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9 Answers to Boost Tax-Free Roth Retirement Income

Joe and Big Al spitball on paying the tax on your Roth conversions: if you take the money out of your retirement account, what does Joe mean that you’ll be “paying the tax to pay the tax to pay the tax”? Can you pay it from the Roth account itself, or from your monthly pension tax withholding? Are the fellas wrong on this whole topic altogether? They also spitball on withdrawing Roth 401(k) contributions that were rolled to an IRA, those infamous 5-year rules for withdrawals from Roth accounts, when to do Roth conversions, saving to tax-deferred, taxable, or tax-free accounts, and how long-term capital gains taxes fit into the picture. Plus, consolidating individual stock investments, the fate of the home office deduction, and what Joe thinks about the Apple Podcasts reviewer who says he’s “checked out”.

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10
DEC
2024
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Rules for Inheritances and Making Roth Contributions for Others

Can Ted and Georgette convert $1.6M in an inherited trust to Roth without distributing it? Should the trust own their home so they can use the home equity? Melissa was added as joint owner on her parents’ bank accounts after a medical event, but what have they done? Should Ralph and Alice use the required minimum distribution from their inherited IRA to pay Roth conversion taxes? Plus, can Theodore contribute to his wife Louise’s Roth IRA? Can Marc make Roth contributions for his grandkids? Joe and Al also come up with a unique way for John to potentially pay the tax on his Roth conversion using his home equity.

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19
NOV
2024
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Spitballing Retirement During the Expensive Kid Years

Market declines just before you retire, or early in your retirement, can really screw up your retirement income strategy. If you’re in the middle of the expensive kid years, how do you avoid this sequence of returns risk when making your retirement plans? That’s “Jaclyn Smith’s” question, today on Your Money, Your Wealth® podcast 485. Plus, can Vern’s wife collect Social Security at age 63, then switch to spousal benefits at age 70? Matt wants to know if 2026 catch-up Roth contributions will be subject to the pro-rata rule, and Tom and Amy are trying to figure out how to avoid Medicare’s monthly income-related adjustment amount, or IRMAA, in their plan for Roth conversions. 

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11
JUN
2024
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What to Do When There’s Too Much Money in Your Traditional IRA

How can you reduce taxes, IRMAA, net investment income tax, and required minimum distributions when you’ve got too much money in your tax-deferred retirement account – and just how much Roth conversion should you do? Plus, can you contribute to a Roth by transferring stocks “in kind”? If the check you send off to pay your estimated taxes isn’t cashed before the deadline, is it late? How does SECURE 2.0 impact 529 plans, and is 529 better than Roth IRA for college savings? Finally, Joe and Big Al spitball a 401(k) in-plan Roth conversion and retirement account consolidation strategy.

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04
APR
2023
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How to Reduce Taxes and Get Better Investing Returns? Asset Location

Generating “tax alpha” to get better returns on your investments: which investments should go in your traditional IRA vs your Roth IRA, and does that asset location depend on your age? Plus, Joe and Big Al spitball whether to roll a TIAA 403(b) to an IRA or take the annuity, and they spitball retirement, Roth conversion, and Roth contribution strategies for an overseas officer with a military pension, and for Americans working abroad who qualify for the foreign earned income exclusion.

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28
MAR
2023
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What to Do When You Get a Huge Pay Increase

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. 

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21
FEB
2023
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  • Financial Planning
  • Investing
  • Retirement Planning

Why You Should Consider Roth Conversions in a Down Market

The first eight months of 2022 have been tough for investors. Stock indexes around the world have declined by double digits, while historically safe bonds have suffered their worst performance in decades. Eventually, markets will resume their upward trend, but unfortunately, no one knows exactly when that time will come, and furthermore, no one can […]

19
AUG
2022
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