Schedule a Free Financial Assessment with an experienced professional:

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Financial situations around early retirement today on YMYW: Shane and Ilya are 38 and 37. Ilya has a big federal pension and lifetime health insurance waiting for him at age 50, but he needs out of his job now. Can they still retire early? Rip and Beth are 35 and 33, and Beth can sell her business for $1.8 million. Is that enough for her to be done for good, or would she end up back at work anyway? Leeroy and Belle are teachers with just shy of a million dollars saved at age 34 and 33. Is it crazy for them to take a gap year? Finally, Jake is in his early 50s with $1.1 million, planning to Coast FIRE his way out at age 58. Does the math hold up? We’ll find out today on Your Money, Your Wealth® podcast number 606 with Joe Anderson, CFP® and Big Al Clopine, CPA.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-606 (full show notes & episode transcript)

LIMITED-TIME SPECIAL OFFER | DIY Retirement Guide: download by Friday, November 6, 2026!

https://purefinancial.com/ymyw/#specialoffer

WATCH Un-Retirement: Why Retirees Are Going Back to Work (And How to Avoid It) - YMYW TV:

https://purefinancial.com/ymyw/episodes/unretirement-mistakes-force-retirees-back-to-work/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep606-description-tv-s12e09

Financial Blueprint (free, self-guided):

https://bit.ly/YMYWblueprintC

REQUEST your Retirement Spitball Analysis:

https://bit.ly/YMYWaskC

DOWNLOAD more free guides:

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Leave your honest reviews and ratings in Apple Podcasts:

https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254

Chapters:

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

00:58 - Quitting Kills My $76K Pension and Health Insurance. Can We Stop Working at 50 Anyway? (Shane & Ilya)

12:23 - Should I Sell My Business for $1.8M and Quit at Age 33? (Rip & Beth, KY)

24:24 - Two Teachers, $1M Saved, and a Gap Year at 34. Is That Crazy? (Leeroy & Belle, IA)

34:21 - Coast FIRE at 52: Can I Stop Saving Now and Retire at 58? (Jake, MI)

42:37 - Outro: Next Week on the YMYW Podcast

43:37 - The Derails: Giant Ice Cube, Dutton Ranch, Wisconsin's Brandy Old-Fashioned

Schedule a Free Financial Assessment with an experienced professional:

https://bit.ly/YMYWassessC

Joe Anderson, CFP® and Big Al Clopine, CPA spitball on how to build your own retirement AND support your kids financially, today on Your Money, Your Wealth® podcast number 605. Lloyd and Diane in Montgomery County are 50 with $8.4 million. Can they retire early and still be generous with their kids? E and T in Missouri are 34 and 31 with $255K, and hopefully some big inheritances in the future. Can they fund the kids' college, and help them buy their first homes, AND retire early? Kent in Kansas City is 73 with 12 million bucks and $2 million in life insurance. Do Joe and Big Al back up his plan to buy an annuity, gift money to his kids now, and still spend freely in retirement, Die With Zero style? Finally, should John in the San Francisco Bay Area sell the family home and move to Nevada, or hold the house for his autistic daughters to inherit later? We’ll have a brand-new episode of tax strategies, retirement planning, and making fun of finance for you next week, but in the meantime, enjoy this encore presentation of an episode from March of this year.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-605 (full show notes & episode transcript)

Estate Plan Organizer - free download:

https://purefinancial.com/white-papers/estate-plan-organizer/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-estate-plan-organizer&utm_content=ymyw-pod-ep605-description-whitepaper

Retirement Readiness Guide - free download:

https://purefinancial.com/white-papers/retirement-readiness-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-retirement-readiness-guide&utm_content=ymyw-pod-ep605-description-whitepaper

Retirement Won't Look Like You Planned: Four Hard Truths About Retirement You Need to Face - YMYW TV:

https://purefinancial.com/ymyw/episodes/4-hard-retirement-truths-about-retirement-you-need-to-face/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep605-description-tv-s11e07

Financial Blueprint (free, self-guided):

https://bit.ly/YMYWblueprintC

REQUEST your Retirement Spitball Analysis:

https://bit.ly/YMYWaskC

DOWNLOAD more free guides:

https://bit.ly/YMYWguidesC

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https://bit.ly/YMYWvidsC

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https://bit.ly/YMYWnewsletterC

