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 Horner, CFP® spitball on these topics for "Beavis and Daria" in Texas and "Clark Kent" in Pennsylvania, today on Your Money, Your Wealth® podcast number 543. Plus, the sooner 56-year-old "Tony Soprano" in New Jersey can retire, the better. What tips do Joe and Marc have for him? By the way, Marc is one of the newest principals here at Pure Financial Advisors. He’s the founder of Fairhaven Wealth Management, which has just become the newest Pure Financial Advisors Chicagoland office in Wheaton, Illinois - so help us welcome him for his YMYW debut.

Free financial resources & episode transcript: https://bit.ly/ymyw-543

Complete the 8th Annual YMYW Podcast Survey for your chance at a $100 Amazon e-gift card! (secret password: ymyw)

DOWNLOAD the Withdrawal Strategy Guide for free

WATCH Withdrawal Trap Doors on YMYW TV

ASK Joe & Big Al for your Retirement Spitball Analysis

SCHEDULE your Free Financial Assessment

LEAVE YOUR HONEST RATINGS AND REVIEWS on Apple Podcasts

SUBSCRIBE or FOLLOW on your favorite podcast app

JOIN THE CONVERSATION on YouTube

DOWNLOAD more free guides

READ financial blogs

WATCH educational videos

SUBSCRIBE to the YMYW Newsletter

Timestamps:

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

01:00 - Spending Higher Earlier in Retirement to Celebrate? How to Convert? Where to Withdraw? (Beavis & Daria, TX)

12:30 - Watch Withdrawal Trap Doors on YMYW TV and Download the Withdrawal Strategy Guide for free

13:36 - Can I Retire at 57 Even With a High Draw Down Rate? Should I Convert After Retirement? Should I Consider an Annuity? (Clark Kent, PA)

28:23 - Complete the 8th Annual YMYW Podcast Survey for your chance at a $100 Amazon e-gift card! (secret password: ymyw)

29:09 - When Can I Retire? The Sooner the Better. (Tony Soprano, NJ)

37:43 - Next Week on the YMYW Podc

"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 542 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, should David in Redondo Beach California use his Roth money to buy a home? And what do the fellas think about "Charlie Pepper" in Colorado using a home equity line of credit (HELOC) for retirement spending, instead of living off of pre-tax money?

Free financial resources & episode transcript: https://bit.ly/ymyw-542

DOWNLOAD the Investing Basics Guide

WATCH Financial Boot Camp on YMYW TV

COMPLETE the 8th Annual YMYW Podcast Survey for your chance at a $100 Amazon e-gift card! (secret password: ymyw)

ASK Joe & Big Al for your Retirement Spitball Analysis

SCHEDULE your Free Financial Assessment

LEAVE YOUR HONEST RATINGS AND REVIEWS on Apple Podcasts

SUBSCRIBE or FOLLOW on your favorite podcast app

JOIN THE CONVERSATION on YouTube

DOWNLOAD more free guides

READ financial blogs

WATCH educational videos

SUBSCRIBE to the YMYW Newsletter

Timestamps:

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

00:43 - $250K Saved, $67K Fixed Income, $65K Spending. Are We Cutting Retirement Too Close? (Rubble & Sky, MN)

05:20 - We Have a $700K Pension, $335K Retirement, Plus Social Security. Will We Be OK? (Atouk and Tala, NJ)

13:14 - Watch Financial Boot Camp on YMYW TV, Download the Investing Basics Guide

14:03 - Should I Use My Roth Money for a Home Purchase? (David, Redondo Beach, CA)

21:03 - Complete the 8th Annual YMYW Podcast Survey for your chance at a $100 Amazon e-gift card! (secret password: ymyw)

22:01 - HELOC vs. Pre-Tax Account for Retirement Spending (Charlie Pepper, CO)

34:23 - Next Week on YMYW Podcast: Guest Co-Host Marc Horner, CFP®

34:53 - YMYW Podcast Outro

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 Clopine, CPA. Plus, do Roth conversions make sense for Will and Jane in New York, given their high income and high tax bracket? Which pension option is best for their circumstances? Finally, the fellas spitball for Juan’s mother in Florida on how long-term capital gains on the installment sale of her company will be taxed.

