Joe and Big Al spitball two sides of the retirement equation, today on Your Money, Your Wealth® podcast number 570. Daniel in Texas is 40 and worrying about how to support Mom and Dad if their money runs out. Can he build some kind of financial safety net for them without ruining his own retirement? Jemma's 82-year-old mom is drawing down her portfolio. Is locking in guaranteed income with an annuity a smart move, or could that create new problems down the road? Plus, "Cookie and Gerry" want to walk away from work before 50 with a big brokerage account and a pension. Are they positioned correctly? How can they avoid pulling the wrong levers at the wrong time? And "Fred and Wilma" are staring at a potential multi-million-dollar ESOP payout. What levers do they need to pull so they can retire at 46 and shout "Yabba Dabba Doo"?

Free Financial Resources in This Episode:

https://bit.ly/ymyw-570 (full show notes & episode transcript)

10 Steps to Improve Investing Success - free download

What to Do When the Stock Market Gets Crazy - YMYW TV

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Chapters:

00:00 - Intro: This Week on the YMYW Podcast

00:57 - Can I Afford to Be My Parents' Retirement Plan? (Daniel, Texas)

07:07 - Will an Annuity Really Save Mom From Running Out of Money? (Jemma)

15:07 - Can We Retire in Our Early 50s With a Pension and a $190K Spend? (Cookie and Gerry)

30:39 - Can We Retire Early at 46 With a $4M ESOP and a $210K Spend? (Fred and Wilma, CA)

44:23 - Outro: Next Week on the YMYW Podcast

When you're standing at a major financial crossroads, the timing of your decisions can mean the difference between success and failure. Joe Anderson, CFP® and Big Al Clopine, CPA spitball on the "when" of five retirement decisions, today on Your Money, Your Wealth podcast number 569. We'll kick things off with a whale of an email: "Fine and Dandy" is 42 years old with a multimillion dollar private equity offer on the table. Should he sell his business now or hold out for a second bite of the apple later? He also wonders if it's crazy to spend more on his vacation home than on his primary residence. David calls himself an "elderly orphan," flying solo at 66 and in need of a plan to protect his million-dollar portfolio as he ages. BB and Shell are trying to time their final year of retirement contributions to save as much as possible before moving to a lower-tax state. Should they go Roth IRA or traditional? Joel wonders when to take required minimum distributions from retirement accounts for the maximum tax benefit, and Brian in New York needs a spitball on when it makes sense to have an emergency fund as a retiree, and for how much.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-569 (full show notes & episode transcript)

Growing Your Wealth Guide - free download

Retirement Readiness Guide - free download

Retire at 62: Great Idea or Huge Mistake? - YMYW TV

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Chapters:

00:00 - Intro: This Week on the YMYW Podcast

01:09 - Should I Sell My Business or Wait? Is It Crazy to Spend More on My Vacation Home Than My Primary Residence? (Fine and Dandy, IL)

20:48 - Saving to Roth IRA vs Traditional IRA in the Final Year Before Retirement (BB and Shell)

23:50 - When to Take Your First RMD for the Maximum Tax Benefit (Joel, CA)

27:33 - Aging Alone in Retirement: How to Protect Assets Before Cognitive Decline (David, 68, Logan, NM)

35:37 - Why Some CPAs Cap Roth Conversions at $500K AGI (Shweta, CA)

37:05 - When Does It Make Sense for Retirees to Have an Emergency Fund - and How Much? (Brian, Albany, NY)

42:03 - Outro - Next Week on the YMYW Podcast

John Q. Taxpayer is in the home stretch of his career, looking for the best way to catch-up and build his tax-free bucket. Meanwhile, a pair of young financial nerds in Omaha are already strong savers, but they're wondering whether a simple "VOO for life" strategy is enough to help them reach multimillionaire status in retirement. Also, Janine retired unexpectedly. Can her remaining savings support a European retirement lifestyle? From Jonas Grumby's "glitch in the matrix" tax strategy to the potential tax nightmare of Dolly's literal sack of inherited gold coins, today on Your Money, Your Wealth® podcast 568, Joe Anderson, CFP® and Big Al Clopine, CPA. spitball on how folks from different generations with different situations can reach the same ultimate goal: positioning assets today to ensure the most tax-free wealth tomorrow. Plus, the fellas spitball on the "double taxation" trap of retirement plan loans for Pete in North Carolina, and the affordability of 50-year mortgages for Semper Fi in Michigan.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-568 (full show notes & episode transcript)

