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What’s the difference between an equity-indexed annuity and an index fund? One needs an army of salespeople. The other sells itself.

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Frittering away Frugality 

"The lines move very fast though Dick."
- Fred Gloeckler
Read more »

Reluctantly Saving Money

"Mark, this gave me a smile and I think Jonathan would have loved it to. There's a certain irony in wanting to spend money and finding nobody willing to take it. More importantly, you reminded us that one of the best investments isn't in the stock market, it's the ability to solve problems yourself. The savings were nice, but the confidence that comes from knowing you can handle life's little crises may prove even more valuable. Thanks for the laugh."
- Andrew Clements
Read more »

Every Writer Has a Beginning: Organ Transplant Fails

"OMG Dana you are so right about the title. I read it and the first paragraph and I said to wife, “Classic Jonathan.”"
- DavidHLancaster
Read more »

Don’t Let a Roth Conversion Trigger a Penalty

"Yep, I think you must be right on that. I've always used last year's number so haven't worried about it."
- Andrew Forsythe
Read more »

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 »

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
Read more »

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
Read more »

Frittering away Frugality 

"The lines move very fast though Dick."
- Fred Gloeckler
Read more »

Reluctantly Saving Money

"Mark, this gave me a smile and I think Jonathan would have loved it to. There's a certain irony in wanting to spend money and finding nobody willing to take it. More importantly, you reminded us that one of the best investments isn't in the stock market, it's the ability to solve problems yourself. The savings were nice, but the confidence that comes from knowing you can handle life's little crises may prove even more valuable. Thanks for the laugh."
- Andrew Clements
Read more »

Every Writer Has a Beginning: Organ Transplant Fails

"OMG Dana you are so right about the title. I read it and the first paragraph and I said to wife, “Classic Jonathan.”"
- DavidHLancaster
Read more »

Don’t Let a Roth Conversion Trigger a Penalty

"Yep, I think you must be right on that. I've always used last year's number so haven't worried about it."
- Andrew Forsythe
Read more »

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 »

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 »

Free Newsletter

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.

humans

NO. 52: WE ENGAGE in mental accounting, viewing our home, investments, car loans and so on as distinct parts of our financial life. But this narrow focus can hurt our finances. Suppose we have a high-interest mortgage. Paying down that loan may be smarter than buying bonds—and yet mental accounting can cause us to overlook this opportunity.

think

TAX DEFERRAL. When you defer taxes on investment gains, you hang onto money earmarked for Uncle Sam—and use it to earn additional gains for yourself. This deferral is a key advantage of retirement accounts. You can also defer taxes in a taxable account—by holding winning investments for longer and thereby delaying the capital-gains tax bill.

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.

My Money Journey

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: Taxes

Investments Tax

MANY PEOPLE don’t know, but there is a net investment income tax of 3.8% that applies to some of your income. Today, I want to discuss what it is, how we can reduce its impact, and how we can save money.
Let’s dive right in:
Net Investment Income Tax (NIIT)
The net investment income tax is imposed on investment income if the modified adjusted gross income (adjusted gross income + foreign income exclusion) is more than $200,000 for single filers or $250,000 for those married filing jointly.

Read more »

Effective vs. Marginal? Nah…..

Perhaps what we should be debating is which is the most important line on the tax return. I can tell you that most would say line 34, “this is the amount you overpaid, or line 37, “this is the amount you owe. I contend line 24 matters most, “this is your total tax”. Rarely, and I mean well under 1% of the time, did a client ask me how much tax they paid. As a matter of fact,

Read more »

Some people are never satisfied

The Washington Post has an article on yet another effort to cut taxes for the wealthy. This time it is stepping up the cost basis for capital gains to account for inflation. You’d think they’d at least wait for the dust to settle from the recent give away.
I don’t know whether the article is behind the pay wall, it’s not giving me an option to share it so I did a straight copy.

Read more »

Home Tax Tips

IF YOU OWN a home or are planning to buy one, there are a few things you need to know from the tax standpoint that could save you money:
1. Mortgage Interest
If you have a mortgage, you can typically deduct the interest you pay on the loan up to $750,000 ($1,000,000 if taken before December 16, 2017) but only if you itemize your deductions (schedule A)
You can also deduct points you paid if you itemize.

Read more »

New Bonus Senior Deduction Impact

The recently enacted One Big Beautiful Bill Act included a number of tax provisions of interest to HumbleDollar readers. Given the emphasis on retirement planning on HumbleDollar, the new bonus Deduction for Seniors has potential to provide a significant tax savings for seniors.
This has been discussed in previous posts over the last few weeks, but the details are worth a quick review.  Taxpayers who reach 65 by the last day of the tax year, starting in 2025,

Read more »

Business and Side Hustle Tax Tips

BUSINESS OWNERS HAVE far more control over their tax bill than W-2 employees. But only if you know how the rules actually work. 
The tax code is structured to reward self employment, business investment, and retirement saving, yet many business owners leave significant money on the table simply because they are unaware of all the strategies.
If you are eligible, a Solo 401(k) plan can be an effective way to lower your taxes or shield your investments from future taxation.

