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Thinking of a possible reason to tap Roth earlier then planned

"One thing I’d check is whether the home-sale proceeds can actually be put back into the Roth. Unless the 60-day rollover rule applies, I believe that Roth space is permanently lost. That said, I’m not sure preserving the Roth is automatically the right answer either. If the alternative is holding highly appreciated taxable assets for heirs, those may receive a step-up in basis at death, potentially making that growth effectively income-tax-free as well. I’d compare the actual borrowing cost against the value of preserving the Roth, the embedded gains in taxable assets, and the estate plan rather than assuming the Roth should never be touched."
- Mark Gardner
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Frittering away Frugality 

"Okay, I have a visual of that now. 😩 I have a membership, but it is hard to get out of there for less than $150 and you only have 10 items. Purchasing gas there pays for the membership."
- Olin
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Reluctantly Saving Money

"Definitely good to have first-world problems lol. I'll admit my ignorance: I have no idea what a smart thermostat actually is. My 'dumb' one works perfectly well—what exactly makes an upgrade smart?"
- Mark Crothers
Read more »

Every Writer Has a Beginning: Jonathan’s First Essay

"Thank you Dana! I had to smile at your fourth-grade opening line, and especially the giant Hershey bar! One thing I’ve discovered during this journey is that every writer really does have a beginning. I’m also glad Jonathan’s title suggestions helped you. He certainly had a gift for them."
- Andrew Clements
Read more »

