunched and YOLO’d away their retirement dreams? That’s today on Your Money, Your Wealth® podcast number 541 with Joe Anderson, CFP® and Big Al…

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Smart Strategies to Retire Early and Spend More - 540 33:14

2M ago33:14

33:14

Can Beth and Rip retire early, spend more, and Die with Zero? When should they claim Social Security? Forrest and Jenny have 10 rental properties at age 31. Can they retire at age 50? (And what makes you a real estate professional from a tax perspective?) Plus, what are the rules for spousal IRA contributions and required minimum distributions? Mem…

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084: Examining the Big Beautiful Tax Bill & What it Means for Your Retirement with Alina Osokhovska 41:43

2M ago41:43

41:43

The "One Big Beautiful Bill Act" has just become law, bringing sweeping tax changes that will directly impact retirees and pre-retirees. From changes to itemized deductions and charitable giving to updates on Social Security taxation and estate planning, the impact is far-reaching. Today, Matthew Peck is joined by one of SHP Financial’s Certified F…

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Where to Invest for Pre-Retirement and a GO-GO Lifestyle? - 539 27:02

2M ago27:02

27:02

Roger in Canton, Ohio, is burnt out. Can he and his wife Jane pre-retire next year in their mid-50s with $2.8 million? Joe and Big Al spitball on whether they’ll still have enough money for their Go-Go years, Joe’s favorite, today on Your Money, Your Wealth® podcast number 539. Roger also has an employee stock purchase plan. For the best asset loca…

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5 Mistake Most Millionaire Retirees Make 31:05

2M ago31:05

31:05

You’ve done the hard work. You saved consistently, built a seven-figure portfolio, and are ready to enjoy retirement. But even millionaire retirees can make mistakes that put their plans at risk. In this episode, Devin shares the five most common retirement mistakes he sees among high-net-worth clients. These include missing long-term tax planning …

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How Much Money Do You Need to Retire in 2026? - 538 35:10

2M ago35:10

35:10

George and Weezy in the land of Lincoln will have deferred compensation and wonder if they can retire in mid-2026, or even earlier. Will they have enough? Should Jenn in Ohio move with work, take a break, or just retire? She asks Joe Anderson, CFP® and Big Al Clopine, CPA for a brutally honest spitball, today on Your Money, Your Wealth® podcast 538…

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Overview of the One, Big, Beautiful Bill 32:11

2M ago32:11

32:11

In this episode, we break down the newly signed One Big Beautiful Bill Act (OBBBA) and what it means for retirees. From the extension of the 2017 tax cuts to new rules around Roth conversions, Social Security taxation, and a brand-new "Senior Deduction"—there’s a lot packed into this legislation. We’ll walk you through the major provisions, highlig…

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Matt's Markets on the Move Q2: July 2025 36:05

2M ago36:05

36:05

Co-Founder, Matt Peck, CFP®, CIMA®, and Investment Analyst, Zach Perkins CFA®, team up to deliver the market update for Q2. Matt and Zach discuss what's currently going on in the markets — where we've been, where we're headed, and how tariffs and the “Big Beautiful Bill” may impact the economy. They'll also address key questions submitted by our cl…

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Asset Location, Investing Property Sale Proceeds, and Maxing Tax-Free Retirement - 537 36:08

3M ago36:08

36:08

You’ve got your tax-free Roth accounts and your tax-deferred retirement accounts. Should you invest the same way in each? Kevin in Denver wants to know. Jim and Pam in Orange County are eligible for combat zone tax exclusions (CZTE). How else can they maximize their tax-free retirement strategy? Susan Brandeis, CFP® spitballs with Big Al Clopine, C…

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Inbox Question | How Filing Early Impacts the Spousal Benefit 3:06

3M ago3:06

3:06

Today we answer a question from Ken, a recent retiree at 63, about how his Social Security claiming decision impacts his wife’s future spousal benefit. We break down how spousal benefits are calculated, whether the FRA (Full Retirement Age) amount is frozen when you claim early, and how COLA (Cost of Living Adjustments) factor into the equation. Al…

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083: Smart Tax Planning Strategies to Keep More of Your Retirement Income with Mike Guthrie 39:52

3M ago39:52

39:52

Most retirees are surprised to learn just how differently their income is taxed once they stop working. From Social Security to pensions, IRAs, dividends, and even rental income, retirement brings a complex new tax landscape that can catch even the most financially savvy off guard. This episode is here to help you stay ahead of the curve. Joining S…

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Social Security vs. Pension No More - 536 17:02

3M ago17:02

17:02

If your pension impacted your ability to collect Social Security benefits, 2025 is a very good year for you and your spouse. The Windfall Elimination Provision and the Government Pension Offset are no more, and you’re now eligible for your full Social Security benefits AND your pension! Today on a quick Your Money, Your Wealth® podcast number 536, …

