FREE NEWSLETTER

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

Latest PostsAll Discussions »

Reluctantly Saving Money

"I'm supposed to get a visit from No. 4 tomorrow. Not holding my breath. Ah, who needs railings anyway."
- Ted Tompkins
Read more »

Frittering away Frugality 

"Heading to Costco today for gas, which is about 50 cents per gallon cheaper than most of the stations around us."
- Ted Tompkins
Read more »

Don’t Let a Roth Conversion Trigger a Penalty

"Thanks, John. I appreciate your contribution to the site."
- Edmund Marsh
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 »

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
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 »

Reluctantly Saving Money

"I'm supposed to get a visit from No. 4 tomorrow. Not holding my breath. Ah, who needs railings anyway."
- Ted Tompkins
Read more »

Frittering away Frugality 

"Heading to Costco today for gas, which is about 50 cents per gallon cheaper than most of the stations around us."
- Ted Tompkins
Read more »

Don’t Let a Roth Conversion Trigger a Penalty

"Thanks, John. I appreciate your contribution to the site."
- Edmund Marsh
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 »

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 »

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: Investing

Interest Rates Battle

EARLIER THIS WEEK, the Federal Reserve’s Open Market Committee met and decided to lower interest rates by a quarter-point. This immediately sparked a war of words.
At a press conference, Fed chair Jerome Powell took a swipe at the White House, blaming the president’s new tariff policies for an uptick in inflation.
President Trump wasted no time in responding. All year, he has been lobbying Fed officials to move rates lower. And while they have been taking steps in that direction,

Read more »

Driving Prices

IN 2020, ELECTRIC car maker Lucid Motors brought in revenue of $4 million. Five years later, sales had risen impressively, to more than $1 billion. In 2025 alone, sales grew 68%. That sounds like a success story, and through that lens, it is. And yet, over that same period, the company’s stock dropped more than 89%.
What happened?
A better question is: What didn’t happen? Despite growing sales, the company has struggled to turn a profit.

Read more »

AI Rally Market Risks

LAST WEEK, OPENAI founder Sam Altman sat down for an interview with venture capitalist Brad Gerstner and Microsoft CEO Satya Nadella. Both are investors in OpenAI, so it seemed like a friendly audience. But Gerstner posed a question that seemed to make Altman uncomfortable.
Since introducing ChatGPT three years ago, OpenAI has posted impressive growth, but Gerstner wondered whether the company was, nonetheless, getting ahead of itself.
“How can a company with $13 billion in revenues make $1.4 trillion of spend commitments?” Gerstner asked.

Read more »

Backdoor Roth Explained

ROTH IRA IS A powerful account. It grows tax-free and withdrawals are tax-free during retirement. Roth IRA also has income limits.
For 2025, if you are filing your taxes as single and make less than $150,000 ($236,000 if married filing jointly) of modified adjusted gross income, you can contribute a maximum amount of $7,000.
But if you make $165,000 (single) or $246,000 (married jointly), you are ineligible to contribute to a Roth IRA directly.

Read more »

Asset Location Decisions

WHERE YOU PUT your investments can make a huge difference for your after-tax wealth. 
As you know, we have 3 main investment accounts:

Taxable account. A traditional brokerage account where you are taxed every time you dividends or sell investments at a gain.
Tax deferred account. Traditional 401(k), 403(b), and traditional IRAs allow taxes to be deferred to the future. You pay taxes when your investments are withdrawn, and generally come with an immediate tax deduction.

Read more »

Navigating the Unknowns of Financial Decisions

WHEN IT COMES to financial decisions, there are, as I’ve argued before, two answers to every question: what the calculator says, and how you feel about it. There’s a fly in the ointment, though: Calculator answers might appear to be based in logic, but they’re still imperfect.
Why?
Ian Wilson, a former executive at General Electric, explained it this way: “No amount of sophistication is going to allay the fact that all knowledge is about the past,

Read more »