Free financial resources & episode transcript: https://bit.ly/ymyw-541

Complete the 8th Annual YMYW Podcast Survey for your chance at a $100 Amazon e-gift card! (secret password: ymyw)

LIMITED TIME OFFER: Download The Money Makeover Guide before this Friday, August 8, 2025!

WATCH Complete Money Makeover on YMYW TV

ASK Joe & Big Al for your Retirement Spitball Analysis

SCHEDULE your Free Financial Assessment

LEAVE YOUR HONEST RATINGS AND REVIEWS on Apple Podcasts

SUBSCRIBE or FOLLOW on your favorite podcast app

JOIN THE CONVERSATION on YouTube

DOWNLOAD more free guides

READ financial blogs

WATCH educational videos

SUBSCRIBE to the YMYW Newsletter

 

Timestamps: 

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

00:44 - We’re Millennials. Have We Brunched and YOLO'd Away Our Retirement Dreams? (Pam & Jim, Phoenix, AZ)

12:10 - We're 39 With $840K. Can We Retire at Age 57? (Matt, PA)

22:57 - Complete the 8th Annual YMYW Podcast Survey for your chance at a $100 Amazon e-gift card!

23:53 - Do Roth Conversions Make Sense Given Our High Income and Tax Bracket? What Pension Option is Best? (Will and Jane, NY - voice)

37:04 - Watch Complete Money Makeover on YMYW TV, Download the Complete Money Makeover Guide before Friday, August 8, 2025!

37:46 - How Will Long Term Capital Gains on the Installment Sale of My Company Be Taxed? (Juan's Mother, FL)

47:50 - YMYW Podcast Outro

 

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? Memphis wants to know. Joe Anderson, CFP® and Big Al Clopine, CPA spitball for YMYW audience members who are definitely not fictional characters, today on Your Money, Your Wealth® podcast number 540.

Free financial resources & episode transcript: https://bit.ly/ymyw-540

Complete the 8th Annual YMYW Podcast Survey for your chance at a $100 Amazon e-gift card! (secret password: ymyw)

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

CALCULATE your free Financial Blueprint

ASK Joe & Big Al for your Retirement Spitball Analysis

SCHEDULE your Free Financial Assessment

LEAVE YOUR HONEST RATINGS AND REVIEWS on Apple Podcasts

SUBSCRIBE or FOLLOW on your favorite podcast app

JOIN THE CONVERSATION on YouTube

DOWNLOAD more free guides

READ financial blogs

WATCH educational videos

SUBSCRIBE to the YMYW Newsletter

 

Timestamps:

00:00 - Complete the 8th Annual YMYW Podcast Survey for your chance at a $100 Amazon e-gift card!

00:35 - Intro: This Week on the YMYW Podcast

01:13 - Can We Retire Early, Spend More, and Die With Zero? When Should We Collect Social Security? (Beth and Rip, FL - voice)

12:06 - Watch Retirement Panic Button: 7 Ways to Avoid Hitting It on YMYW TV

Calculate your Financial Blueprint

Schedule a Free Assessment

13:41 - We Have 10 Rental Properties at Age 31. Are We on Track to Retire at Age 50? (Forrest and Jenny, Cherry Hill, NJ - voice)

20:04 - Spousal IRA Contributions and RMD Rules (Memphis)

32:23 - YMYW Podcast Outro

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 location strategy, should he max out the ESPP at a 15% discount, convert to Roth IRA, build his brokerage account, or a little of all the above? Speaking of asset location, some of our YouTube viewers object to the idea of putting higher performing assets in your Roth account. They say you can’t write off the losses and you’ll be exposed to sequence of returns risk. Stick around for Joe and Al’s response.