Why Asset Location Matters - free guide

All About Asset Location - more free resources

15 Maneuvers to Duck an Unplanned Early Retirement Knockout - YMYW TV

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Chapters:

00:00 - Intro: This Week on the YMYW Podcast

01:05 - After-Tax 401(k) Catch-Ups vs Taxable Investing (John Q Taxpayer)

06:16 - Forced Early Retirement: Social Security and Roth Conversion Timing? (Janine, Bothell, WA)

11:30 - Are 50-Year Mortgages Actually Affordable? (Semper Fi, Stevensville, MI)

17:59 - 401(k) Loan vs Mortgage Payoff (Pete, NC)

21:27 - Can You Manufacture a Step-Up in Basis? (Jonas Grumby, The Colony, TX)

25:03 - Inherited Gold Coins and Capital Gains Taxes (Dolly, 63, TN)

29:35 - Spitball for Young Investors Who Don't Have Millions (Young Financial Nerds, Omaha, NE)

42:13 - Outro: Next Week on the YMYW Podcast

Should Al and Peggy in Illinois keep hammering pre-tax retirement savings or should they pivot to post-tax Roth for better tax diversification? Which pension option is best for their early retirement plans? Long-term care insurance premiums are going up endlessly for Eloise in Connecticut. Is she walking into an insurance industry trap? How do Eric and Tami in Baton Rouge help their kids with college without blowing up their own retirement, and when do student loans make sense? Finally, should Lana and Sterling harvest capital gains or prioritize Roth conversions before moving to a much higher-tax state? The basic question in all of these is the same: how do you protect your future from rising costs and unknowns that are out of your control? We'll find out what it takes, today on Your Money, Your Wealth podcast number 567.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-567 (full show notes & episode transcript)

Key Financial Data Guide - free download

Retirement Panic Button: 7 Ways to Avoid Hitting It - YMYW TV

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

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Chapters:

00:00 - Intro: This Week on the YMYW Podcast

00:55 - Pre-Tax vs. Late Roth Savings? Pension Lump Sum vs. Lifetime Income in Early Retirement? (Al & Peggy, Illinois)

14:14 - Should I Drop Long-Term Care Insurance Now at Age 70? (Eloise, Connecticut)

20:41 - College Costs vs Retirement Security for Parents (Tami & Eric, Baton Rouge, LA)

35:59 - Roth Conversions or Capital Gains Before Moving to a High Tax State? (Lana & Sterling, Nebraska)

48:14 - Next Week on the YMYW Podcast

"Mr and Mrs Smith" have nearly $850,000 saved at age 43, but they're very concerned about retirement. "Lucy and Desi" are 58 and 64 with nearly $7 million saved, but they still lie awake wondering if it's enough for their high-expense life. "Tony and Carmela" are in a similar boat with millions saved at 61 and 59, but they're worried their asset allocation won't get them through their retirement. No matter the numbers, the fears sound exactly the same: will you run out of money in retirement? Turns out overcoming that fear is not about hitting a magic number. We'll find out what it's all about today on Your Money, Your Wealth podcast number 566 with Joe Anderson, CFP®, and Big Al Clopine, CPA. The fellas also spitball Roth conversions, long/short direct indexing capital gains tax strategies for "Juicy Squeeze", working after retirement for Wendi, and how one confusing word can completely change a retirement timing decision for "Jacques and Johana."

