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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 bracket. Plus, zero coupon municipal bonds and the de minimis rule, and target date funds as part of Paul Merriman’s Two Funds for Life strategy. Finally, how do dividends figure into the 4% rule for retirement withdrawals, and should that 4% come from stocks or bonds?

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22
NOV
2022
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Spitballing Retirement Planning in Your 40’s & 50’s

A compilation of some of Joe and Big Al’s retirement plan spitballing specifically for those in their 40s and 50s – a critical time on the path to retirement. Is your financial plan set up so you pay as little tax as possible? Does it take volatile markets and potential future tax increases into account? Have you got a strategy nailed down for Roth conversions, or backdoor Roth, or pension options? Maybe you’re making big decisions about what to do with your money between now and when you retire, like buying a house vs. saving for retirement? Are you comfortable with the retirement lifestyle you’re creating? Do you know what you’ll do with your time once you’re permanently off the clock? 

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27
SEP
2022
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Where to Find Retirement Income When the Stock Market Freaks Out

Equitable accumulators, cash management accounts, and Social Security: with today’s market volatility, how can you squeeze a few more dollars of income out of your retirement savings? Any reason not to use a robo-advisor for decumulation, in other words, spending down those savings? Plus, a pension retirement spitball follow-up, and is it possible to avoid tax liability on a lump sum withdrawal from a 401(k)? Finally, is Joe’s marriage the canary in the Coors Light Party Ball for YMYW?

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21
JUN
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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Retirement Spitball: Social Security, Pension, and Self-Employed

Spitballing retirement for a police officer turning teacher, a self-employed small business owner, an early retiree with an employee stock ownership plan (ESOP) wanting to do Roth conversions and withdraw 5 or 6% in retirement, and a pension and Social Security analysis. Plus, how many months of expenses should you save in your emergency fund? Also, you may know where Ric Edelman and Dave Ramsey stand on 15 vs. 30-year mortgages and using cash vs. credit, but what does YMYW think? Kyle Stacey, CFP® fills in with Big Al Clopine while Joe Anderson is on vacation.

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05
APR
2022
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When Must You Pay Roth Conversion Taxes?

When do you have to pay the taxes on a Roth IRA conversion to avoid any IRS penalties? Was it a mistake to convert to Roth IRA? What percentage of your assets should be in tax-free, tax-deferred, and taxable accounts to give maximum flexibility in retirement? Do Roth conversions count as income toward your eligibility to contribute to a Roth, and finally, how will a pension be taxed?

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Free Financial Assessment

29
MAR
2022
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Retirement Pension Lump Sum or Monthly Annuity Payment?

Should you take your pension all at once in a lump sum when you retire, or spread it out over monthly annuity payments? What if the lump sum choice requires moving your pension to an investment plan? Or maybe your only pension options are either 10-year period certain or joint with rights of survivorship? All of these pension spitball analyses are compiled into this single episode to help you choose between your own pension options.

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Free Financial Assessment

30
NOV
2021
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What to Do When You Own Too Much of One Stock

If your portfolio is overweighted in one or two individual stocks, here are some ways to diversify those concentrated stock positions. Is using a donor-advised fund a good choice? Plus, how does the IRS know if a required minimum distribution is a qualified charitable distribution? From which pool of money should you pull extra retirement income? Also, structured notes, and paying Grandma for daycare without impacting taxes on her pension – lump sum or monthly payments? Finally, the fellas provide their thoughts on starting a career in financial planning.

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Free Financial Assessment

10
AUG
2021
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Should People in High Tax Brackets Save in Roth Retirement Accounts?

Questions answered about Roth 401(k) contributions and “Megatron” (that is, mega backdoor) Roth contributions for highly compensated employees, and the Roth conversion strategy of filling the tax bracket. Plus, moving a pension to an investment plan, owning real estate in a self-directed IRA, paying off the mortgage vs. refinancing, spousal vs. survivor Social Security benefits, rolling a whole life insurance policy to a variable annuity, and more.

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Free Financial Assessment

01
JUN
2021
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Monthly Retirement Pension Vs. Lump Sum Payment: How to Choose

Choosing the pension lump sum or monthly payment: let it ride, roll it, or annuitize it? Plus, spitball analyses involving the 72(t) tax election, a donor-advised fund, 529 plans, and early retirement. Also, is growth on after-tax 401(k) contributions tax-free? How much of the portfolio should be in tax-free, taxable, and tax-deferred accounts? How does […]

09
MAR
2021
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What’s the Best Way to Take Retirement Distributions?

Drilling down into the specifics of retirement distribution strategies: dollar cost averaging, pro-rata withdrawals, and buckets vs. the total return approach. Plus, a retirement withdrawal strategy with a side of pension and Social Security, another mortgage payoff question, the small business solo 401(k) trap, an LLC for a kayak side-hustle, and FIPhysician.com says nice things […]

26
JAN
2021
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How to Choose Your Pension Options and Retirement Withdrawal Strategy

Welcome to 2021! In this first episode of the year, Joe and Big Al go over estate planning strategies for CFP® candidate/Redditor Nate in SC, they do a spitball analysis for John in TN who wants to retire early, a retirement withdrawal and 529 plan strategy for Ace in TX, and a breakdown of pension […]

05
JAN
2021
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YMYW Spitball Analysis 2: Retirement and Social Security

The YMYW Retirement Plan Spitball Analysis was so popular that it’s time for part 2! Where do Roth conversions, your primary residence, and rental real estate investment properties fit in your retirement plan? How much of your Social Security is taxed, and will taking your pension lump sum before taking Social Security have an impact […]

25
AUG
2020
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Tanja Hester on the Flexibility of Financial Independence

“The sooner we can understand the link between our money and how we spend our lives, the better.” Tanja Hester (called the Matriarch of the women’s FIRE movement by the New York Times) returns to YMYW to discuss the value of our time, how it’s connected to our finances, and the options financial independence provides […]

03
DEC
2019
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Mad at the Roller Coaster? Then You Don’t Understand the Ride

Back to investing basics with Matt Balderston, CFP® from Pure Financial Advisors: what makes for a wise investing philosophy while on the market volatility roller coaster? Plus, answers to your money questions: How do you find a financial fiduciary? How do you avoid people with bad financial intentions? What is a good investment policy statement? […]

03
SEP
2019
LISTEN NOW
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