Free financial resources & episode transcript: https://bit.ly/ymyw-539 

DOWNLOAD Why Asset Location Matters for Free

CALCULATE Your Free Financial Blueprint

WATCH Recipe for Retirement | Retirement Plans Explained on YMYW TV

ASK Joe & Big Al for your Retirement Spitball Analysis

SCHEDULE your Free Financial Assessment

LEAVE YOUR HONEST RATINGS AND REVIEWS on Apple Podcasts

SUBSCRIBE or FOLLOW on your favorite podcast app

JOIN THE CONVERSATION on YouTube

DOWNLOAD more free guides

READ financial blogs

WATCH educational videos

SUBSCRIBE to the YMYW Newsletter

Timestamps:

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

02:03 - I’m Burned Out. Can I Pre-Retire Next Year? (Roger & Jane, Canton, OH)

11:46 - Watch Recipe for Retirement | Retirement Plans Explained on YMYW TV and Calculate Your Free Financial Blueprint

12:50 - Would You Rather for Asset Location: Roth vs. Brokerage? Roth vs. ESPP with 15% Discount? (Roger & Jane, Canton, OH, cont'd)

21:08 - Higher Performing Assets in Roth Exposes You To Sequence of Returns Risk and You Can't Write Off  The Losses (YouTube comment)

24:54 - Next Week on the YMYYW Podcast

25:27 - Download Why Asset Location Matters for Free

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. Plus, Seth isn’t sure if he can afford to stay retired at age 52, and whether he should convert his retirement savings to Roth, so he uses an AI voice to ask the fellas for his spitball. And Leon uses his real voice to ask whether REIT ETFs are a good way to get into real estate investing.

Free financial resources & episode transcript: https://bit.ly/ymyw-538 

Test your knowledge: take our Retirement Pop Quiz

Watch Retirement Pop Quiz: 18 Questions To Get You Ready to Retire on YMYW TV

Download the Retirement Readiness Guide for free

Email Us and Request a Free Copy of The Best of Jonathan Clements: Classic Columns on Money and Life on Kindle! 

Watch or Listen to “The Payoff is Huge”: Jonathan Clements’ Final Initiative to Empower Lifelong Savers

ASK Joe & Big Al for your Retirement Spitball Analysis

SCHEDULE your Free Financial Assessment

LEAVE YOUR HONEST RATINGS AND REVIEWS on Apple Podcasts

SUBSCRIBE or FOLLOW on your favorite podcast app

JOIN THE CONVERSATION on YouTube

DOWNLOAD more free guides

READ financial blogs

WATCH educational videos

SUBSCRIBE to the YMYW Newsletter

 

Timestamps:

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

01:03 - Can “George and Weezy” Retire in 2026 or Earlier With Deferred Compensation? (IL)

12:17 - Pop Quiz, Retirement Readines Guide

13:02 - Should I Move With Work, Take a Break, or Retire Now? Be Brutally Honest (Jenn, OH)

17:43 - Can I Stay Retired at Age 52? Should I Convert Retirement Saving

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, CPA, today on Your Money, Your Wealth® podcast number 537. Plus, should Ned in Tokyo sell his Bay Area rental property and invest the proceeds? And Bob and Brigette in Wisconsin got a late start on Roth IRA savings. Should they prioritize saving into a Roth, brokerage account, or 401(k)?

Free financial resources & episode transcript: https://bit.ly/ymyw-537

DOWNLOAD Why Asset Location Matters

DOWNLOAD The Recession Protection Guide

WATCH How to Build a Recession-Proof Portfolio on YMYW TV

ASK Joe & Big Al for your Retirement Spitball Analysis

SCHEDULE your Free Financial Assessment

LEAVE YOUR HONEST RATINGS AND REVIEWS on Apple Podcasts

SUBSCRIBE or FOLLOW on your favorite podcast app

JOIN THE CONVERSATION on YouTube

DOWNLOAD more free guides

READ financial blogs

WATCH educational videos

SUBSCRIBE to the YMYW Newsletter

Timestamps:

