What’s the difference between an equity-indexed annuity and an index fund? One needs an army of salespeople. The other sells itself.
| Scenario | Estimated 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 pattern | Potentially $45,000+ |
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.
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.
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.
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.
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.
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.
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,
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.
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.
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,
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.
Frittering away Frugality
R Quinn | Jul 8, 2026
Reluctantly Saving Money
Mark Crothers | Jul 7, 2026
Every Writer Has a Beginning: Organ Transplant Fails
Andrew Clements | Jul 8, 2026
Don’t Let a Roth Conversion Trigger a Penalty
John Urban | Jul 8, 2026
Thinking of a possible reason to tap Roth earlier then planned
edwardsbruce1 | Jul 5, 2026
A $30,000 Mistake
ArticleJohn Urban | Jul 4, 2026
- 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:- 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.Happy 250th Birthday America
Nick Politakis | Jul 3, 2026
Haunted Head
Dan Smith | Jul 3, 2026
Should I Lock in CD Rates Now or Stay in Money Market?
Mark Crothers | Jan 13, 2026
Reminded of Jonathan’s Grace
rkhamilton920 | Jun 29, 2026
Tempted by the Shiny and New: Another HD Car Post
Mark Crothers | Jul 3, 2026
IRS Notice 2025-68 – I’m trying to understand an aspect of the new tax law
William Perry | Dec 4, 2025