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What’s the next move for a 22-year-old who wants to retire early at 50? Can another YMYW listener afford to retire by the ocean in 10 months? Can Flowergirl and her husband AND her boyfriend retire next year? Joe and Big Al also check extensive retirement spitball math sent in PDF format. Plus, what are the fellas’ philosophies on single vs. married tax rates when one spouse passes, and how does high state income tax impact a retirement strategy?
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Should you convert money from your pre-tax retirement accounts to Roth now, wait until retirement, or until required minimum distributions kick in? Should a mid-30s couple do Roth Conversions or a Backdoor Roth? Should a 93-year-old open his first ever Roth and start converting? What’s a good retirement savings mix between pre-tax and post-tax? And the fellas do a worst-case scenario retirement spitball analysis.
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How do you determine how much you need in retirement when you factor in taxes, and how does the 4% rule apply? Has one YMYW listener spitballed retirement well enough to convince his wife that they can afford a new luxury truck? Can another YMYW listener take advantage of what seems to be a big opportunity to sell company stock, pay no capital gains tax, and do Roth conversions? Can Big Al’s high school friend do a 1031 exchange to buy a rental property, make it his primary residence in 5 or 10 years, and pay no tax when selling? Is earned income from stock trading still taxable for Social Security if your LLC is in a trust? Finally, a compliment comes in, and Joe and Big Al assume it’s for them.
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Should you save for a house down payment or invest for retirement? How much long term capital gains tax do you pay on a rental property when you sell it after 20 years, and how does a 1031 exchange work? Also, opening a Roth IRA with the Backdoor Roth strategy, and the 5 year Roth withdrawal rules explained. Plus, a couple retirement spitball analyses: are you saving too aggressively for retirement? Can you avoid the Medicare IRMAA, or income related monthly adjustment amount, and high taxes from required minimum distributions?
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The time may be right for a giant Roth IRA conversion, especially now while the market is down, to potentially give you more money to spend in retirement. How does that work with long-term capital gains and dividends, and how much should you convert to Roth, and when, and how? Plus, deciding how to invest 529 plan college savings, whether to save to pre-tax or post-tax retirement accounts, and the ever-popular Backdoor Roth strategy.
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Learn how to craft a retirement plan email question that’ll get you a model retirement spitball analysis. Plus, when should you contribute to Roth IRA, and when and how much of a Roth Conversion should you do? Is it hypocritical to prioritize investment returns over your conscience and values? Joe and Big Al talk ESG, or environmental, social, and governance investing, and they evaluate a strategy to keep taxes low while helping your kids buy a house. Finally, your comments about YMYW.
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“Are we on track for retirement?” The ever-popular Retirement Spitball Analysis is all based on that simple question. Joe and Big Al spitball retirement for listeners planning to retire in just a few years, wondering if they should save to pre-tax or post-tax accounts, and strategizing around long-term capital gains, dividends, and Roth conversions.
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Check out YMYW on Feedspot’s Retirement Podcasts and Financial Planning Podcasts!
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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Does it make sense to do larger “Calvin Johnson” (Megatron, aka mega backdoor) Roth conversions when the financial markets are way down? Should you convert to Roth now, or in retirement? How do you spitball the right amount to have in 529 plans for education savings? And are the rules for doing a backdoor Roth the same if you’re married filing separately?
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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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Should those in the 35% tax bracket contribute to traditional 401(k) or Roth 401(k)? Should a self-employed cryptocurrency investor do Roth conversions or tax gain harvesting? Also, a retirement spitball for a couple, age 35, wanting to retire with $5M at age 60. Plus, do the SECURE Act rules for required minimum distributions (RMDs) apply when inheriting an inherited IRA? Finally, comments on some of the proposals in the latest version of the Build Back Better Act, which is currently being considered by the Senate.
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What do Joe and Big Al think of the “Buy, Borrow, Die” strategy of the uber-wealthy, and how could it work on a smaller scale? Plus, stacking capital gains vs. Roth conversions, contributing to a non-deductible IRA vs. a brokerage account given ordinary income tax vs. capital gains tax, and minimizing the tax when a trust is the beneficiary on a thrift savings plan (TSP). Also, how to estimate Social Security benefits with a future salary of $0, and why delay Social Security to age 70 if you don’t need the money? Finally, is it bad etiquette to “ghost” an advisor? Should you hire a financial advisor near you?
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In what order you should contribute into which accounts for retirement? Joe & Big Al explain the reasoning behind the sequence of retirement savings, and where a health savings account (HSA) fits in that sequence. Following some retirement plan spitball analyses and Roth conversion strategizing, the fellas explain whether capital gains are taxed progressively, how required minimum distributions are taxed, and they revisit indexed universal life insurance.
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Questions answered on retiring overseas and foreign earned income exclusion eligibility, using your tax refund thanks to the foreign earned income exclusion for a back door Roth conversion, and working abroad and contributing to a health savings account (HSA). Plus, should you contribute to Roth accounts, pre-tax accounts, or a brokerage account when nearing early retirement? Are substantially equal periodic payments (SEPP) from your retirement savings a good idea to bridge the gap between retiring early and age 59 and a half? And finally, is it ever a good time to time the market?
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You’ve had enough of the 9 to 5 and are ready to punch early. Are you financially prepared for a long and early retirement? Joe and Big Al provide a spitball analysis. And of course, the ever-popular Roth IRA conversions: how much to convert to Roth, when and how to pay the tax on a Roth conversion, and why not pay Roth conversion taxes out of the retirement account you’re converting from?
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