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

00:46 - Should the Asset Location of Our Accounts Be Independent of Each Other? (Kevin, Denver)

08:54 - CTZE - Any Other Ways to Maximize Our Tax-Free Retirement Strategy? (Jim & Pam, Orange County)

17:19 - Watch How to Build a Recession-Proof Portfolio on YMYW TV, Download the Recession Protection Guide

18:00 - Should We Sell a Rental Property and Invest the Proceeds? (Ned, Tokyo, Japan)

25:37 - Got a Late Start on Roth IRA Savings. Should I Prioritize Roth, Brokerage, or 401(k)? (Bob & Bridgette, WI)

34:49 - Next Week on YMYW Podcast

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, while Joe hangs in the North Star State, Big Al Clopine explains what the Social Security Fairness Act means for Cherilyn and her husband, and "Nuke La Loosh" and his wife, with the help of our special guest co-host, Susan Brandeis, CFP®.

Free financial resources & episode transcript: https://bit.ly/ymyw-536

DOWNLOAD The Social Security Handbook (newly updated!) for free

YMYW ranked among the "14 Best Retirement Podcasts and Blogs to Follow" by Due.com, featured on NASDAQ.com

ASK Joe & Big Al for your Retirement Spitball Analysis

SCHEDULE your Free Financial Assessment

SUBSCRIBE to YMYW on YouTube

DOWNLOAD more free guides

READ financial blogs

WATCH educational videos

SUBSCRIBE to the YMYW Newsletter

Timestamps:

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

00:47 - Can I Qualify for Half of My Wife's Social Security Now That WEP and GPO Are Gone? (Nuke La Loosh, Northern CA - voice)

08:16 - Is My Husband Eligible for Spousal Social Security Benefits Now that WEP and GPO Are Gone? (Cherilyn, El Cajon, CA)

12:58 - Comment: Your TV Show and Guide on Social Security Are Out of Date (Helen, San Diego)

14:11 - Comment: Even If the TV Show Doesn't Pertain to You Directly, You Can Inform Someone Else (Catherine)

14:39 - Social Security Handbook (newly updated!) - download for free

15:00 - YMYW ranked among the "14 Best Retirement Podcasts and Blogs to Follow" by Due.com, featured on NASDAQ.com

15:21 - Next Week on the YMYW Podcast

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 Roth conversions no longer make sense? Stay tuned for the 7 reasons to consider NOT converting to Roth, today on Your Money, Your Wealth podcast number 535 with Joe Anderson, CFP® and Big Al Clopine, CPA. First up, a word of Roth conversion thanks from Al in Florida.

Free financial resources & episode transcript: https://bit.ly/ymyw-535

DOWNLOAD The Ultimate Guide to Roth IRAs

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

RETIREMENT CALCULATION TOOLS:

Financial Blueprint

EASIRetirement.com (from Boldin, formerly NewRetirement)

 

ASK Joe & Big Al for your Retirement Spitball Analysis

SCHEDULE your Free Financial Assessment

SUBSCRIBE to YMYW on YouTube

DOWNLOAD more free guides

READ financial blogs

WATCH educational videos

SUBSCRIBE to the YMYW Newsletter

Insult to a Nose (Scene from Steve Martin movie "Roxanne" - warning, language!)

 

Timestamps:

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

00:44 - Thanks for Suggesting a Roth Conversion During the Market Drop (comment from Al, FL)

03:38 - In the 32% Tax Bracket. Where Should I Save for Retirement to Be in a Lower Bracket? (Ryan, TX)

07:57 - In the 37% Bracket: Backdoor Roth or Non-Roth Investments for Retirement Savings? (Weronika, TX)

12:25 - Watch The Last 5 Years Before Retirement Will Decide Your Lifestyle - Here's How on YMYW TV. Calculate your free Financial Blueprint

13:23 - Is There a Point Where Roth Conversions No Longer Make Sense? (Jerry, Phoenix, AZ)

25:26 - YMYW Podcast Outro