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Leave your honest reviews and ratings in Apple Podcasts:

https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254

Chapters:

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

01:10 - 50 with $8.4M. Can We Retire Early and Still Give to Our Kids? (Lloyd Dobler and Diane, Montgomery County, MD)

11:41 - Die With Zero: Spend My $12M or Buy an Annuity? (Kent, 73 & 70, Kansas City)

25:08 - Can We Afford Kids’ College AND Houses AND Our Own Early Retirement? (E & T, 34 & 31, Missouri)

34:17 - Should We Move to Save Money or Keep the House for Our Autistic Kids? (John, 68 & 66, San Francisco Bay Area)

42:29 - Outro: Next Week on the YMYW Podcast

Schedule a Free Financial Assessment with an experienced professional:

https://bit.ly/YMYWassessC

How much can you actually spend in retirement without running out of money? That’s today on Your Money, Your Wealth® podcast 604 with Joe Anderson, CFP® and Big Al Clopine, CPA. Longtime listener E-Dog built a fifty-year backtest spreadsheet to call out Big Al and prove the famous four percent rule is way too cautious. Hot stuff “Donna Summer” wonders if her biggest problem with her $13 million dollar portfolio is going to be the distributions she’ll be required to take from it and how to manage them. “Hansel and Gretel” in Minnesota are trying to figure out now what a lot of good savers never do: how to permit themselves to spend their $4.3 million dollar portfolio? James in Texas needs a spitball on how much to convert to Roth before Social Security and Medicare kick in, and Mark needs a spitball on whether he should save for retirement to his pre-tax 401(k) or his post-tax Roth.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-604 (full show notes & episode transcript)

Withdrawal Strategy Guide - free download:

https://purefinancial.com/white-papers/withdrawal-strategy-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-withdrawal-strategy-guide&utm_content=ymyw-pod-ep604-description-whitepaper

Financial Blueprint - free, self-guided:

https://purefinancial.com/financialblueprint/?utm_source=captivate&utm_medium=podcast&utm_campaign=financial-blueprint&utm_content=ymyw-pod-ep604-description-blueprint

Retirement Panic? Here’s Your 7-Step Escape Plan - YMYW TV:

https://purefinancial.com/ymyw/episodes/retirement-panic-button/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep604-description-tv-s11e04

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Leave your honest reviews and ratings in Apple Podcasts:

https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254

Chapters:

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

01:05 - Is 4% Too Conservative? A Listener’s 50-Year Backtest (E-Dog)

17:10 - Roth Conversion to the Top of 24% Tax Bracket, or Protect My ACA Subsidy? (James, TX)

27:53 - Will RMDs Be My Biggest Problem on a $13M Portfolio? (Donna Summer, CA)

36:47 - $4.35M and Scared to Spend It. What’s Our YOLO Number? (Hansel & Gretel, MN)

44:30 - In My Late 30s With $750K Income: Save to Roth or Pretax 401(k)? (Mark)

49:40 - Outro: Next Week on the YMYW Podcast

51:05 - The Derails: Donna Summer, Hansel & Gretel, Joe's six fridges, and TV

Schedule a Free Financial Assessment with an experienced professional:

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George and Louise in Queens bring in $600,000 a year. Should they keep working just to do Roth conversions? Cher and Sonny in Oregon wonder if they can retire in a couple years at 59 and 60, and whether the mega backdoor Roth belongs in their plans. Joe Anderson, CFP® and Big Al Clopine, CPA spitball retirement planning and Roth conversion strategies for them, today on Your Money, Your Wealth® podcast number 603. Plus, Michelle in Vienna, Virginia, is 56 and ready to retire, but what about her brand-new mortgage? Finally, our friend Marion in Fresno asks about Vanguard's suggestion of an annuity to cover fixed expenses.

