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Can Bauer in Illinois retire at age 57, and when should he collect Social Security? More importantly, can he afford a $300,000 motor home? Can Brad in Michigan coast for the next 10 years and still reach the promised land of retirement somewhere around age 53? Plus, it seems weird to Elizabeth in Connecticut that nearly all of her $5M is in taxable accounts. Is that good or bad? N&N in the San Francisco Bay Area have $10M liquid. Should they make Roth contributions and Roth conversions now, or wait until they retire?
Can Alanis retire early at age 60? With Barney and Betty’s spending patterns, can they retire ASAP? Daisy and Donald need retirement income for 40 years. Can they retire now? Plus, we review the results of the 7th Annual YMYW Podcast Survey (congratulations to jemart for winning the Amazon e-gift card!) And Joe and Big Al take on some critical YouTube comments from Keith, following their interview with Ed Slott, CPA.
Are women better investors and financial planners? Today on YMYW, three different husbands want to retire, while their wives feel they need to work longer. Can Jack and Diane, Mark and Belle, and Mike and his wife hit the slopes now, or do they need to keep wearing their suits? Joe and Big Al spitball on who’s right. Plus, should Ellie take her pension in a lump sum or in monthly annuity payments? The fellas also consider a solo 401(k) contribution strategy for self-employed types from our buddy Will.
Will building a new home delay Janelle’s early retirement? Can Mike and his wife retire early at ages 50 and 55, and how much should they convert to Roth? Maria and her partner keep their finances separate – can Maria cover her own expenses in early retirement? Plus, Joe and Big Al explain the difference between FDIC insurance and SIPC insurance for Edward, who wonders if he should spread his assets between banks for protection. Fajita Willy needs a spitball on his MYGA (multi-year guaranteed annuities) retirement strategy. Nancy wants to know if mandatory seismic retrofit expenses are tax-deductible. And how should Lee manage Roth contributions and IRMAA now that his Social Security disability has finally been approved and he’s received 5 years of back pay?
Jimmy in Wisconsin will have a pension and Social Security. How should he cover his seven year retirement shortfall? Skipper in Texas has some unusual pension options, which one makes the most sense for his retirement needs? Should Mike and Carol in Virginia wait to do Roth conversions if they’ll be in a lower tax bracket in retirement? Where should Duncan in Texas invest in the 10 years before he retires early? Would it be stupid for Jay Z in Minnesota to miss out on free Roth opportunities? Can Ben in San Francisco’s “friend” use the rule of 55 on a rollover retirement plan? And finally, YMYW is fun, but of limited value, according to a recent review.
Big Tex, Paul in Maryland, and Nick in Alabama all need to know how much money they should convert to Roth to pay as little tax as possible. Johnny and June forgot to convert their backdoor Roth money – are they in trouble? Darren in Nevada has no plans at all to do Roth conversions, but surprisingly still listens to YMYW, and still wants a spitball on his retirement and real estate investment strategies. Plus, can Lolly Pop in New Jersey be less miserly and back off on saving for retirement? Can John in South Carolina use this year’s lower income to reduce his Medicare premiums? And finally, if Ordinary Guy in Boston meets an untimely demise, should that change his plans to retire early?
Can Clark Kent’s dad in Hutchinson, Kansas retire at age 50? Will Devin in South Carolina be fat and happy or cutting calories if he retires at 59 and a half? Can Scott Magic in Idaho retire to a good and simple life at age 60? Gina and her wife are 52 and 58. Can they retire in four years, and how much should they be putting in their Roth accounts? Plus, Frenchie in Maine needs a spitball on a Roth conversion strategy with Canadian retirement funds, and Andi shares what she knows about target date funds.
Spitballing on early retirement and Roth conversions to finish 2023. How can Jack and Diane (no, the other, other Jack and Diane, these are the ones in Rochester, MN) bridge the gap to retirement at age 61? Can Michael in San Diego do a Roth conversion without it impacting his taxes? Plus, what should the Flintstones do with their whole life insurance policies? What spitballs of wisdom do the fellas have for Michael, who is “benefit-less” in Kansas City? Then, we wrap up the final episode of the year with the YMYW origin story.
Should Jackson and Elsa from Wyoming fire their financial advisors and shop for lower fees, or switch to do-it-yourself financial planning? Can 34-year-old Bob in Texas retire early at 50, and what’s the best way for him to put an extra $30K to work? How much should 35-year-old Matthew in the middle of nowhere Wisconsin be saving for retirement in pre-tax accounts vs. post-tax accounts? And finally, should Michelle in Minnesota leave excess education savings in a 529 plan or move it to a Roth IRA?
Does the math work for Chris’ early retirement plan? What’s a safe retirement withdrawal rate for Luke, who wants to be part of the financial independence / retire early or FIRE movement? Plus, Jake is about to change jobs, can Joe and Big Al uncover any tax planning opportunities for him? The fellas also explain capital gains tax for our buddy Carl Spackler, they spitball on those capital gains when it comes to selling a house for Olga and for LJ, and Jim wonders about the impact of selling a house on Affordable Care Act subsidies.
Can you retire before age 55 simply by contributing to your 401(k) only up to the company match and then saving to a brokerage account? Joe and Big Al spitball on using this so-called tax “jailbreak” strategy to retire early. Plus, is Christine on track to have $150,000 present value to live on in retirement? Is John stuck just watching his money grow and turn into big required minimum distributions? Can Jackie contribute to a SEP IRA and convert it all to Roth? And what do the fellas think of Lee’s I-Bond emergency fund?
How should your financial strategy change when your income increases dramatically? We’re talking like $450K one year to a million and a quarter the next? (If you guessed Roth conversions might be in the answer you’d be correct!) Joe and Big Al also spitball strategies for when your income is too high to make Roth contributions, and can you use capital gains to contribute to Roth? Can “Alligator Joe” afford to retire early, or does he need to keep gutting it out at his current job wrestling alligators? Should Catherine contribute to her 401(k) or buy company stock before she quits her day job to start a business? The fellas also spitball retirement planning involving structured settlements, inherited assets, and ACA credits, and they discuss transferring annuities to a CD vs. deferring the interest into another annuity.
Asset location strategies, liquidity, and building up tax-free Roth IRA money when retiring early, how growth is taxed in taxable accounts, the pros and cons of rolling an employer retirement plan into a traditional IRA, how stock futures are determined and why stock price matters, and buying 8-week treasuries. And, if you’re planning to make a killing on eBay or at your next garage sale, the fellas get into the weeds on how to maximize your tax savings.
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Setting up your saving and investing strategies when you’re in your 30s can put you on a good path to meeting your retirement goals. Joe and Big Al revisit their financial spitballing over the last couple of years specifically for savers and investors in their 30s and even 20s, some of whom want to retire early.
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Will the Senate pass the SECURE Act 2.0, and will it require a Roth option for retirement savings? Plus, “pandemic unemployment” from the CARES Act and the earned income tax credit. Next, are you eligible to make Roth contributions, and should you contribute only to Roth for retirement? Then, the pros and cons of consolidating retirement accounts, and some early retirement spitball analyses. When you plan to retire early, should you invest in dividend-paying stocks or real estate? And finally, is the bucket investing strategy really that complicated?
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