Free Financial Resources in This Episode:

https://bit.ly/ymyw-566 (full show notes & episode transcript)

Withdrawal Strategy Guide - free download

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

WATCH 6 Signs You Truly Have "Enough" For Retirement on YMYW TV

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Chapters:

00:00 - Intro: This Week on the YMYW Podcast

01:01 - 43 With $850K. Am I Too Late to Build Enough Roth Money? (Mr & Mrs Smith, Dallas, TX)

11:29 - Nearly $7M Saved at 58 and 64. Do We Have Enough for a High-Spend Retirement? (Lucy & Desi, Jersey Shore, NJ)

23:38 - 61 and 59 With $4.5M Saved. Can I Retire Now With a 50/50 Portfolio? (Tony & Carmela, San Ramon, CA)

32:09 - Mid-50s with $685K Saved. Can One Spouse Retire While the Other Works? (Jacques & Johana, Florida)

38:53 - Are Long-Short Direct Indexing Tax Strategies Worth the Fees? (Juicy Squeeze)

47:04 - Should I Work as an Employee or Contractor After 70 on Social Security? (Wendi)

52:04 - Outro: Next Week on the YMYW Podcast

Lucky Lou is 48, burned out and wants to punch at 50. How should he bridge the gap before pensions and Social Security? Joe Anderson, CFP®, and Big Al Clopine, CPA walk through the Rule of 55, 72(t)s, and the psychological reality of spending down a taxable account, today on Your Money, Your Wealth® podcast number 565. Alexei and Anna are high earners in their mid-20s who want to save aggressively and keep taxes low. Which retirement accounts should they prioritize, and can they afford a downpayment on a house? Jay and Gloria are wrestling with the classic question of whether to save to Roth or traditional 401(k), especially since their state doesn't tax retirement income. Is taking the deduction now and backdooring Roths the smarter move? Plus, Sleepless in Seattle wants to know, can her 28-year-old daughter afford to buy a condo in a high-cost housing market? Finally, Jennifer in Texas wonders how to invest and withdraw an inherited IRA over the 10-year rule with the least tax damage.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-565 (full show notes & episode transcript)

The Last 5 Years Before Retirement Will Decide Your Lifestyle - Here's How - YMYW TV

Guides:

• Growing Your Wealth
• Tax-Free Retirement
• One Big Beautiful Bill Act

Blogs:

• A Market of Stocks
• Why AI May Not Be a Bubble
• Should You Own Gold Instead of Stocks?

Financial Blueprint (self-guided)

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Chapters:

00:00 - Intro: This Week on the YMYW Podcast

01:04 - Can I Retire at 50 with $5M and Bridge the Gap to Pensions and Social Security? (Lucky Lou)

10:51 - Which Retirement Accounts Should Young High Earners Max First? Can We Afford a House Downpayment? (Alexei & Anna, Cincinnati)

17:57 - Save to Roth 401(k) or Traditional If Our State Doesn't Tax Retirement Income? (Jay & Gloria, People's Republic of IL)

28:21 - Should a 28-Year-Old Buy a Home in an Expensive Market? (Sleepless in Seattle)

37:15 - How to Invest for Most Growth and Least Tax on an Inherited IRA? (Jennifer, TX)

41:04 - Outro: Next Week on the YMYW Podcast

Hana's mom is 92. Mom's husband is 74, and after years of trying to help a family member, nearly a million dollars is gone. How do they stop the bleeding before it's too late, and how much can they spend each year from what's left? That's today on Your Money, Your Wealth® podcast number 564 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, "Peter and Gwen" from Virginia have a pension, Roths, and a shrinking IRA. With the new tax law, IRMAA, and Social Security decisions all colliding, should they keep converting to Roth, and when should they actually collect Social Security? Also, does it make sense for "Mr. and Mrs. Scarecrow" to claim Social Security early and invest it? Finally, "Rosie and Astro" from Pennsylvania ask if they can retire in just three years with $1.3 million, and whether it's time to hire an advisor to help them get there.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-564 (full show notes & episode transcript)

Social Security Handbook

Retirement Readiness Guide

6 Biggest Financial Pitfalls in America (Avoid These Traps!) - YMYW TV

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

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Chapters:

00:00 - Intro: This Week on the YMYW Podcast

02:21 - Family Wrecking Retirement: How Much Can Benevolent Retirees Afford to Spend? (Hana)

10:30 - We Have a Pension. Should We Do Roth Conversions After the OBBBA? When to Claim Social Security? (Peter Parker & Gwen Stacy)

23:29 - Should We Claim Social Security Early and Invest It? (Mr & Mrs Scarecrow)

