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Frittering away Frugality 

"Thanks, I needed that. We make the 165 mile round trip from Hilo to Kona every couple months. No freeways. Recently the gas pumps were expanded from 16 to 32, on this an Island population around 200k. As a general rule the price of gas in the state, yes we are a state, of Hawaii is 25% less than California. Hilo gas today is $5.29. My sister paid $6.79 in So Ca today. Consider the Hawaii Islands are further from any continent on earth. Another point of interest is the best selection of fish is Costco's flash frozen 3 to 4 lb baged filets, individuality sealed. Unfortunately our remote location among a small population, assures us the mega tons of fish caught in the beautiful Pacific are shipped, flown overnight, to the mainland. From the West Coast to the East Coast, following the money. The only fresh fish in abundance on Hawaii Island is Ahi.Tuna. Sold off the tailgates of pick up trucks by the fisherman who caught it hours ago. A different story on Oahu and Maui as they are tourist destinations, with if I may, world class restaurants, and renown chefs who demand fresh and various kinds of fish. Being born and raised, lived in So. Californian for over 60 yrs., the food I miss most is Mexican. There is wonderful grass fed beef grown on the slopes of Mauna Kea at the Parker Ranch, North of Hilo. It is found in markets throughout Hawaii Is. From what I understand competitively price with mainland rising beef prices. Aloha"
- Bob Smith
Read more »

Reluctantly Saving Money

"One of the things to be concerned about in the US is whether or not the tradesperson has insurance. As others have mentioned for folks in our general age bracket, being on a ladder can be hazardous. If a worker without insurance is on your roof and falls, you might be liable for their injury. Asking for a Certificate of Insurance (CoI) is one of my automatic requests when speaking to contractors."
- Jeff Bond
Read more »

Don’t Let a Roth Conversion Trigger a Penalty

"Thanks! I’ve been doing a bit of digging into this myself because our tax situation is more complicated this year. We’re not doing Roth conversions but will be withdrawing some funds from an IRA to help pay for renovations. I’ve been trying to figure out the most efficient way to pay the taxes on that, and after some calculations, decided that the 2025 safe harbor number is the way to go. We know that number, and it makes all the 2026 complexity less relevant."
- DrLefty
Read more »

Money and Me by Jonathan Clements

"Thank you William for mentioning that. I watched Jonathan’s Hall of Fame induction, and it was both moving and well deserved. I’m glad his words continue to reach people. I hope you enjoy Money and Me, for me, it felt like one last conversation with my brother."
- Andrew Clements
Read more »

What Addiction Couldn’t Take: My Sister’s Story

"Thank you Andy, I appreciate you reading the article and your kind words."
- Andrew Clements
Read more »

Thinking of a possible reason to tap Roth earlier then planned

"That's great! I worked in banking as a lender for several decades, and it was challenging for some retirees to sometimes obtain financing for loan requests due to living on a lower income than working years. I think the OP would need a fairly large loan for a home purchase (rather than a modest HELOC), which was why I thought a securities loan could be an option. Anyways, good luck with your project in the future!"
- Bill C
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 »

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 »

Frittering away Frugality 

"Thanks, I needed that. We make the 165 mile round trip from Hilo to Kona every couple months. No freeways. Recently the gas pumps were expanded from 16 to 32, on this an Island population around 200k. As a general rule the price of gas in the state, yes we are a state, of Hawaii is 25% less than California. Hilo gas today is $5.29. My sister paid $6.79 in So Ca today. Consider the Hawaii Islands are further from any continent on earth. Another point of interest is the best selection of fish is Costco's flash frozen 3 to 4 lb baged filets, individuality sealed. Unfortunately our remote location among a small population, assures us the mega tons of fish caught in the beautiful Pacific are shipped, flown overnight, to the mainland. From the West Coast to the East Coast, following the money. The only fresh fish in abundance on Hawaii Island is Ahi.Tuna. Sold off the tailgates of pick up trucks by the fisherman who caught it hours ago. A different story on Oahu and Maui as they are tourist destinations, with if I may, world class restaurants, and renown chefs who demand fresh and various kinds of fish. Being born and raised, lived in So. Californian for over 60 yrs., the food I miss most is Mexican. There is wonderful grass fed beef grown on the slopes of Mauna Kea at the Parker Ranch, North of Hilo. It is found in markets throughout Hawaii Is. From what I understand competitively price with mainland rising beef prices. Aloha"
- Bob Smith
Read more »

Reluctantly Saving Money

"One of the things to be concerned about in the US is whether or not the tradesperson has insurance. As others have mentioned for folks in our general age bracket, being on a ladder can be hazardous. If a worker without insurance is on your roof and falls, you might be liable for their injury. Asking for a Certificate of Insurance (CoI) is one of my automatic requests when speaking to contractors."
- Jeff Bond
Read more »

Don’t Let a Roth Conversion Trigger a Penalty

"Thanks! I’ve been doing a bit of digging into this myself because our tax situation is more complicated this year. We’re not doing Roth conversions but will be withdrawing some funds from an IRA to help pay for renovations. I’ve been trying to figure out the most efficient way to pay the taxes on that, and after some calculations, decided that the 2025 safe harbor number is the way to go. We know that number, and it makes all the 2026 complexity less relevant."
- DrLefty
Read more »

Money and Me by Jonathan Clements

"Thank you William for mentioning that. I watched Jonathan’s Hall of Fame induction, and it was both moving and well deserved. I’m glad his words continue to reach people. I hope you enjoy Money and Me, for me, it felt like one last conversation with my brother."
- Andrew Clements
Read more »

What Addiction Couldn’t Take: My Sister’s Story

"Thank you Andy, I appreciate you reading the article and your kind words."
- Andrew Clements
Read more »

Thinking of a possible reason to tap Roth earlier then planned

"That's great! I worked in banking as a lender for several decades, and it was challenging for some retirees to sometimes obtain financing for loan requests due to living on a lower income than working years. I think the OP would need a fairly large loan for a home purchase (rather than a modest HELOC), which was why I thought a securities loan could be an option. Anyways, good luck with your project in the future!"
- Bill C
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 »

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 »

Free Newsletter

Get Educated

Manifesto

NO. 46: WE SHOULD favor financial advisors who focus on index funds—and who help not only with investing, but also with broader finance issues like taxes, insurance and estate planning.

