Show Notes
If you plan to punch the clock for the final time decades before "standard" retirement age, you need a financial strategy that goes beyond just saving. Joe Anderson, CFP® and Big Al Clopine, CPA spitball five different early retirement plans to see whose numbers are tight and who is ready to go for it, today on Your Money, Your Wealth® podcast 571. George in South Carolina wants to retire in 8 years at 53. Does he have enough in his brokerage account to bridge the gap to Social Security? Joe in Massachusetts is saving a staggering $200,000 a year, but will his high-spending lifestyle make a multi-million dollar nest egg look small? The fellas help 26-year-old Jonathan in Florida map out a path to retire in his 40s using his 457 plan, and they spitball on whether early exit strategies for both Kris and Rojo in California are a "green light" or a reality check. Plus, Joe explains why the "Rule of 55" and Roth conversions might be some of the most important tools in your early retirement toolbox. Free Financial Resources in This Episode: https://bit.ly/ymyw-571 (full show notes & episode transcript) Withdrawal Strategy Guide - free download: https://purefinancial.com/white-papers/withdrawal-strategy-guide/?utm_source=LibsynDestinations&utm_medium=podcast&utm_campaign=YMYW-571 Long-Term Care Planning Guide - free download: https://purefinancial.com/white-papers/long-term-care-planning-options/?utm_source=LibsynDestinations&utm_medium=podcast&utm_campaign=YMYW-571 The #1 Spending Mistake Ruining Retirements - YMYW TV: https://purefinancial.com/ymyw/episodes/number-one-spending-mistake-ruining-retirements/?utm_source=LibsynDestinations&utm_medium=podcast&utm_campaign=YMYW-571 Financial Blueprint (self-guided): https://bit.ly/PureFinancialBlueprint Financial Assessment (Meet with an experienced professional): https://bit.ly/PureFreeAssessment REQUEST your Retirement Spitball Analysis: https://bit.ly/AskJoeAndAl DOWNLOAD more free guides: https://bit.ly/PureGuides READ financial blogs: https://bit.ly/PureFinBlog WATCH educational videos: https://bit.ly/PureEdVideos SUBSCRIBE to the YMYW Newsletter: https://bit.ly/YMYWNewsletter Connect With Us: Subscribe on YouTube and join the conversation in the comments: https://bit.ly/YMYW-YT 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 01:06 - Is Retiring at 53 With No Pension a Smart Move or a Risky Bet? (George, South Carolina) 11:59 - High Income, High Spend, Early Retirement: Does the Math Still Work? (Joe, MA) 18:39 - At 26, Should I Go All In on a 457 to Retire Way Early? (Jonathan, Florida) 26:41 - Can I Retire Early and Still Cover Health Care and Long Term Care Costs? (Kris, California) 33:33 - I'm a Widowed Parent. Can I Retire at 57 and Still Fund College and Legacy Goals? (Rojo, California) 43:08 - Outro: Next Week on the YMYW Podcast
More from Your Money, Your Wealth
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 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: https://bit.ly/YMYW-YT 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 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: https://bit.ly/YMYWassessC 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: https://bit.ly/YMYW-YT 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 00:50 - 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 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: https://bit.ly/YMYW-YT 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 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: 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: https://bit.ly/YMYW-YT 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 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: 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: https://bit.ly/YMYW-YT 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 00:54 - 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.