29:56 - We're 60 and 57 with $1.3M. Can We Retire in 3 Years? Should We Hire an Advisor? (Rosie & Astro, PA)

41:04 - Outro: Next Week on the YMYW Podcast

YMYW friends, welcome to 2026. What actually mattered most to you in 2025? It turns out to be tax-free gains on investments, retirement timing, and claiming Social Security. Today on Your Money, Your Wealth® podcast number 563, Joe Anderson, CFP® and Big Al Clopine, CPA break down the smartest tax moves, the biggest Roth mistakes to avoid, and how real people solve real retirement problems - with the help of special guests Susan Brandeis CFP® and the IRA guru, Ed Slott, CPA. Find out when Roth conversions help or hurt, how to lower lifetime taxes for you and your heirs, what it really takes to retire confidently, even without a massive portfolio, and more. Watch or listen and steal the financial strategies that made YMYW's most popular episodes of the year.

Free Financial Tools & Resources in This Episode:

https://bit.ly/ymyw-563 (full show notes & episode transcript)

The Complete Roth Papers Package - 3 free downloads in one!

Don't Let These 10 Risks Break Your Retirement - YMYW TV

Financial Blueprint (self-guided)

EASIRetirement (self-guided)

Financial Assessment (Meet with an experienced professional)

LISTEN to the Best of the YMYW Podcast 2021, 2022, 2023, 2024

LISTEN to the Top Funniest Moments from the YMYW Podcast Vol. 1, Vol. 2

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Chapters:

• 00:00 - Intro: This Week on the YMYW Podcast
• 00:54 - Roth IRA is "The Greatest Account Ever" Per Ed Slott. But Why?
  • from ep. 526: YMYW most listeners and plays in 2025 on Apple Podcasts, YMYW most downloaded in 2025 across all podcast platforms
• 20:46 - Is There a Point Where Roth Conversions No Longer Make Sense? (Jerry, Phoenix, AZ)
  • from ep. 535: YMYW most views, watch time, and new subscribers in 2025 on YouTube, most engaged listeners in 2025 on Apple Podcasts
• 32:13 - Roth Conversions vs. Taking Advantage of Zero Percent Cap Gains (Skipper, CA)
  • from ep. 517: YMYW most consumed episode in 2025 on Apple Podcasts
• 43:06 - We're in Our Early 40s with $795K Saved. Can We Retire at 55? (Mr Buckeye, OH)
  • from ep. 546: YMYW longest average view duration in 2025 on YouTube
• 55:12 - Is My Husband Eligible for Spousal Social Security Benefits Now that WEP and GPO Are Gone? (Cherilyn, El Cajon, CA)
  • from ep. 536: YMYW most plays, most listeners, and most viewers in 2025 on Spotify
• 59:53 - Outro: 2025 Stats and Next Week on the YMYW Podcast

Today on Your Money, Your Wealth podcast 562 (an encore of episode 513), Joe Anderson, CFP® and Big Al Clopine, CPA spitball for YMYW listeners in their 40s who are ready to call it quits at work, become financially independent, and retire early. Can they afford to do it? Peter and Joanna want to retire in the next two years. Burned Out and Ready to Retire wants out of his toxic office. If Maryland Chicken Man never earns another dollar, how much can he afford to withdraw from his retirement accounts each year? And Suzanne in Massachusetts is 69 and needs $60K a year for the next 30 years. Is she all right?

(While Joe and Big Al enjoy a little seasonal downtime and Andi recovers from surgery, enjoy this encore presentation of these questions from an early 2025 episode.)