Truths

NO. 66: TWENTY STOCKS aren’t enough. One rule says you need 20 individual stocks to be diversified. With that many, your portfolio's volatility won't be much greater than the broad market's. Problem is, you might still earn returns that differ radically from the market averages. To avoid this tracking error, you need to own hundreds of stocks.

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.

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Manifesto

NO. 46: WE SHOULD favor financial advisors who focus on index funds—and who help not only with investing, but also with broader finance issues like taxes, insurance and estate planning.

Spotlight: Cars

How have you decided when it’s worth it to fix an old car?

My 2014 Honda Accord recently hit 99,000 miles. It’s nothing fancy to look at, but it drives well. Recently I’ve been having an issue with the starter. The push start works intermittently. Sometimes it starts on the first push, sometimes it takes multiple tries. I think the most it has taken is 6 tries.  I’ve kept up with the maintenance, but I drive it infrequently, so the time between service has spread out. It was due for an oil change,

Read more »

Black Beauty

AFTER 20 YEARS, the U.S. military has withdrawn from Afghanistan. The news brought back memories of the year I spent deployed there—and a crucial financial lesson I learned. Perhaps that lesson resonates even more today given the past year’s pandemic and the role deferred gratification has lately played in many of our lives.
When you’re deployed to a combat zone, the government doesn’t tax your wages. Consequently, most soldiers can sock away a lot of money.

Read more »

Just Another Car

ONCE I GRADUATED college and started working fulltime, I knew what my first major purchase would be: a sporty new car. I was jealous of the cars my friends drove in high school. I had just spent four years grinding through an undergraduate engineering program. I was ready to reward myself.
To prepare for the purchase, I minimized my expenses. I shared an apartment with two friends who had also just graduated from college.

Read more »

Diminished Value

A CRUCIAL STEP WHEN buying a preowned car is to scrutinize its Carfax report. A single-owner car with a regular maintenance history and which was driven solely for personal use should be a safe bet, while an accident record gives most people pause. All things being equal, a car that was in an accident, however minor, ought to cost less than a similar one with a clean history.
Some bargain hunters don’t mind taking a chance on a car with an accident history as long as it drives well.

Read more »

About That Fine Print

CAR LEASING WILL likely make a comeback in 2023. But is leasing a good idea?
Before the pandemic, leases represented about 30% of new car sales and as much as 70% or 80% for some luxury vehicles. But during the pandemic, with new vehicles in short supply, manufacturers reduced their generous lease subsidies. This, combined with low interest rates, reduced payment differences between financing and leasing, making leasing less attractive.
But that may be about to change.

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When does leasing a car make financial sense?

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Spotlight: Politakis

Scams

Another day, another article about a scam perpetrated by fraudsters. This one from the New York Times that starts with a retired lawyer having problems with his iPad and connecting to Microsoft outlook and wanting to get technical assistance. He googled Microsoft’s number and wouldn’t you know it, the number google provided was that of a scammer. To read the rest of the story go to: https://www.nytimes.com/2025/12/12/business/tech-support-scam-bank-fraud.html?unlocked_article_code=1.8E8.0Dgr.Bku6U1c1S2Yo&smid=url-share  
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Is AI going to affect our investments

This futuristic Research Report from June 2028 got Wall Street scared a few days ago. It predicts that AI will cause massive disruption and displacement in the economy which will lead to a terrible market decline. It’s very scary reading not for the faint of heart. Personally, with national debt at $38 trillion, I worry more about a looming debt crisis than AI. What is your take on either of these topics? What are you worried about? A debt crisis or disruption to the economy by AI?
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Pig Butchering

Sounds awful doesn’t it? The Article in the WSJ was so painful to read but it led me to the awareness of how to protect myself and those I love. in the article the problem was the spouse trusted the other spouse who was starting the long road of dementia.  How do you protect your financial well being from something like that? HumbleDollar readers, how do you protect yourselves?  I need your wisdom.
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I want to see less of me on the internet

There is an excellent article in the Wall Street Journal about how to find what there is about you on the internet and how to delete it if you want.  Here is the Link. I read the article followed the suggestions and it was very easy.  I hope it works.  Has anyone tried this?
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No financial wisdom here other than ….

From looking at the forum posts, Most HD readers are calm and it seems not worried about the markets.  I really don’t believe that because what has happened in the last week and a half has been unprecedented and there is no end in sight. Without injecting politics into the discussion how are we HD readers going to handle the next 45 months of this turmoil that is caused by the whims of one man who doesn’t understand economics and no one else in his cabinet no matter how bright and successful somehow agreed to be a yes man.  I’m looking for a real discussion about how to protect my retirement savings.  There, I said it.
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Housing options for older Americans

I wanted to share this article and I hope our dear HD readers comment and tell us if they are doing what is suggested in the article and how it’s working out.  I am at the beginning of trying to figure out my housing options and what is described in the article sounds good. https://www.wsj.com/lifestyle/relationships/new-housing-options-emerge-for-older-americans-dfa4c8f5?st=Sp9vyR&reflink=desktopwebshare_permalink
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