LIMITED-TIME SPECIAL OFFER | DIY Retirement Guide - download by Friday, October 16, 2026!

https://purefinancial.com/ymyw/#specialoffer

Free Financial Resources in This Episode:

https://bit.ly/ymyw-603 (full show notes & episode transcript)

Do You Have These 10 Habits of the Quietly Wealthy? - YMYW TV:

https://purefinancial.com/ymyw/episodes/do-you-have-these-10-habits-of-the-quietly-wealthy/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep603-description-tv-s12e08

Financial Blueprint (free, self-guided):

https://bit.ly/YMYWblueprintC

REQUEST your Retirement Spitball Analysis:

https://bit.ly/YMYWaskC

DOWNLOAD more free guides:

https://bit.ly/YMYWguidesC

READ financial blogs:

https://bit.ly/YMYWblogC

WATCH educational videos:

https://bit.ly/YMYWvidsC

SUBSCRIBE to the YMYW Newsletter:

https://bit.ly/YMYWnewsletterC

Connect With Us:

Subscribe on YouTube and join the conversation in the comments:

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Leave your honest reviews and ratings in Apple Podcasts:

https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254

Chapters:

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

00:50 - Should I Keep Working Just to Do Roth Conversions? (George & Louise, Queens, NY)

13:50 - Convert to Roth Now or Wait Until We Leave Oregon? (Cher & Sonny, Oregon)

30:29 - We Built a Dream House. Can I Still Retire? (Michelle, Vienna, VA)

38:38 - Should an Annuity Cover Your Fixed Expenses? (Marion, Fresno, CA)

39:56 - Outro: Next Week on the YMYW Podcast

41:02 - The Derails: Cher, blue cheese olives, Joe's Escalade, iPhone, and new lifestyle

Schedule a Free Financial Assessment with an experienced professional:

https://bit.ly/YMYWassessC

Joe Anderson, CFP® and Big Al Clopine, CPA are spitballing on whether Roth conversions actually pay off as part of your retirement tax strategies, today on Your Money, Your Wealth® podcast number 602. “Ozzie and Harriet” in Lafayette, Louisiana are 67, and Ozzie's spreadsheet says converting from their $7 million IRA costs more than just taking the RMDs. He challenges the fellas to change his mind. They also address BondBeer’s many YouTube comments telling them that their favorite guidance to convert when the market drops is flat wrong. Finally, Alan on Daufuskie Island, South Carolina asks for clarification on paying the tax to pay the tax when you pull money from an IRA, and whether it matters if the tax comes out of the account or out of your brokerage.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-602 (full show notes & episode transcript)

Retirement Accounts Guide - free download:

https://purefinancial.com/white-papers/retirement-accounts-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-retirement-accounts-guide&utm_content=ymyw-pod-ep602-description-whitepaper

Financial Blueprint - free, self-guided:

https://purefinancial.com/financialblueprint/?utm_source=captivate&utm_medium=podcast&utm_campaign=financial-blueprint&utm_content=ymyw-pod-ep602-description-blueprint

5 Years From Retirement? Do These Things Now - YMYW TV:

https://purefinancial.com/ymyw/episodes/last-5-years-before-retirement-decide-lifestyle/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep602-description-tv-s11e03

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Leave your honest reviews and ratings in Apple Podcasts:

https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254

Chapters:

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

01:04 - Do Roth Conversions Actually Lose You Money? (Ozzie & Harriet, Lafayette, LA)

12:08 - Is a Market Downturn Really the Best Time for a Roth Conversion? (bondbeer, YouTube)

23:00 - Do You Pay Tax on the Tax? Roth Withdrawals vs. Roth Conversions Clarified (Alan, Daufuskie Island, SC)

28:04 - Outro: Next Week on the YMYW Podcast

Schedule a Free Financial Assessment with an experienced professional:

https://bit.ly/YMYWassessC

How do you know if you're really on track to retire, especially if you're hoping to get out early? Fred and Wilma in Denver are 33 and 31, earning a small fortune, but sitting on nearly two million dollars in debt. Should they focus on paying it down faster or saving more? Jeremy, in Summerville, South Carolina, is 42 with a hefty military pension. Is that his green light to go all-in on stocks for the next 20 years? And finally, Saver and Spender in Saratoga Springs, New York are 41 and 42 and hoping an early exit. Can part-time work can carry them through their gap years? Joe Anderson, CFP® and Big Al Clopine, CPA spitball for all of them, today on Your Money, Your Wealth® podcast number 601.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-601 (full show notes & episode transcript)