Free Financial Resources in This Episode:

https://bit.ly/ymyw-562 (full show notes & episode transcript)

2025 Key Financial Data Guide - free download

10 Big Retirement Regrets to Avoid (Before It's Too Late) - YMYW TV

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

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Chapters:

00:00 - Intro: This Week on the YMYW Podcast 01:30 - We're 45 and 44. Can We Retire in the Next 2 Years? (Peter & Joanna, NJ) 10:45 - Watch 10 Big Retirement Regrets to Avoid (Before It's Too Late) on YMYW TV, Calculate your Free Financial Blueprint 11:44 - I'm 42 and I Work in a Toxic Office. Can I Afford to Retire? (Burned Out and Ready to Retire, NJ) 21:53 - Download the 2025 Key Financial Data Guide for free 22:53 - I'm 69 and Need $60k/Year for the Next 30 Years. Am I All Right? (Suzanne, MA) 25:40 - I'm 45. If I Never Earn Another Dollar How Much Can I Withdraw Every Year? (Maryland Chicken Man) 35:15 - Outro: Next Week on the YMYW Podcast

Financially speaking, should Old Bear in Northern Kentucky marry his Honey? How should Sebastian in Virginia navigate the financial aspects of his separation? Plus, Famous Missourians want to know, how much is enough for retirement and when can you take your foot off the gas? Can Paul with the Big Wallet Bridge the long gap between retiring and claiming Social Security benefits? And can Aspiring Adventurer in Oregon retire single at age 58?

(While Joe and Big Al enjoy a little seasonal downtime and Andi recovers from surgery, enjoy this encore presentation of these questions from an early 2025 episode.)

Free Financial Resources in This Episode:

https://bit.ly/ymyw-561 (full show notes & episode transcript)

DOWNLOAD The Going Solo Guide for free

WATCH: Going Solo: Navigating Your Financial Future Single on YMYW TV

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

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Chapters:

00:00 - Intro: This Week on the YMYW Podcast

01:01 - Financially Speaking, Should Old Bear Marry His Honey? (Northern Kentucky, near Cincinnati, OH)

08:41 - Navigating Finances When Separating from Your Spouse (Sebastian, VA)

15:13 - Watch Going Solo: Navigating Your Financial Future Single on YMYW TV, Download the Going Solo Guide for free

15:42 - How Much is Enough for Retirement? When Can We Take Our Foot Off the Gas? (JC Penney & Laura Ingalls Wilder, Kansas City, MO)

28:31 - How to Bridge the Long Gap Between Retirement and Social Security (Paul with the Big Wallet)

38:50 - Calculate your free Financial Blueprint

39:20 - Can I Retire at Age 58? Where to Save? Should I Do a Roth Conversion Ladder in Retirement? (Aspiring Adventurer, OR)

51:00 - YMYW Podcast Outro

Today on Your Money, Your Wealth® podcast 560, Joe Anderson, CFP® and Big Al Clopine, CPA spitball business development company (BDC) funds for Edward in Illinois before diving into buckets of cash, T-bills, decumulation, and Roth conversion timing for Pebbles and Bam Bam. Plus, the fellas help 34 year old Keith in Connecticut figure out if he's actually on track, whether he's taking too much risk, or just worrying too much. They also spitball on the six-figure annuity gain that Gus in Philly's 95 year old dad has amassed. Finally, why yelling "never pay an advisor" on the internet doesn't necessarily magically turn MYGAs into the perfect investment for everyone.

(While Joe and Big Al enjoy a little seasonal downtime and Andi recovers from surgery, enjoy this encore presentation of these questions from a January 2025 episode.)

Free Financial Resources in This Episode:

https://bit.ly/ymyw-560 (full show notes & episode transcript)

10 Steps to Improve Investing Success - free download

Tax-Smart Charitable Giving Guide

6 Secrets to Bigger Tax Deductions from Your Non-Profit Donations - YMYW TV

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

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Chapters:

00:00 - Intro: This week on the YMYW Podcast

01:03 - What's the Risk With Business Company Development (BDC) Funds? (Edward, IL)

03:58 - T-Bills, Decumulation, IRAs, and Investing Strategies (Pebbles & Bam Bam, Kentuckystone)

12:02 - I'm 34. Are My Investments Appropriate for My Time Horizon? (Keith, CT)

17:59 - MYGA Retirement Withdrawal Strategy for Dad (Gus in Philly)

23:00 - Just Buy Multi-Year Guaranteed Annuities (MYGAs) and Bonds (comment from Ken, YouTube)

28:04 - YouTube comments: State Taxes, Pro-Rated Sale of Primary Residence, Bonds vs. Pension, and PERMA

35:27 - YMYW Podcast Outro