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Retire Early in Your 40s or 50s: Green Light or Reality Check?

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.

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03
MAR
2026
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Retirement Planning for Aging Parents – and Can You Retire Early?

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”?

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24
FEB
2026
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Tax-Smart Investing at Every Age: Starting Young or Catching Up

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, Joe and Big Al 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.

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10
FEB
2026
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48 and Worried About Early Retirement? This Changes the Math

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.

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20
JAN
2026
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How to Beat the “Fire Hydrant” of Future Taxes: YMYW Best of 2025

What actually mattered most to the YMYW audience in 2025? It turns out to be tax-free gains on investments, retirement timing, and claiming Social Security. In this Best of 2025 episode, Joe and Big Al break down the smartest tax moves, the biggest Roth mistakes to avoid, and how real people solve real retirement problems – with the help of some special guests. 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.

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06
JAN
2026
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I’m 42 and Burned Out with $2.25M. Can I Retire Early from My Toxic Job?

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?

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30
DEC
2025
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Retiring Before Social Security? Consider These Portfolio Changes

Joe Anderson, CFP® and Big Al Clopine, CPA spitball withdrawal strategies, Roth conversion timing, and saving priorities for every stage of life, today on Your Money, Your Wealth® podcast number 555. Christine just retired at 59 and wants the smartest way to draw income before Social Security, without letting taxes take a third of it. Prickly Richard and Margarita Maggie have a plan to “pull ahead” some Roth conversions now to dodge an RMD avalanche later. Will it work? And the Michigan Queen and Mississippi Boy are wondering whether to save harder for retirement or college for three kids currently under the age of 5.

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11
NOV
2025
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Don’t Let Money Anxiety Ruin Your Retirement

Joe and Big Al tackle the fears that mess with even the best-laid financial plans, today on Your Money, Your Wealth® podcast 552. Big Wallet Barbie and Ken from the Midwest have saved millions, but Barbie’s still worried about retiring early, buying a new house, and converting to Roth. Is she second-guessing her plans? The fellas spitball for Dan from Florida, who’s flying high in the 35% tax bracket and trying to decide between Roth 401(k) contributions and future Roth conversions. They also float a surprising idea – one that’s rare on YMYW – for a listener from Chicago who is FIRE’d Up about Roth vs. pre-tax and making a tax-smart wealth transfer. We’ll wrap up with a couple of your comments.

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21
OCT
2025
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What’s the Tax Triangle and How to Find Out if Yours is Lopsided

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. Plus, do Rae or Roy need to get a part-time job? Also, Elwood Blues in Illinois would like to retire in two years, but is willing to go for 3 more to make his retirement plan work. Joe and Marc spitball on when Elwood can really put down that harmonica.

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26
AUG
2025
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SEASON 11, EPISODE 5

15 Maneuvers to Duck an Unplanned Early Retirement Knockout

Famous boxer Mike Tyson said, “Everyone has a plan until you get hit in the face.” If you’re among the 49% of Americans punched in the face by an unplanned early retirement, trainers Joe Anderson, CFP® and Big Al Clopine, CPA are here with 15 defensive maneuvers that’ll help you bob and weave, slip, and […]

24
AUG
2025
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Can You Retire at Age 57 and Spend Big?

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.

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19
AUG
2025
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Smart Strategies to Retire Early and Spend More

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, Memphis wants to know, what are the rules for spousal IRA contributions and required minimum distributions?

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29
JUL
2025
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Retirement Savings: When to Take Your Foot Off the Gas

You’ve been jamming money into your retirement accounts for years now. When is it okay to slow down? Joe and Big Al spitball for Ron and Veronica in Indiana. Plus, how can Scott in Illinois bridge the gap from age 55 to retirement income at 57? How should Big Juan in Texas pay for college? Should he convert his TSP to Roth? Can he retire at 55 And finally, Frank and Jane Drebin in Wisconsin are 46 and 47 and wondering if their plan for retirement in 5 years is just a pipe dream.

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06
MAY
2025
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Haven’t Yet Saved a Million. Can We Still Retire Early?

Martin and Caterina in Green Bay are in their 40s and haven’t yet saved a million bucks. Are they on track to retire at age 58? Can Piggie and Kermit in California retire today at ages 50 and 57 and still build wealth for their children? Can Galahad and Zoot in Chicago retire early in their 50s, or do they need to keep working? Do Bo and Daisy have enough saved to retire now at 61 and 56? Plus, Chuck in South Carolina asks, if you can retire early, why wouldn’t you?

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11
MAR
2025
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Deferred Comp, Roth Strategies, Asset Protection (and Gold)

Mike and his wife in Tampa are 39 and 36, they’ve got nearly a million bucks saved. Are they on track for retirement? Kate in California is 55 and hopes to retire in the next couple of years. How should she manage deferred compensation and retirement withdrawals? Joe and Big Al also answer questions from our YouTube viewers on considering IRMAA when making Roth conversions, paying Roth conversion taxes quarterly or in December or in January, protecting a gifted house from a child’s ex, and the tax impact of rebuilding on an inherited property. Finally, 8 years ago, Joe and Big Al said you shouldn’t have more than 2% of your portfolio in gold, and one YouTube viewer said that did not age too well. What do the fellas think today? We’ll find out.

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28
JAN
2025
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