A $30,000 Mistake

IF YOU’RE IN YOUR early 60s and retired, you probably have a lot of financial questions on your mind. The next few years may be among your lowest-income and lowest-tax-paying years. Your salary and bonus years are behind you. Social Security and required minimum distributions from your IRAs and 401(k)s have not started yet. You are hearing advice about doing Roth conversions during this low-tax window, and the arguments are compelling. You may also be thinking about consulting or part-time work to stay active and bring in some income. This article is about the hidden cost of those decisions: how income choices you make now can affect both your health insurance costs today and your Medicare premiums later. If you don’t understand the interaction, the surprise can cost thousands of dollars. The ACA cliff is back… and it’s steep The enhanced ACA subsidies that softened premium costs from 2021 through 2025 expired at the end of last year. Congress didn’t extend them. That means the hard cliff is back in full effect for 2026. The cliff sits at 400% of the federal poverty level. Cross it by even $1 and you lose your entire premium tax credit. It’s not a partial reduction; it’s all of it. If you aren’t prepared, that can create real cashflow problems. For 2026 coverage, based on the 2025 federal poverty guidelines, those thresholds are:
  • Single filer: $62,600 
  • Married couple: $84,600
  • Family of three: $106,600
Per KFF’s analysis, a 60-year-old earning $62,000 pays roughly $515 a month in health premiums, about 10% of income. The same person earning $64,000, or just $2,000 more, pays around $1,244 a month, roughly 23% of income. That’s not a typo. Two thousand dollars of extra income triggers roughly $8,750 in extra annual premiums.  The income figure that determines your eligibility is your MAGI. It includes everything you might be doing in retirement to manage your finances: Roth conversions, capital gain realizations, dividends, interest, part-time income and Social Security if you’re already drawing it.  The IRMAA clock starts when you’re 63, not 65 The ACA cliff is only part of the issue. Medicare uses a two-year lookback to set your premiums. Your 2028 Medicare Part B and Part D costs will be determined by your 2026 income, the same year you’re managing your ACA cliff right now. The 2026 IRMAA thresholds reflect 2024 income for those already on Medicare. They give us a reasonable proxy for what 2028 will likely look like, as the Centers for Medicare and Medicaid Services won’t publish the actual 2028 brackets until late 2027. The first IRMAA tier kicks in at $109,000 for single filers and $218,000 for couples. Cross that threshold in 2026, and when you turn 65 in 2028, you’ll be looking at roughly an extra $81.20 per month per person in Part B premiums or $974 per person per year, on top of the standard $202.90/month premium. That’s the first tier. The surcharges climb from there. And both Part B and Part D carry their own IRMAA surcharges, so couples can easily see $2,000 to $4,000 in added annual Medicare costs from a single income year that was too high. It is ironic but the income year most likely to push you over an IRMAA threshold is often one of your last years before Medicare when you might be selling an asset, doing a large Roth conversion, or drawing down a pre-tax account to fund living expenses. Why do these two cliffs need to be planned together? Put these two together and you can see the problem clearly. Take a 63-year-old couple with $80,000 of MAGI: they’re under the $84,600 cliff, subsidies intact. Now add a $20,000 Roth conversion. That one decision pushes them to $100,000 and it wipes out the entire ACA subsidy this year. The same conversion, sized larger or stacked with a capital gain that crosses $218,000, would also raise their Medicare premiums starting in 2028. That is why the two cliffs need to be modeled together, not checked separately after the fact. Where the $30,000 comes from:
ScenarioEstimated Cost
Couple crosses the ACA cliff in 2026, full subsidy lost≈ +$21,500/yr
Same 2026 MAGI over the first IRMAA tier triggers the 2028 Medicare surcharge (Part B + D, couple)+$2,297
If 2027 income also stays over the ACA cliff≈ +$21,500 more
Combined two-year exposure from the same income patternPotentially $45,000+
The chart below plots 2026 MAGI against both costs at once: the bars are your annual ACA premium (indigo while subsidized, red past the cliff), and the line is the annual Medicare surcharge that same income locks in for 2028. If you’re 63 in 2026: Too much income this year and you lose ACA subsidies, costing potentially $10,000 to $25,000 more in health premiums in 2026 and 2027. Too much income this year and you trigger IRMAA, paying $2,000 to $8,000+ more in Medicare premiums annually starting in 2028. Both cliffs draw from the same income year at once, not in sequence. Your 2026 MAGI sets your ACA subsidy right now, and that same 2026 return sets your 2028 Medicare premium through the two-year lookback. Because the two systems are run separately (one by the IRS and the Department of Health and Human Services, the other by Social Security and the Centers for Medicare and Medicaid Services) most people never see the combined exposure until it’s already locked in. What you can do about it The goal is to keep your 2026 MAGI below both cliffs where possible, or at least to be deliberate about which cliff you’re willing to cross and why.
  • Traditional IRA contributions: reduce MAGI dollar-for-dollar, if you have earned income
  • HSA contributions: a pre-tax reduction, but watch the Medicare timeline
  • Capital gain timing: deferring a sale past Medicare can bypass the pincer entirely
  • Roth conversions: the opposite, since they add directly to MAGI
For people with earned income, deductible Traditional IRA contributions can be one of the most direct MAGI reducers. If you or your spouse has earned income, you can contribute to a Traditional IRA and deduct it, reducing MAGI dollar-for-dollar. The 2026 limit is $7,500 per person, or $8,600 if you’re 50 or older. For a couple where one spouse is still working, that’s potentially $17,200 off your MAGI. One catch: if you’re covered by a workplace retirement plan, the deduction phases out at higher incomes. For 2026, between $81,000 and $91,000 of MAGI for single filers, or $129,000 and $149,000 for joint filers when the contributing spouse is covered. The counterintuitive part: you’re putting money into a pre-tax account when your tax rate is relatively low, with the understanding that you’ll pay taxes on it later and possibly at higher rates. For some people, that trade doesn’t pencil out. For others, protecting a $10,000 ACA subsidy this year is worth the future tax cost. The math depends on your specific situation, and it’s worth modeling rather than assuming. Health savings account contributions work similarly. Pre-tax contributions reduce MAGI directly. The catch is that you must be on an HSA-eligible high-deductible health plan to contribute. If your ACA marketplace plan qualifies, and you’re not yet on Medicare, this can be a meaningful lever. The 2026 limits are $4,400 for self-only coverage and $8,750 for family coverage, plus an extra $1,000 catch-up if you’re 55 or older. Plan to stop contributions before Medicare begins. Medicare’s Part A coverage can backdate up to six months, which can turn recent contributions into excess contributions, so watch that timeline carefully. Capital gain timing is often the biggest swing. If you’re planning to sell appreciated assets, a taxable brokerage position, a rental property, anything with embedded gain, the year you do it matters enormously. Deferring a large realization from 2026 to 2029, after Medicare begins, sidesteps both the ACA cliff and the IRMAA lookback simultaneously. That’s not always possible, but it’s worth asking whether the transaction needs to happen this year. Roth conversions don’t reduce MAGI, they add to it. If you’re in the pincer zone, aggressive Roth conversion in 2026 can push you over the ACA cliff and set your 2028 IRMAA tier at the same time. That’s not an argument against Roth conversions generally. It’s an argument for sizing them carefully relative to where you are on both cliff structures. If you’re already below both thresholds with room to spare, a modest conversion can make sense. If you’re hovering near either line, the math changes quickly. One longer-horizon point, separate from the two-year window this article is about: if you’re in the pre-pincer years, your late 50s or early 60s, modest Roth conversions now can reduce the size of your future RMDs. Smaller RMDs mean less forced taxable income in your late 60s and beyond, which means less pressure on the IRMAA tiers you’ll face once you’re on Medicare. That is a multi-decade trade, not a fix for the immediate cliff, and it works best when you have a decade or more of runway before Medicare enrollment. Plan this out The two-year lookback means you lose the ability to affect your 2028 Medicare premiums after December 31, 2026. You can’t file an amended return and get a different IRMAA. There is an appeal process through Social Security, but it’s designed for genuine life-changing events like retirement or divorce, not for voluntary income decisions that turned out to be more expensive than expected. For ACA purposes, 2026 is the year in question. January 1, 2027 starts a new calculation. That means the window for planning is now. Not 2027, when you’re closer to Medicare. ________________________________________________________________________________ John Urban is the founder of RetireSmartIRA, a retirement tax-planning app. Earlier, he founded GT Nexus, a supply-chain software company acquired by Infor in 2015. He lives in Northern California with his wife, Kathy, and enjoys time with family, travel, reading, Bay Area sports, and the occasional deep dive into the fine print of the tax code.
Read more »