Ultimate Investing Guide - free download:

https://purefinancial.com/white-papers/the-ultimate-investing-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-ultimate-investing-guide&utm_content=ymyw-pod-ep601-description-whitepaper

Financial Blueprint - free, self-guided:

https://purefinancial.com/white-papers/the-ultimate-investing-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-ultimate-investing-guide&utm_content=ymyw-pod-ep601-description-whitepaper

$1M Retirement Savings: Is It Enough to Retire? - YMYW TV:

https://purefinancial.com/ymyw/episodes/will-your-money-last-through-retirement/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep601-description-tv-s10e16

REQUEST your Retirement Spitball Analysis:

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DOWNLOAD more free guides:

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Connect With Us:

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Leave your honest reviews and ratings in Apple Podcasts:

https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254

Chapters:

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

01:01 - $1.8M in Debt at 33: Pay It Down or Keep Investing? (Fred & Wilma, Denver, CO)

17:07 - My $97K Military Pension: Can I Go 100% Stocks for 20 Years? (Jeremy, Summerville, SC)

26:49 - Can We Bridge Ages 56 to 62 With Part-Time Work? (Saver & Spender, Saratoga Springs, NY)

40:01 - Outro: Next Week on the YMYW Podcast

41:03 - The Derails: The Flintstones, Project Hail Mary

Schedule a Free Financial Assessment with an experienced professional:

https://bit.ly/YMYWassessC

63-year-old Kevin in Denver is pulling $100K a year out of his portfolio. What’s the tax-smart way for him to structure these retirement withdrawals? Tim in Pennsylvania was forced into early retirement, and his wife Jill may be facing a layoff. They have over $2.5M saved, but what about health insurance? And Rocky and Adrian in Tucson have $4M in pre-tax at ages 68 and 69. If they convert to Roth, are they just picking up nickels in front of a steamroller? But first, Jeffrey’s YouTube comment lit a fire when he called a recent episode of YMYW TV on Social Security claiming strategies "cookie-cutter with zero real info." Joe and Big Al have some thoughts!

Free Financial Resources in This Episode:

https://bit.ly/ymyw-600 (full show notes & episode transcript)

2026 Tax Planning Guide - free download:

https://purefinancial.com/white-papers/tax-planning-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-tax-planning-guide&utm_content=ymyw-pod-ep600-description-whitepaper

Withdrawal Strategy Guide - free download:

https://purefinancial.com/white-papers/withdrawal-strategy-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-withdrawal-strategy-guide&utm_content=ymyw-pod-ep600-description-whitepaper

Escape These 11 Tax Traps and Save in Retirement - YMYW TV:

https://purefinancial.com/ymyw/episodes/escape-these-11-tax-traps-save-in-retirement/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep600-description-tv-s10e17

Financial Blueprint (free, self-guided):

https://bit.ly/YMYWblueprintC

REQUEST your Retirement Spitball Analysis:

https://bit.ly/YMYWaskC

DOWNLOAD more free guides:

https://bit.ly/YMYWguidesC

READ financial blogs:

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Connect With Us:

Subscribe on YouTube and join the conversation in the comments:

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Leave your honest reviews and ratings in Apple Podcasts:

https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254

Chapters:

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

00:54 - Claiming Social Security: Is Planning for a 40-Year Retirement a Waste of Time? (jeffreylevin9728, YouTube)

12:31 - How Do I Turn My IRA Into a Monthly Paycheck? (Kevin, Denver)

23:42 - I’m Retired Early Due to Illness and My Wife May be Laid Off. What About Health Insurance? (Tim & Jill, rural PA)

32:30 - Roth Conversions on a $4M IRA at 68: Picking up Nickels in Front of a Steamroller? (Rocky & Adrian, Tucson, AZ)

40:27 - Outro: Next Week on the YMYW Podcast

42:16 - The Derails: Frontier Crucible, The Punisher, Disclosure Day, etc.