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When Do Roth Conversions STOP Making Sense? - 535 26:43

3M ago26:43

26:43

Ryan in Texas is in the 32% tax bracket. Where should he save for retirement so he’ll be in a lower bracket? Should Weronika in Texas pay the taxes now to convert to Roth for lifetime tax-free growth in the future, even though she’s in the 37% tax bracket? And Jerry in Phoenix wonders if there is a point where Joe would come to the conclusion that …

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Why Taxes In Retirement Get More Complicated 34:17

3M ago34:17

34:17

Most retirees think tax planning ends with knowing their tax bracket, but that’s just the beginning. In this episode, we unpack how different income sources interact in retirement, and how seemingly smart decisions can trigger hidden taxes, Medicare surcharges, and other costly surprises. Learn how to avoid the traps and make your retirement income…

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Inbox Question | The Good Life Abroad: Would We Go? 7:15

3M ago7:15

7:15

Today we answer a question from Chris about The Good Life Abroad and whether we plan to take a trip with the company. We share our thoughts on the concept, what interests us about their offerings, and whether a future review might be on the horizon. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin o…

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082: How SMAs Help Optimize Tax Efficiency In Your Portfolio with Cam Iarrobino 35:40

3M ago35:40

35:40

Perhaps you’ve heard of Separately Managed Accounts (SMAs) but aren’t quite sure how they work or if they’re only suitable for high-net-worth investors. In this episode, we’ll break down the truth behind SMAs and why more investors are turning to them as a way to gain control, improve tax efficiency, and tailor their portfolios to their unique fina…

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Roth Conversions vs. IRMAA, Using Retirement Funds to Pay the Mortgage, Retirement Spending Plan - 534 28:02

3M ago28:02

28:02

Ralph and Alice in Monument, Colorado have $4.6 million dollars saved at ages 63 and 58. Should they do Roth conversions? How do they avoid IRMAA? Mary Jo in Escondido, California wonders if she should use her 403(b) money to pay off her mortgage. And Lucas plans to spend from his brokerage, then his 401(k), then his Social Security and pension whe…

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Early Withdrawals, Tech Stocks vs. International, Annuities, ESOP and NUA - 533 33:46

4M ago33:46

33:46

Before she retires next month at age 52, Rowan in Georgia wonders how to maximize growth in her IRA, which will be funded with 72(t) early retirement withdrawals. What do Joe Anderson, CFP® and Big Al Clopine, CPA think of her substantially equal periodic payment plan? And how should she allocate it? Michael in Virginia isn’t interested in any inte…

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Inbox Question | How Much Umbrella Insurance Do You Need? 12:44

4M ago12:44

12:44

Today we answer a question from Sandi about how much umbrella insurance coverage you really need — especially as you approach retirement. We discuss why someone might choose a $2 million policy, how assets like home value, retirement accounts, and savings factor in, and share real-world examples to help you gauge whether you’re over- or underinsure…

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081: How the 2025 Social Security Reforms Will Impact Retirees with Chase Reardon 32:51

4M ago32:51

32:51

The most recent changes to Social Security have left many Americans with questions—and for good reason. A landmark bipartisan bill has repealed the Windfall Elimination Provision (WEP) and Government Pension Offset (GPO), placing more money into the pockets of retirees across the country. But what do these changes really mean for retirees? In this …

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"The Payoff is Huge": Jonathan Clements’ Final Initiative to Empower Lifelong Savers - 532 20:00

4M ago20:00

20:00

Imagine being told you only have 12 months to live. What would you do with your time? Today on Your Money, Your Wealth podcast number 532, Big Al Clopine, CPA and Executive Producer Andi Last are thrilled to welcome Jonathan Clements back for his fourth appearance. For thirty years, Jonathan has been known for his personal finance writing: in his c…

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Inbox Question | How the Small Estate Affidavit Process Works 13:08

4M ago13:08

13:08

Today we answer a question from Peter about what happens when a parent dies with a fully planned estate that avoids probate — and how the Small Estate Affidavit process works in practice. We discuss handling unexpected estate assets like refund checks, whether you can open an estate bank account without letters testamentary, and who’s responsible f…

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Tariffs Killed My Portfolio. Should I Claim Social Security Early? - 531 26:27

4M ago26:27

26:27

Tariffs killed Carl’s investment portfolio and left him wondering if he should claim Social Security early. Joe Anderson, CFP® and Big Al Clopine, CPA spitball for him today on Your Money, Your Wealth® podcast number 531. Kelly and Steve in Pennsylvania ask for a three-fer spitball - when to claim their Social Security, whether they should contribu…

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Listener Q&A: Trusts, IRMAA, Inheritance Taxes, Capital Gains, and More 41:10