Happy 250th Birthday America

"My Irish paternal great-grandfather came in the 1850's and my German maternal great-grandfather came from Germany in the early 1860s. Like you, Nick, my grateful heart knows no bounds."
- Mike Lynch
Read more »

Haunted Head

"Edmund, I think we're all circling the same tension around retirement. Two hundred and fifty years of Western work ethic doesn't loosen its grip easily—I felt that pull too. I'm sixteen months into retirement now. Before I stopped working, I told myself a story: take a full year off, extend it through the following summer, then ease into a part-time, low-pressure job by my second fall. Looking back, it wasn't really a plan. I think it was more a concession to my own anxiety about productivity, a way of promising my future self I wouldn't drift too far from being useful. But somewhere along the way, I fell in love with having full agency over my time. I can say with certainty now: there will be no job waiting for me this fall. What's interesting is that I didn't stop being productive—I just started doing it differently. Without really planning to, I built my own structure: mentoring in sports, then founding and running a new racket sports club. My need for purpose didn't disappear with retirement; it simply went looking for a new form to take. Maybe that's the real trick to a contented post-career life—not the absence of productivity, but trading forced productivity for chosen productivity. Doing the work because it's yours, not because it's required. But most importantly of all: still leaving enough empty space in the week to sit on a cliffside and watch the sharks."
- Mark Crothers
Read more »

Should I Lock in CD Rates Now or Stay in Money Market?

"Yesterday's post on Can I Retire Yet? titled What to do with a Windfall and a current baker's dozen comments addresses many of the same concerns you ask about in this HD forum post. You may find David Champion's post interesting. The what for and when funds will be used seem to be key and would be particular to the specific decisions each of us each of us makes with a windfall of cash. I expect liability matching and liquidity will be key to my decisions along with having a sufficient cash cushion for when my planning turns out wrong."
- William Perry
Read more »

Reminded of Jonathan’s Grace

"It’s always interesting when a book keeps pulling you back in for “just one more chapter.” That usually says a lot about how engaging and thought-provoking the writing is. Thanks for sharing your experience, it’s helpful to hear how a book can leave such a strong impression on a reader."
- Paul Welch
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Tempted by the Shiny and New: Another HD Car Post

"Ha Ha Dunn, Usually I would not even consider a first model year vehicle, HOWEVER: 1) this is a Toyota, and 2) we watched a review of the vehicle by The Care Care Nut, and that convinced us it was OK to purchase it. Main selling points were: 1) most of the components, chassis, hybrid engine, and dash layout are the same as several other Toyota models, and 2) it is assembled in their Lexus plant in Japan. PS, we love it!"
- DavidHLancaster
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Thinking of a possible reason to tap Roth earlier then planned

"One thing I’d check is whether the home-sale proceeds can actually be put back into the Roth. Unless the 60-day rollover rule applies, I believe that Roth space is permanently lost. That said, I’m not sure preserving the Roth is automatically the right answer either. If the alternative is holding highly appreciated taxable assets for heirs, those may receive a step-up in basis at death, potentially making that growth effectively income-tax-free as well. I’d compare the actual borrowing cost against the value of preserving the Roth, the embedded gains in taxable assets, and the estate plan rather than assuming the Roth should never be touched."
- Mark Gardner
Read more »

Frittering away Frugality 

"Okay, I have a visual of that now. 😩 I have a membership, but it is hard to get out of there for less than $150 and you only have 10 items. Purchasing gas there pays for the membership."
- Olin
Read more »

Reluctantly Saving Money

"Definitely good to have first-world problems lol. I'll admit my ignorance: I have no idea what a smart thermostat actually is. My 'dumb' one works perfectly well—what exactly makes an upgrade smart?"
- Mark Crothers
Read more »