Spotlight: Grossman

Rule Your World

I’VE NEVER BEEN a fan of financial planning rules of thumb. To understand why, consider a common shortcut for choosing an asset allocation: The allocation to bonds in a portfolio, according to this rule of thumb, should equal an investor’s age. For example, if an investor is 65 years old, his or her allocation to bonds should be 65%. That sounds reasonable—until you realize that Microsoft founder Bill Gates is 65. Should he have the same asset allocation as everyone else his age? Perhaps he’s an extreme example. But how about a 65-year-old who is retired with a secure government pension? As you can see, rules of thumb can quicky break down. It’s for this reason that I’m skeptical of rules of thumb. But in a recent interview, behavioral scientist Sarah Newcomb cited the work of Gerd Gigerenzer. A professor and the author of Gut Feelings, Gigerenzer challenges the view that rules of thumb are a less-than-optimal way to make decisions. In some ways, he argues, they are superior to a strictly numbers-based, analytical approach. To illustrate, Gigerenzer cites the collapse of the hedge fund firm Long-Term Capital Management. An entire book was written about it. But in short, what happened was that the fund’s managers relied too heavily on statistical models using historical data. They failed to consider the possibility that things might turn out differently—and worse—in the future than in the past. And that’s exactly what happened. In 1998, the fund suffered a spectacular failure, going to zero essentially overnight. Were it not for a bailout by the Federal Reserve, Long-Term Capital might have taken down its trading partners, including some of Wall Street’s biggest banks. This was an extreme but hardly isolated case. It’s why Gigerenzer asserts that rules of thumb shouldn’t be dismissed as an inferior way to think about problems. On the contrary,…
Read more »

Decision Frameworks

IN THE SUMMER of 1966, author John McPhee spent two weeks lying on a picnic table in his backyard. Why? McPhee was suffering from writer’s block. As he described it, “I had assembled enough material to fill a silo, and now I had no idea what to do with it.” Investors find themselves in a similar situation today. There’s no shortage of financial information around us. But that doesn’t make it easier to know what to do with it.  When it comes to financial decision-making, there is, of course, one fundamental problem: None of us can see around corners. But that doesn’t leave us completely empty-handed. Whenever possible, I suggest employing decision frameworks. They can help us to do the best we can in the absence of complete information. Here are four such frameworks you might consider as you look ahead to the new year. Trading decisions Suppose you’re lukewarm on an investment and thinking of selling it. How should you think through this decision? To start, you might evaluate the investment’s merits. If it’s an individual stock, you could examine its valuation and study the company’s financials. If it’s a fund, you could look at its track record and management fees. And if it’s held in a taxable account, you could also check its tax efficiency.  Against those factors, you would then assess the tax impact of selling your shares. But how should you weight each factor in your decision? A fund might be tax-inefficient, for example, but have a good track record. When making decisions like this, the framework I suggest is to evaluate three factors: risk, growth potential and tax impact. And I would consider them in that order. Estate taxes The federal estate tax can be punitive for those with assets over the lifetime exclusion. Under…
Read more »

Know Doubt

ONE SPRING DAY in 1995, McArthur Wheeler walked into two banks near his Pittsburgh home and robbed them at gunpoint. His plan had one critical flaw: The disguise he chose didn't hide his face at all. Instead of the usual stocking cap or hat and sunglasses, Wheeler made an unconventional choice. He applied a coating of lemon juice to his face. His reasoning: Lemon juice could be used to make invisible ink, so Wheeler figured it would have the same effect on his face, making it invisible to surveillance cameras. Because he was so easily identified, Wheeler was arrested just hours later. As police led him away, Wheeler sighed in disbelief. “But I wore the juice,” he said. Wheeler's case is so famously absurd that it was later featured in an academic article, Unskilled and Unaware of It, by David Dunning and Justin Kruger. Their insight: People are often poor judges of their own competence. Worse still, we often get it exactly wrong. Incompetent people think they’re more competent than they actually are, while highly competent people tend to underestimate their skill. While McArthur Wheeler is in a class by himself, Dunning and Kruger's research carries an important message for the rest of us: Overconfidence can be a big problem, especially when it comes to the world of investments, where there’s as much noise as there is data and where there's a strong temptation to predict what will happen next. After all, the hard part about financial planning isn't the math, but rather the uncertainty. What can you do to navigate this uncertainty? Here are three suggestions: 1. Stay the course. At its core, financial planning is simple: You have a set of financial goals, and you want to be sure you're saving enough to reach those goals. But with the stock market's regular ups…
Read more »