Read more »

Spotlight: Lim

Fed Up

IS THE U.S. ECONOMY strong or weak? If you believe it’s strong—and apparently many investors do, judging by the U.S. stock market’s all-time highs—why is the Federal Reserve keeping the federal funds rate at zero? These days, it seems like we take the Fed’s policy of 0% short-term interest rates for granted. Yet such policy measures are truly extraordinary and typically reserved for an economy that’s in the ICU. On the other hand, if you believe the U.S. economy is weak, why did the Fed just announce the tapering of quantitative easing (QE)? The Fed insists that tapering doesn’t mean a higher fed funds rate is around the corner. Instead, raising short-term interest rates would depend on the economy reaching full employment—whatever that is. Still, tapering QE can be viewed as a form of monetary tightening. Researchers Jing Wu and Fan Xia modeled the economic effect of QE, which they dub the “shadow” federal funds rate. This shadow rate attempts to translate the effect of QE by estimating the equivalent fed funds rate necessary to have a similar economic impact. According to the Atlanta Federal Reserve, the current shadow federal funds rate is -1.7%. If the Fed succeeds in tapering QE to zero by June 2022, that might be equivalent to raising interest rates by 1.7% or almost a quarter of a percent per month. Imagine the market’s reaction if the Fed announced a quarter-percent rate hike every month for the next seven months. Whatever your view of the economy, I would contend that the Fed has already erred or is on the verge of erring. If the economy is strong, its zero interest-rate policy makes little sense. In this scenario, the Fed is behind the curve and should have raised interest rates already. But if the economy is so…
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Picking the Fruit

LAST MONTH, the Federal Reserve released the results of its latest stress tests of major financial institutions. As an investor in Wells Fargo, I took special interest in the Fed’s findings. Why? If Wells Fargo passed the Fed’s stress test, it would be allowed to raise its dividend, which currently stands at a paltry 10 cents a share, amounting to a dividend yield of just 0.9%. I’m fully aware that my obsession with stock dividends is less than rational. For one thing, I don’t spend them. My dividends are automatically reinvested in additional Wells Fargo shares. Nor do the dividends necessarily increase the value of Wells Fargo stock. Every dollar in dividends paid out to shareholders lowers the price of a company’s stock by the same amount—at least in theory. That’s why a stock often falls in price on its ex-dividend date, which is the first day a stock trades without the benefit of its next dividend. And since I don’t actually spend my dividends, I really ought to prefer capital gains. After all, dividends are taxed the same year I receive them, but capital gains aren’t taxed until I sell the appreciated stock. In fact, the tax on capital gains may be avoided altogether by donating appreciated shares or bequeathing stock to your heirs, who inherit the stock with a step up in basis. Finally, I can always create “homemade dividends” by simply selling some shares as needed. When economists examine the irrational behavior of dividend lovers like me, they scratch their heads. In 1976, economist Fischer Black pondered the conundrum in a paper titled The Dividend Puzzle. In his words, “The harder we look at the dividend picture, the more it seems like a puzzle, with pieces that just don’t fit together.” But guess what? I still love…
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Ten Tips for 2021

‘TIS THE SEASON FOR making predictions and financial recommendations for the year ahead. Since everyone else is doing it, I figured I’d hop on the bandwagon. Here are my 10 predictions and recommendations for 2021: 1. The stock market will fluctuate, but company dividends will be relatively stable. John Pierpont Morgan was asked what the stock market would do next. According to legend, he answered, “It will fluctuate.” If only financial experts were so truthful today. There’s no doubt that stocks will fluctuate next year, perhaps wildly. I don’t pretend to know whether the market will end 2021 in the black or the red. But there’s one thing you can count on: Company dividends will be much more stable than share prices. In the early 1980s, Nobel laureate Robert Shiller pointed out this phenomenon, noting that—since a stock’s value fundamentally reflects the present value of its future dividends—the wild stock price swings made little sense. Keep that in mind the next time the market throws a tantrum. 2. Wall Street forecasts will be bullish for 2021. You can be sure of two things. First, Wall Street will be bullish on the stock market for 2021 (and 2022 and 2023…). After all, a COVID-19 vaccine is becoming available. Employment is recovering. There’s plenty of pent-up demand. The list is endless. The other thing you can count on: The forecasts are worthless. In fact, they’re worth less than nothing. Acting on stock market predictions from Wall Street strategists or anyone else is a surefire way to lose money. 3. Short-term interest rates will remain very low in 2021. It would usually be hazardous to predict the direction of interest rates. But the Federal Reserve has told us on more than one occasion that, in effect, “We aren’t thinking about raising rates. In…
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Time Is Running Out