Every Writer Has a Beginning: Jonathan’s First Essay

"Thank you Dana! I had to smile at your fourth-grade opening line, and especially the giant Hershey bar! One thing I’ve discovered during this journey is that every writer really does have a beginning. I’m also glad Jonathan’s title suggestions helped you. He certainly had a gift for them."
- Andrew Clements
Read more »

A $30,000 Mistake

IF YOU’RE IN YOUR early 60s and retired, you probably have a lot of financial questions on your mind. The next few years may be among your lowest-income and lowest-tax-paying years. Your salary and bonus years are behind you. Social Security and required minimum distributions from your IRAs and 401(k)s have not started yet. You are hearing advice about doing Roth conversions during this low-tax window, and the arguments are compelling. You may also be thinking about consulting or part-time work to stay active and bring in some income. This article is about the hidden cost of those decisions: how income choices you make now can affect both your health insurance costs today and your Medicare premiums later. If you don’t understand the interaction, the surprise can cost thousands of dollars. The ACA cliff is back… and it’s steep The enhanced ACA subsidies that softened premium costs from 2021 through 2025 expired at the end of last year. Congress didn’t extend them. That means the hard cliff is back in full effect for 2026. The cliff sits at 400% of the federal poverty level. Cross it by even $1 and you lose your entire premium tax credit. It’s not a partial reduction; it’s all of it. If you aren’t prepared, that can create real cashflow problems. For 2026 coverage, based on the 2025 federal poverty guidelines, those thresholds are:
  • Single filer: $62,600 
  • Married couple: $84,600
  • Family of three: $106,600
Per KFF’s analysis, a 60-year-old earning $62,000 pays roughly $515 a month in health premiums, about 10% of income. The same person earning $64,000, or just $2,000 more, pays around $1,244 a month, roughly 23% of income. That’s not a typo. Two thousand dollars of extra income triggers roughly $8,750 in extra annual premiums.  The income figure that determines your eligibility is your MAGI. It includes everything you might be doing in retirement to manage your finances: Roth conversions, capital gain realizations, dividends, interest, part-time income and Social Security if you’re already drawing it.  The IRMAA clock starts when you’re 63, not 65 The ACA cliff is only part of the issue. Medicare uses a two-year lookback to set your premiums. Your 2028 Medicare Part B and Part D costs will be determined by your 2026 income, the same year you’re managing your ACA cliff right now. The 2026 IRMAA thresholds reflect 2024 income for those already on Medicare. They give us a reasonable proxy for what 2028 will likely look like, as the Centers for Medicare and Medicaid Services won’t publish the actual 2028 brackets until late 2027. The first IRMAA tier kicks in at $109,000 for single filers and $218,000 for couples. Cross that threshold in 2026, and when you turn 65 in 2028, you’ll be looking at roughly an extra $81.20 per month per person in Part B premiums or $974 per person per year, on top of the standard $202.90/month premium. That’s the first tier. The surcharges climb from there. And both Part B and Part D carry their own IRMAA surcharges, so couples can easily see $2,000 to $4,000 in added annual Medicare costs from a single income year that was too high. It is ironic but the income year most likely to push you over an IRMAA threshold is often one of your last years before Medicare when you might be selling an asset, doing a large Roth conversion, or drawing down a pre-tax account to fund living expenses. Why do these two cliffs need to be planned together? Put these two together and you can see the problem clearly. Take a 63-year-old couple with $80,000 of MAGI: they’re under the $84,600 cliff, subsidies intact. Now add a $20,000 Roth conversion. That one decision pushes them to $100,000 and it wipes out the entire ACA subsidy this year. The same conversion, sized larger or stacked with a capital gain that crosses $218,000, would also raise their Medicare premiums starting in 2028. That is why the two cliffs need to be modeled together, not checked separately after the fact. Where the $30,000 comes from:
ScenarioEstimated Cost
Couple crosses the ACA cliff in 2026, full subsidy lost≈ +$21,500/yr
Same 2026 MAGI over the first IRMAA tier triggers the 2028 Medicare surcharge (Part B + D, couple)+$2,297
If 2027 income also stays over the ACA cliff≈ +$21,500 more
Combined two-year exposure from the same income patternPotentially $45,000+
