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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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Spitballing Retirement for Fat Wallets

Barney and Betty in Maryland hit the jackpot. How’s Barney’s strategy for net unrealized appreciation, retirement withdrawals, and asset location for his $5 million employee stock ownership plan? Nick in the PNW will have $8 million when he retires early at 53. Should he contribute to his 401(k) or do the good ol’ mega backdoor Roth until then? Those are just a couple of the fat wallets Joe Anderson, CFP® and Big Al Clopine, CPA spitball on in this episode of YMYW. Plus, should Allen in New Braunfels’ recently widowed sister contribute to her traditional IRA and do some Roth conversions? Should Alicia in Denver take Social Security early to pay off her rental property, and how can Vern in Wickenburg Arizona buy a new home before or during the sale of his current home? Finally, Bryan in Washington needs to know the best investment strategy for his thrift savings plan, and Lyse in Georgia wonders when in a market downturn you should start spending your cash. 

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27
FEB
2024
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Unspoken Assumptions About Collecting Social Security

YMYW listener Alan feels that there are two unspoken assumptions that many different podcasters make when it comes to claiming Social Security benefits. Today on Your Money, Your Wealth® podcast 437, Joe Anderson, CFP® and Big Al Clopine, CPA spitball on those assumptions, along with safe retirement withdrawal rates before and after Social Security and pension for Rick and Jen, and a thrift savings plan (TSP) and Social Security retirement strategy for Theresa. Plus, Mark and his wife are semi-retired at 51 and 44. Are they going to run out of money? Where should Mary be saving for retirement, and how should she handle large Roth conversions before required minimum distributions (RMDs) kick in? 

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11
JUL
2023
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Ready to Retire? 5 Retirement Spitball Analyses

Joe and Big Al spitball five different retirement plans: Is Jaybird on track to retire with a decent nest egg? Should Ted and his wife use the retirement smile spending pattern and spend more early in retirement? Is it safe for Aaron to retire at age 59 and a half? How much can Karla convert to Roth for the most tax-efficient retirement withdrawal plan? LEO Jay has Roth TSP retirement strategy questions, and Lynn suggests a super-easy Roth conversion calculator – but Big Al’s got an even easier idea. 

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20
JUN
2023
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Medicare IRMAA, Roth Pro-Rata, & Real Estate Strategies

Joe and Big Al attempt to clearly and succinctly explain modified adjusted income for Medicare and IRMAA, and the pro-rata and aggregation rules for Roth conversions. Will a combat zone TSP transfer be subject to those rules? Plus, joint tenants with rights of survivorship vs. transfer on death for a brokerage account, reducing taxes on the sale of a timeshare, how much to spend on home improvements, and using a reverse mortgage instead of long-term care insurance. And wait ’til you hear the fellas’ thoughts on the best way to pay the least amount of tax when you cash out your retirement savings to buy gold and silver.

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31
JAN
2023
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Roth IRA 5-Year Rules: How to Withdraw Money With No Taxes or Penalties

Joe and Big Al clarify once and for all those 5-year clocks for withdrawing money from your Roth accounts. How do the 5-year Roth IRA rules impact the taxation of dividend income? Do the 5-year rules impact thrift savings plan (TSP) to Roth conversions as well? Plus, why contribute to a Roth in the first place and lose today’s tax savings? Joe and Big Al rise to that challenge and they discuss Roth conversions and required minimum distributions from an inherited IRA. 

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15
NOV
2022
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Roth IRA, 457, TSP, and Retire Early Spitball

Joe & Big Al talk strategy for converting to Roth and paying tax from the IRA when you have limited funds, eliminating required minimum distributions (RMD) on a Roth 457 and avoiding the 5-year Roth clock, and Roth TSP strategies. Plus, the fellas spitball pension options, retiring early, and an intricate – and potentially risky – deferred compensation strategy.

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Free Financial Assessment

10
MAY
2022
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Stock Acquisition, HSA, AMT, TSP, RSU, and Trust as Retirement Beneficiary

Should a trust be the beneficiary of your retirement accounts? Are withdrawal restrictions and required minimum distributions (RMD) good reasons to transfer out of the thrift savings plan (TSP) at retirement? How do you handle the stock acquisition of a company held in your retirement account? Plus, alternative minimum tax (AMT) explained, and strategies for health savings account (HSA) contributions and restricted stock units (RSU).

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Free Financial Assessment

01
FEB
2022
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Estate Planning, Social Security, and TSP Roth Conversions

Is there a step up in basis on, and advantage to, a joint-tenants-with-rights-of-survivorship brokerage account? Is a charitable remainder trust a good way to liquidate property, and what would be the rate of return on it over 20 years? Is there a point to Roth conversions when leaving your entire estate to charity? Should you name your trust as the beneficiary on your retirement accounts? How do ex-spouse and survivor Social Security benefits work? When should you draw from the three-legged stool of Social Security, pension, and annuity in retirement? Plus, Roth conversions from a thrift savings plan (TSP).

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Free Financial Assessment

09
NOV
2021
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Charitable Giving and Roth Conversion Retirement Tax Strategies

How to make the most of a retirement strategy that involves a thrift savings plan, Roth IRA conversions, and charitable giving from a donor-advised fund. (Or maybe a QCD instead.) Also, how to calculate multi-year Roth conversions, and do you lose compound interest when doing Roth conversions? Plus, Joe and Big Al’s thoughts on closed-end […]

16
MAR
2021
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Social Security WEP, GPO & Roth IRA Conversion Strategies

The windfall elimination provision (WEP), government pension offset (GPO), and spousal Social Security benefits. Also, Roth IRA conversions and Medicare, Roth conversions from a thrift savings plan (TSP), and conversions to buy real estate. Plus, asset location and other tax planning strategies beyond Roth IRA conversions, like life insurance and charitable remainder trusts. Subscribe to […]

26
MAY
2020
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Why Not Just Go All in On Vanguard’s Total Stock Market Index Fund VTSAX?

The Vanguard Total Stock Market Index Fund (VTSAX) comes very highly recommended by JL Collins in his book, The Simple Path to Wealth. So why not put all your money into it? Plus, Joe & Big Al answer your questions on the 4% rule for retirement withdrawals, what to do before and after age 59 […]

21
JAN
2020
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Roth Conversions From a Thrift Savings Plan TSP?

The thrift savings plan (TSP) explained, and the rules around Roth conversions from TSPs. Plus, Joe and Big Al answer your questions about, what else, Roth conversions and Roth contributions: age limits on making conversions, backdoor Roth conversions, Roth contribution phase-outs and recharacterizations, and the pro-rata rules. Plus, Joe explains, again, his distaste for fixed […]

31
DEC
2019
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Should You Convert to Roth IRA All at Once or Over Time?

How much of a Roth conversion should you do and when? Does it make sense to convert to a Roth IRA all in one year, or to do it over time, based on your age? Joe and Big Al explain the reasoning behind their answer to this common retirement investing question. Plus, they answer your […]

10
DEC
2019
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Roth Conversions, Life Insurance & More: Email Round-Up

An entire episode dedicated to money questions that run the gamut: from Roth conversions and the Mega Backdoor Roth strategy to IULs to insure future income, reverse mortgages in recession, divorce and retirement accounts, and much more. Listen to the podcast on YouTube:  Subscribe to the YMYW podcast  Subscribe to the YMYW podcast newsletter FOLLOW […]

10
SEP
2019
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