INFLATION CONTINUES to sizzle. November’s Producer Price Index (PPI) rose 9.6% from a year earlier. Even after removing food and energy, PPI was up 7.7%. Both figures are the highest since 2010, when such data were first compiled. This follows last week’s Consumer Price Index report, which showed inflation climbing 6.8% over the past 12 months. Since consumer prices lag producer prices, we can expect little relief from inflation in 2022. All this must be foremost on the minds of Federal Reserve members as they meet this week. Price stability is one of its two mandates, so it’s widely expected that the Fed will accelerate the tapering of its bond purchases. This will position the Fed to raise interest rates sooner as it seeks to quell inflation. Unfortunately, time is running out. A number of factors conspire to make the job of Federal Reserve Chair Jerome Powell a lot more difficult: 1. Inflation expectations are climbing. According to the Federal Reserve Bank of New York, inflation expectations one year out are 6%. This number has doubled since the beginning of the year. This is concerning because, once entrenched, inflation expectations can become a self-fulfilling prophecy. 2. Wages are on the rise. Wages are companies’ largest expense and hence a major determinant of prices. Wages also tend to be sticky, meaning workers are loath to accept cuts in wages. According to a recent survey by the Conference Board, companies plan to raise salaries by 3.9% in 2022. That’s the fastest pace since 2008. 3. The yield curve is flattening. The difference in yield between five-year and 30-year Treasurys was just 0.54 percentage point as of last week. The last time the spread was so small was during the depths of the COVID-19 pandemic in March 2020. A flattening yield curve has…
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12 Financial Sins

FINANCIAL MARKETS are often quick to punish investment sins. By contrast, if we err with our borrowing, spending and other personal-finance issues, problems might not show up until years later—but the damage can be just as great. Here, to complement last week’s list of 12 deadly investment sins, are 12 deadly personal-finance sins: 1. Pride: Keeping up with the Jones by buying luxury cars and fancy clothes. Antidote: Realize the folly of buying depreciating assets you don’t need, with money you don’t have, to impress people you don’t like. 2. Greed: Operating with a “never enough” money mentality. A reporter asked billionaire John D. Rockefeller, “How much money is enough?” His response: “Just a little bit more.” Antidote: Generosity. Giving away money will loosen its emotional grip on you—and make you happier as well. 3. Lust: Getting divorced. Antidote: Invest more time and energy in your marriage. 4. Envy: Comparing your financial state to that of others. Since there will always be someone with apparently greater wealth, such comparisons often lead to envy and discontent. Antidote: Instead of comparing yourself to others, work to develop gratitude for what you have. 5. Gluttony: Falling into debt. If money saved is financial progress, money borrowed is often a step backward. As I’ve mentioned before, going into debt to pay for today’s consumption is the path to financial slavery. Antidote: With the exception of taking out a mortgage or student loans, if you don’t have the cash to pay for something in full, save up until you do. 6. Impatience: Claiming Social Security early. Delaying benefits can be one of the best financial deals out there. Antidote: Make an informed decision about when to claim Social Security benefits. A great place to start is Mike Piper’s excellent book, Social Security Made Simple. 7. Sloth:…
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My Sentence

THREE YEARS AGO, I decided to write a book about money for my children, then ages 9 and 11. Raising Your Child’s Financial IQ: The Most Important Things is now finished. Here are six things I learned along the way—which apply not just to writing a book, but also to life more generally: 1. Yes, you can find the time I’m a physician, working 50 to 60 hours a week. When I get home, greeting me are two children eager for my attention. Where would I find the time and energy to write? My solution: Wake up at 5 a.m. and write for just 25 minutes. My experience shattered the romance I had always associated with being a writer. I discovered that writing a book is an extremely lonely and slow endeavor. At times, a voice in my head would whisper: “This is rubbish. You’re wasting your time. Who do you think you are, writing a book?” 2. Jerry Seinfeld’s hack A young comedian, Brad Isaac, asked Seinfeld if he had any advice: “He said the way to be a better comic was to create better jokes and the way to create better jokes was to write every day.” Isaac continued: “He told me to get a big wall calendar that has a whole year on one page and hang it on a prominent wall. The next step was to get a big red magic marker. He said for each day that I do my task of writing, I get to put a big red X over that day. After a few days you'll have a chain. Just keep at it and the chain will grow longer every day. You'll like seeing that chain, especially when you get a few weeks under your belt. Your only job is to not break the chain.”…
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