The chart below plots 2026 MAGI against both costs at once: the bars are your annual ACA premium (indigo while subsidized, red past the cliff), and the line is the annual Medicare surcharge that same income locks in for 2028. If you’re 63 in 2026: Too much income this year and you lose ACA subsidies, costing potentially $10,000 to $25,000 more in health premiums in 2026 and 2027. Too much income this year and you trigger IRMAA, paying $2,000 to $8,000+ more in Medicare premiums annually starting in 2028. Both cliffs draw from the same income year at once, not in sequence. Your 2026 MAGI sets your ACA subsidy right now, and that same 2026 return sets your 2028 Medicare premium through the two-year lookback. Because the two systems are run separately (one by the IRS and the Department of Health and Human Services, the other by Social Security and the Centers for Medicare and Medicaid Services) most people never see the combined exposure until it’s already locked in. What you can do about it The goal is to keep your 2026 MAGI below both cliffs where possible, or at least to be deliberate about which cliff you’re willing to cross and why.
  • Traditional IRA contributions: reduce MAGI dollar-for-dollar, if you have earned income
  • HSA contributions: a pre-tax reduction, but watch the Medicare timeline
  • Capital gain timing: deferring a sale past Medicare can bypass the pincer entirely
  • Roth conversions: the opposite, since they add directly to MAGI
For people with earned income, deductible Traditional IRA contributions can be one of the most direct MAGI reducers. If you or your spouse has earned income, you can contribute to a Traditional IRA and deduct it, reducing MAGI dollar-for-dollar. The 2026 limit is $7,500 per person, or $8,600 if you’re 50 or older. For a couple where one spouse is still working, that’s potentially $17,200 off your MAGI. One catch: if you’re covered by a workplace retirement plan, the deduction phases out at higher incomes. For 2026, between $81,000 and $91,000 of MAGI for single filers, or $129,000 and $149,000 for joint filers when the contributing spouse is covered. The counterintuitive part: you’re putting money into a pre-tax account when your tax rate is relatively low, with the understanding that you’ll pay taxes on it later and possibly at higher rates. For some people, that trade doesn’t pencil out. For others, protecting a $10,000 ACA subsidy this year is worth the future tax cost. The math depends on your specific situation, and it’s worth modeling rather than assuming. Health savings account contributions work similarly. Pre-tax contributions reduce MAGI directly. The catch is that you must be on an HSA-eligible high-deductible health plan to contribute. If your ACA marketplace plan qualifies, and you’re not yet on Medicare, this can be a meaningful lever. The 2026 limits are $4,400 for self-only coverage and $8,750 for family coverage, plus an extra $1,000 catch-up if you’re 55 or older. Plan to stop contributions before Medicare begins. Medicare’s Part A coverage can backdate up to six months, which can turn recent contributions into excess contributions, so watch that timeline carefully. Capital gain timing is often the biggest swing. If you’re planning to sell appreciated assets, a taxable brokerage position, a rental property, anything with embedded gain, the year you do it matters enormously. Deferring a large realization from 2026 to 2029, after Medicare begins, sidesteps both the ACA cliff and the IRMAA lookback simultaneously. That’s not always possible, but it’s worth asking whether the transaction needs to happen this year. Roth conversions don’t reduce MAGI, they add to it. If you’re in the pincer zone, aggressive Roth conversion in 2026 can push you over the ACA cliff and set your 2028 IRMAA tier at the same time. That’s not an argument against Roth conversions generally. It’s an argument for sizing them carefully relative to where you are on both cliff structures. If you’re already below both thresholds with room to spare, a modest conversion can make sense. If you’re hovering near either line, the math changes quickly. One longer-horizon point, separate from the two-year window this article is about: if you’re in the pre-pincer years, your late 50s or early 60s, modest Roth conversions now can reduce the size of your future RMDs. Smaller RMDs mean less forced taxable income in your late 60s and beyond, which means less pressure on the IRMAA tiers you’ll face once you’re on Medicare. That is a multi-decade trade, not a fix for the immediate cliff, and it works best when you have a decade or more of runway before Medicare enrollment. Plan this out The two-year lookback means you lose the ability to affect your 2028 Medicare premiums after December 31, 2026. You can’t file an amended return and get a different IRMAA. There is an appeal process through Social Security, but it’s designed for genuine life-changing events like retirement or divorce, not for voluntary income decisions that turned out to be more expensive than expected. For ACA purposes, 2026 is the year in question. January 1, 2027 starts a new calculation. That means the window for planning is now. Not 2027, when you’re closer to Medicare. ________________________________________________________________________________ John Urban is the founder of RetireSmartIRA, a retirement tax-planning app. Earlier, he founded GT Nexus, a supply-chain software company acquired by Infor in 2015. He lives in Northern California with his wife, Kathy, and enjoys time with family, travel, reading, Bay Area sports, and the occasional deep dive into the fine print of the tax code.
Read more »