4M ago41:10

41:10

In this special episode, we catch up on a backlog of insightful listener questions—covering everything from estate planning and Social Security taxation to Roth conversions and Medicare rules. If you’ve been wrestling with real-world retirement planning decisions, you’re not alone. Today’s episode delivers practical answers to the kinds of issues m…

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080: How Financial Plans Help Navigate Volatile Markets and Create Peace of Mind with Kyle Britton 28:46

4M ago28:46

28:46

In times like these, when there's market volatility and financial insecurity, it's more important than ever to have a financial plan to know that you can weather the storm and wild swings in the markets. It's the difference between having a plan vs just having a portfolio. In today's episode, Derek Gregoire is joined by SHP Financial's Lead Advisor…

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Portfolio Drift, Avoiding Capital Gains, and a $6M Retirement - 530 36:48

4M ago36:48

36:48

What should you do when the asset allocation of your retirement portfolio drifts? Joe Anderson, CFP® and Big Al Clopine, CPA spitball on rebalancing for DJ in St. Louis, today on Your Money, Your Wealth® podcast number 530. Plus, Coach Dobber in Minnesota is curious about municipal bonds in a brokerage account, and Daniel in Stevensville, Michigan …

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The 3 Parts to a Perfect Estate Plan – Part 3: Protecting the Beneficiaries’ Inheritance (Estate Planning Series Finale) 47:55

4M ago47:55

47:55

In the final installment of our 3-part estate planning series, we dive into one of the most overlooked—but critically important—aspects of planning: protecting your heirs’ inheritance. It’s not enough to simply leave assets to your loved ones. Without proper planning, those assets could be exposed to divorce, lawsuits, creditors, or mismanagement. …

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Inbox Question | Home Equity for Long Term Care 13:05

4M ago13:05

13:05

Today we answer Jeff’s question about using home equity to pay for end-of-life care — from tapping into equity for in-home support to selling the home to cover nursing home costs. In high-cost states like California, many seniors are house rich and cash poor, and this episode explores strategies to help families navigate that challenge. Although th…

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When to HOLD OFF on Doing Roth Conversions - 529 37:26

4M ago37:26

37:26

John in Boston is in the 32% tax bracket. Should he do Roth conversions? Flight Deck Dad and Irish Girl in Pensacola have a lot of tax-free pension income. Should they do Roth conversions? Bert and Ernie in New Jersey wonder if they should convert to Roth or take advantage of zero percent capital gains tax rates. Joe Anderson, CFP® and Big Al Clopi…

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The 3 Parts to a Perfect Estate Plan – Part 2c: Common Mistakes & Oversights 28:47

5M ago28:47

28:47

In this episode, we shine the light on common estate planning mistakes that can derail even the best intentions. We discuss the risks of failing to update beneficiary designations and why relying solely on joint ownership can create unexpected complications. Although this show does not provide specific tax, legal, or financial advice, you can engag…

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Inbox Question | Medicaid for Parents 12:05

5M ago12:05

12:05

Today we answer a question from Cathy about helping aging parents in California navigate care costs, preserve limited resources, and explore options like pro bono legal support. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 📍Contact Devin’s team at https://…

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079: How Practicing Gratitude Builds Deeper Connections and Relationships with John Israel 45:53

5M ago45:53

45:53

Many people nearing retirement focus on their portfolios but neglect one of the most important components of a fulfilling life—genuine human connection. Especially in today’s world, where negativity dominates the headlines and technology often replaces personal interactions, gratitude can help us build more meaningful relationships and improve our …

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Retirement Savings: When to Take Your Foot Off the Gas - 528 34:12

5M ago34:12

34:12

You’ve been jamming money into your retirement accounts for years now. When is it okay to slow down? Joe Anderson, CFP®® and Big Al Clopine, CPA spitball for Ron and Veronica in Indiana today on Your Money, Your Wealth® podcast 528. Plus, how can Scott in Illinois bridge the gap from age 55 to retirement income at 57? How should Big Juan in Texas p…

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The 3 Parts to a Perfect Estate Plan – Part 2b: Tax Considerations 38:58

5M ago38:58

38:58

In this episode, we cover key tax considerations around wealth transfer. We cover the differences between federal estate tax and state inheritance tax, and explain why the stepped-up basis is such a powerful tool for minimizing capital gains taxes for heirs. Although this show does not provide specific tax, legal, or financial advice, you can engag…

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Inbox Question | Company Stock in 401K 8:45

5M ago8:45

8:45

In this episode, Brian asks some great questions about using Net Unrealized Appreciation (NUA) for company stock inside a 401(k). We dive into the rules, timing, and strategies that could lead to major tax savings—if you do it right. We cover: What exactly is NUA and why it matters Can you use NUA before retirement? Do you need to be age 59½? Can y…