Our children are more likely to follow our financial example than our financial advice.
| 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.
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. 109: RETIREMENT isn’t a hard deadline, like buying a home or paying for college. Instead, we might spend down our portfolios over 30 years. The upshot: While it’s prudent to move 100% of your house down payment and kid’s college fund into bonds and cash as you approach those goals, you might start retirement with, say, 60% invested in stocks.
OPEN A DONOR-advised fund. You can deduct contributions to the fund this year, and then disburse the money to your favorite charities over time. A popular strategy: Donate, say, three years’ worth of charitable gifts in a single year, so your total itemized deductions are well above the standard deduction—and thus you get a large tax break for your generosity.
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.
WHEN I WAS GROWING up, I’d receive Series E savings bonds as birthday gifts from my parents. It was the start of many to come. My parents had great respect for savings bonds and, as I got older, I came to hold them in high regard as well.
Savings bonds never offered the highest interest rate. At a defense plant where I worked, a guy in the accounting department questioned my bond buying. He noted that savings bonds paid less interest than the certificates of deposit then available.
I HAVE MY MOTHER to thank for my good savings habits. She opened a savings account in my name when I was a kid. She also made sure I had a Christmas Club savings account every year. I was required to make deposits regularly.
I didn’t mow my neighbor’s lawn, have a newspaper route or sell lemonade on my front lawn. Instead, the money I saved came from the allowance my mother paid me.
SECTION 415(D) OF the IRC requires the Secretary of the Treasury (IRS) to annually adjust limitations for cost-of-living increases. So, let’s dive into some of the changes:
401(k), 403(b), and Most 457 Plans:
For 2026, the 401(k)/403(b)/457(b) amount you can contribute is increasing from $23,500 to $24,500. If you are in a 24% marginal tax rate, that’s an additional $240 of federal taxes you can defer. If you are over age 50, the catch-up contributions are also increasing by $500,
MANY PEOPLE ARE familiar with tax loss harvesting, where you sell a losing security/ETF and rebuy a similar, not identical, security/ETF.
But often we don’t really think about the opposite side of the coin: sell a winning security/ETF and rebuy the exact same, or a different, security/ETF.
That strategy is called tax gain harvesting, and because it’s a gain, the wash sale rule doesn’t apply.
Execution
Long-term capital gains can be taxed at 0% depending on your income.
I’VE ALWAYS BEEN a saver, and perhaps even pathologically frugal. Growing up, it pained me to spend money, even on food when I was hungry. Today, I have more than enough money, but I still resist paying full price for food.
Perhaps I’m just genetically frugal, or perhaps my feelings about money reflect my parents and my upbringing. My mom once shared that her aunt predicted that she’d make lots of money, but it would be like grains of rice and slip through her fingers. Meanwhile,
JEFF WAS A NEW engineer who began his nuclear power career a couple of decades ago as part of my group. He’d graduated from a middling engineering school with a stellar grade point average. Quiet, though not shy, he had a serious demeanor.
Jeff had a goal of purchasing a house as soon as possible. Needless to say, this was a tall order for someone just starting his career. He lived a spartan lifestyle,
Frittering away Frugality
R Quinn | Jul 8, 2026
Thinking of a possible reason to tap Roth earlier then planned
edwardsbruce1 | Jul 5, 2026
Every Writer Has a Beginning: Jonathan’s First Essay
Andrew Clements | Jul 8, 2026
Reluctantly Saving Money
Mark Crothers | Jul 7, 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
Mr Market visits Art Basel
ricardodiaque | Jun 29, 2026