Happy 250th Birthday America

"My Irish paternal great-grandfather came in the 1850's and my German maternal great-grandfather came from Germany in the early 1860s. Like you, Nick, my grateful heart knows no bounds."
- Mike Lynch
Read more »

Haunted Head

"Edmund, I think we're all circling the same tension around retirement. Two hundred and fifty years of Western work ethic doesn't loosen its grip easily—I felt that pull too. I'm sixteen months into retirement now. Before I stopped working, I told myself a story: take a full year off, extend it through the following summer, then ease into a part-time, low-pressure job by my second fall. Looking back, it wasn't really a plan. I think it was more a concession to my own anxiety about productivity, a way of promising my future self I wouldn't drift too far from being useful. But somewhere along the way, I fell in love with having full agency over my time. I can say with certainty now: there will be no job waiting for me this fall. What's interesting is that I didn't stop being productive—I just started doing it differently. Without really planning to, I built my own structure: mentoring in sports, then founding and running a new racket sports club. My need for purpose didn't disappear with retirement; it simply went looking for a new form to take. Maybe that's the real trick to a contented post-career life—not the absence of productivity, but trading forced productivity for chosen productivity. Doing the work because it's yours, not because it's required. But most importantly of all: still leaving enough empty space in the week to sit on a cliffside and watch the sharks."
- Mark Crothers
Read more »

Should I Lock in CD Rates Now or Stay in Money Market?

"Yesterday's post on Can I Retire Yet? titled What to do with a Windfall and a current baker's dozen comments addresses many of the same concerns you ask about in this HD forum post. You may find David Champion's post interesting. The what for and when funds will be used seem to be key and would be particular to the specific decisions each of us each of us makes with a windfall of cash. I expect liability matching and liquidity will be key to my decisions along with having a sufficient cash cushion for when my planning turns out wrong."
- William Perry
Read more »

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Get Educated

Manifesto

NO. 31: WE SHOULD plan for returns below the historical averages. Today’s rich stock valuations and modest bond yields don’t guarantee low returns—but it’s prudent to assume that’s what we’ll get.

act

IMAGINE STOCKS plunged 20%, which happens every four years, on average. That isn't a prediction, but it's always a possibility. Think about your portfolio’s loss in dollar terms, so it seems more real. Ponder whether the financial hit would unnerve you—and whether it would imperil any upcoming goals. If the answer is “yes,” you might want to lighten up on stocks.

Truths

NO. 109: RETIREMENT isn’t a hard deadline, like buying a home or paying for college. Instead, we might spend down our portfolios over 30 years. The upshot: While it’s prudent to move 100% of your house down payment and kid’s college fund into bonds and cash as you approach those goals, you might start retirement with, say, 60% invested in stocks.

act

OPEN A DONOR-advised fund. You can deduct contributions to the fund this year, and then disburse the money to your favorite charities over time. A popular strategy: Donate, say, three years’ worth of charitable gifts in a single year, so your total itemized deductions are well above the standard deduction—and thus you get a large tax break for your generosity.

Manage that tax bill

Manifesto

NO. 31: WE SHOULD plan for returns below the historical averages. Today’s rich stock valuations and modest bond yields don’t guarantee low returns—but it’s prudent to assume that’s what we’ll get.

Spotlight: Spending

Our $1000’s Of Dollars Mistake: A Lesson Learned

My wife, Suzie, and I have just uncovered the biggest financial oversight mistake we’ve probably made in a very long time.
Since entering retirement, we have been reorganizing our everyday finances, including consolidating our two separate current accounts (a checking a/c without a checkbook) into one for the majority of our recurring bills. During this process, we realized we were paying for three mobile phone plans, two coming from my wife’s account. It turns out Suzie had always assumed my plan was taken from her account.

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Consumer Advocate

When I experience an issue with a food product, I don’t suffer in silence. While eating lunch at work in the late 1980s, I found what I thought to be a bug in my frozen turkey dinner. I mailed the specimen to the manufacturer, along with a cover letter that included a subtle attempt to mimic the comic style of the Lazlo Letters. I received some coupons and a boiler-plate apology, along what I thought was an unsatisfactory reply: “We sent your exhibit to our lab and they have informed us that it was a piece of fatty tissue with dark brown meat fibers adhering to the piece of fat.”
I showed the company’s letter to my co-workers and–goaded on a bit by them–I sent a response that stated in part: “Madam,

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Frugality, Minimalism, and Aligning Values

I’ve always been a minimalist – even as a teenager I had no interest in having lots of clothes, shoes, or other trappings of high school life in the 80s. That pull toward minimalism was reinforced during the 2 years I spent teaching English in Japan after college. No dedicated bedroom that sits empty and unused all day? My bed folds up and is stored in the closet? A tiny fridge forcing me to buy fresh fruit and vegetables every other day?

