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Rising Costs and Retirement Unknowns? Here’s What to Do

Should Al and Peggy in Illinois keep hammering pre-tax retirement savings, or should they pivot to post-tax Roth for better tax diversification? Which pension option is best for their early retirement plans? Long-term care insurance premiums are going up endlessly for Eloise in Connecticut. Is...

03
FEB
2026
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Roth Conversions: When to Make ‘Em, When to Take ‘Em

A YMYW listener from Missouri and his wife are retired at 69 and 67, with less than $2 million dollars. Should they continue converting retirement savings to Roth for the tax-free growth? What should they do about long term care insurance? More importantly, is our...

16
SEP
2025
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Are These Millennials Saving Enough to Retire Before 60?

Pam and Jim in Phoenix are 38 and 41 and want to retire at 59 and 62. Matt and his wife in Pennsylvania are both 39 and want to retire at 57. Are these millennials on the right financial path, or have they brunched and...

05
AUG
2025
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When to HOLD OFF on Doing Roth Conversions

John in Boston is in the 32% tax bracket. Should he do Roth conversions? Flight Deck Dad and Irish Girl in Pensacola have a lot of tax-free pension income. Should they do Roth conversions? Bert and Ernie in New Jersey wonder if they should convert...

13
MAY
2025
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Defusing a Future Tax Bomb With Roth Conversions

Does it make sense for Alex and his wife in Massachusetts to do Roth conversions now to the top of their eventual tax bracket? Steve in San Diego got serious about saving for retirement after Joe and Big Al gave him some tough love 5...

31
DEC
2024
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Exchange Funds Explained, Roth Conversion Timing

What is an exchange fund and is it a good thing if you have a lot of capital gains, like Bryan in New York? What should be the timing and ordering of Billy Joe and Bobby Sue’s Roth conversion strategy to help them achieve 33...

27
AUG
2024
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Which Account Should Fund Living Expenses in Retirement?

Should 70-year-old Bob live off of capital gains and dividends from his mutual funds plus Social Security, or should he sell poor-performing mutual funds for living expenses and reinvest the cap gains and dividends? Which account should Neal’s 76-year-old Mother use for living expenses? Should...

14
MAY
2024
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How to Manage Taxes When You Win the Lottery

So you won the lottery – congratulations! After you celebrate, should you rip off the band-aid and convert the entire lump sum payment to a Roth IRA? Also, Bucky in WA is required to have the same asset allocation in his traditional and Roth 401(k)....

23
APR
2024
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Does Your Financial Advisor Just Want to Collect Fees?

Why would a financial advisor suggest that Frank in Lake Wobegon sell a piece of inherited property, pay 25% tax, and invest the lump sum? Mark in Florida is 72 and invested in CDs. Should he go back to his financial advisor, or just buy...

19
MAR
2024
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Market Timing, Pension & Roth Conversion Retirement Spitball

How will a diet COLA on a pension affect retirement plans for Joe and Barb in Tulsa? Percy in South Carolina has a pension too. He’s timing the market, but should he change his investing strategy as he approaches retirement? Plus, Michael in Virginia needs...

05
SEP
2023
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Early Retirement Withdrawals & Capital Gains Tax Explained

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...

08
AUG
2023
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Capital Gains vs Dividends: What’s the Difference? | Financial Tip

Pure’s Senior Financial Planner, Richard Alexander, CFP®, AIF®, explains the difference between capital gains and dividends. Capital gains are profits from selling investments at a higher price, while dividends are income paid out by corporations to stockholders. FREE GUIDE | 10 Tips for Real Estate Investors Transcript Capital Gains vs Dividends. Both are sources of […]

02
JUN
2023
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Mutual Funds vs. ETFs, SECURE 2.0, & Capital Gains Strategies

Are low-cost mutual funds or ETFs better investments in a tax-advantaged account? Also, more strategizing from that SECURE Act 2.0 529 plan provision, the pros and cons of selling a rental house now or holding it until you pass, and an easy-breezy self-employed retirement account...

14
MAR
2023
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How to Forecast Your Expenses in Retirement

What will you actually need to spend in retirement? Joe and Big Al explain how to really think about and calculate your retirement expenses. Plus, if you want to reduce your tax-deferred account balances, does it make more sense to do Roth conversions or reinvest?...

29
NOV
2022
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Life Insurance, Muni Bonds, and Dividend Stocks in Retirement

Joe and Big Al discuss LIRPs, or life insurance retirement plans, they spitball whether to take full pension survivor benefits or buy a life insurance policy, and whether to sell losing stocks for even bigger losers to take advantage of the 0% capital gains tax...

22
NOV
2022
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