Schedule a Free Financial Assessment with an experienced professional:

https://bit.ly/YMYWassessC

How do you buy a house as a young person, without wrecking your long-term retirement plan? That’s today on Your Money, Your Wealth® podcast 599, as Joe Anderson, CFP® and Big Al Clopine, CPA spitball for 35-year-old Gord in New York City. He's got $300,000 saved, and a home purchase is coming soon thanks to a new relationship. Should he liquidate his brokerage account and pull the trigger? Carrie Bradshaw in California is 33 and wants to buy a roughly $1.5M home. When should she move the down payment money out of the market, and can she avoid derailing early retirement? Finally, Archie and Veronica in Missouri are 41 and 34, pulling in $600,000 a year and saving close to $200,000 of it. Are they saving too much? Should they pay off their mortgage or keep investing?

Free Financial Resources in This Episode:

https://bit.ly/ymyw-599 (full show notes & episode transcript)

Financial Blueprint (free, self-guided):

https://bit.ly/YMYWblueprintC

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

https://purefinancial.com/ymyw/episodes/10-big-retirement-regrets-to-avoid-before-its-too-late/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep599-description-tv-s10e15

REQUEST your Retirement Spitball Analysis:

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DOWNLOAD more free guides:

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Connect With Us:

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Leave your honest reviews and ratings in Apple Podcasts:

https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254

Chapters:

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

01:02 - I’m 35 in NYC. Do I Cash Out My ETFs to Buy a House? (Gord, NYC)

15:21 - How Much of My $900K Goes to the Down Payment? ("Carrie Bradshaw", CA)

24:12 - We Make $600K With a $1.1M Mortgage. Pay It Off or Keep Investing? ("Archie & Veronica", MO)

35:55 - Outro: Next Week on the YMYW Podcast

Schedule a Free Financial Assessment with an experienced professional:

https://bit.ly/YMYWassessC

Today on Your Money, Your Wealth® podcast 598, Joe Anderson, CFP® and Big Al Clopine, CPA spitball early retirement planning for Shua in Phoenix, who has a million dollars saved at age 42. Can he stop saving right now, coast until age 55, and still spend $170,000 a year in retirement? But first, Michael in Texas is a stay-at-home dad who does the stock market. His wife wants out of her job at age 47. Will their $5 million last through retirement? And then Homer and Marge in North Carolina make 640K in sales and want to spend up to 25K a month, and Seth in Illinois wants to retire at 58 on a pension and a Roth. Some of these plans work and some of ‘em aren't even close.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-598 (full show notes & episode transcript)

Withdrawal Strategy Guide - free download:

https://purefinancial.com/white-papers/withdrawal-strategy-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-withdrawal-strategy-guide&utm_content=ymyw-pod-ep598-description-whitepaper

Retirement Readiness Guide - free download:

https://purefinancial.com/white-papers/retirement-readiness-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-retirement-readiness-guide&utm_content=ymyw-pod-ep598-description-whitepaper

10 Assumptions Pre-Retirees Get Wrong About Retirement - YMYW TV:

https://purefinancial.com/ymyw/episodes/10-assumptions-pre-retirees-get-wrong-about-retirement/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep598-description-tv-s12e07

Financial Blueprint (free, self-guided):

https://bit.ly/YMYWblueprintC

REQUEST your Retirement Spitball Analysis:

https://bit.ly/YMYWaskC

DOWNLOAD more free guides:

https://bit.ly/YMYWguidesC

READ financial blogs:

https://bit.ly/YMYWblogC

WATCH educational videos:

https://bit.ly/YMYWvidsC

SUBSCRIBE to the YMYW Newsletter:

https://bit.ly/YMYWnewsletterC

Connect With Us:

Subscribe on YouTube and join the conversation in the comments:

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Subscribe or follow YMYW in your favorite podcast app:

https://lnk.to/ymyw

Leave your honest reviews and ratings in Apple Podcasts:

https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254

Chapters:

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

00:52 - Wife Wants to Retire at 47. What Are We Missing? (Michael, TX)

14:03 - $3M Saved, $640K Income: Can We Retire at 50? (Homer & Marge, Northern California)

21:19 - Pension + $1.45M: Can I Retire at 58 and Spend $11K a Month? (Seth, North Central IL)

26:51 - Can We Stop Saving Now at 42 and 45 and Still Retire at 55? (Shua, Phoenix, AZ)

36:07 - Outro: Next Week on the YMYW Podcast

37:19 - The Derails: Big Al Canoeing on the Russian River