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Is frugality all it’s cracked up to be? A lifetime of frugality, I have claimed that, Jonathan has written it. Many comments on HD have also made that claim, but is it true?  RDQ

Are we all on the same frugality page?
From what I found, frugal living involves  prioritizing needs over wants, spending less than earned, valuing quality, and embracing resourcefulness like DIY. Common practices include planning meals, buying used items, and seeking discounts.
I read that a cheap person focuses on price and a frugal person on value. Well, that doesn’t make sense. You could spend a lot of money achieving what you value – like a car or a cruise.

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Bah Humbug! It’s Not Even September Yet

I was in a large discount retailer yesterday with my grandson, picking up some school supplies for his return to school after the summer break. Bearing in mind it’s late August, around 20% of the store was roped off while staff were busy unboxing and displaying Christmas merchandise. Unbelievable!
I overheard a few people asking staff when the display would be open for business, and you could sense a general excitement within the store about this new buying opportunity.

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A Record Journey

I went on a little shopping spree last week for some new tunes, ordering some records from a reputable online music store. Like a little kid who just ordered PlayStation 5 from Amazon, I’ve been anxiously tracking my order on the fine United States Post Office website.
I cannot make the following story up. 
On 8/11 I placed my order.
On 8/12 the retailer delivered my records to the USPS origin facility in Louisville KY. 
So far so good.

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Spotlight: Ferris

A Rental House? Questions to Consider

So we’re thinking about buying a rental home, either in our college town or the town 10 miles north of us. I’ve written here before that we were briefly landlords in the late 90s when we moved to a larger home and rented out our starter home. But we felt we didn’t have the bandwidth to be landlords, so we sold the place after a year. That was a major financial mistake. Why are we considering this now? I won’t bore you with all the details, but we’re planning to have our daughter and her pets, with a paying roommate or two, live there while she finishes school and establishes herself in more steady work. We’ve been financially supporting her while she’s been recovering from serious injuries sustained in car accidents in 2022 and 2023. But paying rent, especially in the expensive part of California in which she now lives, is not only a drain on our finances as we approach retirement but also feels like flushing money down the toilet. We’d rather re-direct that money to an actual asset that could be worth something over time. Anyway, here are the practical questions I feel we need to research before we (possibly) take this leap in the next few months. (We’ll wait until interest rates drop, as predicted, this fall.) The questions: How much can we pay, how much down payment will we need, and from which source(s) will we free up that cash? What kind of property should we buy? For example, a two-bedroom condo in our town with a small yard should be adequate for our daughter, but a modest home (with no HOA) in the next town up might be a better long-term financial decision. Do we need a realtor to represent us in the purchase, or…
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Estrangement & Estates

I've been thinking about family dynamics and how they affect financial decisions, and this will be the first of several posts on various applications of this topic. This first one is a hard one to talk about: It's family estrangement, specifically a family member(s) going "no contact" with or otherwise walking away from other family member(s). It's not as unusual as you might think--there is growing research on the topic, and some estimate that more than 30% of American families have an estranged family member. The reasons for this alarming trend are sociologically complex. One expert on the topic is psychologist Joshua Coleman, who's written a couple of books and many articles based on insights from his own practice and his research. He notes that while about half of the estrangement situations happen for reasons we'd all consider legitimate (e.g., clearly abusive behavior), others are harder to peg, and what one adult child might consider a "toxic" on the part of their parents might be incomprehensible to their sibling. As I said, it's complicated. Sometimes, according to Coleman, the estranged family members might find a way back to each other. In other cases, the person is (most likely) gone forever. The question arises as to the implications estrangement has for one's estate. Coleman urges parents with an estranged adult child not to cut them out of their will, arguing that this will just exacerbate an already painful situation. However, others might argue that if a family member has chosen to exit the family, causing pain by so doing, they are no longer entitled to family resources--and including them in an estate plan might even seem or be disrespectful to other family members who have been hurt by their actions. I'll be vague, but we have an estrangement situation in my…
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In Short-Term Limbo

As I shared a few weeks ago, I’m in the process of moving the money from my workplace retirement accounts at Fidelity to my rollover IRA at Schwab. This, like other aspects of my retirement transition, has had its bumps in the road. Fidelity will only mail a check to your home, no electronic or direct transfers, so I called them a couple of days before we left San Diego last week to begin the process. The phone call went smoothly, and we had already completed the process of transferring my 403B account, when the agent said, “Oh. You can’t roll over your 457 or DCP accounts until you’ve been separated (he actually said “terminated,” which I balked at) for 31 days.” So now I have to call again next week to do the other half of the transfer. So I paid $25 to have my check from the 403B expedited and got a UPS notification that it would be delivered on Monday (7/21). I (wrongly) thought someone would have to sign for it, so I made sure someone was home all day, though it didn’t arrive until 8:40 p.m.—and then was just tossed on our doorstep with a doorbell ring. The envelope made it clear that it was financial papers. I hate the idea that such a large check could have been sitting in front of our condo if we hadn’t been there (or worse, in front of our building—some UPS drivers don’t bother looking up the code to get in). On advice of the Schwab rollover specialist, I hand-delivered the check to the local Schwab branch yesterday rather than putting it back into the mail. The guy there told me it should get deposited into my IRA by this afternoon and then I’d have to decide how to…
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A Rental House? By the Numbers