Three Risks

ON DEC. 17, 2002, Harry Markopolos walked out of his Boston office wearing an oversized trench coat and a pair of white cotton gloves. His destination: the John F. Kennedy Presidential Library.  A quiet figure, Markopolos worked as the chief investment officer at a small firm that specialized in trading stock options. He had heard about a New York-based competitor that was apparently doing similar work, but with much greater success. Following his boss’s recommendation, Markopolos tried one day to replicate his competitor’s strategy. But when he did, a funny thing happened. He realized that he couldn’t—not because he wasn’t capable, but because it simply wasn't possible. As Markopolos tells the story, it was just five minutes before he began to suspect something fishy about the New York firm’s numbers. By the end of day, with just a little more work, he was sure of it. So sure, in fact, that Markopolos decided to alert the authorities. Markopolos prepared a detailed written report. His objective that December day: to hand deliver it, anonymously, to the New York State Attorney General, who happened to be speaking at the Kennedy Library. Markopolos’s analysis was dense, packed with math. But the bottom line was clear: It was mathematically impossible for the New York firm to be doing what it claimed to be doing. If that was the case, the only alternative was that the firm—Bernard L. Madoff Investment Securities—was a giant fraud, running the world’s largest Ponzi scheme. In Markopolos’s words, he “gift wrapped" the Madoff case for the government. In addition to the New York Attorney General, Markopolos also contacted the SEC. Yet none of these regulators took any action. Madoff was able to continue his fraud for another six years before it finally unraveled. Markopolos was recently in the news again—this…
Read more »

The Other Answer

THERE ARE USUALLY TWO answers to every personal-finance question: There’s what the calculator says—and then there’s how you feel about it. What does that mean in practice? Let’s look at an example. Suppose you’re considering when to claim Social Security. Many retirees struggle with this question. On the one hand, the government offers a strong incentive to wait: For each year you forgo Social Security—up to age 70—your future benefit will grow by some 8%. That’s on top of inflation. But those who wait also pay a price. Each year that you delay is also a year during which you don’t receive benefits. Result: For those who delay claiming Social Security, it takes some number of years to break even on that decision. Consider an individual who would be eligible for a benefit of $30,000 at age 67. To maximize his benefit, he could wait until 70. Then he’d receive $37,200—a substantial increase. But in the meantime, he’d be giving up three years of benefits totaling $90,000. How long would it take to break even? Putting aside inflation, the math is straightforward: Starting at age 70, he’d receive an extra $7,200 per year. To make up the $90,000 he earlier gave up would thus take about 12 years ($90,000 ÷ $7,200 = 12.5). To break even, he’d have to wait until age 82 or 83. While 12 years might sound like a long time, this tradeoff still makes sense for a lot of people. Yes, 82 is only a few years less than the average U.S. life expectancy, which is age 84 for a 65-year-old man and age 87 for a 65-year-old woman. But that overlooks two factors: First, life expectancies differ dramatically among demographic groups. Education and profession are also key factors. As a result, your own life expectancy could easily…
Read more »

Portfolio Insurance

A TEL AVIV WOMAN named Anat decided to surprise her elderly mother with a gift. Noticing that her mother had been sleeping on the same worn-out mattress for decades, Anat replaced it while her mother was away from the house. She then took the old mattress out to the curb. It wasn't until the next morning that her mother noticed the change and asked what had happened to the old mattress. Anat explained that she had put it out with the trash, which had since been picked up. This sent her mother into a panic. It turned out she had hidden her life's savings in the old mattress—more than $1 million. According to news reports about the 2009 incident, they searched three different dumpsites across the city but never found it. When I mentioned this story to a colleague, he described something similar. When his grandfather passed away, he helped clean out his house. In the freezer they found several packages labeled “fish.” These packages caught his eye because, he said, “there were a lot of them, and they didn’t look like fish.” As you can probably guess, when he opened them, he found piles of cash. These stories are both funny and not funny at the same time. They’re also not unusual. According to a Marist College poll, people hide money in all kinds of places. More than 10% hide cash under the mattress. Even more hide money in the freezer. Other popular spots include the sock drawer and the cookie jar. There's also the backyard. I don’t recommend keeping cash in your home like this—unless it's in a safe—but I understand the emotional appeal. A pile of cash is tangible in a way that a bank balance isn’t. Especially in a volatile world, it's comforting to have a stable asset. But…
Read more »