Thanks so much for the great comments and advice on my previous post about this topic. As I said in a reply, I’m making a list of all the ideas commenters shared to discuss with my husband. We may or may not move forward with this idea—there are some complicated family dynamics that I won’t get into in this particular post. But if we do, here are some of the numbers we’re considering. I’ve been looking at small starter homes or condos in either our town or the one 10 miles north of us. They’re mostly 3 bedrooms, but some are 2 and a couple are 4. The price range I’ve set is $450-650K. (I know that’s horrifying. It’s California.) Zillow does a pretty good job of estimating what your monthly payment would be, and you can adjust it for a larger or smaller down payment. If interest rates drop, we could make a smaller down payment. At this point, we’re looking at a down payment in the $200-300K range. Zillow also estimates what kind of rent could be charged for the property. I’d like our total house payment, including HOA (if applicable), property taxes, etc., to be $2500-3000. How much rent we could charge will depend on the size of the home and whether it’s one or two paying roommates. According to the Zillow estimates, the types of properties I’m looking at should rent for that range. We won’t charge our daughter rent if she’s going to school, and since we’ve been paying her rent since her latest car accident, this will be a wash for us. If she finishes school and is working full-time and wants to stay in the house, we’ll start charging her rent. So we’d make a down payment large enough to get the monthly…
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Final Arrangements: A Learning Curve

As I’ve written here before, my mother-in-law has been dealing with Alzheimer’s, and this last year has been a constant learning curve of navigating long-term care policies, trying out in-home caregivers (pretty major fail), and finally a memory care residential facility. Well, this past week was a new challenge. My MIL passed away suddenly on Tuesday night. We got a call from the memory care facility that she’d fainted several times,  so they’d called an ambulance. We were concerned, but she’d had issues with fainting before. 20 minutes later, a hospital nurse called and said she’d arrested (she had an DNR order) and died on the way to the hospital. It was very abruptly conveyed, and the nurse barely took a breath before asking which local mortuary we’d like the body transferred to.  We said we’d have to call her husband (my husband’s stepfather) and get back to them. It was a traumatic few minutes. Alzheimer’s notwithstanding, she’d otherwise been in good health and had never had heart problems. She was 84. Anyway, the real drama involved the final arrangements. My in-laws had purchased cemetery plots in Palo Alto, CA, where other family members have been laid to rest. But they live in Southern California, some 400 miles from this cemetery. Nothing had been set up with a local mortuary. We had to really quickly find one that (a) would take the body from the hospital (b) prepare the body for a 400-mile road trip and (c) transport the body. Then we had to figure what would happen on the other end after the transport. My father-in-law also had to go to the local mortuary and fill out lots of paperwork as next-of-kin to get the body released. He’s 82 and gets easily confused and frustrated. My husband had offered…
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Final Countdown

I'VE DECIDED UPON MY retirement date: July 1, 2025. We just passed the one-year countdown point, so I thought I’d share some of my ideas and plans for my final year in the workforce. This countdown idea, of course, isn’t original with me. Indeed, there are apps that you can put on your phone to count down the time until retirement. I was primarily inspired by a retirement blogger named Fritz Gilbert. He’s way more decisive than I am. Gilbert started his blog several years before his planned retirement date, and has meticulously documented his journey leading up to retirement and the time since. Besides setting a date, I’ve already completed a couple of preparatory steps. I’ve attended several retirement webinars offered by my current university’s retirement program and my previous university’s program. I now understand the timelines for filing retirement paperwork, and I have those dates on my calendar for next spring. One year to go: Financial tasks. One thing I thought I’d be doing during this final year is stress-testing our retirement spending plan. We have a spreadsheet of sorts that roughs out what we think our monthly expenses will be. But since my husband may not retire next year when I do, we don’t need a trial run of our more austere spending plan—yet. Instead, I’ll need to think about a household budget that will change in two distinct and related ways. First, my take-home income will go up. I’ll be receiving pensions from two university systems, and together they will replace more than 80% of my current gross income. Meanwhile, I’ll no longer be making contributions to my university pension, Social Security and Medicare, and my 403(b) and 457 retirement plans. These contributions, together with federal and state tax withholding, easily devour more than 50% of…
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